MXPA06005334A - Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of light - Google Patents
Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of lightInfo
- Publication number
- MXPA06005334A MXPA06005334A MXPA/A/2006/005334A MXPA06005334A MXPA06005334A MX PA06005334 A MXPA06005334 A MX PA06005334A MX PA06005334 A MXPA06005334 A MX PA06005334A MX PA06005334 A MXPA06005334 A MX PA06005334A
- Authority
- MX
- Mexico
- Prior art keywords
- naphthalene
- alkyl
- tert
- dicarboxylic
- mixtures
- Prior art date
Links
- 239000011368 organic material Substances 0.000 title claims abstract description 46
- 230000000254 damaging effect Effects 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title claims description 80
- NRXUWZCOERPIOT-UHFFFAOYSA-N 1,3-dioxobenzo[de]isoquinoline-6-carbonitrile Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=C(C#N)C3=C1 NRXUWZCOERPIOT-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 233
- GRVIMBYDMARKEZ-UHFFFAOYSA-N 8-carbamoylnaphthalene-1-carboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)N)=CC=CC2=C1 GRVIMBYDMARKEZ-UHFFFAOYSA-N 0.000 claims abstract description 108
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000004429 atom Chemical group 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 150000001721 carbon Chemical group 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
- -1 cyano, amino, hydroxyl Chemical group 0.000 claims description 288
- 229920000642 polymer Polymers 0.000 claims description 116
- 239000006096 absorbing agent Substances 0.000 claims description 67
- 229920000515 polycarbonate Polymers 0.000 claims description 62
- 239000004417 polycarbonate Substances 0.000 claims description 60
- 229920003023 plastic Polymers 0.000 claims description 55
- 239000004033 plastic Substances 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- 239000003381 stabilizer Substances 0.000 claims description 42
- 229920001577 copolymer Polymers 0.000 claims description 41
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 41
- 150000001412 amines Chemical class 0.000 claims description 38
- 239000003963 antioxidant agent Substances 0.000 claims description 33
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 239000000654 additive Substances 0.000 claims description 29
- 230000003078 antioxidant effect Effects 0.000 claims description 29
- 239000000975 dye Substances 0.000 claims description 28
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 28
- 150000001565 benzotriazoles Chemical class 0.000 claims description 27
- 239000000049 pigment Substances 0.000 claims description 26
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 150000002989 phenols Chemical class 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 22
- 229920002223 polystyrene Polymers 0.000 claims description 21
- 239000004793 Polystyrene Substances 0.000 claims description 20
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 20
- 229920000728 polyester Polymers 0.000 claims description 20
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 19
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 19
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 claims description 18
- 229920001155 polypropylene Polymers 0.000 claims description 18
- RXELBMYKBFKHSM-UHFFFAOYSA-N 2-phenyl-1,3,5-triazine Chemical class C1=CC=CC=C1C1=NC=NC=N1 RXELBMYKBFKHSM-UHFFFAOYSA-N 0.000 claims description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000004743 Polypropylene Substances 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- VSXIZXFGQGKZQG-UHFFFAOYSA-N 2-cyano-3,3-diphenylprop-2-enoic acid Chemical class C=1C=CC=CC=1C(=C(C#N)C(=O)O)C1=CC=CC=C1 VSXIZXFGQGKZQG-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000006069 physical mixture Substances 0.000 claims description 14
- 229920000098 polyolefin Polymers 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 150000001993 dienes Chemical class 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 9
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- 239000004416 thermosoftening plastic Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000002667 nucleating agent Substances 0.000 claims description 7
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 7
- 229940045997 vitamin a Drugs 0.000 claims description 7
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 229920001903 high density polyethylene Polymers 0.000 claims description 6
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 claims description 6
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 claims description 6
- 229920008790 Amorphous Polyethylene terephthalate Polymers 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 5
- 239000004700 high-density polyethylene Substances 0.000 claims description 5
- 238000003303 reheating Methods 0.000 claims description 5
- 229920008651 Crystalline Polyethylene terephthalate Polymers 0.000 claims description 4
- 230000001627 detrimental effect Effects 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 239000000123 paper Substances 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- YAAQEISEHDUIFO-UHFFFAOYSA-N C=CC#N.OC(=O)C=CC=CC1=CC=CC=C1 Chemical compound C=CC#N.OC(=O)C=CC=CC1=CC=CC=C1 YAAQEISEHDUIFO-UHFFFAOYSA-N 0.000 claims description 3
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 3
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 230000002939 deleterious effect Effects 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical class O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 claims 2
- 150000001241 acetals Chemical class 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 229920000638 styrene acrylonitrile Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 235000006708 antioxidants Nutrition 0.000 description 28
- 230000005540 biological transmission Effects 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 150000002148 esters Chemical class 0.000 description 26
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 25
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 22
- 239000004611 light stabiliser Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 21
- 238000000465 moulding Methods 0.000 description 21
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 20
- 150000003254 radicals Chemical group 0.000 description 20
- 239000010408 film Substances 0.000 description 19
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 230000005855 radiation Effects 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- ZFUOUGCLKHYEIY-UHFFFAOYSA-N 1,1'-biphenyl;2,4-ditert-butylphenol;trichlorophosphane Chemical compound ClP(Cl)Cl.C1=CC=CC=C1C1=CC=CC=C1.CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ZFUOUGCLKHYEIY-UHFFFAOYSA-N 0.000 description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 14
- CVSXFBFIOUYODT-UHFFFAOYSA-N 178671-58-4 Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=C(C#N)C(=O)OCC(COC(=O)C(C#N)=C(C=1C=CC=CC=1)C=1C=CC=CC=1)(COC(=O)C(C#N)=C(C=1C=CC=CC=1)C=1C=CC=CC=1)COC(=O)C(C#N)=C(C=1C=CC=CC=1)C1=CC=CC=C1 CVSXFBFIOUYODT-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000005842 heteroatom Chemical group 0.000 description 13
- 229920000573 polyethylene Polymers 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 150000005846 sugar alcohols Polymers 0.000 description 13
- OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 12
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 12
- 239000004698 Polyethylene Substances 0.000 description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 11
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- 239000002585 base Substances 0.000 description 10
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 10
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 description 10
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- 239000000178 monomer Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
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- 125000001624 naphthyl group Chemical group 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 8
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- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 6
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 6
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- IMXRBCGZTVENAC-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical class C=1C=CC=CC=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 IMXRBCGZTVENAC-UHFFFAOYSA-N 0.000 description 1
- NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical class C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- IXVLEAZXSJJKFR-UHFFFAOYSA-N octadecyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CSCC1=CC(C)=C(O)C(C)=C1 IXVLEAZXSJJKFR-UHFFFAOYSA-N 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
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- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
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- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006302 stretch film Polymers 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920006230 thermoplastic polyester resin Polymers 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910021573 transition metal iodide Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- RZLBWJFZKYADKB-UHFFFAOYSA-N tridecan-4-yl 2-[(3,5-ditert-butylphenyl)methylsulfanyl]-2-hydroxyacetate Chemical compound OC(C(=O)OC(CCC)CCCCCCCCC)SCC1=CC(=CC(=C1)C(C)(C)C)C(C)(C)C RZLBWJFZKYADKB-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Abstract
A description is given of the use of naphthalene-1,8-dicarboxylic monoimides of the formula (I), in which R1 is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl and R2 is a radical containing at least one&pgr;electron system containing a carbon atom and at least one further atom selected from carbon, oxygen, and nitrogen, with the proviso that the radical contains at least one atom other than carbon;to protect organic material from the damaging effects of light, of compositions which comprise at least one naphthalene-1,8-dicarboxylic monoimide of the formula (I) in an amount which provides protection from the damaging effects of light, and at least one organic material, and of new naphthalene-1,8-dicarboxylic monoimides (I).
Description
USE OF DERIVATIVES OF 4-CYANO-NAFTALEN-1, 8-DICARBOXAMIDE AND
RELATED COMPOUNDS TO PROTECT ORGANIC MATERIAL A
STARTING FROM HARMFUL EFFECTS OF LIGHT
DESCRIPTION OF THE INVENTION The present invention relates to the use of naphthalene-1, 8-dicarboxylic monoimides to protect organic material against the damaging effects of light, to compositions which comprise at least one organic material and at least one monoimide naphthalene-1 , 8-dicarboxylic of the formula I in an amount that provides protection from the damaging effects of light, and new monoimides naphthalene-1, 8-dicarboxylic. Living and inanimate organic material such as human or animal skin, human or animal hair, paper, food, perfumes, cosmetics, plastics, polymer dispersions, paints, photographic emulsions, photographic layers, etc., is often sensitive to the damaging effects of light, and particularly to the fraction of ultraviolet (UV) radiation which occurs in daylight. The damage may be due to the UVA fraction of the UV radiation, that is, the region of approximately 320 to 400 nm, the UVB fraction of the UV radiation, ie the region from 280 to 320 nm, and the fractions even shorter wavelength of UV radiation. There is therefore a substantial and constant demand for new substances which provide effective protection against such harmful effects. In this application, the substances employed have to comply increasingly with a complex profile of requirements designed for the specific nature of the organic material that is protected, the circumstances under which protection is required and the desired protective effect. It is known that the mechanical, chemical and / or aesthetic properties of organic material, particularly plastics, can deteriorate under the effect of light. This deterioration usually manifests as yellowing, discoloration, cracking or cracking in the material. An important field of use for light stabilizers is therefore the protection of plastics. Plastic containers and plastic films find widespread use as packaging materials, for example. For aesthetic reasons, plastics that exhibit light intensity transmission in the visible wavelength range from 400 to 750 nm are increasingly gaining importance as packaging materials. Clear plastics with or without light coloration, however, are generally transparent to the UV fractions of daylight, with the consequence that, under light, both the packaging material and the packaged products suffer from aging.
Depending on the specific packaged contents, the adverse alteration to the contents may be manifested, for example, in a change of appearance, such as yellowing and discoloration, in a change in taste and / or odor, and / or in the decomposition of ingredients . In the case of food, perfumes and cosmetics, shelf life and preservation properties can be abruptly reduced. The stabilizers that are added to the plastic for packaging must therefore provide satisfactory protection both in the plastic itself and in the packaged product with respect to aging processes induced by light. Plastics are also in widespread use in combination with glass in composite materials which are transparent in the visible wavelength range. Composite systems of this kind find use in automotive or architectural varnishing, for example. The windows of cars of this class increasingly require absorbing radiation in the wavelength range below 400 nm, in order to protect the interior of the car and its occupants from UV radiation, for example. GB 1,003,083 describes 4-alkoxynaphthalene-1, 8-dicarboxylic monoimides and their use as optical brighteners for fabrics. The fabrics may consist of natural or synthetic fibers, including polyamides, polyesters, polyurethanes, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile or polyvinyl alcohols. EP 0682145 describes a method for improving the sun protection factor in fabrics, wherein the woven fiber is treated with a composition comprising at least one optical brightener which is absorbed in the wavelength range of 280-400 nm. In addition to a host of the additional compounds, the suitable optical brighteners specified include (by way of a formula) naphthalene-1, 8-dicarboxylic monoimides which carry in the 4 or 5 position a C 4 -C 4 alkoxy , S03M (wherein the definitions of M include H, Na, K, Ca, Mg, ammonium or mono-, di-, tri- or tetra-alkylammonium of C? -C) or an NHCO-C-alkyl group? C4 The only specific substituted 4 compound described is the 4-methoxy compound. There are no usable examples for this class of compound. EP 0263705 discloses the use of naphthaletracarboxylic acid or its derivatives as light stabilizers in thermoplastic polyester resin compositions, wherein additional components that may be used include naphthalene monoimides. The imide group of the monoimides may be in positions 1,8, 2,3 or 3,4 of the naphthalene ring. Additionally, the naphthalene ring is not substituted or can transport up to 6 additional substituents, selected from halo, hydroxyl, amino, nitro, cyano, sulfonic acid or metal salts thereof, optionally substituted alkyl, optionally substituted alkenyl, optionally aralkyl substituted and optionally substituted alkylaryl. Preferably, the naphthalene ring of naphthalen monoimides does not carry any of the additional substituents. EP 0335595 discloses thermoplastic polyester compositions comprising as UV absorbers a diimide compound, more so if desired, a naphthalene monoimide. The imide group of the monoimide can be located in positions 1,2, 1,8 or 2,3 of the naphthalene ring. The naphthalene ring can carry up to 6 additional substituents, selected from halo, carboxyl or an ester thereof, hydroxyl, -0-C (= 0)) CH3, amino, nitro, cyano, sulfonic acid or a metal salt thereof , optionally substituted alkoxy, optionally substituted aliphatic groups and optionally substituted aromatic groups. JP1024852 describes the use of substituted or unsubstituted naphthalenedicarboxylic and tetracarboxylic acids or their esters, imides and anhydrides as light stabilizers for polyamide resins. The polyamide resins can be used as packaging material for food. JP-7247978 describes rinsing compositions for synthetic fibers, comprising a mixture of 4-substituted naphthalene-1, 8-dicarboxylic monoimides and, if desired, alkylnaphthalenesulfonates. The mixture comprises naphthalenecarboxylic monoimides wherein the substituent at the 4-position is an unsubstituted lower alkoxy or phenoxy or a benzyloxy group and compounds wherein the substituent at the 4-position is an alkylthio, phenylthio or benzylthio group. The imide nitrogen atom can in each case be replaced by a hydrogen atom or by an alkyl or hydroxyl group. A significant disadvantage of the naphthalene-1, 8-dicarboxylic monoimides substituted and unsubstituted with phenoxy and / or substituted with lower alkoxy described is their low compatibility with plastics. The light stabilizers of the prior art have a number of disadvantages. A substantial disadvantage is the period of the protective effect, which is often too short, since the known light stabilizers often have inadequate UV stability. Another disadvantage is that many known light stabilizers have an intrinsic color clearly discernible in the visible wavelength range, with the consequence that a plastic stabilized with these light stabilizers appears to have a pale yellow coloration. further, many light stabilizers are unable to filter the long wave fraction of UVA radiation. Many light stabilizers exhibit low solubility in the application medium. The resulting crystallization of the light stabilizer may render the polymer opaque. Additional advantages are the often deficient synthetic availability of light stabilizers, their inadequate formulation properties, their low resistance to sublimation and / or their low migration strength. There is therefore still a need for stabilizers and stabilizer compositions which have improved performance properties and / or are easier to prepare. It is an object of the present invention, therefore, to provide stabilizers which are suitable as UV absorbers for protecting organic material such as plastics, polymer dispersions, paints, photographic emulsions, photographic layers, paper, human or animal skin, human hair or animal, food, etc., for a relatively long period of time. The stabilizers should preferably be absorbed with high extinction in the UVA region, and particularly also in the long wave UVA region above 360 nm, they should be photostable and / or thermally stable, and they should have little or no intrinsic color in the range of visible wavelength. Surprisingly, it has now been found that the use of naphthalene-1, 8-dicarboxylic monoimides of the formula I
wherein R1 is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl and R2 is a radical containing at least one electron system p containing a carbon atom and at least one further atom selected from carbon, oxygen and nitrogen, with the proviso that the radical contains at least one atom other than carbon to protect the organic material against the damaging effects of light. The present invention consequently provides the use of naphthalene-1, 8-dicarboxylic monoimides of the formula I to protect organic material against the damaging effects of light. The present invention further provides a composition comprising at least one organic material and at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I in an amount that provides protection against the detrimental effects of light.
The present invention further provides a method for protecting the organic material against the deleterious effects of light, which involves adding to the material at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I. The present invention also provides compounds of the formula I
wherein R1 is hydrogen, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl, preferably C5-C8 cycloalkyl or phenyl, the two radicals mentioned at the end, each is not substituted or carries one, two, three, four or five alkyl groups of C_-C4, and R2 is cyano, -C (0) NR5R5a or phenyloxy which carries one, two, three, four or five C alquilo-C_2 alkyl groups; and R 5 and R 5a are each independently of one another hydrogen, C 1 -C 8 alkyl, aryl or heteroaryl, aryl and heteroaryl each being unsubstituted or carrying one or more substituents preferably selected from C 1 -C 6 alkyl, alkoxy of C_-Cg, hydroxyl, carboxyl and cyano. The term "protection" is to be broadly construed in the context of the present invention. This covers on the one hand the stabilization of an organic material with respect to the damaging effects of light in order to avoid and / or retard the degradation processes initiated with light in the organic material. For this purpose, an agent which protects against light is added to the organic material. On the other hand, the aforementioned term, in the context of the present invention, also encompasses the indirect protection of materials, wherein a material containing, an agent that protects against light at least partially surrounds other organic material which does not it is protected against the effects of light, so that it reduces the damaging effects of light to the organic material behind which it is not protected from light. For the purpose of explaining the present invention, the term "alkyl" embraces straight and branched chain alkyl. The alkyl is preferably straight or branched chain C_-c30 alkyl, particularly C_-C2o alkyl, and especially C_-C_2 alkyl. Examples of alkyl groups are, in particular, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 2-methylbutyl, 3-methylbutyl, 1/2 -dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 2-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl , 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, -ethyl-2-methylpropyl, n-heptyl, 2-heptyl, 3-heptyl, 2-ethylpentyl, 1-propylbutyl, n-octyl, 2-ethylhexyl, 2-propylheptyl, 1, 1,3, 3-tetramethylbutyl, nonyl , decyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl. The alkyl also encompasses an alkyl whose carbon chain can be interrupted by one or more non-adjacent groups selected from -O-, -S-, -NR3-, -CO- and / or -S02-; that is, the terms of the alkyl group are formed by the carbon atoms. The above observations apply equally to alkoxy and alkylamino. The term "alkenyl" refers in the sense of the present invention to straight-chain and branched alkenyl groups, which depending on the chain length can carry one or more double bonds. These are preferably C2-C20 alkenyl groups, more preferably C2-C_0, such as vinyl, allyl or methylallyl. "Alkenyl" also encompasses substituted alkenyl groups, which may carry, for example, 1, 2, 3, 4 or 5 substituents. Examples of suitable substituents include cycloalkyl, heterocycloalkyl, aryl, heteroaryl, nitro, cyano, halo, amino and mono- and di (C_-C2o) alkyl amino. Cycloalkyl for the purposes of the present invention encompasses both substituted and unsubstituted cycloalkyl groups, preferably C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, and especially C5-C8 cycloalkyl. When the cycloalkyl groups are substituted, they can carry one or more - for example, one, two, three, four or five C_-C6 alkyl groups. The C5-C8 cycloalkyl, which is unsubstituted or can carry one or more C_-C6 alkyl groups, is for example, cyclopentyl, 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclopentyl, cyclohexyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 3- and 4-propylcyclohexyl, 3- and 4-isopropylcyclohexyl, 3- and 4-butylcyclohexyl, 3- and 4-sec-butylcyclohexyl, 3- and 4-tert-butylcyclohexyl, cycloheptyl, 2-, 3- and 4-methylcycloheptyl, 2-, 3- and 4-ethylcycloheptyl, 3- and 4-propylcycloheptyl, 3- and 4-isopropylcycloheptyl, 3- and 4-butylcycloheptyl, 3 - and 4-sec-butylcycloheptyl, 3- and 4-tert-butylcycloheptyl, cyclooctyl, 2-, 3-, 4- and 5-methylcyclooctyl, 2-, 3-, 4- and 5-ethylcyclooctyl and 3-, 4- and 5-propylcyclooctyl.
Aryl for the purposes of the present invention encompasses monocyclic or polycyclic aromatic hydrocarbon radicals which may be substituted or unsubstituted. The aryl is preferably phenyl, tolyl, xylyl, mesityl, duryl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl or naphthyl, more preferably phenyl or naphthyl, it being possible for these aryl groups when substituted to carry generally 1, 2, 3, 4 or 5, preferably 1, 2 or 3 substituents selected from C 1 -C 8 alkyl, C 1 -C 6 alkoxy, cyano, C0NR 4 Ra, C 0 2 R 4, arylazo and heteroarylazo, with arylazo and heteroarylazo themselves being unsubstituted or carrying one or more radicals selected independently from one another from C_-C_8 alkyl, C_-C6 alkoxy and cyano. The aryl, unsubstituted or carrying one or more radicals selected independently from each other from C 1 -CS alkyl, Ci-C alkoxy. and cyano, is for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3 - and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dipropylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and 2 , 6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 2-, 3- and 4-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dibutylphenyl, 2,4,6- tributylphenyl, 2-, 3- and 4-isobutylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisobutylphenyl, 2,4,6-triisobutylphenyl, 2-, 3- and 4-sec -butylphenyl, 2,4-2,5-, 3,5- and 2,6-di-sec-butylphenyl, 2,, 6-tri-sec-butylphenyl, 2-, 3- and 4-tert-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di-tert-butylphenyl and 2,4,6-tri-tert-butylphenyl, 2-, 3- and 4-methoxyphenyl, 2,4 -, 2,5-, 3,5- and 2,6-dimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-, 3- and 4-ethoxyphenyl, 2,4-, 2,5-, 3,5- and 2, 6-diethoxyphenyl, 2,4,6-triethoxyphenyl, 2-, 3- and 4-propoxyphenyl, 2,4-, 2 , 5-, 3,5- and 3,6-dipropoxyphenyl, 2-, 3- and 4-isopropoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisopropoxyphenyl, 2-, 3 - and 4-butoxyphenyl; and 2-, 3- and 4-cyanophenyl. The heterocycloalkyl for the purposes of the present invention encompass unsaturated or unsaturated cycloaliphatic, non-aromatic groups, generally having 5 to 8 ring atoms, preferably 5 or 6 ring atoms, wherein 1, 2 or 3 of the atoms in the ring are replaced by heteroatoms selected from oxygen, nitrogen, sulfur and a group -NR3- and are not replaced or replaced by one or more - for example, 1, 2, 3, 4, 5 or 6 groups C_-C3 alkyl. Examples which may be given of such heterocycloaliphatic groups include pyrrolidinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, morpholinyl, thiazolidinyl, isothiazolidinyl, isoxazolidinyl, piperazinyl, tetrahydrothiophenyl, dihydrothien-2-yl, tetrahydrofuranyl, dihydrofuran. -2-yl, tetrahydropyranyl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl and dioxanyl. Heteroaryl for the purposes of the present invention encompasses substituted or unsubstituted monocyclic or polycyclic, heteroaryl groups, preferably the pyridyl, quinolinyl, acridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, indolyl, purinyl, indazolyl groups. , benzotriazolyl, 1,2,3-triazolyl, 1, 3, 4-triazolyl and carbazolyl, which when substituted can generally carry 1, 2 or 3 substituents. The substituents are selected from C_-C6 alkyl, C_-Cg alkoxy, hydroxyl, carboxyl and cyano. 5- to 7-membered heterocycloalkyl or heteroaryl radicals linked by a nitrogen atom and optionally containing additional heteroatoms are, for example, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, pyrrolidinyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, pyridinyl, pyridazinyl, pyrimidinyl. , pyrazinyl, triazinyl, piperidinyl, piperazinyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, indolyl, quinolinyl, isoquinolinyl or quinaldinyl. According to the invention, the radical R2 includes at least one electron system p having one carbon atom and at least one additional atom selected from carbon, oxygen and nitrogen. It should be understood in the context of the present invention to encompass electron p systems with both p junctions located and misplaced. P electron systems with mismatched p-junctions include aromatic compounds, heteroaromatic compounds and polyenes. An electron p system is generally possible only in the case of polyatomic groups. Examples of electron systems p composed of carbon atoms are groups having one or more C = C double bonds such as alkenyl, cycloalkenyl or aryl, and groups having at least one triple C = C bond such as in alkynyl or cycloalkynyl. Examples of groups with an electron system p having at least one carbon atom and at least one additional atom selected from oxygen and nitrogen are aryloxy, corresponding heteroaryls and the carbonyl group, for example, the keto group or the aldehyde group , the carboxyl group and also the carboxylate group, the ester group, the amide group and the anhydride group, groups having a double C = N bond such as in imines, and groups having a triple C = N bond as in nitriles. It will be appreciated that R2 can contain two or more electron systems p selected independently from each other from the aforementioned groups. Preferably R2 contains only one electron system p. The electron p system is preferably in combination with the naphthalene backbone. The expression "wherein R2 is a radical which contains at least one electron system p having one carbon atom and at least one additional atom selected from carbon, oxygen and nitrogen, with the proviso that the radical contains less an atom other than carbon "is understood in the context of the present invention to mean that R2 has at least one carbonless atom, ie, at least one heteroatom - one or two heteroatoms, for example. The heteroatom can be an oxygen, nitrogen or sulfur atom, for example. The heteroatom can in principle be in any position within R2. For example, the heteroatom can be part of the electron system p. The electron system p may also consist solely of carbon atoms, so that the heteroatom must be at a different position in R2. R 2 can be attached to the skeleton of the naphthalene-1, 8-dicarboxylic monoimide in the form of a carbon atom or as a heteroatom, an oxygen atom for example. A first preferred embodiment of the present invention is re-aligned to the use of at least one compound I wherein R1 is C_-C30 alkyl whose carbon chain can be interrupted by one or more non-adjacent groups selected from -O-, -S -, -NR3-, -CO- and / or -S02-, and / or which is replaced or is not replaced one or more times by identical or different radicals selected from cyano, amino, hydroxyl, carboxyl, aryl, heterocycloalkyl and heteroaryl, with aryl, heterocycloalkyl and heteroaryl groups which are not substituted or carry one or more substituents selected independently from each other from C_-C_8 alkyl and C_-C6 alkoxy; or R1 is C5-C3 cycloalkyl which is not substituted or carries one or more C_C6 alkyl groups, or R1 is 5- to 8-membered heterocycloalkyl which is not substituted or carries one or more C_- alkyl groups C6; or R1 is aryl or heteroaryl, with aryl or heteroaryl which is not substituted or carries one or more radicals independently selected from C_-C_8 alkyl, C_-C6 alkoxy, cyano, C0NR4R4a, C02R4, arylazo and heteroarylazo, with arylazo and heteroarylazo in turn being unsubstituted or carrying one or more radicals independently selected from C 1 -C 8 alkyl, C 1 -C 6 alkoxy and cyano; R3 is hydrogen or C_-C6 alkyl; and R4 and Ra each independently are hydrogen, alkyl, aryl or heteroaryl of C_-C_8, with aryl and heteroaryl in each case being unsubstituted or carrying one or more substituents selected from C_-C6 alkyl, C_-CS alkoxy, hydroxyl, carboxyl and cyano. Particular preference is given to compounds I wherein R 1 is C 1 -C 2 alkyl, C 5 -C 8 cycloalkyl or phenyl, the two radicals mentioned at the end, each being unsubstituted or carrying one, two, three, four or five alkyl groups of C_-C4. Particularly preferred compounds I are those in which R 1 is C 1 -C 12 alkyl or C 5 -C 8 cycloalkyl, especially cyclohexyl, which is not substituted or carries a C 1 -C 4 alkyl group, or R 1 is phenyl which is not substituted or carries one, two or three C_-C4 alkyl groups. If the phenyl carries two or three C_-C4 alkyl groups, then two of these are preferably attached in the 2 and 6 positions. If R1 is an alkyl radical having at least one heterocycloalkyl substituent of a heteroaryl substituent, the radical in The subject matter is preferably a 5- to 7-membered heterocycloalkyl which is attached to the alkyl radical through a nitrogen atom, or a 5- to 7-membered heteroaryl which is attached to the alkyl radical via a nitrogen atom. R1 is, for example, 2-ethylhexyl, cyclohexyl, 4-tert-butylcyclohexyl, phenyl, 2,6-diisopropylphenyl or 2,4,6-trimethylphenyl. A characteristic aspect of the compounds I is the radical R2 with at least one electron system p and at least one heteroatom. The electron system p may contain one or more, for example, one or two - heteroatoms. In a preferred embodiment of the present invention, the electron system p comprises at least one nitrogen and / or oxygen heteroatom. In this case, the radical R2 is preferably linked via a carbon atom of the electron p system to the monoimide naphthalene-1, 8-dicarboxylic skeleton. The radical R2 which characterizes the compound I is in particular cyano or -C (0) NR5R? A, wherein R5 and R5 are as defined above. Preferably R5 and R5a each independently of the other are hydrogen or C_-C18 alkyl, and in particular are each hydrogen. Compounds I wherein R2 is cyano are sometimes referred to later as compounds I-A. Compounds I wherein R2 is -C (0) NR5R5a wherein R5 and R5a are as defined above, are sometimes referred to later as compounds I-B. In a further preferred embodiment of the present invention, the p-electron system is linked through a heteroatom to the monoimide naphthalene-1, 8-dicarboxylic skeleton. A particularly suitable heteroatom is oxygen. In that case, the radical R2 is preferably phenoxy which carries one, two, three, four or five substituents. Substituents of the phenoxy radical are preferably selected from the alkyl of C_C_2, C1_C12 alkoxy, -COOR6, -S03Rs, halo, hydroxyl, carboxyl, cyano, -C0NR5R5a and -NHCOR5, wherein R5, RSa and Rd are as defined above. Particularly preferred alkyl substituents are alkyl radicals of Ca-C 0, especially C 3 -C 0 alkyl radicals. In particular, substituents on the phenyl ring are selected from substituents containing only carbon atoms, so that radical R2 contains only 1 heteroatom. In a particularly preferred embodiment of the present invention, the phenoxy group carries in the 4-position an alkyl group of Cj.-C? O, in particular a C3-C? Alkyl group or such as isopropyl, 1, 1- dimethylpropyl (tert-pentyl) or 1,1,3,3-tetramethylbutyl (tert-octyl). Compounds I wherein R2 is substituted phenoxy are sometimes referred to later as compounds I-C. Especially preferred among the naphthalene-1, 8-dicarboxylic monoimides are those in which R 1 and R 2 in combination have the definitions given below: R 1 is C 1 -C 8 alkyl, especially C 1 -C 8 alkyl, C 5 -C 8 cycloalkyl which an alkyl group of C_-C4, especially cyclohexyl, which is not substituted or carries an alkyl group of C_-C4, or phenyl which is not substituted or carries one, two or three of the alkyl group (s) is not substituted or substituted. of C_-C4, and R2 is cyano, -C (0) NH2 or phenyloxy which carries an alkyl group of C_-C_0, preferably a C3-C10 alkyl group. Examples of suitable naphthalene-1, 8-dicarboxylic monoimides I include 4-cyano-N- (cyclohexyl) -phthalen-1,8-dicarboximide, 4-cyano-N- (4-tert-butylcyclohexyl) -naphthalene-1, 8- dicarboximide, 4-cyano-N- (2,6-diisopropylphenyl) -phthalen-1,8-dicarboximide, 4-cyano-N- (phenyl) -naphthalene-1,8-dicarboximide, 4-cyano -N- (2, 4,6-trimethylphenyl) naphthalene-1,8-dicarboximide, 4-aminocarbonyl-N- (2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide, N- (2,6-diisopropylphenyl) -4- (4- tert-octylphenoxy) naphthalene-1,8-dicarboximide, N- (2,6-diisopropylphenyl) -4- (4-isopropylphenoxy) -phthalen-1,8-dicarboximide, N- (2,6-diisopropylphenyl) -4- ( 4-tert-pentylphenoxy) naphthalene-1, 8-dicarboxy ida, N- (phenyl) -4- (4-tert-octylphenoxy) -naphthalene-1,8-dicarboximide, N- (phenyl) -4- (4- isopropylphenoxy) naphthalene-1, 8-dicarboximide, N- (phenyl) -4- (4-tert-pentylphenoxy) naphthalene-1,8-dicarboximide, N- (2-ethylhexyl) -4- (4-tert-octylphenoxy) naphthalene-1, 8-dicarboximide, N- (2-ethylhexyl) -4- (4-isopropylphenoxy) aftalen-1 , 8-dicarboximide, N- (2-ethylhexyl) -4- (4-tert-pentylphenoxy) naphthalene-1,8-dicarboximide and N- (2,4,6-trimethylphenyl) -4- (4-tert-octylphenoxy) ) naphthalen-1, 8-dicarboximid. Compounds of the formula I-A
wherein R1 has the suitable and preferred definitions specified above can be prepared for example by reacting 4-halonaphthalen-1,8-dicarboximides II with copper cyanide (I) according to scheme 1.
Scheme 1
(ll) (I-A) In scheme 1 Hal is halogen, such as fluorine, bromine, chlorine or iodine, particularly bromine or iodine. R1 is as defined above. R 1 is preferably C 1 -C 2 alkyl, cycloalkyl or C 5 -C 8 phenyl, the two radicals mentioned at the end each being unsubstituted or carrying one, two, three, four or five C 4 alkyl groups. The reaction has place usually in an organic solvent which contains nitrogen and is inert under the reaction conditions. Examples of suitable organic solvents which contain nitrogen include aromatic nitrogen heterocycles such as pyridine, 2-methylpyridine, 3-methylpyridine or 4-methylpyridine, quinoline or isoquinoline, N, N-dialkylcarboxamides such as N, N-dimethylformamide or N, N -dimethylacetamide and N-alkyl-lactams such as N-methylpyrrolidone. The reaction generally takes place at a temperature between room temperature and the boiling temperature of the solvent, preferably at temperatures between 40 ° C and the boiling temperature of the solvent, and in particular at the boiling temperature of the solvent. Compound II and copper (I) cyanide are usually employed in approximately equimolar amounts. It may also be advantageous, however, to use one of the two reagents in excess. In a preferred embodiment, copper (I) cyanide is used in excess, relative to compound II. It may be advantageous to carry out the reaction in the presence of metal iodides, preferably transition metal iodides, and in particular copper iodide (I).
The reaction mixture is generally developed by diluting with water and the product is isolated by filtration.
Where appropriate, the product can be purified in a customary manner, by crystallization or chromatography for example. In order to remove the copper salts, particularly the copper (I) salts, it can be advantageous to convert the salts within the copper (II) salts by oxidation in aqueous solution, with acid peroxide or salts of the product, from the product. Iron (III), for example, and then isolate the product by extraction with a water-immiscible, organic solvent. In addition, the copper salts can be removed by treatment with aqueous solutions of compound reagents, such as ammonia, monoamines or organic diamines, and soluble cyanide salts. An alternative option is to extract the product with organic solvents, for example, chlorinated hydrocarbons such as dichloromethane or 1,2-dichloroethane or ketones such as acetone, with the aid, for example, of a Soxhlet apparatus, from the unpurified product. The 4-halonaphthalen-1,8-dicarboximides II can be prepared, for example, by reacting anhydrides III 4-halonaphthalen-1,8-dicarboxylic acids with a primary IV amine according to the reaction sequence described in scheme 2.
Scheme 2:
(III) (IV) (ID
In scheme 2 Hal is halogen, such as fluorine, bromine, chlorine or iodine, particularly bromine or iodine, and R1 is as defined above. The reaction according to scheme 2 is carried out if desired in the presence of a catalyst. Examples of suitable catalysts are Lewis acids, such as metal ions in the form of their salts, Zn (II) acetate being, for example, Bronstedt acids, such as organic carboxylic or sulfonic acids, examples being acetic acid, atypical acid and p-toluenesulfonic or mineral acids such as sulfuric acid, Bronstedt bases, such as tertiary amines, triethylamine being an example, or mixtures of Brónstedt bases and Brónstedt acids. The reaction is usually carried out in an organic solvent which is inert under the reaction conditions. Examples of suitable inert solvents include nitrogen-containing solvents, for example, aromatic nitrogen heterocycles such as pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, quinoline or isoquinoline, N, N-dialkylcarbcxamides such as N, N-dimethylformamide or N, N-dimethylacetamide, N-alkyl -lactams such as N-methylpyrrolidone or aromatic solvents such as toluene or xylene. In general, the reaction takes place at a temperature between room temperature and the boiling temperature of the solvent, preferably at elevated temperature, and in particular at the boiling temperature of the solvent. It is normal to use compound III and amine IV in approximately equimolar amounts. It can, however, be advantageous to use one of the two reagents in excess. It may be advantageous to remove the water formed during the reaction from the reaction mixture, using a water separator, for example. The reaction mixture is developed by cooling it, diluting it with water when appropriate, and isolating the product by filtration. The product can, if desired, be purified in a customary manner, by crystallization or chromatography, for example. The anhydrides III 4-halonaphthalen-1, 8-dicarboxylic anhydrides are known from the literature or can be prepared by known methods. For bromine derivatives, see for example, Graebe, Guinsbourg, Justus Liebigs Ann.
Chem. 1903, 327, 86 or Rule, Thompson, J. "Chem. Soc. 1937, 1764. For the chlorine derivatives see, for example, Xuhong, Shengwu, J". Chem. Eng. Data 1998, 33, 528-529.
The compounds I-B
... uuuuc R1 is as defined above and R5 and R5a each independently of the other are hydrogen, C_-C18 alkyl, aryl or heteroaryl, with aryl and heteroaryl in each case being unsubstituted or carrying one or more sustituyent.es selected from C_-Cs alkyl, C_-C6 alkoxy, hydroxyl, carboxyl and cyano; they can be prepared, for example, by hydrolyzing the I-A 4-cyanonaphthalen-1, 8-dicarboxylic monoimides. Where R5 and R5a are radicals other than hydrogen, the hydrolysis is followed by alkylation of the compound L-B 4-aminocarbonyl. The hydrolysis can take place under atmospheric pressure or superatmospheric pressure. The hydrolysis can be accelerated by superatmospheric pressure, elevated temperature and / or addition of a catalyst. In a preferred embodiment, the hydrolysis takes place in the presence of a catalyst. Suitable catalysts are transition metal oxides, such as iron oxides, concentrated acids such as sulfuric acid or phosphoric acid or acid peroxide in basic solution. Where concentrated acids are used as catalysts, they can act as solvents at the same time. Preference is given to the use of sulfuric acid as a catalyst. The hydrolysis normally takes place at temperatures between room temperature and the boiling point of the mixture: for example, at temperatures between 50 and 90 ° C. The compounds of formula IB, wherein R5 and / or R5a are different from hydrogen can be obtained by, for example, first subjecting a compound IB wherein R5 and R5a are hydrogen to reaction (a) with an alkylating agent R5-L (V ) wherein R5 is as defined above and L is a nucleophilically displaceable leaving group and, if desired, the monoalkylated reaction product obtained in the step to reaction (b) is subsequently subjected to an alkylating agent R5a-L ( VI) wherein R5a is as defined above and L is a nucleophilically displaceable leaving group. Examples of a nucleophilically displaceable leaving group L are halide, preferably chloride, bromide or iodide, sulfate, C 1 -C 8 alkylsulfonyloxy, C 1 -C 8 haloalkylsulfonyloxy, C 1 -C 18 alkoxysulfonyloxy or phenylsulfonyloxy, wherein the phenyl radical is substituted or it is not replaced one or more times by halo, nitro or Ci-Cg alkyl, such as phenylsulfonyloxy, p-toluenesulfonyloxy, p-chlorophenylsulfonyloxy, p-bromophenylsulfonyloxy or p-nitrophenylsulfonyloxy. The alkylation is carried out normally in the presence of a base. Suitable bases include in principle any compounds capable of deprotonation of the amide nitrogen atom. Examples of suitable bases include alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate or alkali metal and alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide. . The base can be used in a substoichiometric, superstoichiometric or equimolar amount, relative to compound I-B. It is preferred to employ at least an equimolar amount of the base, relative to the compound I-B.
The reaction of compounds I-B wherein R5 and R5a = hydrogen with the alkylating agent (V) is advantageously carried out in the presence of a solvent. The solvents used for these reactions - depending on the temperature range - are aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, cyclohexane, toluene and xylene, chlorinated aliphatic and aromatic hydrocarbons such as dichloromethane and chlorobenzene, open chain dialkyl ethers such as diethyl ether, -n-propyl ether and methyl tert-butyl ether, cyclic ethers such as tetrahydrofuran and 1,4-dioxane and glycol ethers such as dimethyl glycol ether, or mixtures of these solvents. It may be advantageous to carry out the reaction in the presence of a base transfer catalyst, especially when using inorganic bases whose solubility in the reaction medium is poor. Examples of suie phase transfer catalysts in this context include quaternary ammonium salts or phosphonium salts. Suie quaternary ammonium salts include chlorides, bromides and fluorides of tetra (C 1 -C 8 alkyl) ammonium, and tetrafluoroborates, such as tetraethylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide and tetrabutylammonium tetrafluoroborate, benzyltriol chlorides C_-C_8) ammonium, bromides and fluorides, an example is benzyltriethylammonium chloride.
Suitable phosphonium salts are chlorides or bromides of tetra (C 1 -C 8 alkyl) phosphonium such as tetrabutylphosphonium bromide or tetraphenylphosphonium chloride or bromide. Additional suitable phase transfer catalysts are crown ethers, an example is 18-crown-6. The reaction temperature is generally between room temperature and the boiling temperature of the solvent. The reaction of the resulting compound I-B, where
R5? hydrogen with the alkylating agent VI for the preparation of the compounds wherein Rs and R5a? hydrogen takes place by a process comparable to that described above, for the preparation of the compounds I-B wherein R5? hydrogen. With respect to the appropriate bases, the solvates and reaction temperatures refer to the comments made above.
Compounds of the formula I-C
wherein R1 is as defined above, R represents identical or different C_C_2 alkyl groups; and n is 1, 2, 3, 4 or 5 can be obtained for example by reacting a compound II with a phenol VII according to the reaction sequence shown in scheme 3.
(it) (Vil) (l-C)
In scheme 3 Hal is halogen, such as fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine. R, n and R1 have the definitions given above, preferably the preferred definitions. The reaction of compound II with compound VII is preferably carried out in the presence of a base. Examples of suitable inorganic bases are alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate or cesium carbonate, acid alkali metal carbonates and alkaline earth metal carbonates such as lithium acid carbonate, sodium, potassium acid carbonate or cesium acid carbonate, alkali metal and alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkali metal and alkaline earth metal hydrides, such as sodium hydride and potassium hydride. Examples of suitable organic bases include tertiary amines such as trialkylamines, for example triethylamine, tri-n-propylamine, N-ethyldiisopropylamine, cycloaliphatic amines such as N, N-dimethylcyclohexylamine, cyclic amines such as N-methylpyrrolidine, N-ethylpiperidine, diazabicycloundecene and diazabicyclooctane, and aromatic nitrogen heterocycles such as pyridine, a-, β- or β-picoline, 2,4- and 2,6-lutidine, quinoline, quinazoline, quinoxaline, p-dimethylaminopyridine, pyrimidine and the like. In the case of salts whose solubility in the reaction medium is poor, it may be advantageous to carry out the reaction in the presence of a phase transfer catalyst. Examples of suitable phase transfer catalysts in this context include quaternary ammonium salts or phosphonium salts. Suitable quaternary ammonium salts include chlorides, bromides and fluorides of tetra- (C 1 -C 8 alkyl) ammonium, and tetrafluoroborates, such as tetraethylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide and tetrabutylammonium tetrafluoroborate, chlorides, bromides and fluorides of benzyltri (C?-C__ 8 alkyl) ammonium, an example being benzyltriethylammonium chloride. Suitable phosphonium salts are tetrachloro (C 8 -alkyl) phosphonium chlorides or bromides such as tetrabutylphosphonium bromide or tetraphenylphosphonium chloride or bromide. Suitable phase transfer catalysts are crown ethers, an example is 18-crown-6. The reaction is usually carried out in an organic solvent. Examples of suitable organic solvents are nitrogen-containing solvents, such as aromatic nitrogen heterocycles similar to pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, isoquinoline or quinoline, N, N-dialkylcarboxamides such as N, N-dimethylformamide or N, N-dimethylacetamide, N-alkyl-lactams such as N-methylpyrrolidone and aromatic solvents such as xylene or toluene. Generally speaking, the reaction takes place at a temperature between room temperature and the boiling temperature of the solvent, preferably at elevated temperature, and in particular at the boiling temperature of the solvent. Compound II and phenol VII are normally used in approximately equimolar amounts. It may also be advantageous to use one of the two reagents in excess.
The reaction mixture is generally developed by cooling it, diluting it, where appropriate with water or a lower alcohol, and isolating the product by filtration. Where appropriate, the product can be purified in a customary manner, by crystallization or chromatography for example. The naphthalene-1, 8-dicarboxylic monoimides of the formula I are capable of being absorbed in the wavelength range below 400 nm preferably, and below 390 nm in particular. The transmission of the stabilized material for electromagnetic radiation with a wavelength between 340 nm and 380 nm is preferably not greater than 10%. The naphthalene-1, 8-carboxylic monoimides used according to the invention are suitable for protecting the organic material. The organic material for the purposes of the present invention encompasses both the living organic material and the inanimate organic material. The protection means in the sense of both stabilization, when obtained by mixing the material that is protected with at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I, and the protection of the materials which are surrounded at least partially by a directly protected material (in the form of packaging, for example). An example of living organic material is skin and an example of inanimate organic material is hair. Examples of inanimate organic material also include, for example, food, cleaning products, perfumes, fabrics, paper, furniture, carpets, plastic moldings such as electrical coatings, preparations for cosmetics such as ointments, creams, gels, emulsions and lotions, formulations for drugs such as drops, emulsions, solutions, pills, tablets and suppositories, paints, photographic emulsions, photographic layers and particularly plastic and polymer dispersions. A preferred embodiment of the present invention relates to the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I to protect inanimate organic material. Naphthalene-1, 8-dicarboxylic monoimides are used in particular to protect plastics. The naphthalene-1, 8-dicarboxylic monoimides used according to the invention are shown to be highly compatible with plastics, so that the optical properties of the polymer are not affected. In addition, many of the naphthalene-1, 8-dicarboxylic monoimides used according to the invention display a weak fluorescence, so that by adding the plastic with at least one monoimide I naphthalene-1, 8-dicarboxylic is able to mask or reduce any intrinsic yellow coloring of the plastic. Preferred plastics are those that are transparent in the colorless state in the visible wavelength range. These include not only homopolymers and copolymers, but also physical mixtures of polymers (polymer blends). Copolymers for the purposes of the present invention are copolymers formed by copolymerization (connection) of two or more different monomers. It will be appreciated that copolymers such as polyesters can also include transesterification products, depending on their preparation and / or processing. With regard to the preparation and / or processing of interest, in the case of the copolymers it is also possible that grafting or graft transfer operations take place. The monoimide I naphthalene-1, 8-dicarboxylic used according to the invention protects the plastic against the consequences of exposure to light and in the case of transparent plastics also protects the living and / or inanimate organic material surrounding at least partially by the plastic directly protected against the damaging effects of light. One embodiment of the present invention relates to the use of naphthalene-1, 8-dicarboxylic monoimides I in plastics used as packaging materials. The plastics preferably comprise at least one polymer selected from polyesters, polycarbonates, polystyrene, copolymers of styrene or α-methylstyrene with dienes and / or acrylic derivatives, polyurethanes, polyvinylacetals, polyolefins, polyacrylates, polymethacrylates and physical mixtures of such polymers. Preference is given to polymers and polymer blends (polymer preparations) which can be processed to clear, highly transparent packages or packaging materials. In a preferred embodiment of the present invention, the polyvinylacetal is a polyvinyl butyral. In another preferred embodiment of the present invention, the thermoplastic molding compound comprises at least one polycarbonate polymer selected from polycarbonates, polycarbonate copolymers and physical blends based on polycarbonates with acrylonitrile-butadiene-styrene copolymers, acrylonitrile-styrene copolymers acrylate, polymethyl methacrylates, polybutyl acrylates, polybutyl methacrylates, polybutylene terephthalate and polyethylene terephthalates. In a further preferred embodiment of the present invention, the polyester is a polyethylene terephthalate. In another preferred embodiment of the present invention, the polyolefin is a high density polyethylene or a polypropylene. In another preferred embodiment of the present invention, the styrene copolymer with dienes and / or acrylic derivatives is a copolymer of acrylonitrile-butadiene-styrene or a styrene-acrylonitrile copolymer. In a preferred embodiment of the invention, the plastic comprises as a polymer at least one polyester, preferably at least one linear polyester. Suitable polyesters and copolyesters are described in EP-A-0678376, EP-A-0 595 413 and US 6,096,854, whereby it is incorporated for reference. The polyesters, as is known, are condensation products of one or more polyols and one or more polycarboxylic acids. In linear polyesters, the polyol is a diol and the polycarboxylic acid is a dicarboxylic acid. The diol component can be selected from ethylene glycol, 1,4-cyclohexanedimethanol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 2,2-dimethyl-1,3-propanediol, 1,6- hexandiol, 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexanedimethanol and 1,3-cyclohexanedimethanol. Also suitable are diols whose alkylene chain is interrupted one or more times by non-adjacent oxygen atoms. Such diols include diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol and the like. In general, the diol contains from 2 to 18 carbon atoms, preferably 2 to 8 carbon atoms. Cycloaliphatic diols can be used in the form of their cis or trans isomers or as an isomeric mixture. The acid component can be an aliphatic, alicyclic or aromatic dicarboxylic acid. The acid component of the linear polyesters is generally selected from terephthalic acid, isophthalic acid, 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, 1,2-dodecandioic acid, 2,6-naphthalenedicarboxylic acid and mixtures thereof. It will be appreciated that the functional derivatives of the acid component can also be used, such as esters, the methyl ester for example, anhydrides or halides, preferably chlorides. Preferred polyesters are polyalkylene terephthalate and polyalkylene naphthalates obtainable by condensing terephthalic acid or naphthalenedicarboxylic acid, respectively, with an aliphatic diol. Particularly preferred polyalkylene terephthalates are polyethylene terephthalates (PET), which are obtained by condensing terephthalic acid with diethylene glycol. PET is also obtainable by trans-esterifying dimethyl terephthalate with ethylene glycol, with the removal of methanol, to form bis (2-hydroxyethyl) terephthalate, and subjecting the product to polycondensation, liberating ethylene glycol. The preferred additional polyesters are polybutylene terephthalates (PBT), obtainable by condensing terephthalic acid with 1,4-butanediol, polyethylene 2,6-naphthalate (PEN), poly-1,4-cyclohexanedimethylene terephthalates (PCT) and also copolyesters of polyethylene terephthalate with cyclohexanedimethanol (PDCT) and polybutylene terephthalate with cyclohexanedimethanol. Preference is likewise given to copolymers, transesterification products and physical mixtures (preparations) of the aforementioned polyalkylene terephthalates. Particularly suitable thermoplastic molding compounds are selected from polycondensates and copolycondensates of terephthalic acid, such as poly- or copolyethylene terephthalate (PET or CoPET or PETG), poly (2,6-naphthalene naphthalates) (PEN) or copolymers of PEN / PET and mixtures of PEN / P? T. Such copolymers and mixtures, depending on their preparation process, may also include fractions of transesterification products. In a further preferred embodiment of the invention, the plastic comprises polycarbonates as polymers. The polycarbonates are formed, for example, by condensation of phosgene or carbonic esters such as diphenyl carbonate or dimethyl carbonate with dihydroxy compounds. Suitable dihydroxy compounds are dihydroxy aliphatic or aromatic compounds. Examples of aromatic dihydroxy compounds include bisphenols such as 2,2-bis (4-hydroxyphenyl) propane (bisphenol A), tetraalkylbisphenol A, 4, - (meta-phenylenedisopropyl) diphenol (bisphenol M), 4,4-para-phenylene diisopropyl) diphenol, 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane (BP-TMC), 2,2-bis (4-hydroxyphenyl) -2-phenylethane, 1,1-bis (4-hydroxyphenyl) ) cyclohexane (bisphenol Z) and, where appropriate, mixtures thereof. The polycarbonates can be branched using small amounts of branching agents. Suitable branching agents include phloroglucinol, 4,6-dimethyl-2,4,6-tri (4-hydroxyphenyl) hept-2-ene, 4,6-dimethyl-2,4,6-tri (4-hydroxyphenyl) heptane; 1,3,5-tri (4-hydroxyphenyl) benzene; 1,1,1- tri (4-hydroxyphenyl) heptane; 1, 3,5-tri (4-hydroxyphenyl) benzene; 1,1, 1-tri (4-hydroxyphenyl) -ethane; tri (4-hydroxyphenyl) phenylmethane, 2,2-bis [4, 4-bis (4-hydroxyphenyl) -cyclohexyl] propane; 2,4-bis (4-hydroxyphenylisopropyl) phenol; 2, 6-bis (2-hydroxy-5'-methylbenzyl) -4-methylphenol; 2- (4-hydroxyphenyl) -2- (2,4-dihydroxyphenyl) propane; hexa (4- (4-hydroxyphenylisopropyl) phenyl orthothephthalate); tetra (4-hydroxyphenyl) -methane; tetra (4- (4-hydroxyphenylisopropyl) phenoxy) methane; a, a ', a "-tris (4-hydroxyphenyl) -1,3,5-triisopropylbenzene, 2,4-dihydroxybenzoic acid, trimesic acid, cyanuric chloride, 3,3-bis (3-methyl-4-hydroxyphenyl) -2 -oxo-2, 3-dihydroindole, 1,4-bis (4 ', 4"-dihydroxytriphenyl) methyl) benzene and, in particular, 1, 1, 1-Tri (-hydroxyphenyl) ethane and bis (3-) methyl-4-hydroxyphenyl) -2-0x0-2, 3-dihydroindole. For the termination of the chain, the suitability is possessed by, for example, phenols such as phenol, alkylphenols such as cresol and 4-tert-butylphenol, chlorophenol, bromophenol, cumylphenol or mixture thereof. The fraction of the chain terminators is generally from 1 to 20 mol%, per mol of the dihydroxy compound. In another suitable embodiment of the invention, the plastic comprises polymers derived from α, 3-unsaturated acids and derivatives thereof, for example, poly (meth) acrylates such as polymethyl methacrylate (PMMA) and polyethyl methacrylate. In a further suitable embodiment of the invention, the plastic comprises as a polymer a homopolymer or a vinylaromatic copolymer such as polystyrene (PS) or copolymers of styrene or an α-methylstyrene with dienes and / or acrylic derivatives, such as styrene-butadiene, styrene acrylonitrile (SAN), styrene-ethyl methacrylate, styrene-butadiene-ethyl acrylate, styrene-acrylonitrile-methacrylate, acrylonitrile-butadiene-styrene (ABS) or methyl methacrylate-butadiene-styrene (MBS). In a further suitable embodiment of the invention, the plastic comprises polymers derived from unsaturated alcohols and amines or their acrylic derivatives or acetates, such as polyvinyl acetate (PVAC) and polyvinyl alcohol (PVAL). The reaction of polyvinyl alcohol with an aldehyde forms polyvinylacetals: for example, polyvinylformalee (PVFM) in the reaction with formaldehyde, or polyvinylbutyrals (PVB) with butyraldehyde. In laminated glass, two or more sheets of glass are bonded together adhesively through polyvinyl butyral films. The polyvinyl butyral molding compound generally has an average molecular mass of more than 70,000, preferably from about 100,000 to 250,000. The polyvinyl butyral generally has a residual hydroxyl group content of less than 19.5%, preferably from about 17% to 19% by weight, calculated as the polyvinyl alcohol, and a residual ester group content of 0 to 10%, preferably from 0 to 3%, calculated as the polyvinyl ester. An exemplary PVB is commercially available under the name Butvar® from Solutia, Inc., of St. Louis, Mo. Any glass is suitable as long as it is transparent to light in the visible wavelength range. Such glasses include normal transparent soda lime glass, an IR reflect coated glass or an IR absorption glass; see for example, US 3,944,352 and US 3,652,303. With respect to the configuration of laminated glass, the entirety of WO 02/077081, and in particular pages 28 to 32, is therefore incorporated for reference. For the purposes of the present invention, the term "polyolefin" embraces all polymers synthesized from olefins without additional functionality, such as low or high density polyethylene, polypropylene, linear olibut-1-ene or polyisobutylene or polybutadiene. , and also copolymers of monoolefins or diolefins. The preferred polyolefins are the homopolymers and copolymers of ethylene and also the homopolymers and copolymers of propylene.
Ethylene polymers: Suitable polyethylene (PE) homopolymers are, for example: PE-LD (LD = low density), obtainable for example by the high pressure process (IC) of 1000 to 3000 bar and 150 to 300 ° C with oxygen or peroxide catalysts in autoclaves or tube reactors. Highly branched with branches of different length, crystallinity of 40 to 50%, density 0.915 to 9.35 g / cm3, average molar mass of up to 600 000 g / moles. - PE-LLD (LLD = linear low density) obtainable with metal complex catalysts in the process of low pressure from the gas phase, from a solution (for example, mineral spirit) in a suspension or with a modified high pressure process . The light branching with the side chains which are themselves, unbranched, molar masses higher than for PE-LD. PE-HD (HD = high density) obtainable by intermediate pressure (Phillips) and low pressure processes
(Ziegler) According to Phillips at 30 to 40 bar, 85 to 180 ° C, chromium oxide catalyst, molar masses of approximately 50,000 g / moles. According to Ziegler in 1 a
50 bar, 20 to 150 ° C, titanium halide, titanium ester or aluminum-alkyl catalysts, molar mass of about 200,000 to 400,000 g / mol. Carried out in suspension, solution, gas phase or volume. Very light branch, cristallity 60 to 80%, density 0.942 a
0. 965 g / cm3. PE-HD-HMW (HMW = high molecular weight), obtainable by Ziegler, Phillips or gas phase method. High density and high molar mass. - PE-HD-UHMW (UHMW = ultra-high molecular weight) obtainable with a modified Ziegler catalyst, molar mass 3,000,000 to 6,000,000 g / moles. The particular suitability for the polyethylene prepared in a gas-phase fluidized bed process using (normally supported) catalysts, for example Lupolen® (Basell), is possessed. Particular preference is given to polyethylene prepared using metallocene catalysts. Polyethylene of this class is commercially available as Luflexen® (Basell), for example. Suitable ethylene copolymers include all commercially customary ethylene copolymers, examples being Luflexen® grades (Basell), Nordel® and Engage® (Dow, DuPont). Examples of suitable comonomers include α-olefins having 3 to 10 carbon atoms, especially propylene, but-1-ene, hex-1-ene and oct-1-ene and also alkyl acrylates and methacrylates having 1 to 20 atoms of carbon in the alkyl radical, especially butyl acrylate. Additional suitable comonomers are dienes such as butadiene, isoprene and octadiene, for example. Other suitable comonomers are cycloolefins, such as cyclopentenc, norbornene and dicyclopentadiene. The ethylene copolymers are normally random copolymers or block or impact copolymers. Suitable block or impact copolymers of ethylene and comonomers are, for example, polymers for which, in the first step, a homopolymer of the comonomer or a random copolymer of the comonomer is prepared, containing up to 15% by weight of ethylene, for example, and then a comonomer-ethylene copolymer with ethylene contents of 15 to 80% by weight is polymerized in the second stage. Normally, enough of the comonomer-ethylene copolymer is polymerized for the copolymer produced in the second stage having a fraction from 3 to 60% by weight in the final product.
The polymerization to prepare the ethylene-comonomer copolymers can take place by means of the Ziegler-Natta catalyst system. However, it is also possible to use catalyst systems based on metallocene compounds or based on polymerization active metal complexes.
Propylene Polymers: Polypropylene should be understood after it refers to both homopolymers and propylene copolymers. Propylene copolymers contain minor amounts of monomers copolymerizable with propylene, examples being C2-C8 alk-1-ennes such as ethylene, but-1-ene, pent-1-ene or hex-1-ene, among others. Two or more different comonomers can also be used. Suitable polypropylenes include propylene homopolymers or propylene copolymers with up to 50% by weight of other copolymerized alk-1-ene having up to 8 carbon atoms. The propylene copolymers are in this case random copolymers or block or impact copolymers. When the propylene copolymers are randomly constructed, they generally contain up to 15% by weight, preferably up to 6% by weight, of other alk-1-ene having up to 8 carbon atoms, especially ethylene, but-1-ene or a mixture of ethylene and but-1-ene.
Suitable block or impact copolymers of propylene are, for example, polymers for which in the first stage a propylene homopolymer or a random copolymer of propylene with up to 15% by weight, preferably up to 6% by weight, of others alkyl-1 having up to 8 carbon atoms is prepared and then in the second stage a propylene-ethylene copolymer having ethylene contents of 15 to 80% by weight is polymerized, being possible for the propylene-ethylene copolymer also include other C4-C8 alkyl-1-enynes. Normally, enough of the propylene-ethylene copolymer is polymerized where the copolymer produced in the second stage has a fraction of 3 to 60% by weight in the final product. The polymerization for the preparation of the polypropylene can take place by means of a Ziegler-Natta catalyst system. The use is made in particular of catalyst systems which in addition to a solid component a) which contains titanium also contains co-catalysts in the form of organic aluminum compounds b) and electron donor compounds c). It is also possible, however, to use systems based on metallocene compounds or based on active metal complexes by polymerization. The preparation of the polypropylenes is usually carried out by the polymerization in at least one reaction zone or, frequently, in two or more reaction zones connected in series (a reactor cascade), in the gas phase, in a suspension, or in a liquid phase (bulky phase). The reactors used may be the normal reactors used to polymerize C2-C8 alk-1-ennes. Suitable reactors include continuous stirred tanks, loop reactors, powder bed reactors or fluidized bed reactors. The polymerization to prepare the polypropylenes used is operated under normal reaction conditions at temperatures from 40 to 120 ° C, in particular from 50 to 100 ° C, and pressures from 10 to 100 bar, in particular from 20 to 50 bar. Suitable polypropylenes typically have a melt flow index (MFR) in accordance with ISO 1133 from 0.1 to 200 g / 10 minutes, in particular from 0.2 to 100 g / 10 minutes, at 230 ° C and under a weight of 2.16 kg. . In another embodiment of the invention, the plastic comprises at least one polyolefin. Preferred polyolefins contain at least one copolymerized monomer selected from ethylene, propylene, but-1-ene, isobutylene, 4-methyl-1-pentene, butadiene, isoprene and mixtures thereof. Suitability is possessed by homopolymers, copolymers of the established olefin monomers, and copolymers of at least one of such olefins as the main monomer, with other monomers (such as vinylaromatics for example) as comonomers. Preferred polyolefins are low density polyethylene (PE-LD) homopolymers and polypropylene homopolymers and polypropylene copolymers. Preferred polypropylenes are, for example, biaxially oriented polypropylene (BOPP) and crystallized polypropylene. In another embodiment of the invention, the plastic comprises at least one polyurethane as the polymer. Polyurethanes are, generally speaking, addition products of at least one diisocyanate and at least one diol component, which may also contain higher polyfunctional isocyanates, triisocyanates for example, and higher polyfunctional polyols. Suitable isocyanates are aromatic diisocyanates such as 2,4- and 2,6-toluene diisocyanate (TDI) and isomeric mixtures thereof, tetramethylxylylene diisocyanate (TMXDI), xylene diisocyanate (XDI) and 4,4'-diisocyanate. of diphenylmethane (MDI), and aliphatic diisocyanates, such as 4,4 '- dicyclohexylmethane diisocyanate (H 2 MDI), tetramethylene diisocyanate, hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI), trimethylhexamethylene diisocyanate and mixtures of the same. Preferred diisocyanates include hexamethylene diisocyanate (HMDI) and isophorone diisocyanate. Also suitable for preparing polyurethanes are triisocyanates, for example, 4 ', 4"triphenylmethane tricyanate and cyanurates and biurets of the aforementioned diisocyanates Suitable diols are glycols preferably having 2 to 25 carbon atoms, including 1,2-ethanediol, 1, 2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1, 10-decanediol, diethylene glycol, 2,2,4-trimethylpentan-l, 5-diol, 2, 2-dimethylpropan-l, 3-diol, 1,4-dimethylcyclohexane, 1,6-dimethylolcyclohexane, 2,2-bis (4-hydroxyphenyl) propane (bisphenol A), 2,2-bis (4-hydroxyphenyl) butane (bisphenol B), or 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane (bisphenol C) Polyols are also useful starting materials for preparing polyurethanes Polyols are trivalent alcohols ( known as trioles) and higher polyfunctional alcohols, these generally have 3 to 25, preferably 3 to 18, carbon atoms, which include glycerol, trimethylolethane, trimethylolpropane, erythritol. l, pentaerythritol, sorbitol and alkoxylates thereof. In a preferred embodiment of the present invention, the plastic is a thermoplastic molded composite. The transmission of the non-colored thermoplastic molding compound for electromagnetic radiation with a wavelength between 420 nm and 800 nm is preferably greater than 90%. The present invention further provides the use of at least one naphthalene-1, 8-dicarboxylic monoimide I to prepare a layer which absorbs ultraviolet light. The absorbent layer is preferably transparent in the wavelength range between 420 and 800 nm. The preferably transparent layer, which absorbs ultraviolet light, is based on a thermoplastic molded compound. Suitable thermoplastic molded compounds include thermoplastics comprising at least one polymer selected from polyesters, polycarbonates, polyolefins, polyvinylacetals, polystyrene, copolymers of styrene or of α-methylstyrene with dienes and / or acrylic derivatives, and also hybrid forms of the aforementioned polymers . In a preferred embodiment of the present invention, the transparent layer is part of an architectural or automotive lacquering system or is a sheet intended for adhesive bonding to a glass or plastic for insulation or filtration purposes; in particular it is part of a laminated window in automotive varnish. In a particularly preferred embodiment, the plastic sheet comprises a polyvinylacetal, in particular polyvinyl butyral. The monoimide I naphthalene-1, 8-dicarboxylic in the laminated glass acts as a UV absorber to protect a living organic material and an inanimate organic material, so that for example, the conductor and the inanimate organic material present inside the The car is protected against damaging damages of ultraviolet radiation. Examples of possible damage include erythema or sunburn in the case of living organic material and yellowing, discoloration, cracking or cracking in the case of inanimate organic material. Optionally, the plastic further comprises at least one light stabilizer which absorbs light radiation in the UV-A and / or UV-B region, and / or (co) additional stabilizers. The light stabilizer and, where appropriate, the additional (co) stabilizers used should of course be compatible with the monoimide I naphthalene-1, 8-dicarboxylic acid. In the visible range, these are preferably colorless or have only a slight inherent coloration. The light stabilizers and / or (co) stabilizers, where they are used, preferably have high firmness to migration and stability to temperature. Suitable light stabilizers and additional (co) stabilizers are selected, for example, from groups a) s): a) 4, -diarylbutadienes, b) cinnamic esters, c) benzotriazoles, d) hydroxybenzophenones, e) diphenylcyanacrylates, f) oxamides , g) 2-phenyl-1,3,5-triazines; h) antioxidants, i) nickel compounds, j) spherically hindered amines, k) metal deactivators, 1) phosphites and phosphonites, m) hydroxylamines, n) nitrones, o) amine oxides, p) benzofuranones and indolinones, q) thiosynergists , r) peroxide destroying compounds, and s) basic co-stabilizers The group a) of the 4,4-diarylbutadienes includes for example the compounds of the formula A.
The compounds are known from EP-A-916 335. The substituents Rio and / or Rn are preferably C? -C8 alkyl and C5-C8 cycloalkyl.
Group b) of the cinnamic esters includes, for example, 2-isoamyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, methyl a-methoxycarbonylcinnamate, methyl a-cyano- / 3-methyl-p-methoxymethylformate, butyl a-cyano- / 3-methyl-p-methoxycinnamate and methyl-methoxycarbonyl-p-methoxycinnamate. Group c) of the benzotriazoles includes for example 2- (2'-hydroxyphenyl) -benzotriazoles such as 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (3 ', 5'-di-ter- butyl-2 '-hydroxyphenyl) benzotriazole, 2- (5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5' - (1,1,3,3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5- chlorobenzotriazole, 2- (3 '-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-4'-octyloxyphenyl) benzotriazole, 2- (3', 5 '- di-tert-amyl-2'-hydroxyphenyl) -benzotriazole, 2- (3 ', 5'-bis- (a, a-dimethylbenzyl) -2'-hydroxyphenyl) benzotriazole, 2- (3'-tert-butyl- 2 '-hydroxy-5' - (2-octyloxycarbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) - 5-chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonylethyl) phenyl) -5- chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonylethyl) phenyl) -benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5' - (2 -octyloxycarbonylethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) -benzotriazole, 2- (3'-dodecyl-2' - hydroxy-5'-methylphenyl) -benzotriazole and 3- (3'-tert-butyl-2'-hydroxy-5 '- (2-isooctyloxy-carbonylethyl) phenylbenzotriazole, 2,2'-methylenebis [4- (1,1 , 3,3-tetramethylbutyl) -6-benzotriazol-2-ylphenol]; the product for esterifying 2- [3'-tert-butyl-5 '- (2-methoxycarbonylethyl) -2'-hydroxyphenyl] -2H-benzotriazole with polyethylene glycol 300; [R-CH2CH2-COO (CH2) 3] 2 wherein R = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl and mixtures thereof. Group d) of the hydroxybenzophenones includes, for example, 2-hydroxybenzophenones such as 2-hydroxy-4-methoxybenzophenone, 2,2 '-dihydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2, 2', 4, 4 '- tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4- (2-ethylhexyloxy) benzophenone, 2-hydroxy-4 - (n-octyloxy) benzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-3-carboxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid and its sodium and acid salt 2, 2'-dihydroxy-4, '-dimethoxybenzophenone-5,5'-bisulfonic acid and its sodium salt. The group e) of the diphenylcyanoacrylates includes, for example, ethyl 2-cyano-3, 3-diphenylacrylate obtainable commercially, for example, under the name Uvinul® 3035 from BASF AG, Ludwigshafen, 2-cyano-3, 3-diphenylacrylate 2-ethylhexyl. , commercially available for example as Uvinul® 3039 from BASF AG, Ludwigshafen and 1,3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2,2-bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] metd 1} propane, commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen. Group f) of the oxamides includes, for example, 4'-dioctyloxyoxanilide, 2,2'-diethyloxyanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxyanilide, 2,2'-didodecyloxy-5 , 5'-di-tert-butoxyanilide, 2-ethoxy-2'-ethoxyanilide, N, N'-bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxyanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, and also mixtures of ortho-, para-methoxy-disubstituted oxanilides and mixtures of ortho- and para-methoxy-disubstituted oxanilides. The group g) of the 2-phenyl-1,3,5-triazines includes, for example, 2- (2-hydroxyphenyl) -1,3,5-triazines such 2, 4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1 , 3, 5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) ) -6- (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (4-methylphenyl) 1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxypropoxy) phenyl] -4,6-bis (2,4-dimethyl) - 1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-octyloxypropoxy) phenyl] -4,6-bis (2,4-dimethyl) 1,3,5-triazine, 2 - [4- (dodecyloxy / tridecyloxy-2-hydroxypropoxy) -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- ( 2-hydroxy-3-dodecyloxypropoxy) phenyl] -4,6-bis- (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-hexyloxyphenyl) -4-6- diphenyl-1,3,5-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4,6-diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy-4-] (3-butoxy-2-hydroxypropoxy) phenyl] -1,3,5-triazine, and 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1,3,5-triazine. Group h) of the antioxidants comprises, for example: hl) alkylated monophenols such as, for example, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6 -di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol , 2- (a-methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols of chain lateral branched or unbranched such as, for example, 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6- (1-methylundec-1-yl) phenol, 2,4-dimethyl-6- (1) -methylheptadec-1-yl) phenol, 2,4-dimethyl-6- (1-methyltridec-1-yl) phenol, and mixtures thereof. h.2) alkylthiomethylphenols such as, for example, 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol and 2,6-didodecylthiomethyl-4- nonylphenol. h.3) Hydroquinones and alkylated hydroquinones such as, for example, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, , 6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydrosianisole, 3,5-di-tert-butyl-4-hydroxyanisole, stearate 3, 5-di-tert-butyl-4-hydroxyphenyl and bis- (3,5-di-tert-butyl-4-hydroxyphenyl) adipate. h.4) Tocopherols, such as, for example, a-tocopherol, jS-tocopherol, α-tocopherol, d-tocopherol and mixtures thereof (vitamin E). h.5) Hydroxylated thiodiphenyl ether such as, for example, 2,2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-) tert-butyl-3-methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-sec-amylphenol) and 4,4 '- bis (2,6-dimethyl-4-hydroxyphenyl) disulfide. h.6) The alkyldenbisphenols such as, for example, 2,2 '-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2 '-methylenebis [4- methyl-6- (a-methylcyclohexyl) phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl-4-methylphenol), 2, 2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidebisbis (4,6-di-tert-butylphenol), 2,2'-ethylidebisbis (6-tert-butyl-4) isobutylphenol), 2,2'-methylenebis [6- (a-methylbenzyl) -4-nonylphenol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonylphenol], 4,4 ' - methylenebis (2,6-di-tert-butylphenol), 4,4'-methylenebis (6-tert-butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-) ethylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy-2-met) .ylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecyl mercaptobutane, ethylene glycol bis [3, 3-bis (3-tert-butyl-4-hydroxyphenyl) butyrate], bis (3-tert-butyl-4-hydroxy-5-methyl-phenyl) d-cyclopentadiene, bis [2- (3'-tert-butyl-2-hydroxy-5-yl-benzyl) -6-tert-butyl- 4- methylphenyl] terephthalate, 1,1-bis (3,5-dimethyl-2-hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4-hydroxyphenyl) propane, 2, 2- bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -4-n-dodecyl mercaptobutane, 1,1,5,5-tetra- (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane . h.7) Benzyl compounds such as, for example, 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzylether, octadecyl 4-hydroxy-3, 5-dimethylbenzylmercaptoacetate, 4- Tridecyl hydroxy-3, 5-di-tert-butylbenzylmercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) amine, 1, 3, 5-tri (3,5-di-tert-butyl- 4-hydroxybenzyl) -2,4,6-trimethylbenzene, di (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isobutyl 3,7-di-tert-butyl-4-hydroxybenzylmercaptoacetate, bis terephthalate (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiol, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-Butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 3,5-di-tert-butyl-4-hydroxybenzyl phosphoric acid dioctadecylester, and 3,5-di-tert-alkyl monoethyl ester Butyl-4-hydroxybenzyl-phosphoric, calcium salt. h.8) Hydroxybenzylated malonates, such as, for example, 2,2-bis- (3, 5-di-tert-butyl-2-hydroxybenzyl) malonate of dioctadecyl, dioctadecyl-2- (3-tert-butyl-4-hydroxy) 4-methylbenzyl) malonate, mercaptoethyl-2, 2-bis (3, 5-di-tert-butyl-4-hydroxybenzyl) alonate of didodecyl and 2,2-bis (3,4-di-tert-butyl-4-) hydroxybenzyl) bis [4- (1,1,3,3-tetramethylbutyl) phenyl] malonate]. h.9) Hydroxybenzyl aromatics such as, for example, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3 , 5-di-tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene and 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol. h.10) Triazine compounds such as, for example, 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto- 4,6-bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4) -hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris (3, 5-di-tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1 , 3, 5-triazine, and 1, 3, 5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate. h.ll) Benzyl phosphonates such as, for example, dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate (3, 5-bis (1, Diethyl 1-dimethylethyl) -4-hydroxyphenyl) methylphosphonate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate and the calcium salt of the 3, 5-di-tert-butyl-4-hydroxybenzylphosphonate monoethyl. h.12) Acylaminophenols such as, for example, 4-hydroxylauranylide, 4-hydroxysteatenylidene, 2,4-bisoctylmercapto-6- (3,5-tert-butyl-4-hydroxyanilino) -s-triazine and N- (5). Octyl-di-tert-butyl-4-hydroxyphenyl) carbamate. h.13) Esters of ß- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols, such as with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1, 6 hexandiol, 1, 9-nonanediol, ethylene glycol, 1,2-propandiol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxalamide, 3-thiaundecanol, 3- tiapentadecanol, trimethylhexandiol, trimethylolpropane and 4-hydroxymethyl-l-phospha-2,6,6-trioxabicyclo [2.2.2] octane. h.14) Esters of ß- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with monohydric or polyhydric alcohols, such as methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonandiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxalamide , 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane and 4-hydroxymethyl-1-phospha-2,6,7-thioxabicyclo [2.2.2] octane. h.15) Esters of β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol , 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane and 4-hydroxymethyl -l-phospha-2, 6, 7-thioxabicyclo [2.2.2] octane. h.16) Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with monohydric or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonandiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane and 4- hydroxymethyl-l-phospha-2, 6, 7-thioxabicyclo [2.2.2] octane. h.17) β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid amides, such as N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylenediamide , N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylenediamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazide, N, N '-bis [2- (3- [3,5-di-tert-butyl-4-hydroxyphenyl] propionyloxy) ethyl] oxamide (for example, Naugard®XL-1 from Uniroyal). h.18) Ascorbic acid (vitamin C) h.19) Amine antioxidants, such as, for example, N, N'-diisopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N '-bis (1,4-dimethylpentyl) -p-phenylenediamine, N, N'-bis (l-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl) -p- phenylenediamine, N, N'-dicyclohexyl-p-phenylenediamine, N, N '-diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N' -phenyl-p phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N- (1-methylheptyl) -N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p- phenylenediamine, 4- (p-toluenesulfamoyl) diphenylamine, N, N '-dimethyl-N, N' -di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-1 -naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example, p.p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4- butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecan oilaminophenol, bis (4-methoxyphenyl) amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetramethyl- 4,4'-diaminodiphenylmethane, 1,2-bis [(2-methylphenyl) amino] ethane, 1,2-bis (phenylamine) propane, o-tolyl biguanide, bis [4- (1 ', 3'-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- and dialkylated ter-butyl / tert-octyldiphenylamines, a mixture of mono- and dialkylated nonildiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl / isohexyldiphenylamines, a mixture of mono- and dialkylated ter-butyldiphenylamines, 2,3-dihydro-3, 3-dimethyl-4H-1, 4-benzothiazine, phenothiazine, a mixture of tert-butyl / ter- octylphenothiazine mono- and dialkylated, a mixture of mono- and dialkylated ter-octylphenothiazines, N-allylphenothiazine, N, N, N ', N' -tetraphenyl-1,4-diaminobut-2-ene, N, N-bis (2) , 2,6,6-tetramethylpiperidin-4-yl) hexamethylenediamine, seb bis (2, 2, 6, 6-tetramethylpiperidin-4-yl), 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol, the polymer of dimethyl succinate with 4-hydroxy-2, 2, 6, 6-tetramethyl-1-piperidinetanol [CAS number 65447-77-0], (for example Tinuvin® 622 from Ciba Specialty Chemicals, Inc.), the 2, 2, 4, 4-tetramethyl- 7-oxa-3, -20-diazadispiro [5.1.11.2] heneicosan-21-one and epichlorohydrin [CAS No .: 202483-55-4], (for example, Hostavin®30 from Ciba Specialty Chemicals, Inc.). Group i) of the nickel compounds includes, for example, 2, 2'-thiobis [4- (1,1,3,3-tetramethylbutyl) phenol] nickel complexes, such as the 1: 1 or 1: 2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of monoalkyl esters of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid such as methyl or ethyl esters, for example , ketoxim nickel complexes such as, for example, 2-hydroxy-4-methylphenyl undecyl ketoxime, and the nickel complex of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.
Group j) of the spherically hindered amines includes, for example, 4-hydroxy-2,2,6,6-tetramethylpiperidine, l-allyl-4-hydroxy-2,6,6,6-tetramethylpiperidine, l-benzyl-4 -hydroxy-2, 2,6,6-tetramethylpiperidine, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2, 2, 6,6-tetramethyl-4-piperidyl) succinate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (l-octyloxy-2, 2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1, 2,2,6) , 6-pentamethyl-4-piperidyl) n-butyl-3, 5-di-tert-butyl-4-hydroxybenzyl-acidic acid (n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonic acid bis (1,2 , 2,6,6-pentamethylpiperidyl) ester, condensation product of 1- (2-hydroxyethyl) -2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensation products of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-l, 3,5-triazine, tris (2, 2, 6 , 6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6,6-tetramethyl- 4-piperidyl) 1,2,3,4-butanedicarboxylate, 1,1'- (1,2-ethanediyl) bis (3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6 -tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis (1,2, 2,6,6-pentamethylpiperidyl) 2-n-butyl-2- (2-hydroxy-3,5-dihydroxy) tert-butylbenzyl) malonate, 3-n-octyl-7,7,9,9-tetramethyl-l, 3,8-triazaspiro [4.5] decan-2,4-dione, bis (l-octyloxy-2, 2, 6,6-tetramethylpiperidyl) sebacate, bis (l-octyloxy-2, 2,6,6-tetramethylpiperidyl) succinate, linear or cyclic condensation products of N, N'-bis (2, 2, 6,6-tetramethyl) 4-piperidyl) hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, condensation products of N, N'-bis (2, 2, 6,6-tetramethyl-4-piperidyl) hexamethylenediamine and formic esters (CAS No. 124172-53-8, for example., Uvinul® 4050H from BASF AG, Ludwigshafen), condensation product 2-chloro-4,6-bis (4-n-butylamino-2, 2, 6,6-tetramethylpiperidyl) -1, 3, 5-triazine and 1,2-bis (3-aminopropylamino) eta no, condensation product of 2-chloro-4,6-di- (4-n-butylamino-l, 2,2,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2-bis ( 3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7, 7,9, 9-tetramethyl-l, 3,8-triazaspiro [4.5] decan-2,4-dione, 3-dodecyl-1- (2 , 2,6,6-tetramethyl-4-piperidyl) pyrrolidin-2, 5-dione, 3-dodecyl-1- (1,2,2 / 6,6-pentamethyl-4-piperidyl) pyrrolidin-2, 5- dione, mixture of 4-hexadecyloxy- and 4-stearyloxy-2, 2,6,6,6-tetramethylpiperidine, condensation product of N, N'-bis (2, 2, 6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, condensation product of 1,2-bis (3-aminopropylamino) ethane and 2,4,6-trichloro-1,3,5-triazine and also 4-butylamino-2, 2,6,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]); N- (2, 2, 6, 6-tetramethyl-4-piperidyl) -n-dodecyl succinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl) -n-dodecyl succinimide, 2-undecyl- 7, 7,9, 9-tetramethyl-l-oxa-3,8-diaza-4-oxospiro [4.5] decane, reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-l-oxa- 3, 8-diaza-4-oxospiro [4.5] decane and epichlorohydrin, 1,1-bis (1, 2, 2, 6, 6-pentamethyl-4-piperidyloxycarbonyl) -2- (4-methoxyphenyl) ethene, N, N '-bisformyl-N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, 4-methoxymethylenemalonic acid diester with 1, 2, 2, 6, 6-pentamethyl-4-hydroxypiperidine , poly [methylpropyl-3-oxo-4- (2,2,6,6-tetramethyl-4-piperidyl)] siloxane, reaction product of maleic anhydride-α-olefin copolymer and 2, 2, 6,6-tetramethyl 4-aminopiperidine or 1, 2, 2, 6, 6-pentamethyl-4-aminopiperidine, copolymers of (partially) maleimide of N-piperidin-4-yl-substituted and a mixture of α-olefins such as Uvinul® 5050H
(BASF AG), 1- (2-hydroxy-2-methylpropoxy) -4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 1- (2-hydroxy-2-methylpropoxy) -4-hexedecanoyloxy-2, 2 , 6,6-tetramethylpiperidine, the reaction product of l-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and a carbon radical of t-amyl alcohol, 1- (2-hydroxy-2-methylpropoxy) -4-hydroxy-2, 2,6,6-tetramethylpiperidine, 1- (2-hydroxy-2-methylpropoxy) -4-oxo-2, 2,6,6 -tetramethylpiperidine, bis (1- (2-hydroxy-2-methylpropoxy) -2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis (1- (2-hydroxy-2-methylpropoxy) -2, 2 , 6,6-tetramethylpiperidin-4-yl) adipate, bis (1- (2-hydroxy-2-methylpropoxy) -2,2,6,6-tetramethylpiperidin-4-yl) succinate, bis (1- (2- hydroxy-2-methylpropoxy) -2,2,6,6-tetramethylpiperidin-4-yl) glutarate, 2,4-bis. { N [1- (2-hydroxy-2-methylpropoxy) -2,2,6,6-tetramethylpiperidin-4-yl] -N-butylamino} -6- (2-hydroxyethylamino) -s-triazine, N, N '-bisformyl-N, N' -bis (1,2,2,6,6-pentamethyl-4-piperidyl) hexamethylenediamine, hexahydro-2, 6 bis (2,2,6,6-tetramethyl-4-piperidyl) 1H, 4H, 5H, 8H-2,3a, 4a, 6,7a, 8a-hexaazacyclopenta [def] fluoren-4,8-dione (by Uvinul® 4049 from BASF AG, Ludwigshafen), poly [[6- [(1,1,3, 3-tetramethylbutyl) amino] -1,3,5-triazine-2,4-diyl] [(2, 2,6,6-tetramethyl-4-piperidinyl) imino] -1,6-hexandiyl [(2, 2, 6,6-tetramethyl-4-piperidinyl) imino]]) [CAS No. 71878-19-8] , 1, 3, 5-triazine-2,4,6-triamine, N, N '' '- [1,2-ethanediylbis [[4,6-bis [butyl] (1,2,2,6,6- pentamethyl-4-piperidinyl) amino] -1,3,5-triazin-2-yl] imino] -3,1-propandiyl]] bis [N ', N "-dibutyl-N', N" -bis (1 , 2,2,6,6-pentamethyl-4-piperidinyl) (CAS No .106990-43-6) (for example, Chimassorb 119 from Ciba Specialty Chemicals, Inc.). The group k) of the metal deactivators includes, for example, N, N'-diphenyloxalamide, N-salicylal-N '-salicyloylhydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3, 5) di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,4-triazole, bis (benzylidene) oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoylbisphenyl hydrazide, dihydrates N, N'-diacetyladipic, dihydrazide N, N '-bis (salicyloyl) oxalic and N, N'-bis (salicyloyl) thiopropionyl dihydrazide. Group 1) of the phosphites and phosphonites include, for example, triphenyl phosphite, diphenylalkylphosphites, phenyldialkyl phosphites, tris (nonylphenyl) phosphite, trilaurylphosphite, trioctadecylphosphite, distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis (2) , 4-di-tert-butylphenyl) pentaerythritholdiphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyl oxypentarythritol diphosphite, bis (2,4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2) , 4,6-tris (tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitoltriphosphite, tetrakis (2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphonium, 6-isooctyloxy-2,4,8,10-tetra-tert-butyldibenzo [ d, f] [1, 3, 2] dioxaphosphepine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo [d, g] [1,3,2] -dioxaphosphocin , bis (2,4-di-tert-butyl-6-methylphenyl) methylphosphite, bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 2,2 ', 2"-nitrile [trie iltris ( 3,3 ', 5,5'-tetra-ter-butyl-1, 1 '-biphenyl-2, 2'-diyl) phosphite], and 2-ethylhexyl 3, 3', 5, 5 'tetra-tert-butyl-1,1'-biphenyl-2, 2'-diylphosphite. The group m) of the hydroxylamines includes, for example, N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N-dihexadecylhydroxylamine, N, N -dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N-methyl-N-octadecylhydroxylamine and N, N-dialkylhydroxylamine from fatty amines of hydrogenated tallow. The group n) of the nitrones include for example N-benzyl a-phenyl nitrona, N-ethyl a-methyl nitrone, N-octyl a-heptyl nitrona, N-lauryl a-undecyl nitrone, N-tetradecyl a-tridecyl nitrone, N-hexadecyl a-pentadecyl nitrone, N-octadecyl a-heptadecyl nitrone, N-hexadecyl a-heptadecyl nitrone, N-octadecyl a-pentadecyl nitrone, N-heptadecyl-heptadecyl nitrone, N-octadecyl a-hexadecyl nitrone, N- methyl a-heptadecyl nitrona and nitrones derived from N, N-dialkylhydroxylamines prepared from fatty amines of hydrogenated talc. The group o) of the amine oxides includes, for example, amine oxide derivatives as described in US Pat. Nos. 5., 844.029 and 5,880,191, dodecylmethylamine oxide, tridecylamine oxide, tridodecylamine oxide and trihexadecylamine oxide. The group p) of the bensofuranones and indolinones includes, for example, those described in US Patents 4,325,863; 4,338; 244; 5,175; 312; 5,216,052; 5,252,643; in DE-A-4316611; in DE-A-4316622; in DE-A-4316876; in EP-A-0589839 or EP-A-0591102, or 3- [4- (2-acetoxyethoxy) phenyl] -5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butyl -3- [4- (2-stearoyloxyethoxy) phenyl] benzofuran-2-one, 3,3'-bis [5,7-di-tert-butyl-3- (4- [2-hydroxyethoxy] phenyl) benzofuran- 2 -one], 5, 7-di-tert-butyl-3- (4-ethoxyphenyl) benzofuran-2-one, 3- (4-acetoxy-3,5-dimethylphenyl) -5,7-di-ter- butylbenzofuran-2-one, 3- (3,5-dimethyl-4-pivaloyloxyphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3- (3,4-dimethylphenyl) -5, 7-di-tert-butyl-benzofuran-2-one, Irganox® HP-136 from Ciba Specialty Chemicals, and 3- (2,3-dimethylphenyl) -5,7-di-tert-butyl-benzofuran-2 -one . The group q) of the thiosynthetists includes, for example, dilauryl thiodipropionate or distearyl thiodipropionate. The group r) of the peroxide destroying compounds includes, for example, esters of β-thiodipropionic acid, for example, lauryl, stearyl, myristyl or tridecylester, mercaptobenzimidazole or the zinc salt of 2-mercaptoenzymidoazole, dibutyldithiocarbamate zinc, dioctadecyl disulfide and pentaerythritol tetrakis (β-dodecyl mercapto) ropionate. The group s) of the basic co-stabilizers include, for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallylcyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal of higher fatty acids, example, calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatechol or zinc pyrocatechol. A preferred embodiment of the present invention utilizes at least one compound I together with at least one light stabilizer having at least one absorption maximum in the wavelength range from 280 to 400 nm. The light stabilizer is preferably selected from compounds of groups b), c), d), e) and g). The light stabilizer in question, in particular has at least a maximum absorption in the wavelength range from 280 to 320 nm. Accordingly, the light stabilizer employed additionally has at least an absorption maximum in the UVB range. The absorption maximum for the purposes of the present invention are the bands associated with the corresponding local or absolute maximum in the UV spectrum of the respective compounds, as measured in common organic solvents such as dichloromethane, acetonitrile or methanol at room temperature . The extinction of the UVB absorbers at the maximum, which is measured in solution, usually in dichloromethane, at a concentration of 1% by weight and a path length of 1 cm, is at least 100, in particular at least 200. Examples of light stabilizers used in particular in particular are the aforementioned diphenylcyanacrylates of group e).
In another preferred embodiment of the present invention, at least one naphthalene-1, 8-dicarboxylic monoimide I as defined above is used as a single light stabilizer from the group of naphthalene derivatives having at least one absorption maximum in the wavelength range over 320 to 400 nm in order to protect the organic material from the damaging effects of light. Typical representatives of the group of naphthalene derivatives are the naphthalene-1, 8-dicarboxylic monoimides used according to the invention and also the naphthalenedicarboxylic acids, the naphthalenedicarboxylic esters, the naphthalenedicarboxylic anhydrides, the naphthalenetetracarboxylic acids, the naphthalenetetracarboxylic anhydrides and the naphthaletracarboxylic esters. In a further preferred embodiment of the present invention, at least one naphthalene-1, 8-dicarboxylic monoimide I as defined above is used as a single light stabilizer (s) to protect the organic material from the damaging effects of light. The plastic may also comprise other additives and auxiliaries. Suitable additives of group t) are the usual additives, such as pigments, dyes, nucleating agents, fillers, reinforcing agents, anti-fogging agents, biocides and antistatics, for example.
Suitable pigments are inorganic pigments, examples being titanium dioxide in its three modifications - rutile, anatase or brookite; ultramarine blue, iron oxides, bismuth vanadates or carbon black and also the class of organic pigments, examples being compounds of the class of phthalocyanines, perylenes, azo compounds, isoindolines, quinophthalones, diketopyrrolopyrroles, quinacridones, dioxazines and indantrones. By dyes it is meant all dyes which are completely dissolved in the plastic used or are presented in a molecularly dispersed distribution and can therefore be used for the non-scattered coloration of high transparency of the polymers. It is also estimated that dyes are organic compounds that exhibit fluorescence in the visible part of the electromagnetic spectrum, such as fluorescent dyes. Suitable nucleating agents include, for example, inorganic substances, examples being talc, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates, preferably alkaline earth metals; organic compounds such as monocarboxylic or polycarboxylic acids and also their salts, such as 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; and polymeric compounds, such as ionic copolymers ("ionomers") for example. Suitable fillers and reinforcing agents include, for example, calcium carbonate, silicates, talc, mica, kaolin, barium sulfate, metal oxides and metal hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products , and synthetic fibers. Additional suitable examples of the powdered fibers or fillers include carbon or glass fibers in the form of glass fabrics, glass carpets or glass filament fibers, glass in pieces, virgin beads and wollastonite. The glass fibers can be incorporated either in the form of short glass fibers or in the form of continuous fibers (yarns). Examples of suitable antistats include amine derivatives such as N, N-bis (hydroxy-alkyl) alkylamines or -alkyleneamines, polyethylene glycol esters and ethers, ethoxylated carboxylic esters and carboxamides, and glyceryl mono- and distearate and also mixtures thereof . Typically, the plastic is mixed with at least one naphthalene-1, 8-dicarboxylic monoimide in an amount from 0.01 to 10% by weight, preferably from 0.01 to 5% by weight, and more preferably from 0.01 to 1.0% by weight. weight, based on the total weight of the plastic. The total weight of the plastic means the weight of the plastic added with the monoimide I naphthalene-1, 8-dicarboxylic and, where appropriate, with additional (co) stabilizers (plastic + the sum of all the (co) stabilizers + the sum of all the other additives). The light protection achieved is dependent on the path length in the plastic. This is illustrated by Lambert-Beer law E = e 'c d (e: molar extinction coefficient (absorbance), c: concentration, d: path length). In thin layers of plastic, therefore, it is usual to use a higher proportion of the UV absorber than in a thick layer of plastic. Compounds are used from groups a) to s), with the exception of benzofuranones of group p), in customary amounts: for example, in amounts from 0. 0001 to 10% by weight, preferably from 0.01 to 1% by weight, based on the total weight of the plastic. The additives of group t) are used in customary amounts. These are normally used in an amount from 0 to 60% by weight, based on the total weight of the plastic. The monoimide I-naphthalene-1, 8-dicarboxylic acid used according to the invention can also be added in the form of a pre-mixture (basic or compound concentration) containing at least one monomide I, naphthalene-1,8-dicarboxylic acid. a concentration of from 1 to 20% by weight to the materials that are stabilized, usually a plastic The pre-mix may further comprise the above-mentioned compounds of groups a) as) and other additives of group t) The present invention provides in addition compositions comprising at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above in an amount providing protection from the damaging effects of light, and at least one organic material. preferably a polymer selected from polyesters, polycarbonate polymers, polyolefins, polyvinylacetals, polystyrene, copolymers of styrene or of α-methylstyrene with die US and / or acrylic derivatives, and physical mixtures of the aforementioned polymers. The following text relates to the compositions of the invention concerning suitable and preferred embodiments equally applied to the corresponding use of such monoimide naphthalene-1, 8-dicarboxylic in such a thermoplastic molded composite. A preferred embodiment of the present invention relates to a composition comprising: - at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above; - at least one polyvinyl butyral (PVB); - at least one oligoalkylene glycol alkylcarboxylic diester as plasticizers; at least one carboxylic, aliphatic salt to control adhesion; if desired, at least one UV absorber selected from benzotriazoles, 2-phenyl-1,3,5-triazines, hydroxybenzophenones, diphenylcyanoacrylates and mixtures thereof, and if desired, at least one additional component selected from of fillers, dyes, pigments and additional additives. Particular preference is given to employing at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I in sheets of PVB in laminated glass, for automotive coating systems for example. Particular preference is given to the naphthalene-1, 8-dicarboxylic monoimide of the formula I selected from the I-C naphthalene-1, 8-dicarboxylic monoimides. With respect to the preparation of polyvinyl butyral, the above text is incorporated in its entirety for reference. The polyvinylbutyrals used in the polymer composition generally have an average molecular mass of more than 70,000, preferably from about 100,000 to 250,000. The polyvinylbutyral normally has a residual hydroxyl group content of less than 19.5%, preferably from about 17 to 19% by weight, calculated as the polyvinyl alcohol, and a residual ester group content from 0 to 10%, preferably from 0 to 3%, calculated as the polyvinyl ester. An advantageous polyvinyl butyral is that obtainable under the name Butvar® from Solutia, Inc., from St. Louis, Mo. Molded polyvinyl butyral compound is normally used in the form of a sheet with a thickness of 0.13 to 1.5 mm. The polyvinyl butyral can be formed to the desired thickness in a sheet extrusion line, for example. Suitable oligoalkylene glycol carboxylic diesters comprise the esters of the branched or unbranched C2-C?? Branched or unbranched monocarboxylic acids, preferably C6-C8 monocarboxylic acids, with C2-C3 tri-alkylene glycols or C2-C3 tetra-alkylene glycols . Suitable plasticizers are, for example, triethylene glycol di (2-ethylbutyrate), triethylene glycol di (2-ethylhexanoate), triethylene glycol diheptanoate or tetraethylene glycol diheptanoate. The fraction of the plasticizer is generally from 20 to 80% by weight preferably from 25 to 45% by weight, based on the total weight of the polymer composition. The aliphatic carboxylic salts suitable for controlling the adhesion are, for example, the polyvalent metal salts of the branched or unbranched C4-C22 monocarboxylic acids. Suitable metals include, for example, zinc, aluminum, lead or alkaline earth metals such as magnesium or calcium. A suitable example of an aliphatic carboxylic salt for controlling adhesion is for example, the magnesium salt of 2-ethylbutyric acid. The salts reduce the stickiness and viscosity of the polyvinylbutyral. The fraction of the aliphatic carboxylic salt is generally from 0.0001 to 0.5% by weight, preferably from 0.0001 to 0.1% by weight, based on the total weight of the polymer composition. The polyvinylbutyral polymer composition may further comprise at least one additional UV absorber, preferably selected from benzotriazoles, 2-phenyl-1,3,5-triazines, hydroxybenzophenones, diphenylcyanoacrylates and mixtures thereof. Examples of benzotriazoles are 2- (2'-hydroxyphenyl) benzotriazoles, preferably those mentioned above. Particular preference is given to the following: 2 (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5-chlorobenzotriazole [CAS No. 3896-11-5), commercially available for example as Tinuvin® 326 from Ciba Specialty Chemicals, Inc .; 2,4-di-tert-butyl-6- (5-chlorobenzotriazol-2-yl) phenol [CAS No. 3864-99-1], commercially available for example as Tin? Vin® 327 from Ciba Specialty Chemicals, Inc.;
2 (2H-benzotriazol-2-yl) -4,6-di-ter-pentyphenol [CAS No. 25973-55-1], commercially available for example as Tinuvin® 328 from Ciba Specialty Chemicals, Inc .; and - 2-be:? zotriazol-2-yl-4-methylphenol [CAS No. 2440-22-4], commercially available for example as Tinuvin® P from Ciba Specialty Chemicals, Inc. Examples of 2-phenyl-1, Suitable 3, 5-triazines are 2- (2'-hydroxyphenyl) -1,3,5-triazines, preferably those mentioned above. Particular preference is given to the following: 2- (4,6-diphenyl-1, 3,5-triazin-2-yl) -5-hexyloxyphenol [CAS 147315-50-2], commercially available for example as Tinuvin® 1577 of Ciba Specialty Chemicals, Inc.; and - 2,4-bis (2,4-dimethylphenyl) -6- (2-hydroxy-4-octylphenyl) -1,3,5-triazine [CAS No. 2725-22-6], commercially available for example as Cyasorb® UV 1164 by Cytec. Examples of suitable hydroxybenzophenones are 2-hydroxybenzophenones, preferably those mentioned above. Particular preference is given to the following: - 2-hydroxy-4-n-octoxybenzophenone [CAS No. 1843-05-6], commercially available for example as Chimassorb® 81 from Ciba Specialty Chemicals, Inc. Examples of suitable diphenylcyanacrylates are those mentioned above. Particular preference is given to the following: - 1, 3-bis [(2'-cyano-3 ', 3'-diphenylacryloxy) oxy] -2,2-bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen; Ethyl 2-cyano-3, 3-diphenylacrylate [CAS No. 5232-99-5], commercially available for example under the name Uvinul® 3035 from BASF AG, Ludwigshafen; and 2-ethylhexyl 2-cyano-3, 3-diphenylcyanoacrylate
[CAS 6197-30-4], commercially available for example under the name Uvinul® 3039 from BASF AG, Ludwigshafen. Generally speaking, the fraction of another UV absorber, depending on the thickness of the sheet used, is from 0.05 to 2% by weight, preferably from 0.1 to 1% by weight, based on the total weight of the polymer composition. In the case of thin polymeric layers, the fraction of the UV absorber used is generally higher than in the case of coarse polymer layers. The polyvinylbutyral polymer composition may further comprise at least one additional component selected from additional fillers, dyes, pigments and additives. With respect to suitable fillers, dyes and pigments, the above text is incorporated in its entirety for reference.
Another preferred embodiment of the present invention relates to a composition comprising - at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above; - at least one polycarbonate polymer selected from polycarbonates, polycarbonate copolymers and physical blends of polycarbonates with acrylonitrile-butadiene-styrene copolymers, acrylonitrile-styrene-acrylate copolymers, polymethyl methacrylates, polybutyl acrylates, polybutyl methacrylates, poly butylene terephthalates) and polyethylene terephthalates; - at least one stabilizer selected from phosphites, phosphonites and mixtures thereof, - - if desired, at least one UV absorber selected from benzotriazoles, 2-phenyl-1,3,5-triazines, diphenylcyanoacrylates and mixtures thereof; - if desired, at least one 2,6-dialkylated phenol antioxidant, and - if desired, at least one additional component selected from fillers, dyes, pigments and other additives. Also preferred is the use of at least one naphthalene-1, 8 -dicarboxyl monoimide of the formula I as defined above in a polycarbonate polymer composition. For the purposes of the present invention, the term "polycarbonate copolymers" encompasses polycarbonates obtainable by condensing phosgene or carbonic esters with at least two different dihydroxy compounds: different bisphenols, for example. A fraction of halogenated bisphenols, tetrabromobisphenol for example, increases the flame retardancy; a fraction of bisphenol S (dihydroxydifenyl sulphide) increases the impact resistance to the notch. Polycarbonate copolymers include, for example, polycarbonate copolymers based on bisphenol A and bisphenol C, or polycarbonate copolymers based on bisphenol A and bisphenol TMC (trimethylcyclohexane). For the purposes of the present invention, the term "polycarbonate copolymers" also includes polyester carbonates, which are obtainable for example, by reacting bisphenols with phosgene and aromatic dicarbonyl bichlorides, and block copolymers comprising polycarbonate blocks and blocks of polyalkylene oxide. The polycarbonate polymer composition comprises at least one stabilizer selected from phosphites and phosphonites. As for the appropriate phosphites and phosphonites, the above observations are incorporated in their entirety for reference. The preferred phosphites and phosphonites are tris (2,4-di-tert-butylphenyl) phosphite [CAS No.31570-04-4], which is commercially available for example as Irgafos® 168 from Ciba Specialty Chemicals, Inc., tetrakis (2,4-di-tert-butylphenyl) -4,4'-diyl bisphosphonite [CAS No. 119345-01-6], commercially obtainable for example as Irgafos® P-EPQ from Ciba Specialty Chemicals, Inc., and mixtures thereof. The fraction of the phosphite and / or the phosphonite is generally up to 2000 ppm, preferably from 500 to 1500 ppm, based on the total weight of the polymer composition. The polymer composition of the polycarbonate may further comprise at least one other UV absorber. Other suitable UV absorbers are those mentioned above. The other UV absorbers are preferably selected from benzotriazoles, 2-phenyl-1,3,5-triazines, diphenylcyanacrylates and mixtures thereof. Examples of suitable benzotriazoles are 2- (2'-hydroxyphenyl) benzotriazoles, preferably those mentioned above. Particular preference is given to the following: - 2 (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol [CAS No. 70321-86-7], commercially available for example as Tinuvin® 234 from Ciba Specialty Chemicals, Inc .; -2,4-di-tert-butyl-6- (5-chlorobenzotriazol-2-yl) phenol [CAS No. 3864-99-1], commercially available for example as Tinuvin® 327 from Ciba Specialty Chemicals, Inc .; 2- (2H-benzotriazol-2-yl) -4- (1, 1,3,3-tetramethylbutyl) phenol [CAS No. 3147-75-9], commercially available for example as Tinuvin® 329 from Ciba Specialty Chemicals, Inc .; 2- (2H-benzotriazol-2-yl) -4- (tert-butyl) -6- (sec-butyl) phenol [CAS No. 36437-37-3], commercially available for example as Tinuvin® 350 from Ciba Specialty Che nicals, Inc; - 2, 2 '-methylenebis- (6- (2H-benzotriazol-2-yl) -4-l, l, 3,3-tetramethylbutyl) phenol) [CAS No. 103597-45-1], commercially available for example as Tinuvin® 360 from Ciba Specialty Chemicals, Inc .; and transesterification products of methyl 3- (3-2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyphenyl) propionate with polyethylene glycol, obtainable for example as Tinuvin® 213 from Ciba Specialty Chemicals, Inc., (containing 52% of the compound R-COO- [(CH2) 2 ~ 0] nH (molar mass: 637 g / mol) [CAS No. 104810-48-2], 35% of the compound of the formula R-COO- [(CH2) 2-0] n-C0-R (molar mass: 975 g / moles) [CAS No. 104810-47-1] with
R = and 13% of the compound HO- [(CH2) 2-0] n-H [CAS No. 25322-68-3]. Examples of 2-phenyl-1,3,5-triazines are 2- (2'-hydroxyphenyl) -1,3,5-triazines, preferably those mentioned above. Particular preference is given to the following: - 2 (4,6-diphenyl-1,3,5-triazin-2-yl) -5-hexyloxyphenol [CAS No. 147315-50-2], commercially available for example as Tinuvin ® 1577 from Ciba Specialty Chemicals, Inc. Examples of suitable diphenylcyanacrylates are those mentioned above. Preference is given to the following: 1, 3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxyl] -2,2-bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen; and -ethyl-2-cyano-3,3-diphenylacrylate [CAS No. 5232-99-5], commercially available for example under the name Uvinul® 3035 from BASF AG, Ludwigshafen. In general, the fraction of other UV absorbers is up to 10% by weight, preferably 0.001-10% by weight, in particular 0.05-10% by weight, most preferably 0.1-10% by weight, based on the weight total of the polymer composition. In the case of the thin polymeric layers, the fraction of the UV absorber used is generally higher than in the case of the thick polymeric layers. The polycarbonate polymer composition may further comprise at least one 2,6-dialkylated phenol antioxidant. Suitable 2, 6-dialkylated phenols are those mentioned above and, in particular, the esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with the monohydric or polyhydric alcohols. Preferred esters of ß- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic with the monohydric or polyhydric alcohols are pentaerythritol tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate] [CAS No. 6683- 19-8], commercially available for example as Irganox® 1010 from Ciba Specialty Chemicals, Inc., octadecyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate [CAS No. 2082-79-3 ], commercially available for example as Irganox® 1076 from Ciba Specialty Chemicals, Inc., and mixtures thereof. The antioxidant fraction is generally up to 2000 ppm, preferably from 500 to 2000 ppm, based on the total weight of the polymer composition. In a further preferred embodiment, the polymer composition comprises not only at least one 2,6-dialkylated phenol antioxidant but also at least one phosphite stabilizer and / or a phosphonite. The ratio of the antioxidant to the co-stabilizer is in that case generally in the range from 1:10 to 10: 1.
An especially preferred embodiment of the present invention relates to a polymer composition which comprises at least one polycarbonate, at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above and, as (a) the additional components, the substance (s) indicated in a line of Table A (compositions 1.1 to 1.60). The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1,8-dicarboxylic monoimides of the formula I-C. The weight fractions of the individual constituents in compositions 1.1 to 1.60 are placed with the ranges indicated above, based on the total weight of the polymer composition.
Table A:
A further especially preferred embodiment of the present invention relates to a polymer composition 2.1 to 2.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a polycarbonate copolymer. A further, particularly preferred embodiment of the present invention relates to a polymer composition 3.1 to 3.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a physical mixture of the polycarbonates with acrylonitrile copolymers -butadiene-styrene. A further, particularly preferred embodiment of the present invention relates to a polymer composition 4.1 to 4.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a physical mixture of the polycarbonates with acrylonitrile copolymers -styrene-acrylate. A further, particularly preferred embodiment of the present invention relates to a polymer composition 5.1 to 5.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a physical mixture of polycarbonates with polymethyl methacrylates. An especially preferred embodiment of the present invention relates to a polymer composition 6.1 to 6.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a physical mixture of polycarbonates with polybutyl acrylates. A further, particularly preferred embodiment of the present invention relates to a polymer composition 7.1 to 7.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a physical mixture of polycarbonates with polybutyl methacrylates. A particularly preferred, additional embodiment of the present invention relates to a polymer composition 8.1 to 8.60, which differs from the corresponding compositions 1.1 to 1.60 only in that the polycarbonate is replaced by a physical mixture of polycarbonates with poly (terephthalates of butylene). A particularly preferred, additional embodiment of the present invention relates to the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above in a polymer composition 9.1 to 9.60, which differs from the corresponding compositions 1.1. to 1.60 only in that the polycarbonate is replaced by a physical mixture of the polycarbonates with polyethylene terephthalates. The polycarbonate polymer composition may further comprise at least one additional component selected from dyes, pigments and other additives. With respect to suitable dyes and pigments, the above observations are incorporated herein in their entirety for reference. In a preferred embodiment, the dye and / or the pigment is an indigo agent. Suitable indigo agents are, for example, ultramarine blue, phthalocyanines, anthraquinones and indantrones. When an indigo agent is used as well as the fraction of the indigo agent is up to 500 ppm (0.05% by weight), preferably 0.5-100 ppm, based on the total weight of the polymer composition. Preferred applications for the polycarbonate polymeric compositions of the invention are as lenses for headlight covers, as windshields in automobiles and as other lens / varnishing systems in automobiles and architecture. A further preferred embodiment of the present invention relates to a composition comprising - at least one naphthalene-1, 8-dicarboxylic monoimide as defined above; - at least one polyethylene terephthalate (PET); at least one 2,6-dialkylated phenol antioxidant; if desired, at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; and if desired, at least one additional UV absorber selected from diphenylcyanoacrylates, phenyl-1,3,5-triazines and benzotriazoles and mixtures thereof. Likewise, the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above in a PET composition is preferred. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the I-C naphthalene-1, 8-dicarboxylic monoimides. Suitable 2, 6-dialkylated phenol antioxidants are those mentioned above. Preference is given to the esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols and particularly tetrakis [3- (3,5-di-tert-butyl-4-) hydroxyphenyl) propionate] of pentaerythritol [CAS No. 6683-19-8], commercially available for example as Irganox® 1010 from Ciba Specialty Chemicals, Inc., hexamethylene-bis- (3- (3,5-di-tert-butyl) -4-hydroxyphenyl) propionate [CAS No. 35074-77-2], commercially available for example as Irganox® 259 from Ciba Specialty Chemicals, Inc., and 3, 5-dialkylated hydroxyphenyl ethyl esters, preferably ((3, 5 diethyl bis (1, 1-dimethylethyl) -4-hydroxyphenyl) methyl) phosphonate [CAS No. 976-56-7], commercially available for example as Irganox® 1222 from Ciba Specialty Chemicals, Inc. The fraction of the antioxidant is generally up to 2000 ppm, preferably from 500 to 2000 ppm, based on the total weight of the polymer composition. The polyethylene terephthalate comprises at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof. Suitable phosphites and phosphonites are those mentioned above. A preferred phosphite is tris (2,4-di-tert-butylphenyl) phosphite [CAS No. 31570-04-4], commercially available for example as Irgafos® 168 from Ciba Specialty Chemicals, Inc. The fraction of the phosphite and / or of the phosphonite is generally up to 2000 ppm, preferably from 500 to 2000 ppm, in particular from 750 to 2000 ppm, based on the total weight of the polymer composition. In a further preferred embodiment, the polyethylene terephthalate polymer composition comprises not only at least one 2,6-dialkylated phenol, preferably at least one 3,5-dialkylated hydroxyphenylmethylphosphonic ester and / or at least one ester of β- ( 3, 5-di-tert-butyl-4-hydroxyphenyl) propionic with monohydric or polyhydric alcohols, as an antioxidant, but also at least one phosphite and / or a phosphonite as a co-stabilizer. The ratio of the antioxidant to the co-stabilizer is in that case in general in the range from 1:10 to 10: 1. The polymer composition of polyethylene terephthalate may further comprise at least one other UV absorber. Other suitable UV absorbers are those mentioned above. The other UV absorbers are preferably selected from benzotriazoles, phenyl-1,3,5-triazines, diphenylcyanacrylates and mixtures thereof. Examples of suitable benzotriazoles are 2- (2'-hydroxyphenyl) benzotriazoles, preferably those mentioned above. Particular preference is given to the following: 2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol [CAS No. 70321-86-7], commercially available for example as Tinuvin® 234 from Ciba Specialty Chemicals, Inc .; 2,4-di-tert-butyl-6- (5-chlorobenzotriazol-2-yl) phenol [CAS No. 3864-99-1], commercially available for example as Tinuvin® 327 from Ciba Specialty Chemicals, Inc .; 5-2,2 '-methylenebis- (6- (2H-benzotriazol-2-yl) -4,1,1,3,3, -tetramethylbutyl) phenol [CAS No. 103597-45-1], commercially available from example as Tinuvin® 360 from Ciba Specialty Chemicals, Inc.; and transesterification products of methyl 3- (3- (2H-10-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyphenyl) propionate with polyethylene glycol, obtainable for example as Tinuvin® 213 from Ciba Specialty Chemicals, Inc. Examples of suitable 2-phenyl-1,3,5-triazines are 2- (2'-hydroxyphenyl) -1,3,5-triazines, preferably those mentioned above. Particular preference is given to the following: 2- (4,6-diphenyl-l, 3,5-triazin-2-yl) -5-hexyloxyphenol [CAS No. 147315-50-2], commercially available for example as Tinuvin® 1577 from Ciba Specialty 20 Chemicals, Inc. Examples of suitable diphenylcyanacrylates are those mentioned above. Preference is given to the following: -1,3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2,2-25 bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] methyljpropane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen; - ethyl 2-cyano-3, 3-diphenylacrylate [CAS No. 5232-99-5], commercially available for example under the name Uvinul® 3035 from BASF AG, Ludwigshafen; and 2-ethylhexyl 2-cyano-3, 3-diphenylacrylate [CAS No. 6197-30-4], commercially available for example under the name Univul® 3039 from BASF AG, Ludwigshafen. In general, the fraction of other UV absorbers is up to 2% by weight, preferably 0.01-5% by weight, in particular 0.1 - 0.15% by weight, based on the total weight of the polymer composition of polyethylene terephthalate . In the case of the thin polymeric layers, the fraction of the UV absorber used is generally higher than in the case of the thick polymeric layers. An especially preferred embodiment of the present invention relates to polyethylene terephthalate polymer compositions which comprise at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above, and as (a) the additional component (s) , the one or more substances indicated in a line of Table B (compositions 10.1 to 10.54). The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. The weight fractions of the individual constituents in the compositions 10.1 to 10.54 are within the ranges indicated above, based on the total weight of the polymer composition.
Table B
In a further preferred embodiment of the present invention, polyethylene terephthalate is an amorphous polyethylene terephthalate and the polyethylene terephthalate polymer composition further comprises at least one acetaldehyde scavenger. An example of a suitable acetaldehyde scavenger is anthranilamide [CAS No. 88-68-6]. A further particularly preferred embodiment of the present invention relates to polyethylene terephthalate polymer compositions 11.1 to 11.54, which differ from the corresponding compositions 10.1 to 10.54 only in that the polyethylene terephthalate is an amorphous polyethylene terephthalate and the composition additionally includes an acetaldehyde scrubber. In particular, the naphthalene-1, 8-dicarboxylic monoimide of the formula I is a naphthalene-1,8-dicarboxylic monoimide of the formula I-C. The polymeric composition comprising the amorphous polyethylene terephthalate may further include at least one additional component, selected from reheating agents, dyes, pigments and other additives. For the purposes of the present invention, a reheating agent is a substance which on absorption of energy accelerates plasticization of the polymer and thus allows the polymer mass to be formed by assemblies downstream (eg, a bottle blow mold) . Carbon black is an example of a suitable reheating agent. Carbon black can be used in the form of powder or granules. The fraction of the reheating agent is generally from 0.1 to 2% by weight, based on the total weight of the polymer composition. The dyes, pigments and other suitable additives are those mentioned above. Particular preference is given to the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I in the compositions comprising an amorphous polyethylene terephthalate, at least one 2,6-dialkylated phenol antioxidant, and at least one scrubber of acetaldehyde for packaging materials such as bottles or containers. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. In another preferred embodiment of the present invention, polyethylene terephthalate is a partially crystalline polyethylene terephthalate and the polymer composition further includes at least one nucleating agent. Suitable nucleating agents are those mentioned above. The fraction of the nucleating agent is generally from 0.05 to 1% by weight, based on the total weight of the polymer composition. A further particularly preferred embodiment of the present invention relates to polymer compositions of polyethylene terephthalate 12.1 to 12.54, which differ from the corresponding compositions 10.1 to 10.54 only in that the polyethylene terephthalate is a partially crystalline polyethylene terephthalate and the The composition further includes at least one nucleating agent. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. Application areas for polymeric compositions comprising partially crystalline polyethylene terephthalate for example are optical films for projection. In particular, the naphthalene-1, 8-dicarboxylic monoimide of the formula I is a naphthalene-1,8-dicarboxylic monoimide of the formula I-C. A further particularly preferred embodiment of the present invention relates to compositions comprising at least one naphthalene-1, 8-dicarboxylic monoimide as defined above; - at least one high density polyethylene or polypropylene; at least one 2,6-dialkylated phenol antioxidant, - if desired, at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; if desired, at least one UV absorber, selected from diphenyl cyanoacrylates, hydroxybenzophenones, phenyl-1,3,5-triazines, benzotriazoles and mixtures thereof, - if desired, at least one sterically hindered amine; and - if desired, an additional component selected from dyes, pigments and other additives. Also preferred is the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above in a composition comprising a polyethylene or a high density polypropylene. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from I-C naphthalene-1, 8-dicarboxylic monoimides. Examples of suitable 2,6-dialkylated phenols are those specified above, preferably the esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols, particularly tetrakis [3- ( 3, 5-di-tert-butyl-4-hydroxyphenyl) propionate] of pentaerythritol [CAS No. 6683-19-8], commercially available for example as Irganox® 1010 from Ciba Specialty Chemicals, Inc., and 3- (3 Octadecyl-5-di-tert-butyl-4-hydroxyphenyl) propionate [CAS No. 2082-79-3], commercially available for example as Irganox® 1076 from Ciba Specialty Chemicals, Inc., and mixtures thereof. The antioxidant fraction is generally up to 4000 ppm, preferably 1000 to 4000 ppm, based on the total weight of the polymer composition. If desired, the composition includes a co-stabilizer selected from phosphites, phosphonites, and mixtures thereof. With respect to the appropriate phosphites and phosphonites the above text is incorporated in its entirety for reference. The preferred phosphites and phosphonites are tris (2,4-di-tert-butylphenyl) phosphite [CAS No. 31570-04-4], commercially available for example as Irgafos® 168 from Ciba Specialty Chemicals, Inc., and tetrakis (2). , 4-di-tert-butylphenyl) (1,1-biphenyl) -4,4'-diylbisphosphonite [CAS No. 119345-01-6], commercially available for example as Irgafos® P-EPQ from Ciba Specialty Chemicals, Inc ., and mixtures thereof. The fraction of the phosphite and / or the phosphonite is generally up to 2000 ppm, preferably from 500 to 2000 ppm, in particular from 750 to 2000 ppm, based on the total weight of the polymer composition. In a further preferred embodiment, the polymer composition comprises not only at least one 2,6-dialkylated phenol antioxidant, but also at least one phosphite and / or phosphonite co-stabilizer. The ratio of the antioxidant to the co-stabilizer is in that case generally in the range from 1:10 to 10: 1. The polymer composition may further comprise at least one other UV absorber. Other suitable UV absorbers are those mentioned above. The other UV absorbers are preferably selected from diphenylcyanoacrylates, hydroxybenzophenones, phenyl-1,3,5-triazines, benzotriazoles and mixtures thereof. Examples of suitable benzotriazoles are 2- (2'-hydroxyphenyl) benzotriazoles, preferably those mentioned above. Particular preference is given to the following: 2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol [CAS No. 70321-86-7], commercially available for example as Tinuvin® 234 from Ciba Specialty Chemicals Inc .; 2,4-di-tert-butyl-6- (5-chlorobenzotriazol-2-yl) phenol [CAS No. 3864-99-1], commercially available for example as Tinuvin® 327 from Ciba Specialty Chemicals, Inc .; 2- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol [CAS No. 3147-75-9], commercially available for example as Tinuvin® 329 from Ciba Specialty Chemicals , Inc.; 2- (2H-benzotriazol-2-yl) -4- (tert-butyl) -6- (sec-butyl) phenol [CAS No. 36437-37-3], commercially available for example as Tinuvin® 350 from Ciba Specialty Chemicals, Inc; 2,2'-methylenebis- (6- (2H-benzotriazol-2-yl) -4-1,1,3,3-tetramethylbutyl) phenol) [CAS No. 103597-45-1], commercially available for example as Tinuvin® 360 from Ciba Specialty Chemicals, Inc.; and transesterification products of methyl 3- (3- (2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyphenyl) ro-pionate with polyethylene glycol, obtainable for example as Tinuvin® 213 from Ciba Specialty Chemicals, Inc. Examples of suitable 2-phenyl-1,3,5-triazines are 2- (2'-hydroxyphenyl) -1,3,5-triazines, preferably those mentioned above. Particular preference is given to the following: 2- (4,6-diphenyl-1, 3,5-triazin-2-yl) -5-hexyloxyphenol [CAS No. 147315-50-2], commercially available for example as Tinuvin® 1577 from Ciba Specialty Chemicals, Inc .; and 2,4-Bis (2,4-dimethylphenyl) -6- (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine [CAS No. 2725-22-6], commercially available for example as Cyasorb ® UV 1164 by Cytec. Examples of suitable hydroxybenzophenones are the 2-hydroxybenzophenones, preferably those mentioned above. Particular preference is given to: - 2-hydroxy-4-n-octoxybenzophenone [CAS No. 1843-05-6], commercially available for example as Chimassorb® 81 from Ciba Specialty Chemicals, Inc. Examples of suitable diphenylcyanacrylates are those mentioned above . Preference is given to the following: 1, 3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2, 2-bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen; and -ethyl-2-cyano-3,3-diphenylacrylate [CAS No. 5232-99-5], commercially available for example under the name Uvinul® 3035 from BASF AG, Ludwigshafen. In general, the fraction of other UV absorbers is up to 2% by weight, preferably from 0.01 to 1.5% by weight, and in particular from 0.05-1% by weight, based on the total weight of the polymer composition. In the case of the thin polymeric layers, the fraction of the UV absorber used is generally higher than in the case of the thick polymeric layers.
The polymer composition comprising a polyethylene or a high density polypropylene may further comprise at least one sterically hindered amine. Suitable sterically hindered amines (HALS) are sterically hindered, oligomeric and monomeric amines, examples are those mentioned above. The sterically hindered amines are: (partially) maleimide N-piperidin-4-yl-substituted copolymers and a mixture of α-olefins, obtainable for example as Uvinul® 5050H [CAS 152261-33-1] (molar mass approximately 3500 g / moles) of the formula
from BASF AG, Ludwigshafen; the sterically hindered amine of the formula
[CAS No. 124172-53-8]
which is obtainable for example under the name Uvinul® 4050 H from BASF AG, Ludwigshafen; poly [[6 - [(1,1,3,3-tetramethylbutyl) amino] -1,3,5-triazin-2,4-diyl] [(2,2,6,6-tetramethyl-4-piperidinyl)] imino] -1,6-hexandiyl [(2, 2, 6, 6-tetramethyl-4-piperidinyl) imino]]) [CAS No. 71878-19-8], commercially available for example as Chimassorb® 944 (molar mass : 2000 to 3100 g / moles) from Ciba Specialty Chemicals, Inc .; the polymer of dimethyl succinate with 4-hydroxy-2, 2, 6, 6-tetramethyl-l-piperidinetanol [CAS number
65447-77-0], commercially available for example as
Tinuvin® 622 (molar mass: 3100 - 4100 g / moles) of Ciba
Specialty Chemicals, Inc .; - sebacate of bis (2, 2, 6, 6-tetramethyl-4-piperidyl) [CAS No. 52829-07-9], commercially available for example as Tinuvin® 770 from Ciba Specialty Chemicals, Inc .; and the polymer of 2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro [5.1.11.2] eneicosan-21-one and epichlorohydrin of the formula
[CAS No. 202483-55-4], commercially available for example as Hostavin® N30 from Ciba Specilty Chemicals, Inc. In general, the fraction of the sterically hindered amine is up to 2% by weight, preferably 0.1-2% by weight, in particular 0.1-0.15% by weight, most preferably 0.1-1% by weight, based on the total weight of the polymer composition. In the case of the thin polymeric layers, the fraction of the sterically hindered amine used is generally higher than in the case of the thick polymeric layers. The polymer composition may further comprise at least one additional component selected from dyes, pigments and other additives. Suitable dyes and pigments are those mentioned above. An especially preferred embodiment of the present invention relates to compositions which comprise at least one polyethylene or a high density polypropylene, at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above, and, as ( a) additional component or components, the substance (s) indicated in a line of Table C (compositions 13.1 to 13.108). The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1,8-dicarboxylic monoimides of the formula I-C. The weight fractions of the individual constituents in compositions 13.1 to 13.108 are within the ranges indicated above, based on the total weight of the polymer composition.
Table C:
Particular preference is given to the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I in the polymer compositions comprising at least one polyethylene or a high density polypropylene for packaging materials such as bottles or containers. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. A further particularly preferred embodiment of the present invention relates to compositions comprising - at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above; - at least one polystyrene; - at least one 2,6-dialkylated phenol antioxidant; if desired, at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; - if desired, at least one additional UV absorber, selected from benzotriazoles, diphenylcyanoacrylates and mixtures thereof; if desired, at least one sterically hindered amine; and - if desired, at least one additional component selected from dyes, pigments and other additives. Also preferred is the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above in a polystyrene polymer composition. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the I-C naphthalene-1, 8-dicarboxylic monoimides. Examples of suitable 2, 6-dialkylated phenols are those specified above. Preferred 2,6-dialkylated phenols are the esters of / 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols, particularly tetrakis [3- (3,5-dihydro)). pentaerythritol tert-butyl-4-hydroxyphenyl) propionate]
[CAS No. 6683-19-8], commercially available for example as Irganox® 1010 from Ciba Specialty Chemicals, Inc., and octadecyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate.
[CAS No. 2082-79-3], commercially available for example as Irganox® 1076 from Ciba Specialty Chemicals, Inc., and mixtures thereof. The antioxidant fraction is generally up to 2000 ppm, preferably from 500 to 2000 ppm, based on the total weight of the polymer composition. With respect to the appropriate phosphites and phosphonites, the above text is incorporated in its entirety for reference. A preferred phosphite is tris (2,4-di-tert-butylphenyl) phosphite [CAS No. 31570-04-4], commercially available for example, as Irgafos® 168 from Ciba Specialty Chemicals, Inc. The fraction of the phosphite and / or the phosphonite is generally up to 2000 ppm, preferably from 500 to 2000 ppm, based on the total weight of the polymer composition. Preference is also given to mixtures comprising at least a 2,6-dialkylated phenol, preferably an ester of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols, as an antioxidant , and also a phosphite and / or a phosphonite as a co-stabilizer. In that case the ratio of the co-stabilizer to the antioxidant is generally in the range from 10: 1 to 1:10. Among such mixtures, particular preference is given to those which comprise as co-stabilizer tris- (2,4-di-tert-butylphenyl) phosphite [CAS No. 31570-04-4], commercially available for example as Irgafos® 168 from Ciba Specialty Chemnicals, Inc., and as antioxidant tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate pentaerythritol [CAS No. 6683-19-8], commercially available for example, as Irganox® 1010 from Ciba Specialty Chemicals, Inc., or octadecyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate [CAS No. 2082-79-3], commercially available for example as Irganox® 1076 from Ciba Specialty Chemicals, Inc. A preferred mixture is, for example, a mixture of 1 part of octadecyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate and 4 parts of tris (2,4-di). -tert-butylphenyl) phosphite, this mixture is commercially available for example, as Irganox B900 from Ciba Specialty Chemicals, Inc. The polystyrene polymer composition may further comprise at least one other UV absorber. Other suitable UV absorbers are those mentioned above. The other UV absorber is preferably selected from benzotriazoles, diphenylcyanoacrylates and mixtures thereof. Examples of benzotriazoles are 2- (2'-hydroxyphenyl) benzotriazoles, preferably those mentioned above. Particular preference is given to the following: 2- (2H-benzotriazol-2-yl) -4,6-di-ter-pentiphenol
[CAS No. 25973-55-1], commercially available for example as Tinuvin® 328 from Ciba Specialty Chemicals, Inc .; and - 2-benzotriazol-2-yl-4-methylphenol [CAS No. 2440-22-4], commercially available for example as Tinuvin® P from Ciba Specialty Chemicals, Inc., and mixtures thereof. Examples of suitable diphenylcyanacrylates are those mentioned above. Preference is given to the following: 1, 3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2, 2-bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen; and -ethyl-2-cyano-3,3-diphenylacrylate [CAS No. 5232-99-5], commercially available for example under the name Uvinul® 3035 from BASF AG, Ludwigshafen. In general, the fraction of the other UV absorbers is up to 2% by weight, preferably from 0.01 -1.5% by weight, and in particular from 0.05-1% by weight, based on the total weight of the polymer composition . In the case of the thin polymeric layers, the fraction of the UV absorber used is generally higher than in the case of the thick polymeric layers. The styrene polymer composition may further comprise at least one spherically hindered amine. Suitable sterically hindered amines are those mentioned above. The sterically hindered amine is preferably a compound of the formula RNH- (CH2) 3-NR- (CH2) 2-NR- (CH2) 3-NHR [CAS No. 106990-43-6] where
which is commercially available for example as Chimassorb® 119 from Ciba Specialty Chemicals, Inc., bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate [CAS No. 52829-07-9], commercially available from example as Tinuvin® 770 from Ciba Specialty Chemicals, Inc., or mixtures thereof. In general, the fraction of the sterically hindered amine is up to 2% by weight, preferably 0.1-1.5% by weight, in particular 0.1-0.5% by weight, based on the total weight of the polymer composition. The polystyrene polymer composition may further comprise at least one additional component selected from dyes, pigments and other additives. Suitable dyes and pigments are those mentioned above. An especially preferred embodiment of the present invention relates to polystyrene polymer compositions comprising at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above, and, as additional components, the substances indicated in a line of Table D
(compositions 14.1 to 14.45). The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. The weight fractions of the individual constituents in compositions 14.1 to 14.45 are within the ranges indicated above, based on the total weight of the polymer composition.
Table D:
Particular preference is given to the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I in the polystyrene polymeric packaging compositions such as yoghurt cups and electric instrument linings. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. A further particularly preferred embodiment of the present invention relates to compositions comprising - at least one naphthalene-1, 8-dicarboxylic monoimide as defined above; at least one acrylonitrile-butadiene-styrene copolymer or a styrene-acrylonitrile copolymer; at least one 2,6-dialkylated phenol antioxidant; if desired, at least one co-stabilizer selected from phosphites, phosphonites and mixtures; if desired, at least one additional UV absorber, selected from benzotriazoles, hydroxybenzophenones, diphenylcyanoacrylates and mixtures thereof; if desired, at least one sterically hindered amine; and - if desired, an additional component selected from dyes, pigments and other additives. Also preferred is the use of at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above in an acrylonitrile-butadiene-styrene copolymer or styrene-acrylonitrile copolymer composition. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the I-C naphthalene-1, 8-dicarboxylic monoimides. Examples of suitable 2, 6-dialkylated phenols are the esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols and in particular 3- (3, 5-dihydrate). octadecyl tert-butyl-4-hydroxyphenyl) propionate [CAS No. 2082-79-3], commercially available for example as Iganox® 1076 from Ciba Specialty Chemicals, Inc. The fraction of the antioxidant is generally up to 2000 ppm, preferably from 500 to 2000 ppm, based on the total weight of the polymer composition. With respect to the appropriate phosphites and phosphonites, the above text is incorporated in its entirety for reference. The preferred phosphites and phosphonites are tris (2,4-di-tert-butylphenyl) phosphite [CAS No. 31570-04-4], commercially available for example, as Irgafos® 168 from Ciba Specialty Chemicals, Inc., and tetrakis ( 2,4-di-tert-butylphenyl) [1,1-biphenyl] -4,4'-diylbisphosphonite [CAS No. 119345-01-6], commercially available for example as Irgafos® P-EPQ from Ciba Specialty Chemicals, Inc., and mixtures thereof. The phosphite fraction and / or the phosphonite is generally up to 2000 ppm, preferably from 500 to 2000 ppm, based on the total weight of the polymer composition. In another preferred embodiment, the polymer composition comprises not only at least one 2,6-dialkylated phenol, preferably an ester of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols. as an antioxidant, but also at least one phosphite and / or a phosphonite as a co-stabilizer. In that case, the ratio of the antioxidant to the co-stabilizer is generally in the range from 1:10 to 10: 1. The polymer composition which comprises at least one acrylonitrile-butadiene-styrene copolymer or a styrene-acrylonitrile copolymer can additionally comprise at least one additional UV absorber. The other suitable UV absorbers are those mentioned above. The other UV absorbers are preferably selected from benzotriazoles, hydroxybenzophenones, diphenylcyanoacrylates and mixtures thereof. Examples of suitable benzotriazoles are 2- (2'-hydroxyphenyl) benzotriazoles, preferably those mentioned above. Particular preference is given to the following: 2,4-di-tert-butyl-6- (5-chlorobenzotriazol-2-yl) phenol [CAS No. 3864-99-1], commercially available for example as Tinuvin® 327 from Ciba Specialty Chemicals, Inc., 2-benzotriazol-2-yl) -4-methylphenol [CAs No. 2440-24-4] commercially available for example as Tinuvin® P from Ciba Specialty Chemicals, Inc. Examples of suitable hydroxybenzophenones They are
2-hydroxybenzophenones. Particular preference is given to -2-hydroxy-4-n-octoxybenzophenone [CAS No. 1843-05-6], commercially available for example as Chimassorb® 81 from Ciba Specialty Chemicals, Inc. Examples of suitable diphenylcyanacrylates are: - 1 , 3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2,2-bis. { [2'-cyano-3 ', 3'-diphenyl-acryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen; and -ethyl-2-cyano-3,3-diphenylacrylate [CAS No. 5232-99-5], commercially available for example under the name Uvinul® 3035 from BASF AG, Ludwigshafen. In general, the fraction of other UV absorbers is up to 2% by weight, preferably 0.01 - 1.5% by weight, and in particular 0.05 - 1% by weight, based on the total weight of the polymer composition. In the case of thin polymeric layers, the fraction of the UV absorber used is generally higher than in the case of thick polymer layers. The composition of acrylonitrile-butadiene-styrene copolymer or styrene-acrylonitrile copolymer may further comprise at least one sterically hindered amine. Suitable sterically hindered amines are those mentioned above. The sterically hindered amine is preferably a compound of the formula RNH- (CH2) 3-NR- (CH2) 2-NR- (CH2) 3-NHR [CAS No. 106990-43-6] wherein
which is commercially available, for example, as Chimassorb® 119 from Ciba Specialty Chemicals, Inc., bis (2, 2,6,6,6-tetramethyl-4-piperidyl) sebacate [CAs No. 528929-07-9], commercially available for example, as Tinuvin® 770 from Ciba Specialty Chemicals, Inc., or mixtures thereof. In general, the fraction of the sterically hindered amine is up to 2% by weight, preferably 0.1-1.5% by weight, in particular 0.1-1% by weight, most preferably 0.1-0.5% by weight, based on the weight total of the polymer composition. The composition of the acrylonitrile-butadiene-styrene copolymer or the styrene-acrylonitrile copolymer may additionally comprise at least one additional component selected from dyes, pigments and other additives. Suitable dyes and pigments are those mentioned above.
An especially preferred embodiment of the present invention relates to acrylonitrile-butadiene-styrene copolymer or styrene-acrylonitrile copolymer compositions comprising at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above, and as additional components, the substances indicated in a line of Table E (compositions 15.1 to 15.54). The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. The weight fractions of the individual constituents in compositions 15.1 to 15.54 are within the ranges indicated above, based on the total weight of the polymer composition.
Table E:
Composition Antioxidant / Co-stabilizer Absorber of amine sterically CAS No. UV CAS No. prevented CAS No. 15.37 2082-79-3 and 119345-01-6 1843-05-6 52829-07-9 15.38 2082-79-3 and 119345-01-6 2440-22-2 52829-07-9 15.39 2082-79-3 and 119345-01-6 178671-58-4 52829-07-9 15.40 2082-79-3 and 119345-01-6 5232 -99-5 52829-07-9 15.41 2082-79-3 and 31570-04-4 3864-99-1 15.42 2082-79-3 and 31570-04-4 1843-05-6 15.43 2082-79-3 and 31570-04-4 2440-22-2 15.44 2082-79-3 and 31570-04-4 178671-58-4 15.45 2082-79-3 and 31570-04-4 5232-99-5 15.46 2082-79-3 and 31570-04-4 106990-43-6 15.47 2082-79-3 and 31570-04-4 52829-07-9 15.48 2082-79-3 and 119345-01-6 3864-99-1 15.49 2082-79- 3 and 119345-01-6 1843-05-6 15.50 2082-79-3 and 119345-01-6 2440-22-2 15.51 2082-79-3 and 119345-01-6 178671-58-4 15.52 2082-79 -3 and 119345-01-6 5232-99-5 15.53 2082-79-3 and 119345-01-6 106990-43-6 15.54 2082-79-3 and 119345-01-6 52829-07-9
Particular preference is given to the use of at least one monoimide naphthalene-1, 8-dicarboxylic of the formula I in compositions of the acrylonitrile-butadiene-styrene copolymer or the styrene-acrylonitrile copolymer in automotive components and linings of electric instruments. The naphthalene-1, 8-dicarboxylic monoimide of the formula I is preferably selected from the naphthalene-1, 8-dicarboxylic monoimides of the formula I-C. The present invention further provides a process for protecting organic material against detrimental effects of light, which involves adding to the material at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined above. The present invention further provides a process for protecting inanimate organic material against ultraviolet radiation, which involves producing the packaging using a plastic comprising at least one naphthalene-1, 8-dicarboxylic monoimide. The present invention further provides the use of a UV radiation absorbing layer to protect the organic material from ultraviolet radiation. The monoimide I naphthalene-1, 8-dicarboxylic acid used according to the invention and, where the compounds of groups a) to s) and / or the other additives of group t) are present are added to the plastic. The addition is made in a customary manner, for example, by mixing with plastic. Thus, the monoimide I naphthalene-1, 8-dicarboxylic acid used in accordance with the invention and, where appropriate, the additional stabilizers can also be added to the starting monomers, and the mixture of monomers and stabilizers can be polymerized. It is also possible to add the monoimide I naphthalene-1, 8-dicarboxylic acid used according to the invention and, where appropriate, the compounds of groups a) as) and / or the other additives of group t) to the monomers during the polymerization. A pre-condition for the addition before or during the polymerization is that the naphthalene-1, 8-dicarboxylic monoimide I used according to the invention and, where appropriate, the compounds of groups a) as) and / or the others additives of group t) are stable under the polymerization conditions: that is, they exhibit little or no decomposition. It is preferred to add the naphthalene-1, 8-dicarboxylic monoimide I used according to the invention and, where present, the compounds of groups a) to s) and / or the other additives of group t) to the finished plastic. This is effected in a usual manner by mixing methods which are known per se: for example, with melting at temperatures from 150 to 300 ° C. However, the components can also be mixed in "cold", without melting, and the powder or granular mixture does not melt and is evenly homogenized during processing. It will be appreciated that the naphthalene-1, 8-dicarboxylic monoimide I used according to the invention and, where present, the compounds of groups a) as) and / or the other additives of group t) can be added together or separated from each other, all at once, in portions, or continuously, in a constant relationship or next to a gradient. For example, part of the naphthalen-1, 8-dicarboxylic monoimide used according to the invention can be added to the monomers during the current polymerization, and the remainder can be added only to the finished polymer, or all the monoimide naphthalene-1, 8- Dicarboxylic can be added to the finished polymer. The mixing preferably takes place in a conventional extruder, with the components being able to be introduced into the extruder for example as a mixture or individually, completely, as a hopper or otherwise introduced proportionally at a later point in the extruder in the molten or solid product in the extruder. For particular adaptation of melt extrusion it is possessed by, for example, twin screw, single screw extruders. A twin screw extruder is preferred. The mixtures obtained can be granulated or pelletized, for example, or processed by methods which are common knowledge: for example, by extrusion, injection molding, foaming with blowing agents, thermoforming, hollow body blowing or calendering. The plastics can preferably be used to produce moldings (including semi-finished products, films, sheets and foams) of all kinds, examples are packaged and films for fabrics for example, particularly packaging for cosmetics, perfumes and pharmaceuticals, and packaging and films for food, bottles for drinks, or packaging for cleaning products. It is also possible to produce stretch films from thermoplastic molded compounds. Any product can in principle be protected by a package which comprises the naphthalene-1, 8-dicxylic monoimide used according to the invention. The product that is protected is preferably selected from cosmetic products, drugs, perfumes, food and cleaning. Suitable cosmetics include soap, body lotion, skin cream, bath gel, foam bath, body spray, makeup, eyeliner, mascara, blusher, lipstick, shampoo, hair conditioner, hair gel, Wax epilator, hair lotion, varnish for nails, varnish remover for nails, etc. Suitable pharmaceutical products include pharmaceutical compositions or drugs in the form of tablets, pills, film-coated tablets, suppositories, solutions, concentrates, suspensions and the like. Suitable comestibles include cnated and non-cnated beverages, examples being cnated beverages such as lemonade, beer, cnated fruit juice drinks, cnated water, non-cnated beverages such as wine, fruit juice, tea or coffee, fruit, meat, embodies , dairy products such as milk, yogurt, butter or cheese, animal and vegetable fats, bakery products, pasta, condiments, sauces, pastes, pestos, broths, purees, catsups, dressings, etc. Suitable cleaning products include household cleaners and industrial cleaners. The naphthalene-1, 8-dicxylic monoimide used in accordance with the invention is used with particular preference in thermoplastic molded compounds comprising polyolefins for agricultural films and packaging films, in biaxially oriented polypropylene for flexible-wrapped films in terephthalate polyethylene or polyethylene naphthalate for bottles and other packaging for containers, in polyvinyl butyral for laminated glass, in polystyrene for packaging with blister and other packaging containers, in polycnate for bottles, jars and other packaging containers and moldings, in polyvinyl chloride for containers and packaging films, or in polyvinyl alcohol to produce films. Where appropriate, the films of different polymers can be combined together by rolling or in the form of extrusion laminates to form composite films. The monoaxial or biaxial expansion is possible where it is appropriate to improve the properties. This is used, for example, in order to produce reduction films. Reducing films, for example, can be produced from polyethylene terephthalate, polyethylene, polyvinylidene chloride or polyvinyl chloride. Stabilized materials using at least one naphthalene-1, 8-dicxylic monoimide exhibit characteristics of particular quality compared to non-stabilized materials and stabilized materials with prior art stabilizers. The stabilized materials according to the invention have a prolonged exposure time, since the damage induced by the light does not start until later. In addition, the stabilized material using at least one naphthalene-1, 8-dicxylic monoimide protects not only the material that is stabilized but also the packaged contents. The following examples are intended to illustrate the invention, but without restricting it.
I. Preparation examples
Example 1: Preparation of 4-cyano-N- (2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide (Compound IA.l) 1.1 Preparation of 4-bromo-N- (2,6-diisopropylphenyl) - naphthalene-1, 8-dicarboximide. 27.7 g of 4-bromonaphthalene-1,8-dicarboxylic anhydride, 19.0 g of 2,6-diisopro-ilanyline and 9.2 g of anhydrous zinc acetate in 65 ml were heated at 200 ° C for 3 hours. of N-methylpyrrolidone. After cooling, the formed precipitate was filtered off, washed and dried to give 26.2 g of 4-bromo-N- (2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide having a melting point of 277. ° C.
1. 2 Preparation of 4-cyano-N- (2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide. 24.8 g of 4-bromo-N- (2,6-diisopropylphenyl) naphthalene were heated at 210 ° C for 4 hours. -1,8-dicarboximide and 7.5 g of copper cyanide (I) in 150 ml of N-methylpyrrolidone. After cooling, water was added to the reaction mixture, producing a precipitate. The precipitate was removed by filtration, washed and dried. Column chromatography of the precipitate on silica gel (eluent: dichloromethane) gave 15.6 g of 4-cyano-N- (2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide having a melting point of 291 ° C. Elemental analysis: C25H __? 202 (382.5 g / moles): calculated: C 78.5; H 5.8; ? 7.3; O 8.4. found: C 78.5; H 5.9; ? 7.0; O 8.4; UV (dichloromethane):? Max (Ig e) 352 nm (4.16). Following the method described in Example 1, in Examples 2 to 5, the monoimides I-A.2 to I-A.5 were prepared 4-cyano-substituted naphthalene-1, 8-dicarboxylic acids. The melting points and spectroscopic properties of monoamides I-A.l to I-A.5 4-cyano-substituted naphthalene-1, 8-dicarboxylics are summarized in Table 1. Dichloromethane was used as the solvent for UV spectroscopy.
Table 1 :
Example 6: Preparation of 4-aminocarbonyl-N ~ (2,6-diisopropylphenyl) -phthalen-1,8-dicarboximide (compound IB.l) 8 g of 4-cyano-N- were heated at 80 ° C for 3 hours. (2,6-diisopropylphenyl) naphthalene-1,8 -dicarboximide from Example 1 in 130 ml of concentrated sulfuric acid. The reaction mixture was subsequently poured into ice water and the formed precipitate was filtered off, washed and dried. This gave 5.1 g of the 4-aminocarbonyl-N- (2,6-diisopropylphenyl) -naphthalene-1,8-dicarboximide having a melting point of 233 ° C. UV (dichloromethane):? Max (Ig e): 336 nm (4.18).
Example 7: Preparation of N- (2,6-diisopropylphenyl) -4- (4-tert-octylphenoxy) -naphthalene-1,8-dicarboximide (compound IC.l) 7.1 Preparation of 4-chloro-N- ( 2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide A mixture of 23.3 g of 4-chloronaphthalene-1, 8-dicarboxylic anhydride, 19.0 g of 2,6-diisopropylaniline and 9.2 g was heated at 200 ° C for 3 hours. of anhydrous zinc acetate in 65 ml of N-methylpyrrolidone. After cooling, the formed precipitate was filtered off, washed and dried. This gave 22.4 g of the 4-chloro-N- (2,6-diisopropylphenyl) naphthalen-1,8-dicarboximide having a melting point of 289 ° C.
7. 2 Preparation of N- (2,6-diisopropylphenyl) -4- (4-tert-octylphenoxy) naphthalene-1,8-dicarboximide A mixture of 5.0 g of 4-chloro-N was heated at 80 ° C for 24 hours. - (2,6-diisopropylphenyl) naphthalene-1,8-dicarboximide from 7.1, 3.5 g of 4- (1,1,3,3-tetramethylbutyl) phenol (tert-octylphenol) and 1.2 g of potassium carbonate in 60 ml of N-methylpyrrolidone. This was cooled and methanol and water were added to the reaction mixture, producing a precipitate. The precipitate thus obtained was extracted by filtration, washed and dried to give 6.2 g of N- (2,6-diisopropylphenyl) -4- (4-tert-octylphenoxy) naphthalene-1,8-dicarboximide having a point of fusion of 217 ° C. ^? - NMR (DMSO-dg) d [ppm]: 0.78 (s, 9 H), 1.12 (t, J = 7.3 Hz, 6H), 1.42 (s, 6H), 1.80 (s, 2H), 2.75 ( septet, J = 6.8Hz, 2H), 6.93 (d, J = 8.5 Hz, ÍH), 7.15 (d, J = 8.5 Hz, 2H), 7.32 (d, J = 7.5 Hz, 2H), 7.48 (t, J = 7.5 Hz, 1H), 7.52 (d, J = 9.0 Hz, 2H), 7.82 (dd, J = 8.0, 7.0 Hz, ÍH), 8.48 (d, J = 9.5 Hz, ÍH), 8.68 (dd, J = 7.0, 1.0 Hz, ÍH), 8.80 (dd, J = 8.5, 1.5 Hz, ÍH); 13 C-NMR (DMSO-dg): d [ppm]: 24.1 (q), 29.4 (d); 31.8 (q), 31.9 (q), 32.6 (s), 38.8 (s), 57.4 (t), 110.6 (d), 116.6 (s), 120.4 (d), 123.0 (s), 124.3 (d), 124.5 (s), 126.8 (d), 128.6 (d), 129.3 (d), 129.6 (d), 130.7 (s) 132.0 (s), 135.5 (d), 133.6 (d), 146.5 (s), 148.2 (s), 152.6 (s), 161.0 (s), 164.2 (s), 164.8 (s); UV (dichloromethane):? P.a (Ig e) 364 nm (4.22). Following the method described in Example 7, in Examples 8 to 16, the monoimides I-C.2 to I-CIO were prepared, 4-phenoxy-substituted naphthalene-1,8-dicarboxylic acids. The melting points and the spectroscopic properties of the monoimides I-C.l to I-C.10 naphthalen-1, 8-dicarboxylic 4-phenoxy substituted are summarized in Table 2. Dichloromethane was used as the solvent for UV spectroscopy.
R1 (1-C) II: Examples of use Examples 17-20: Incorporation of the UV absorbers into the polyethylene terephthalate (PET) film A mixture of polyethylene terephthalate (Polyclear T94 from Ter Hell &Co) was homogenized. GmbH, Hamburg) and the concentration of compound I set forth in Table 3 in a Berstorff twin-screw extruder (melting temperature: 275 ° C) and then granulated. The resulting granules were subsequently extruded in a Weber single screw extruder through a fluted die (melting temperature: 225 ° C) and pressed to a thickness of 300 μm through a roller graft. The results are summarized in Table 3. The parameters reported are the wavelengths below which less than 10% or 20% of the radiation passes through the film. A value below and preferably close to 400 nm means that the material under the film is effectively protected against UV radiation.
Table 3:
maximum wavelength with a transmission of less than 10% maximum wavelength with a transmission of less than 20%. The examples show that the naphthalene-1, 8-dicarboxylic monoimide I used according to the invention can be effectively incorporated into PET films. The monoamino I naph alen-1, 8-dicarboxylic monoimides used according to the invention filter out most of the harmful UV radiation from the spectrum and are therefore suitable as effective UV filters.
Example 22: Exposure of an addition PET film The PET film was exposed from Example 17 (containing 0.4% of compound IA.l) for 1000 hours in accordance with DIN 54004. The transmission profile of the film was measured at regular intervals and is shown in Table 4.
Table 4:
maximum wavelength with a transmission of less than 105 maximum wavelength with a transmission of less than 20!
Example 23: Exposure of an addition PET film. The PET film from Example 20 (containing 20% of compound IC.l) was exposed for 1000 hours in accordance with DIN 54004. The transmission profile of the film was measured at regular intervals and is shown in Table 5 .
Table 5
at maximum wavelength with a transmission of less than 10% b maximum wavelength with a transmission of less than 20%. Examples 22 and 23 show that naphthalene-1, 8-dicarboxylic monoimides I are photostable, ie they do not spoil. Accordingly, the naphthalene-1, 8-dicarboxylic monoimides I are suitable long-term UV filtering substances. Examples 24 to 30: Production of PET moldings (thickness: 1 mm) As described in Examples 17 to 20, in Examples 24 to 28, PET granules and the concentration of compound I indicated in Table 6, and in Examples 29 and 30 (comparative), PET pellets were produced and the concentration indicated in Table 6 of a commercially conventional UV absorber (2- (2H-benzotriazol-2-yl) -4,6-bis ( 1-methyl-1-phenylethyl) phenol (CAS number 70321-86-7), commercially available for example under the name Tinuvin® 234 from Ciba Specialty Chemicals). Subsequently, injection moldings with a thickness of 1 mm were produced in an Arburg 220M injection molding machine. In Example 24 (control) the PET molding does not contain a UV absorber. In Example 28, PET molding contains an additional 0.1% by weight of an additional UV absorber, i.e. 1,3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2 , 2-bis. { [2'-cyano-3 '3' -diphenylacryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen. The yellowing indices (Yl, according to DIN 6167) of the injection moldings of Examples 24 to 30 are reported in Table 6. A zeroing index of zero means that the specimen is pure white. Negative YI values mean that the specimen is bluish (the more negative Yl, the more blue). Positive Yl values indicate that the specimen is yellowish. The more positive Yl, the more yellow the specimen looks to the viewer. The addition of a UV absorber to a plastic generally implies an increase in Yl.
Table 6
maximum wavelength with a transmission of less than 10s maximum wavelength with a transmission of less than 20%.
Example 31: Protection of Vitamin A An ethanolic solution of vitamin A (c = 10-5 moles / 1) in a tube was exposed to a xenon lamp. The PET plates of Examples 24-26 were placed in the beam path of the xenon lamp. During irradiation, the remaining concentration of vitamin A was measured from its absorbance at 323 nm. Figure 1 shows the effect of the filter of the compounds I used according to the invention, as a graph. Since the emission spectrum of a xenon lamp is similar to that of the sun, Figure 1 strongly demonstrates the filter effect of the naphthalen-1, 8-dicarboxylic monoimides I used in accordance with the invention. Without the protection of the naphthalene-1, 8-dicarboxylic monoimides a solution of vitamin A rapidly disintegrates by light. In contrast, there is only slight disintegration of the vitamin A solution under the effect of light if the vitamin A solution is protected by a naphthalene-1, 8-dicarboxylic monoimide used in accordance with the invention.
Examples 32 to 37: Production of polycarbonate moldings As described in Examples 17 to 20, in Examples 32 to 35, polycarbonate granules (Makrolon 2800 from Bayer AG, Leverkusen) and the concentration of compound IC.l indicated in Table 7, and in Examples 36 and 37 (comparative), the polycarbonate granules (Makrolon 2800 from Bayer AG, Leverkusen) and the concentration indicated in Table 7 of a commercially conventional UV absorber (2- (2H) were produced. -benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol (CAS number 70321-86-7), commercially available for example under the name Tinuvin® 234 from Ciba Specialty Chemicals). Later, injection moldings with a thickness of 1 mm were produced in an Arburg 220M injection molding machine. In Example 32
(control) the polycarbonate molding does not contain UV absorber. In Example 35 the polycarbonate moldings contain 0.1% by weight additional of an additional UV absorber, ie 1,3-bis [(2'-cyano-3'-3'-diphenylacryloyl) oxy] -2, 2 -Bis. { [2'-cyano-3 ', 3'-diphenylacryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example, under the name Uvinul® 3030 from BASF AG, Ludwigshafen. The yellowing indexes (Yl, according to
DIN 6167) and the transmission properties of the moldings of Examples 32-37 are reported in Table 7 below.
Table 7: less than 10% b maximum wavelength with a transmission of less than 20%. c The transmission of the moldings does not fall below the corresponding value for the measured wavelengths
(250-1000 nm).
Examples 38 -43: Production of polystyrene moldings As described in Examples 17-20, in Examples 38 to 41 the polystyrene granules (Polystyrol 144C from BASF AG, Ludwigshafen) and the concentration of compound I-C.l. indicated in Table 8, and in Examples 42 and 43 (comparative), the polystyrene granules (Polystyrol 144C from BASF AG, Ludwigshafen) and the concentration indicated in Table 8 of a commercially conventional UV absorber (2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol (CAS number 70321-86-7), commercially available for example, under the name Tinuvin® 234 from Ciba Specialty Chemicals ). Subsequently, injection moldings with a thickness of 1 mm were produced in an Arburg 220M injection molding machine. In Example 38 (control) the molding with polystyrene does not contain UV absorber. In Example 41 the polystyrene molding contains 0.1 additional weight by weight of an additional UV absorber, i.e. 1,3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] 2, 2- Bis. { [2'-cyano-3 ', 3'-diphenylacryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BASF AG, Ludwigshafen. The yellowness indices (Yl, according to DIN 6167) and the transmission properties of the moldings of Examples 38-43 are reported in Table 8 below.
Table 8
at maximum wavelength with a transmission of less than 10% b maximum wavelength with a transmission of less than 20%. c The transmission of the moldings does not fall below the corresponding value for the measured wavelengths (250-1000 nm).
Examples 44-49: Production of acrylonitrile-butadiene-styrene copolymer moldings
As described in Examples 17-20, in Examples 44 to 47 the granules of the acrylonitrile-butadiene-styrene copolymer (Terluran GP22 from 'BASF AG, Ludwigshafen) and the concentration of the compound I -Cl indicated in Table 9, and in Examples 48 and 49 (comparative), the granules of the acrylonitrile-butadiene-styrene copolymer (Terluran GP22 from BASF AG, Ludwigshafen) and the concentration indicated in Table 9 of a commercially conventional UV absorber (2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol (CAS number 70321-86-7), commercially available for example, under the name Tinuvin® 234 from Ciba Specialty Chemicals ). Subsequently, injection moldings with a thickness of 1 mm were produced in an Arburg 220M injection molding machine. In Example 44 (control) ABS molding does not contain a UV absorber. In Example 47 ABS molding contains an additional 0.1% by weight of an additional UV absorber in a ratio of 1: 1, i.e., 1,3-bis [(2'-cyano-3 ', 3' - diphenylacryloyl) oxy] -2, 2-bis. { (2'-cyano-3 ', 3'-diphenylacryloyl) oxy] methyl} propane [CAS No. 178671-58-4], commercially available for example under the name Uvinul® 3030 from BAF AG, Ludwigshafen. The yellowing indices (Yl, according to DIN 6167) and the transmission properties of the moldings of Examples 44-49 are reported in Table 9 below.
Table 9
maximum wavelength with a transmission of less than 10% b maximum wavelength with a transmission of less than 20%. c The transmission of the moldings does not fall below the corresponding value for the measured wavelengths (250-1000 nm). Examples 26 to 49 show that the naphthalene-1, 8-dicarboxylic monoimides of the formula I used according to the invention can be effectively incorporated into a variety of polymers. Mixtures with UVB absorbers are also highly compatible with polymers. The injection molders comprising the absorbers of the invention filter out most of the harmful UV radiation and still the greater part has a much lower yellowness index than the injection molded ones without the absorber. The samples stabilized with the naphthalene-1, 8-dicarboxylic monoimide of the formula I in particular showed a much lower yellow coloration than the samples stabilized with a commercially conventional stabilizer.
Examples 50 to 54: Transmission profiles of glass laminates comprising an addition polyvinyl butyral film A polyvinyl butyral film of 0.76 mm thick was prepared as described in Example 6 of WO 02/077081 and was then used to produce a vitreous laminate - there was a deviation from Example 6 of WO 02/077081 in which no IR absorber was observed, and the benzotriazole derivative Tinuvin (15.8 g (0.5% by weight)) was replaced by: (a) a mixture of 0.1% by weight of 1,3-bis [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2, 2-bis. { [2-cyano-3 ', 3'-diphenylacryloyl) oxy] methyl} propane and 0.1% by weight of I.C.l. (Example 50), (b) a. 0.1% by weight mixture of 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5-chlorobenzotriazole and 0.1% by weight of IC.l (Example 51), (c) a mixture 0.1% by weight of 2-hydroxy-4-n-octoxybenzophenone and 0.1% by weight of IC.l (Example 52), or (d) 0.2% by weight of IC.l (Example 53). For comparison, in Example 54 a polyvinyl butyral film of 0.76 mm was produced in the same way, and a vitreous laminate was produced therefrom, without using an IR absorber or a UV absorber. The transmission profiles of the vitreous laminates produced in Examples 50 to 54 are reported in Table 10.
Table 10
at maximum wavelength with a transmission of less than 10% maximum wavelength with a transmission of less than 20%. Examples 50 to 54 show that a vitreous laminate comprising the naphthalene-1, 8-dicarboxylic monoimides used according to the invention or mixtures of the naphthalene-1, 8-dicarboxylic monoimides used according to the invention with absorbers of UV short wave absorption is able to absorb UV radiation almost completely and therefore effectively protect the area that lies behind it against the effects of such radiation.
Claims (25)
- CLAIMS 1. The use of naphthalene-1, 8-dicarboxylic monoimides of the formula I wherein R1 is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl and R2 is a radical containing at least one electron system p containing a carbon atom and at least one further atom selected from carbon, oxygen and nitrogen, with the proviso that the radical contains at least one atom other than carbon to protect the organic material against the damaging effects of light.
- 2. The use as claimed in claim 1, wherein R1 is C? -C30 alkyl whose carbon chain can be interrupted by one or more non-adjacent groups selected from -O-, -S-, -NR3- , -CO- and / or -S02-, and / or which is replaced or is not replaced one or more times by identical or different radicals selected from cyano, amino, hydroxyl, carboxyl, aryl, heterocycloalkyl and heteroaryl, with aryl, heterocycloalkyl and heteroaryl groups which are not substituted or bear one or more substituents selected independently from each other from C_-C_8 alkyl and C_-C6 alkoxy; or R1 is C5-C8 cycloalkyl which is not substituted or carries one or more C6-C6 alkyl groups; or R1 is 5- to 8-membered heterocycloalkyl which is not substituted or carries one or more C_-C6 alkyl groups; or R1 is aryl or heteroaryl, with aryl or heteroaryl which is unsubstituted or carries one or more radicals selected independently of one another alkyl of C-C_8 alkoxy C-C6 alkyl, cyano, CONR4R4a, C02R4, arylazo and heteroarylazo, with arylazo and heteroarylazo in turn being unsubstituted or carrying one or more radicals independently selected from C 1 -C 18 alkyl, C 1 -C 6 alkoxy and cyano; R3 is hydrogen or C_-C6 alkyl; and R4 and R4 < each are independently hydrogen, alkyl of c_-C18, aryl or heteroaryl, with aryl and heteroaryl in each case are unsubstituted or carry one or more substituents selected from alkyl of C-C6 alkoxy, C-Cs, hydroxyl, carboxyl and cyano.
- 3. The use as claimed in claim 1, wherein R1 is phenyl which is not substituted or carries one, two or three C_-C4 alkyl groups.
- 4. The use as claimed in one of the previous claims, wherein R2 is cyano, -C (0) NR5R5a or phenyloxy which carries one or more substituents selected from C_C_2 alkyl, C_C_2 alkoxy, - COOR6, -S03R6, halogen, hydroxyl, carboxyl, cyano, -CONR5R5a and -NHCOR5; R5 and R5a each independently of one another are hydrogen, alkyl of C-C_8, aryl or heteroaryl, the aryl and heteroaryl are unsubstituted or carry one or more substituents selected from alkyl C ~ CS, alkoxy C-C6 alkyl, hydroxyl , carboxyl and cyano; and R6 is hydrogen or C_-Cg alkyl.
- 5. The use as claimed in one of the preceding claims, wherein the organic material for protection is selected from plastics, polymer dispersions, paints, photographic emulsions, photographic layers, paper, human or animal skin, human hair or animal, cosmetic products, pharmaceutical products, cleaning products and foodstuffs.
- 6. The use as claimed in claim 5, to protect plastics, wherein the plastic comprises at least one selected from polyester polymer, polycarbonates, polyolefins, polyvinyl acetals, polystyrene, styrene copolymers of a-methylstyrene with dienes and / or acrylic derivatives, polyurethanes, polyacrylates, polymethacrylates and physical mixtures of the aforementioned polymers.
- 7. The use of at least one naphthalene-1, 8-dicarboxylic monoimide as defined in one of claims 1 to 4 for preparing a layer which absorbs ultraviolet light.
- 8. The use as claimed in claim 7, wherein the layer is composed of a thermoplastic molded composite, which comprises at least one polymer selected from polyesters, polycarbonates, polyolefins, polyvinylacetals, polystyrene, copolymers of styrene or of -methylstyrene with dienes and / or acrylic derivatives, and physical mixtures of the aforementioned polymers.
- 9. The use as claimed in one of the previous claims, wherein the organic material contains at least one monoimide I naphthalene-1, 8-dicarboxylic acid in an amount from 0.01 to 10% by weight, based on the total weight of the product. material .
- A composition comprising at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined in one of claims 1 to 4, in an amount which provides protection from the detrimental effects of light, and at least one organic material, wherein the organic material comprises a polymer selected from polyesters, polycarbonate polymers, polyolefins, polyvinylacetals, polystyrene, copolymers of styrene or of α-methylstyrene with dienes and / or acrylic derivatives, and physical mixtures of the polymers mentioned above.
- 11. A composition as claimed in claim 10, wherein the polyvinylacetal is a polyvinyl butyral.
- 12. A composition as claimed in claim 10, wherein the polycarbonate polymer is selected from polycarbonates, polycarbonate copolymers and physical blends of polycarbonates with acrylonitrile-butadiene-styrene copolymers, acrylonitrile-styrene-acrylate copolymers, polymethyl methacrylates, polybutyl acrylates, polybutyl methacrylates, poly (butylene terephthalates) and polyethylene terephthalates.
- 13. A composition as claimed in claim 10, wherein the polyester is a polyethylene terephthalate.
- 14. A composition as claimed in claim 10, wherein the polyolefin is a high density polyethylene or a polypropylene.
- 15. A composition as claimed in claim 10, wherein the copolymer of styrene with dienes and / or acrylic derivatives is a copolymer of acrylonitrile-butadiene-styrene or a copolymer of styrene-acrylonitrile.
- 16. A composition as claimed in claim 11, comprising - at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined in one of claims 1 to 4; - at least one polyvinyl butyral; - at least one oligoalkylene glycol alkylcarboxylic diester plasticizer; at least one carboxylic, aliphatic salt to control adhesion; if desired, at least one UV absorber selected from benzotriazoles, 2-phenyl-1,3,5-triazines, hydroxybenzophenones, diphenylcyanoacrylates and mixtures thereof; and if desired, at least one additional component selected from additional fillers, dyes, pigments and additives.
- 17. A composition as claimed in claim 12, comprising - at least one naphthalene-1, 8-dicarboxylic monoimide of the formula I as defined in one of claims 1 to 4; at least one polycarbonate polymer selected from polycarbonates, polycarbonate copolymers and physical blends of polycarbonates with acrylonitrile-butadiene-styrene copolymers, acrylonitrile-styrene-acrylate copolymers, polymethyl methacrylates, polybutyl acrylates, polybutyl methacrylates, methacrylates of polymethyl, polybutyl acrylates, polybutyl methacrylates, poly (butylene terephthalates) and polyethylene terephthalates; - at least one stabilizer selected from phosphites, phosphonites and mixtures thereof; if desired, at least one UV absorber selected from benzotriazoles, 2-phenyl-1,3,5-triazines, diphenylcyanoacrylates and mixtures thereof; - if desired, at least one phenol antioxidant 2, 6-dialkylated, and if desired, at least one additional component selected from fillers, dyes, pigments and other additives.
- 18. A composition as claimed in claim 13, comprising - at least one naphthalene-1, 8-dicarboxylic monoimide as defined in one of claims 1 to 4; - at least one polyethylene terephthalate; - at least one 2,6-dialkylated phenol antioxidant, - at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; and if desired, at least one additional UV absorber selected from diphenyl cyanoacrylates, phenyl-1,3,5-triazines and benzotriazoles and mixtures thereof.
- 19. A composition as claimed in claim 18, wherein the polyethylene terephthalate is an amorphous polyethylene terephthalate and the composition further includes at least one acetaldehyde scavenger.
- 20. A composition as claimed in one of claims 18 and 19, wherein the composition further includes at least one additional component selected from reheating agents, dyes, pigments and additional additives.
- 21. A composition as claimed in claim 18, wherein the polyethylene terephthalate is a partially crystalline polyethylene terephthalate and the composition further includes at least one nucleating agent.
- 22. A composition as claimed in claim 14, comprising - at least one naphthalene-1, 8-dicarboxylic monoimide as defined in one of claims 1 to 4; - at least one high density polyethylene or polypropylene; at least one 2,6-dialkylated phenol antioxidant; - at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; if desired, at least one additional UV absorber selected from diphenyl cyanoacrylates, hydroxybenzophenones, phenyl-1,3,5-triazines and benzotriazoles, and mixtures thereof; if desired, at least one sterically hindered amine; and - if desired, an additional component selected from dyes, pigments and additional additives.
- 23. A composition as claimed in claim 10, comprising - at least one naphthalene-1,8-dicarboxylic monoimide of the formula I as defined in one of claims 1 to 4; - at least one polystyrene; at least one 2,6-dialkylated phenol antioxidant; at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; - if desired, at least one UV absorber selected from benzotriazoles, diphenylcyanoacrylates and mixtures thereof; if desired, at least one sterically hindered amine; and - if desired, at least one additional component selected from dyes, pigments and additional additives.
- 24. A composition as claimed in claim 15, comprising - at least one naphthalene-1, 8-dicarboxylic monoimide as defined in one of claims 1 to 4; at least one acrylonitrile-butadiene-styrene copolymer or a styrene-acrylonitrile copolymer; at least one 2,6-dialkylated phenol antioxidant; at least one co-stabilizer selected from phosphites, phosphonites and mixtures thereof; if desired, at least one additional UV absorber selected from benzotriazoles, hydroxybenzophenones, diphenylcyanoacrylates and mixtures thereof; if desired, at least one sterically hindered amine; and - if desired, an additional component selected from dyes, pigments and additional additives.
- 25. The compounds of the formula I (wherein R1 is hydrogen, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl, and R2 is cyano, -C (0) NR5R5a or phenyloxy which carries one, two, three, four or five C_- alkyl groups. C12; and R5 and R5a each independently of the other are hydrogen, C_-C18 alkyl, aryl or heteroaryl, the aryl and the heteroaryl each is not substituted or carries one or more substituents selected from C_-C6 alkyl, C 1 -C 3 alkoxy, hydroxyl, carboxyl and cyano. SUMMARY OF THE INVENTION A description is given of the use of naphthalene-1, 8-dicarboxylic monoimides of the formula (I), wherein R 1 is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl and R 2 is a radical containing at least one system in the electron p containing one carbon atom and at least one additional atom selected from carbon, oxygen and nitrogen, with the proviso that the radical contains at least one atom other than carbon; to protect the organic material from the deleterious effects of light, of the compositions comprising at least one naphthalene-1, 8-dicarboxylic monoimide of the formula (I) in an amount which provides protection from the detrimental effects of light, and at least one organic material, and of new naphthalen-1, 8-dicarboxylic monoimides (I). o Dissolution of vitamin a (ethanolic solution) Time [seconds]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10353328.1 | 2003-11-14 | ||
| US10770603 | 2004-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06005334A true MXPA06005334A (en) | 2006-10-17 |
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