DE69605925T2 - Verwendung amphiphiler Copolymere, enthaltend fluorhaltige Monomer zur wasserfesten Ausrüstung von Leder - Google Patents
Verwendung amphiphiler Copolymere, enthaltend fluorhaltige Monomer zur wasserfesten Ausrüstung von LederInfo
- Publication number
- DE69605925T2 DE69605925T2 DE69605925T DE69605925T DE69605925T2 DE 69605925 T2 DE69605925 T2 DE 69605925T2 DE 69605925 T DE69605925 T DE 69605925T DE 69605925 T DE69605925 T DE 69605925T DE 69605925 T2 DE69605925 T2 DE 69605925T2
- Authority
- DE
- Germany
- Prior art keywords
- leather
- repeating units
- group
- amphiphilic copolymer
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000010985 leather Substances 0.000 title claims description 105
- 229920001577 copolymer Polymers 0.000 title claims description 65
- 239000000178 monomer Substances 0.000 title claims description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 6
- 229910052731 fluorine Inorganic materials 0.000 title description 6
- 239000011737 fluorine Substances 0.000 title description 6
- 238000004078 waterproofing Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 14
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000005647 linker group Chemical group 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000126 substance Chemical group 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical class 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000012360 testing method Methods 0.000 description 24
- 239000000758 substrate Substances 0.000 description 22
- -1 alkyl methacrylates Chemical class 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- 239000003921 oil Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000149 penetrating effect Effects 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- IAXXETNIOYFMLW-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C(=C)C)CC1C2(C)C IAXXETNIOYFMLW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- FIQBJLHOPOSODG-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxycarbonyl]benzoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=CC=C1C(O)=O FIQBJLHOPOSODG-UHFFFAOYSA-N 0.000 description 2
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000004815 dispersion polymer Substances 0.000 description 2
- 125000006162 fluoroaliphatic group Chemical group 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 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 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical class [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 208000019899 phobic disease Diseases 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- ROEHNQZQCCPZCH-UHFFFAOYSA-N tert-butyl 2-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OC(C)(C)C ROEHNQZQCCPZCH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96117814A EP0841405B1 (en) | 1996-11-07 | 1996-11-07 | Use of amphilic copolymers containing a fluorinated monomer to impart waterproofness to leather |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69605925D1 DE69605925D1 (de) | 2000-02-03 |
| DE69605925T2 true DE69605925T2 (de) | 2000-07-20 |
Family
ID=8223375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69605925T Expired - Lifetime DE69605925T2 (de) | 1996-11-07 | 1996-11-07 | Verwendung amphiphiler Copolymere, enthaltend fluorhaltige Monomer zur wasserfesten Ausrüstung von Leder |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0841405B1 (pt) |
| JP (1) | JP3911549B2 (pt) |
| KR (1) | KR100475495B1 (pt) |
| CN (1) | CN1152142C (pt) |
| AR (1) | AR009410A1 (pt) |
| AU (1) | AU4899897A (pt) |
| BR (1) | BR9712754A (pt) |
| DE (1) | DE69605925T2 (pt) |
| ES (1) | ES2143125T3 (pt) |
| TW (1) | TW419524B (pt) |
| WO (1) | WO1998020170A1 (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7049379B2 (en) | 1999-05-11 | 2006-05-23 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| US6525127B1 (en) | 1999-05-11 | 2003-02-25 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| US7250456B2 (en) * | 2002-01-31 | 2007-07-31 | Tfl Ledertechnik Gmbh | Composition and its use for imparting water repellency to leather or furskins, textiles and other fibrous materials |
| KR20030073514A (ko) * | 2002-03-12 | 2003-09-19 | 강석일 | 방수막을 가지는 먹장어 가죽 및 그 제조방법 |
| EP1801133A1 (en) | 2005-12-19 | 2007-06-27 | Lanxess Deutschland GmbH | Curable fluorinated copolymers and coatings and processes thereof |
| EP1820809A1 (en) | 2006-02-17 | 2007-08-22 | Lanxess Deutschland GmbH | Coating of substrates with curable fluorinated copolymers |
| DE102006027400A1 (de) * | 2006-06-13 | 2007-12-20 | Wacker Chemie Ag | Verfahren zur Behandlung von proteinhaltigen, faserartigen Stoffen mit beta-Ketocarbonyl-funktionellen Siloxanpolymeren |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2803615A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US3923715A (en) | 1973-07-26 | 1975-12-02 | Du Pont | Aqueous dispersions of perfluoroalkyl esters and vinyl polymers for treating textiles |
| US4525305A (en) | 1982-10-25 | 1985-06-25 | Minnesota Mining And Manufacturing Company | Leather with fluorochemical finish |
| US4539006A (en) | 1983-09-13 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Leather treatment |
| EP0213580B1 (de) | 1985-08-30 | 1990-07-18 | Hoechst Aktiengesellschaft | Perfluoralkyl- und Epichlorhydrin-Gruppen enthaltende Urethane, diese Urethane enthaltende wässrige Dispersionen und ihre Verwendung |
| FR2588555B1 (fr) | 1985-10-16 | 1987-12-11 | Atochem | Monomeres acryliques fluores, polymeres en derivant et leur application au traitement hydrofuge et oleofuge de substrats divers |
| FR2590895B1 (fr) | 1985-12-03 | 1988-01-15 | Atochem | Monomeres acryliques fluores, polymeres en derivant et leur application comme agents hydrophobes et oleophobes |
| DE3622284A1 (de) | 1986-07-03 | 1988-01-07 | Hoechst Ag | Urethane aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3722375A1 (de) | 1987-07-07 | 1989-01-19 | Hoechst Ag | Fluor und polysiloxan enthaltende urethane, verfahren zu ihrer herstellung und ihre verwendung |
| DE3800629A1 (de) | 1988-01-12 | 1989-07-20 | Basf Ag | Verfahren zum hydrophobieren von leder, pelzen und lederaustauschmaterialien |
| DE3800845A1 (de) * | 1988-01-14 | 1989-07-27 | Bayer Ag | Pfropfcopolymerisate, ein verfahren zu deren herstellung und deren verwendung |
| TNSN89128A1 (fr) | 1988-12-02 | 1991-02-04 | Rohn And Haas Company Independance Mall West | Traitement du cuir avec des copolymeres amphiphites choisis |
| DE3931039A1 (de) | 1989-09-16 | 1991-03-28 | Basf Ag | Verwendung von copolymerisaten auf basis von langkettigen ungesaettigten estern und ethylenisch ungesaettigten carbonsaeuren zum hydrophobieren von leder und pelzfellen |
| FR2653772B1 (fr) * | 1989-11-02 | 1992-01-17 | Atochem | Telomeres acryliques fluores et leur application au traitement hydrofuge et oleofuge de substrats divers. |
| CA2071596A1 (en) | 1991-07-10 | 1993-01-11 | Frederick E. Behr | Perfluoroalkyl halides and derivatives |
| JP3333511B2 (ja) | 1991-11-12 | 2002-10-15 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | フルオロ脂肪族二量体酸誘導体およびその使用 |
| DE4223111A1 (de) | 1992-07-14 | 1994-01-20 | Henkel Kgaa | Neue Lederfettungsmittel und ihre Verwendung |
| DE4240274B4 (de) * | 1992-12-01 | 2004-02-12 | Minnesota Mining And Manufacturing Co., Saint Paul | Polysiloxane mit fluoraliphaten- und carboxylhaltigen terminalen Gruppen, ihre Herstellung und ihre Verwendung bei der Behandlung von Fasersubstraten |
| DE4244951C2 (de) | 1992-12-01 | 1998-08-06 | Minnesota Mining & Mfg | Fasersubstrat mit Wasser-, Öl-, Schmutzabweisungsvermögen und Weichgriffigkeit |
| DE4416415A1 (de) | 1994-05-10 | 1995-11-16 | Hoechst Ag | Copolymere auf Basis von ethylenisch ungesättigten Dicarbonsäureanhydriden, langkettigen Olefinen und Fluorolefinen |
-
1996
- 1996-11-07 EP EP96117814A patent/EP0841405B1/en not_active Expired - Lifetime
- 1996-11-07 DE DE69605925T patent/DE69605925T2/de not_active Expired - Lifetime
- 1996-11-07 ES ES96117814T patent/ES2143125T3/es not_active Expired - Lifetime
-
1997
- 1997-10-15 JP JP52140298A patent/JP3911549B2/ja not_active Expired - Fee Related
- 1997-10-15 CN CNB971995338A patent/CN1152142C/zh not_active Expired - Fee Related
- 1997-10-15 KR KR10-1999-7004022A patent/KR100475495B1/ko not_active Expired - Fee Related
- 1997-10-15 AU AU48998/97A patent/AU4899897A/en not_active Abandoned
- 1997-10-15 WO PCT/US1997/018386 patent/WO1998020170A1/en not_active Ceased
- 1997-10-15 BR BR9712754-0A patent/BR9712754A/pt not_active IP Right Cessation
- 1997-11-05 TW TW086116460A patent/TW419524B/zh not_active IP Right Cessation
- 1997-11-06 AR ARP970105170A patent/AR009410A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| ES2143125T3 (es) | 2000-05-01 |
| CN1236397A (zh) | 1999-11-24 |
| KR20000053098A (ko) | 2000-08-25 |
| WO1998020170A1 (en) | 1998-05-14 |
| AR009410A1 (es) | 2000-04-12 |
| KR100475495B1 (ko) | 2005-03-10 |
| TW419524B (en) | 2001-01-21 |
| DE69605925D1 (de) | 2000-02-03 |
| EP0841405B1 (en) | 1999-12-29 |
| JP2001504874A (ja) | 2001-04-10 |
| AU4899897A (en) | 1998-05-29 |
| CN1152142C (zh) | 2004-06-02 |
| JP3911549B2 (ja) | 2007-05-09 |
| EP0841405A1 (en) | 1998-05-13 |
| BR9712754A (pt) | 1999-10-19 |
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