JP2011168724A - Pigment dispersant composition, colorant composition and method for producing colored thermoplastic resin - Google Patents
Pigment dispersant composition, colorant composition and method for producing colored thermoplastic resin Download PDFInfo
- Publication number
- JP2011168724A JP2011168724A JP2010035284A JP2010035284A JP2011168724A JP 2011168724 A JP2011168724 A JP 2011168724A JP 2010035284 A JP2010035284 A JP 2010035284A JP 2010035284 A JP2010035284 A JP 2010035284A JP 2011168724 A JP2011168724 A JP 2011168724A
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- Prior art keywords
- pigment
- group
- thermoplastic resin
- pigment dispersant
- carbon atoms
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 175
- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 86
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 83
- 239000003086 colorant Substances 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- -1 sulfosuccinic acid ester Chemical class 0.000 claims abstract description 49
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 25
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 238000004898 kneading Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 34
- 230000000704 physical effect Effects 0.000 abstract description 7
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- 239000004743 Polypropylene Substances 0.000 description 20
- 238000002156 mixing Methods 0.000 description 20
- 229920001155 polypropylene Polymers 0.000 description 20
- 239000008188 pellet Substances 0.000 description 17
- 238000011156 evaluation Methods 0.000 description 12
- 125000000962 organic group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 7
- 239000004595 color masterbatch Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000011575 calcium Substances 0.000 description 5
- 239000001023 inorganic pigment Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- QLZJUIZVJLSNDD-UHFFFAOYSA-N 2-(2-methylidenebutanoyloxy)ethyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OCCOC(=O)C(=C)CC QLZJUIZVJLSNDD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- SOANRMMGFPUDDF-UHFFFAOYSA-N 2-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=CC=C1N SOANRMMGFPUDDF-UHFFFAOYSA-N 0.000 description 2
- BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 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 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 2
- 239000005042 ethylene-ethyl acrylate Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- DBIJGSRXWPQTLH-UHFFFAOYSA-N n-butyloctan-1-amine Chemical compound CCCCCCCCNCCCC DBIJGSRXWPQTLH-UHFFFAOYSA-N 0.000 description 2
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 2
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 2
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
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- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
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- 150000004696 coordination complex Chemical class 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=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
- 125000002704 decyl 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])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
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- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
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- 235000013980 iron oxide Nutrition 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
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- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
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- 238000003475 lamination Methods 0.000 description 1
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- 125000005645 linoleyl group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 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
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 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
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid 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
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
本発明は、顔料分散剤組成物、着色剤組成物、及び着色熱可塑性樹脂の製造方法に関する。 The present invention relates to a pigment dispersant composition, a colorant composition, and a method for producing a colored thermoplastic resin.
熱可塑性樹脂の着色剤には、顔料と分散剤とを混合した粉末状のドライカラー、常温で液状の分散剤中若しくは液状のビヒクルを併用した中に顔料を分散させたペーストカラー又はリキッドカラー、顔料、分散剤及びベース樹脂を溶融混練したカラーマスターバッチがあり、カラーマスターバッチに使用するベース樹脂としては、一般に被着色熱可塑性樹脂への分散、分配性を考慮して被着色熱可塑性樹脂と同一の樹脂が使用されている。
これらの着色剤は、顔料を高濃度に含有しており着色熱可塑性樹脂を製造する際に被着色熱可塑性樹脂によって希望する濃度に希釈して使用されている。
熱可塑性樹脂の着色方法には、（１）着色剤を用いる方法と、（２）直接添加法があり、（１）着色剤を用いる方法とは、上述の着色剤と未着色の被着色熱可塑性樹脂及び樹脂劣化防止等の用途の添加剤とを溶融混練して着色熱可塑性樹脂を得る方法であり、取り扱いの容易さ、使用時の作業環境保全の面から、着色剤としてカラーマスターバッチを使用する方法が好んで用いられている。
（２）直接添加法とは、顔料、上記添加剤及び未着色の熱可塑性樹脂を直接混合、溶融混練して着色熱可塑性樹脂を得る方法である。直接添加法は、その製造方法の容易さから非常に経済性に優れるといった特徴がある。
The colorant of the thermoplastic resin includes a powdery dry color in which a pigment and a dispersant are mixed, a paste color or a liquid color in which the pigment is dispersed in a liquid dispersant at room temperature or in combination with a liquid vehicle, There is a color masterbatch in which a pigment, a dispersant and a base resin are melt-kneaded, and the base resin used for the color masterbatch is generally a colored thermoplastic resin in consideration of dispersion and distribution in the colored thermoplastic resin. The same resin is used.
These colorants contain a pigment in a high concentration, and are used after being diluted to a desired concentration by a thermoplastic resin to be colored when producing a colored thermoplastic resin.
There are (1) a method using a colorant and (2) a direct addition method as a method for coloring a thermoplastic resin. (1) The method using a colorant includes the above-mentioned colorant and uncolored heat to be colored. It is a method to obtain a colored thermoplastic resin by melting and kneading plastic resin and additives for applications such as resin deterioration prevention. From the viewpoint of ease of handling and preservation of the working environment at the time of use, a color master batch is used as a colorant. The method used is preferred.
(2) The direct addition method is a method for obtaining a colored thermoplastic resin by directly mixing, melting and kneading a pigment, the above-mentioned additive and an uncolored thermoplastic resin. The direct addition method is characterized by being very economical because of its ease of production.
熱可塑性樹脂の着色は、顔料を樹脂に練り込むことによって行われるが、その顔料には有機物、無機物から構成される様々な種類が存在し、樹脂中の顔料の分散性に違いがあるため、顔料の種類や熱可塑性樹脂の着色方法により適正な分散剤が必要とされる。元来からの一般的な顔料分散剤としては、特許文献１及び特許文献２に挙げられているとおり、金属石鹸や低分子ポリエチレン等が使用され、コスト面を重視して、金属石鹸が通常使用されている。金属石鹸としては、通常ステアリン酸の金属塩（アルミニウム塩、マグネシウム塩、亜鉛塩、カルシウム塩等）が用いられている。 The thermoplastic resin is colored by kneading the pigment into the resin, but there are various types of pigments composed of organic and inorganic substances, and there is a difference in the dispersibility of the pigment in the resin. An appropriate dispersant is required depending on the type of pigment and the coloring method of the thermoplastic resin. As a general pigment dispersant from the beginning, as mentioned in Patent Document 1 and Patent Document 2, metal soap, low molecular weight polyethylene, etc. are used, and metal soap is usually used with emphasis on cost. Has been. As the metal soap, a metal salt of stearic acid (aluminum salt, magnesium salt, zinc salt, calcium salt, etc.) is usually used.
また、特許文献３では、高濃度の無機顔料を含有する熱可塑性樹脂中の無機顔料の分散性の改善のために、スルホコハク酸ジオクチルナトリウム塩を用いて無機顔料を表面処理する方法が開示されている。 Patent Document 3 discloses a method for surface-treating an inorganic pigment using dioctyl sodium sulfosuccinate in order to improve the dispersibility of the inorganic pigment in a thermoplastic resin containing a high concentration of inorganic pigment. Yes.
ドライカラー、ペーストカラー、リキッドカラーは、常温の攪拌混合のみで製造可能であり、製造コストが安く熱可塑性樹脂用の着色剤、特に汎用着色剤として有用であるが、着色成型の際の顔料分散性に劣る傾向があり、成型品の品質安定性が低下する傾向にある。またドライカラーは、その製造の際に飛散・汚染性が大であり、貯蔵した際の安定性も充分とはいえない。
カラーマスターバッチを用いる方法は、着色成型の際の顔料分散性に優れるが、直接添加法と比べて工程数が多く、熱可塑性樹脂へ顔料分散するためのコストが大きいことが問題である。さらに特許文献３に開示される表面処理でも、工程数が増加し、製造コストが高くなる問題がある。
Dry color, paste color, and liquid color can be manufactured only by stirring and mixing at room temperature, and the manufacturing cost is low, and it is useful as a colorant for thermoplastic resins, especially as a general-purpose colorant. Tend to be inferior in quality, and the quality stability of the molded product tends to be lowered. In addition, the dry color is highly scattered and contaminated during production, and the stability when stored is not sufficient.
The method using a color masterbatch is excellent in pigment dispersibility during color molding, but has a problem that the number of steps is larger than that in the direct addition method and the cost for dispersing the pigment in the thermoplastic resin is large. Furthermore, even the surface treatment disclosed in Patent Document 3 has a problem that the number of steps increases and the manufacturing cost increases.
そこで、このような問題を解決するためには、直接添加法を用いることが考えられる。しかし、従来の顔料分散剤を使用して、直接添加法により熱可塑性樹脂の着色を行った場合、色再現性が乏しく、成型品に色むらが出やすくなり、その着色性を改善するために顔料分散剤の使用量を増やす、混練時間を伸ばすといった対策をとらざるを得なかった。また、顔料分散剤の使用量が多いと、余分な製造コストがかかる上、成型品の物性に影響を及ぼすおそれがあるため、直接添加法でかつ少ない使用量で顔料分散性、着色性を付与できる顔料分散剤が求められていた。さらに、着色熱可塑性樹脂の用途の一つである自動車分野においては、燃費向上を目的として成型品の厚さを小さくする要望が依然として強く、成型品が薄くなると顔料の凝集がより目立つことになり、こうした分野では特により高い顔料分散性の向上が求められていた。 In order to solve such a problem, it is conceivable to use a direct addition method. However, when a conventional pigment dispersant is used and the thermoplastic resin is colored by the direct addition method, the color reproducibility is poor and uneven color tends to appear on the molded product, in order to improve the colorability. Measures such as increasing the amount of pigment dispersant used and extending the kneading time had to be taken. In addition, if a large amount of pigment dispersant is used, extra manufacturing costs are required and the physical properties of the molded product may be affected. There has been a need for a pigment dispersant that can be used. Furthermore, in the automotive field, which is one of the uses of colored thermoplastic resins, there is still a strong demand for reducing the thickness of molded products for the purpose of improving fuel efficiency, and the aggregation of pigments becomes more noticeable when the molded products become thinner. In these fields, particularly higher pigment dispersibility has been demanded.
本発明は、上記事情に鑑みてなされたものであり、直接添加法に用いた場合であっても、成型品の物性に影響を及ぼさないよう顔料分散剤の使用量を低減でき、低コストでかつ良好な顔料分散性を得ることができる顔料分散剤組成物、着色剤組成物、及び着色熱可塑性樹脂の製造方法を提供することを目的とする。 The present invention has been made in view of the above circumstances, and even when used in the direct addition method, the amount of pigment dispersant used can be reduced so as not to affect the physical properties of the molded product, and at low cost. It is another object of the present invention to provide a pigment dispersant composition, a colorant composition, and a method for producing a colored thermoplastic resin capable of obtaining good pigment dispersibility.
本発明者は、上記課題に鑑み、直接添加法においても良好な着色性、顔料分散性を発現することができる新規な顔料分散剤組成物について鋭意検討した結果、本発明を完成するに至った。すなわち、本発明では、下記式［１］又は下記式［２］で表されるスルホコハク酸エステルと、１価の金属イオン又は置換基を有していてもよいアンモニウムイオンと、の塩、及び下記式［３］で表されるカルボニル基含有芳香族化合物を含む顔料分散剤組成物が提供される。 In view of the above problems, the present inventors have intensively studied a novel pigment dispersant composition capable of expressing good colorability and pigment dispersibility even in the direct addition method, and as a result, the present invention has been completed. . That is, in the present invention, a salt of a sulfosuccinic acid ester represented by the following formula [1] or the following formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and the following A pigment dispersant composition comprising a carbonyl group-containing aromatic compound represented by the formula [3] is provided.
（式［１］中、Ｒ１及びＲ２は同一であっても異なっていてもよく、直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２のアリールアルキル基、あるいはこれらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基を表す。）
(In the formula [1], R 1 and R 2 may be the same or different and are linear or branched alkyl groups having 2 to 22 carbon atoms, alkenyl groups having 3 to 22 carbon atoms, carbon The aryl group having 6 to 22 or the arylalkyl group having 7 to 22 carbon atoms, or a group in which any one of these groups is bonded to the terminal of the polyoxyalkylene group having 2 to 30 repeating units.
（式［２］中、Ｒ３は直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２のアリールアルキル基、あるいはこれらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基を表す。）
(In the formula [2], R 3 represents a linear or branched alkyl group having 2 to 22 carbon atoms, an alkenyl group having 3 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, or 7 to 22 carbon atoms. An arylalkyl group or a group in which any of these groups is bonded to the end of a polyoxyalkylene group having 2 to 30 repeats.
（式［３］中、Ｒ４は水素原子、直鎖若しくは分岐鎖状の炭素数１〜６のアルキル基、炭素数２〜６のアルケニル基、炭素数７〜１３のアリールアルキル基、又は金属イオン若しくは置換基を有していてもよいアンモニウムイオンを表し、ｎは１〜３の整数を示す。）
(In the formula [3], R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group having 7 to 13 carbon atoms, or a metal. Represents an ammonium ion which may have an ion or a substituent, and n represents an integer of 1 to 3.)
本発明の顔料分散剤組成物によれば、直接添加法を用いた場合であっても、高い顔料分散性を有する着色熱可塑性樹脂を得ることができる。また、本発明の顔料分散剤組成物は、金属石鹸や低分子ポリエチレン等の顔料分散剤と比較して、その高い顔料分散性により、熱可塑性樹脂の着色に要する顔料分散剤の使用量を低減でき、成型品の物性向上に寄与できる。 According to the pigment dispersant composition of the present invention, a colored thermoplastic resin having high pigment dispersibility can be obtained even when the direct addition method is used. In addition, the pigment dispersant composition of the present invention reduces the amount of pigment dispersant used for coloring thermoplastic resins due to its high pigment dispersibility compared to pigment dispersants such as metal soap and low molecular weight polyethylene. Can contribute to improving the physical properties of the molded product.
顔料分散剤組成物は、上記スルホコハク酸エステルと１価の金属イオン又は置換基を有していてもよいアンモニウムイオンとの塩と、上記カルボニル基含有芳香族化合物と、を１：０．０５〜１：１の質量比で含むことが好ましい。配合比率が上記範囲内にある場合には、さらに優れた顔料分散性を発現する。 The pigment dispersant composition comprises a salt of the sulfosuccinic acid ester and a monovalent metal ion or an ammonium ion optionally having a substituent, and the carbonyl group-containing aromatic compound. It is preferable to include by mass ratio of 1: 1. When the blending ratio is within the above range, further excellent pigment dispersibility is exhibited.
また、本発明では、上記顔料分散剤組成物及び顔料を含む着色剤組成物が提供される。 Moreover, in this invention, the coloring agent composition containing the said pigment dispersant composition and a pigment is provided.
また、上記着色剤組成物は、さらに熱可塑性樹脂を含むことが好ましい。 Moreover, it is preferable that the said colorant composition contains a thermoplastic resin further.
また、本発明では、上記顔料分散剤組成物、顔料及び熱可塑性樹脂を、溶融混練することを特徴とする着色熱可塑性樹脂の製造方法が提供される。本発明の製造方法によれば、式［１］又は式［２］で表されるスルホコハク酸エステルと、１価の金属イオン又は置換基を有していてもよいアンモニウムイオンと、の塩、及び式［３］で表されるカルボニル基含有芳香族化合物を含む顔料分散剤組成物、顔料、並びに熱可塑性樹脂を、原料のまま又は混合物として直接溶融混練した（直接添加法）場合であっても、着色熱可塑性樹脂の顔料分散性を高く維持できる。 Moreover, in this invention, the manufacturing method of the colored thermoplastic resin characterized by melt-kneading the said pigment dispersant composition, a pigment, and a thermoplastic resin is provided. According to the production method of the present invention, a salt of a sulfosuccinic acid ester represented by the formula [1] or the formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and Even when the pigment dispersant composition containing the carbonyl group-containing aromatic compound represented by the formula [3], the pigment, and the thermoplastic resin are directly melt-kneaded as a raw material or as a mixture (direct addition method) The pigment dispersibility of the colored thermoplastic resin can be maintained high.
本発明の顔料分散剤組成物によれば、金属石鹸や低分子ポリエチレン等の顔料分散剤と比較して優れた顔料分散性が得られ、熱可塑性樹脂を着色する際の顔料分散剤の使用量を減少させることができる。そして、顔料分散剤の使用量を少なくできることによって、成型品の物性低下を防ぐことが可能となる。これによって、成型品の厚さを小さくし、成型品ごとの色再現性の向上、不良率の低減をすることができるだけでなく、着色熱可塑性樹脂を構成する様々な顔料やその他の配合物の分散が容易になるため、成型品の意匠の多様化が可能となる。
本発明の着色熱可塑性樹脂の製造方法によれば、直接添加法を採用した場合であっても、高い顔料分散性と着色力を有する着色熱可塑性樹脂を得ることができる。
According to the pigment dispersant composition of the present invention, excellent pigment dispersibility is obtained as compared with pigment dispersants such as metal soap and low molecular weight polyethylene, and the amount of pigment dispersant used when coloring a thermoplastic resin Can be reduced. And it becomes possible to prevent the physical property fall of a molded article by reducing the usage-amount of a pigment dispersant. This can not only reduce the thickness of the molded product, improve the color reproducibility of each molded product, and reduce the defective rate, but also the various pigments and other compounds that make up the colored thermoplastic resin. Since the dispersion becomes easy, the design of the molded product can be diversified.
According to the method for producing a colored thermoplastic resin of the present invention, a colored thermoplastic resin having high pigment dispersibility and coloring power can be obtained even when the direct addition method is employed.
以下、本発明の顔料分散剤組成物、着色剤組成物、及び着色熱可塑性樹脂の製造方法に関してその好適な実施形態に即して詳細に説明する。 Hereinafter, the pigment dispersant composition, the colorant composition, and the method for producing the colored thermoplastic resin of the present invention will be described in detail according to preferred embodiments thereof.
（顔料分散剤組成物）
本発明における顔料分散剤組成物は、下記式［１］又は下記式［２］で表されるスルホコハク酸エステルと、１価の金属イオン又は置換基を有していてもよいアンモニウムイオンと、の塩、及び下記式［３］で表されるカルボニル基含有芳香族化合物を含む。
(Pigment dispersant composition)
The pigment dispersant composition in the present invention comprises a sulfosuccinic acid ester represented by the following formula [1] or the following formula [2], and a monovalent metal ion or an ammonium ion optionally having a substituent. A salt and a carbonyl group-containing aromatic compound represented by the following formula [3].
（式［１］中、Ｒ１及びＲ２は同一であっても異なっていてもよく、直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２のアリールアルキル基、あるいはこれらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基を表す。）
(In the formula [1], R 1 and R 2 may be the same or different and are linear or branched alkyl groups having 2 to 22 carbon atoms, alkenyl groups having 3 to 22 carbon atoms, carbon The aryl group having 6 to 22 or the arylalkyl group having 7 to 22 carbon atoms, or a group in which any one of these groups is bonded to the terminal of the polyoxyalkylene group having 2 to 30 repeating units.
（式［２］中、Ｒ３は直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２のアリールアルキル基、あるいはこれらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基を表す。）
(In the formula [2], R 3 represents a linear or branched alkyl group having 2 to 22 carbon atoms, an alkenyl group having 3 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, or 7 to 22 carbon atoms. An arylalkyl group or a group in which any of these groups is bonded to the end of a polyoxyalkylene group having 2 to 30 repeats.
（式［３］中、Ｒ４は水素原子、直鎖若しくは分岐鎖状の炭素数１〜６のアルキル基、炭素数２〜６のアルケニル基、炭素数７〜１３のアリールアルキル基、又は金属イオン若しくは置換基を有していてもよいアンモニウムイオンを表し、ｎは１〜３の整数を示す。）
(In the formula [3], R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group having 7 to 13 carbon atoms, or a metal. Represents an ammonium ion which may have an ion or a substituent, and n represents an integer of 1 to 3.)
式［１］及び式［２］中のＲ１、Ｒ２及びＲ３のアルキル基の炭素数は、通常２〜２２であるが、２〜１８が好ましく、２〜１２がより好ましい。こうしたアルキル基としては、例えば、エチル基、プロピル基、ブチル基、ヘキシル基、オクチル基、イソオクチル基、２−エチルヘキシル基、ノニル基、デシル基、ラウリル基、ミリスチル基、ヘキサデシル基、ステアリル基、エイコシル基、シクロペンチル基、シクロヘキシル基等を挙げることができ、好ましくオクチル基、イソオクチル基、２−エチルヘキシル基、ラウリル基である。 The number of carbon atoms in the alkyl group of R 1, R 2 and R 3 in the formula [1] and formula [2] is normally 2 to 22, 2 to 18 are preferred, 2 to 12 is more preferable. Examples of such alkyl groups include ethyl, propyl, butyl, hexyl, octyl, isooctyl, 2-ethylhexyl, nonyl, decyl, lauryl, myristyl, hexadecyl, stearyl, eicosyl. Group, cyclopentyl group, cyclohexyl group and the like, and octyl group, isooctyl group, 2-ethylhexyl group and lauryl group are preferable.
アルケニル基の炭素数は、通常３〜２２であるが、３〜１８が好ましく、３〜１２がより好ましい。こうしたアルケニル基としては、例えば、アリル基、プロペニル基、ブテニル基、ヘキセニル基、オクテニル基、ノネニル基、デセニル基、ドデセニル基、テトラデセニル基、ヘキサデセニル基、オクタデセニル基、シクロペンテニル基、シクロヘキセニル基、リノレイル基、ベヘニル基等が挙げられる。 Although carbon number of an alkenyl group is 3-22 normally, 3-18 are preferable and 3-12 are more preferable. Examples of such alkenyl groups include allyl, propenyl, butenyl, hexenyl, octenyl, nonenyl, decenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl, cyclopentenyl, cyclohexenyl, linoleyl. Group, behenyl group and the like.
アリール基の炭素数は６〜２２であり、アリール基としては、例えば、フェニル基、ナフチル基、４−メチルフェニル基等のアルキル若しくはアルケニルフェニル基、又はアルキル若しくはアルケニルナフチル基等が挙げられる。 The aryl group has 6 to 22 carbon atoms, and examples of the aryl group include alkyl or alkenyl phenyl groups such as a phenyl group, a naphthyl group, and a 4-methylphenyl group, or an alkyl or alkenyl naphthyl group.
アリールアルキル基の炭素数は７〜２２であり、アリールアルキル基としては、例えば、ベンジル基、フェネチル基、アルキル若しくはアルケニルベンジル基、又はアルキル若しくはアルケニルフェネチル基等が挙げられる。 The arylalkyl group has 7 to 22 carbon atoms, and examples of the arylalkyl group include a benzyl group, a phenethyl group, an alkyl or alkenylbenzyl group, and an alkyl or alkenylphenethyl group.
また、Ｒ１、Ｒ２及びＲ３の「これらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基」は、換言すると一般式Ｒ’Ｏ（ＡＯ）ｍ−で表される基である。式中Ｒ’は末端に置換基を有していてもよい直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２アリールアルキル基であり、Ａは炭素数２〜４の直鎖状又は分岐鎖状のアルキレン基であり、ｍは２〜３０の整数であり、繰り返し数を示す。ポリオキシアルキレン基としては、例えば、ポリオキシエチレン基、ポリオキシプロピレン基、ポリオキシブチレン基等が挙げられる。
顔料及び熱可塑性樹脂を溶融混練する際に、上記顔料分散剤組成物を加えることにより、直接添加法においても均一着色が可能となる。
In addition, the “group in which any of these groups is bonded to the terminal of a polyoxyalkylene group having 2 to 30 repeats” of R 1 , R 2 and R 3 is, in other words, the general formula R′O (AO) m −. It is group represented by these. In the formula, R ′ is a linear or branched alkyl group having 2 to 22 carbon atoms, an alkenyl group having 3 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, which may have a substituent at the terminal, or It is a C7-22 arylalkyl group, A is a C2-C4 linear or branched alkylene group, m is an integer of 2-30, and shows the number of repetitions. Examples of the polyoxyalkylene group include a polyoxyethylene group, a polyoxypropylene group, and a polyoxybutylene group.
When the pigment and the thermoplastic resin are melt-kneaded, by adding the pigment dispersant composition, uniform coloring is possible even in the direct addition method.
式［１］又は式［２］で表されるスルホコハク酸エステルと塩を形成する１価の金属イオンとしては、例えば、リチウム、ナトリウム、カリウム等の金属イオンを挙げることができる。また、式［１］又は式［２］で表されるスルホコハク酸エステルと塩を形成する、置換基を有していてもよいアンモニウムイオンとは、ＮＨ４ ＋イオン、Ｎ原子上に置換基として有機基を１つ有するアンモニウムイオン、有機基を２つ有するアンモニウムイオン又は有機基を３つ有するアンモニウムイオンである。有機基としては、脂肪族基、芳香族基又はヒドロキシアルキル基等が挙げられる。脂肪族基の炭素数は、通常１〜３０であるが、１〜１８が好ましく、１〜１２がより好ましく、１〜６がさらに好ましい。芳香族基の炭素数は、通常６〜３０であるが、６〜２０が好ましい。ヒドロキシアルキル基の炭素数は、通常２〜１２であるが、２〜８が好ましい。また有機基を２つ以上有する場合は、複数の有機基は互いに同一であっても、異なっていてもよく、さらに互いに結合して環を形成していてもよい。このようなアンモニウムイオンを形成するアミンとしては、例えば、メチルアミン、エチルアミン、ブチルアミン、オクチルアミン、ドデシルアミン、オクタデシルアミン、ジメチルアミン、ジエチルアミン、ジオクチルアミン、ジオクタデシルアミン、メチルドデシルアミン、ブチルオクチルアミン、トリエチルアミン、トリブチルアミン、トリ（２−エチルヘキシル）アミン等の脂肪族アミン；エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、ヘキサメチレンジアミン等の脂肪族ポリアミン；アニリン、メチルアニリン、エチルアニリン、ドデシルアニリン、メチルベンジルアミン等の芳香族アミン；モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等のアミノアルコール；ピリジン、モルホリン、ピロリジン、ピペリジン等の複素環式アミン等が挙げられる。
上記顔料分散剤組成物には、上述の式［１］又は式［２］で表されるスルホコハク酸エステルと１価の金属イオン又は置換基を有していてもよいアンモニウムイオンとの塩を、単独で又は２種類以上を組み合わせて用いることができる。
Examples of the monovalent metal ion that forms a salt with the sulfosuccinic acid ester represented by the formula [1] or the formula [2] include metal ions such as lithium, sodium, and potassium. The ammonium ion optionally having a substituent that forms a salt with the sulfosuccinate represented by the formula [1] or [2] is an NH 4 + ion, a substituent on the N atom. An ammonium ion having one organic group, an ammonium ion having two organic groups, or an ammonium ion having three organic groups. Examples of the organic group include an aliphatic group, an aromatic group, and a hydroxyalkyl group. Although carbon number of an aliphatic group is 1-30 normally, 1-18 are preferable, 1-12 are more preferable, and 1-6 are more preferable. The carbon number of the aromatic group is usually 6-30, but 6-20 is preferable. The carbon number of the hydroxyalkyl group is usually 2 to 12, but 2 to 8 is preferable. In the case of having two or more organic groups, the plurality of organic groups may be the same or different from each other, and may be bonded to each other to form a ring. Examples of amines that form such ammonium ions include methylamine, ethylamine, butylamine, octylamine, dodecylamine, octadecylamine, dimethylamine, diethylamine, dioctylamine, dioctadecylamine, methyldodecylamine, butyloctylamine, Aliphatic amines such as triethylamine, tributylamine, tri (2-ethylhexyl) amine; Aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, hexamethylenediamine; aniline, methylaniline, ethylaniline, dodecylaniline, methylbenzylamine, etc. Aromatic amines; amino alcohols such as monoethanolamine, diethanolamine, and triethanolamine; pyridine, morpholine , Pyrrolidine, heterocyclic amines such as piperidine.
In the pigment dispersant composition, a salt of the sulfosuccinate represented by the above formula [1] or [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, It can use individually or in combination of 2 or more types.
式［３］中の、Ｒ４のアルキル基の炭素数は、通常１〜６であるが、好ましくは１〜４である。こうしたアルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基等が挙げられる。アルケニル基の炭素数は、通常２〜６であるが、好ましくは２〜４である。こうしたアルケニル基としては、ビニル基、アリル基、プロペニル基、ブテニル基等が挙げられる。アリールアルキル基の炭素数は、通常７〜１３であるが、好ましくは７〜９である。こうしたアリールアルキル基としては、ベンジル基、フェネチル基、フェニルベンジル基、ナフチルメチル基等が挙げられる。 The carbon number of the alkyl group of R 4 in formula [3] is usually 1 to 6, but preferably 1 to 4. Examples of such an alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. The carbon number of the alkenyl group is usually 2-6, but preferably 2-4. Such alkenyl groups include vinyl, allyl, propenyl, butenyl and the like. The carbon number of the arylalkyl group is usually from 7 to 13, but preferably from 7 to 9. Examples of such arylalkyl groups include a benzyl group, a phenethyl group, a phenylbenzyl group, and a naphthylmethyl group.
Ｒ４の金属イオンとしては、例えば、リチウム、ナトリウム、カリウム、カルシウム、マグネシウム、亜鉛、鉄、コバルト、ニッケル、銅、錫、カドミウム、バリウム又はアルミニウム等の１〜３価の金属イオンが挙げられる。
また、Ｒ４の置換基を有していてもよいアンモニウムイオンは、ＮＨ４ ＋イオン、Ｎ原子上に置換基として有機基を１つ有するアンモニウムイオン、有機基を２つ有するアンモニウムイオン又は有機基を３つ有するアンモニウムイオンである。有機基は、脂肪族基、芳香族基又はヒドロキシアルキル基を表す。脂肪族基の炭素数は、通常１〜３０であるが、１〜１８が好ましく、１〜１２がより好ましく、１〜６がさらに好ましい。芳香族基の炭素数は、通常６〜３０であるが、６〜２０が好ましい。ヒドロキシアルキル基の炭素数は、通常２〜１２であるが、２〜８が好ましい。また有機基を２つ以上有する場合は、複数の有機基は互いに同一であっても、異なっていてもよく、さらに互いに結合して環を形成していてもよい。このようなアンモニウムイオンを形成するアミンとしては、例えば、メチルアミン、エチルアミン、ブチルアミン、オクチルアミン、ドデシルアミン、オクタデシルアミン、ジメチルアミン、ジエチルアミン、ジオクチルアミン、ジオクタデシルアミン、メチルドデシルアミン、ブチルオクチルアミン、トリエチルアミン、トリブチルアミン、トリ（２−エチルヘキシル）アミン等の脂肪族アミン；エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、ヘキサメチレンジアミン等の脂肪族ポリアミン；アニリン、メチルアニリン、エチルアニリン、ドデシルアニリン、メチルベンジルアミン等の芳香族アミン；モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等のアミノアルコール；ピリジン、モルホリン、ピロリジン、ピペリジン等の複素環式アミン等が挙げられる。
顔料分散剤組成物に上記カルボニル基含有芳香族化合物を含むことにより、上記スルホコハク酸エステルの塩のみを有する場合と比べて、得られる着色熱可塑性樹脂の顔料分散性が向上する。
上記顔料分散剤組成物には、上記式［３］で表されるカルボニル基含有芳香族化合物を、単独で又は２種類以上を組み合わせて用いることができる。
Examples of the metal ion for R 4 include 1 to 3 metal ions such as lithium, sodium, potassium, calcium, magnesium, zinc, iron, cobalt, nickel, copper, tin, cadmium, barium, and aluminum.
In addition, an ammonium ion which may have a substituent of R 4 is an NH 4 + ion, an ammonium ion having one organic group as a substituent on the N atom, an ammonium ion having two organic groups, or an organic group. Is an ammonium ion. The organic group represents an aliphatic group, an aromatic group or a hydroxyalkyl group. Although carbon number of an aliphatic group is 1-30 normally, 1-18 are preferable, 1-12 are more preferable, and 1-6 are more preferable. The carbon number of the aromatic group is usually 6-30, but 6-20 is preferable. The carbon number of the hydroxyalkyl group is usually 2 to 12, but 2 to 8 is preferable. In the case of having two or more organic groups, the plurality of organic groups may be the same or different from each other, and may be bonded to each other to form a ring. Examples of amines that form such ammonium ions include methylamine, ethylamine, butylamine, octylamine, dodecylamine, octadecylamine, dimethylamine, diethylamine, dioctylamine, dioctadecylamine, methyldodecylamine, butyloctylamine, Aliphatic amines such as triethylamine, tributylamine, tri (2-ethylhexyl) amine; Aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, hexamethylenediamine; aniline, methylaniline, ethylaniline, dodecylaniline, methylbenzylamine, etc. Aromatic amines; amino alcohols such as monoethanolamine, diethanolamine, and triethanolamine; pyridine, morpholine , Pyrrolidine, heterocyclic amines such as piperidine.
By including the carbonyl group-containing aromatic compound in the pigment dispersant composition, the pigment dispersibility of the obtained colored thermoplastic resin is improved as compared with the case where only the salt of the sulfosuccinic acid ester is included.
In the pigment dispersant composition, the carbonyl group-containing aromatic compound represented by the formula [3] can be used alone or in combination of two or more.
なお、Ｒ４が水素原子であるカルボニル基含有芳香族化合物と、スルホコハク酸エステルの塩とを混合した場合には、Ｒ４の水素原子は、式［１］又は式［２］で表されるスルホコハク酸エステルと塩を形成する１価の金属イオン又は置換基を有していてもよいアンモニウムイオンにより、置換され得る。 When a carbonyl group-containing aromatic compound in which R 4 is a hydrogen atom and a sulfosuccinate salt are mixed, the hydrogen atom of R 4 is represented by the formula [1] or [2]. It can be substituted with a monovalent metal ion that forms a salt with a sulfosuccinate or an ammonium ion that may have a substituent.
上記スルホコハク酸エステルの塩と上記カルボニル基含有芳香族化合物との配合比は、質量比で１：０．０５〜１：１であることが好ましく、より好ましくは１：０．１〜１：０．５である。配合比率が上記範囲内にある場合には、より優れた顔料分散性を発現することができる。 The mixing ratio of the sulfosuccinic acid ester salt to the carbonyl group-containing aromatic compound is preferably 1: 0.05 to 1: 1, more preferably 1: 0.1 to 1: 0 in terms of mass ratio. .5. When the blending ratio is within the above range, more excellent pigment dispersibility can be exhibited.
顔料分散剤組成物は、様々な用途に適用するために、粉末状若しくはフレーク状等の固体、ペースト状又は液体といった形態をとることができ、それぞれにおいて高い顔料分散性を発揮することができるが、取り扱い、顔料との配合のし易さ、混合した際の均一性や顔料分散性の点から、粉末状であることが好ましい。また、各種形態の顔料分散剤組成物を得るためにはそれぞれに適した既存の製造方法を採用することができる。 The pigment dispersant composition can take the form of a solid such as a powder or flake, a paste or a liquid in order to be applied to various uses, and can exhibit high pigment dispersibility in each. From the viewpoints of handling, ease of blending with pigments, uniformity when mixed, and pigment dispersibility, powder is preferred. Moreover, in order to obtain the pigment dispersant composition of various forms, existing production methods suitable for each can be employed.
顔料分散剤組成物が粉末の場合の嵩密度は０．０１〜１ｇ／ｃｍ３であることが好ましく、より好ましくは０．０５〜０．８ｇ／ｃｍ３であり、特に好ましくは０．１〜０．６ｇ／ｃｍ３である。なお、嵩密度は、以下の方法により算出することができる。すなわち、１００ｍｌ（ｃｍ３）のメスシリンダーに顔料分散剤組成物の粉末を、振動を与えずに徐々に加えて、メスシリンダーを顔料分散剤組成物の粉末で満たす。顔料分散剤組成物の粉末を入れる前後のメスシリンダーの質量の差を測定し、以下の式より嵩密度を算出することができる。
（嵩密度（ｇ／ｃｍ３））＝（質量差（ｇ））÷１００（ｃｍ３）
Preferably the pigment dispersion composition is bulk density when the powder is 0.01 to 1 g / cm 3, more preferably from 0.05~0.8g / cm 3, particularly preferably 0.1 0.6 g / cm 3 . The bulk density can be calculated by the following method. That is, the pigment dispersant composition powder is gradually added to a 100 ml (cm 3 ) graduated cylinder without vibration, and the graduated cylinder is filled with the pigment dispersant composition powder. The difference in mass of the graduated cylinder before and after putting the pigment dispersant composition powder is measured, and the bulk density can be calculated from the following formula.
(Bulk density (g / cm 3 )) = (mass difference (g)) ÷ 100 (cm 3 )
顔料分散剤組成物の粉末の嵩密度が０．０１ｇ／ｃｍ３より小さい場合には、添加、混合・溶融混練の際に飛散し易くなり、作業性、作業環境を悪くさせる傾向がある。一方、嵩密度が１ｇ／ｃｍ３より大きい場合には、混合・溶融混練の際、顔料分散剤の凝集が起こり易くなり、着色熱可塑性樹脂中の顔料分散性が上記範囲内にある場合と比べて低下する傾向がある。 When the bulk density of the powder of the pigment dispersant composition is less than 0.01 g / cm 3 , the powder tends to be scattered during addition, mixing / melt kneading, and the workability and working environment tend to be deteriorated. On the other hand, when the bulk density is greater than 1 g / cm 3 , the pigment dispersant tends to aggregate during mixing and melt-kneading, and the pigment dispersibility in the colored thermoplastic resin is within the above range. Tend to decline.
（着色剤組成物）
着色剤組成物は、式［１］又は式［２］で表されるスルホコハク酸エステルと、１価の金属イオン又は置換基を有していてもよいアンモニウムイオンと、の塩、及び式［３］で表されるカルボニル基含有芳香族化合物を含む顔料分散剤組成物並びに顔料を含有する。
(Colorant composition)
The colorant composition includes a salt of a sulfosuccinic acid ester represented by the formula [1] or the formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and the formula [3]. ] The pigment dispersant composition containing the carbonyl group containing aromatic compound represented by this, and a pigment are contained.
また、着色剤組成物は、式［１］又は式［２］で表されるスルホコハク酸エステルと、１価の金属イオン又は置換基を有していてもよいアンモニウムイオンと、の塩、及び式［３］で表されるカルボニル基含有芳香族化合物を含む顔料分散剤組成物、顔料並びに熱可塑性樹脂（ベース樹脂）を含有していてもよい。着色剤組成物がカラーマスターバッチの場合に用いられる熱可塑性樹脂（ベース樹脂）としては、被着色熱可塑性樹脂の物性を損なわない限り特に制限はないが、被着色熱可塑性樹脂への分散性、分配性に優れるので、被着色熱可塑性樹脂と同一の樹脂を用いることが好ましい。着色剤組成物に用いられる熱可塑性樹脂（ベース樹脂）の配合量は、用いる顔料や熱可塑性樹脂（ベース樹脂）の種類、着色剤組成物の被着色熱可塑性樹脂に対する使用量、成型品の色濃度等によっても異なるが、着色剤組成物１００質量部に対して通常２０〜９９質量部である。以下に、着色剤組成物を構成する材料について説明する。 Further, the colorant composition includes a salt of a sulfosuccinic acid ester represented by the formula [1] or the formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and a formula It may contain a pigment dispersant composition containing the carbonyl group-containing aromatic compound represented by [3], a pigment, and a thermoplastic resin (base resin). The thermoplastic resin (base resin) used when the colorant composition is a color masterbatch is not particularly limited as long as the physical properties of the thermoplastic resin to be colored are not impaired, but the dispersibility in the thermoplastic resin to be colored, Since the distribution property is excellent, it is preferable to use the same resin as the thermoplastic resin to be colored. The amount of the thermoplastic resin (base resin) used in the colorant composition is the type of pigment or thermoplastic resin (base resin) used, the amount of the colorant composition used for the thermoplastic resin to be colored, and the color of the molded product. Although it varies depending on the concentration and the like, it is usually 20 to 99 parts by mass with respect to 100 parts by mass of the colorant composition. Below, the material which comprises a coloring agent composition is demonstrated.
（顔料）
顔料は、熱可塑性樹脂の着色に使用される顔料であれば特に限定されず、対象とすることができる。顔料としては、例えば酸化チタン系、酸化鉄系、複合酸化物系等の金属酸化物；それ以外であるクロム酸塩系、硫化物系、ケイ酸塩系、炭酸塩系、フェロシアン化物、カーボンブラック等の金属酸化物以外の無機顔料；溶性アゾ系、不溶性アゾ系（モノアゾ、ジスアゾ）等のアゾ化合物；縮合アゾ系金属錯塩アゾ系、ベンズイミダゾロン系、多環系であるフタロシアニン系、アントラキノン系、インジゴ系、ペリノン系、ペリレン系、キナクリドン系、イソインドリノン系、金属錯塩系、メチン・アゾメチン系、ジケトピロロピロール系からなる有機顔料が挙げられる。また水溶性である塩基性、酸性系染料や油溶性であるアゾ系、アントラキノン系、ペリレン系染料を用いることもできる。これらの中でも特に、キナクリドン系、アントラキノン系、ペリレン系、イソインドリノン系、ジケトピロロピロール系、キノフタロン系、スレン系あるいは銅フタロシアニン系等の有機顔料；赤色酸化鉄、黒色酸化鉄、酸化チタン、酸化亜鉛、チタンブラック、チタンイエロー、群青、コバルトブルー、カーボンブラック等の無機顔料；タルク、炭酸カルシウム、硫酸バリウム等の体質顔料等が好ましい。
(Pigment)
The pigment is not particularly limited as long as it is a pigment used for coloring a thermoplastic resin, and can be a target. Examples of the pigment include metal oxides such as titanium oxides, iron oxides, and complex oxides; other chromates, sulfides, silicates, carbonates, ferrocyanides, carbons Inorganic pigments other than metal oxides such as black; soluble azo-based, insoluble azo-based (monoazo, disazo), etc .; condensed azo-based metal complex azo-based, benzimidazolone-based, polycyclic phthalocyanine-based, anthraquinone And organic pigments composed of a pigment, an indigo, a perinone, a perylene, a quinacridone, an isoindolinone, a metal complex, a methine / azomethine, and a diketopyrrolopyrrole. Further, basic and acidic dyes that are water-soluble, and azo, anthraquinone, and perylene dyes that are oil-soluble can also be used. Among these, organic pigments such as quinacridone, anthraquinone, perylene, isoindolinone, diketopyrrolopyrrole, quinophthalone, selenium or copper phthalocyanine; red iron oxide, black iron oxide, titanium oxide, Inorganic pigments such as zinc oxide, titanium black, titanium yellow, ultramarine blue, cobalt blue and carbon black; extender pigments such as talc, calcium carbonate and barium sulfate are preferred.
顔料に対する顔料分散剤組成物の配合量は、顔料１００質量部に対して０．０１〜１００質量部であることが好ましく、より好ましくは０．０５〜７５質量部であり、さらに好ましくは０．１〜５０質量部である。顔料分散剤組成物の配合量が顔料１００質量部に対して１００質量部より多い場合、それ以上の顔料分散性の向上は認められない傾向があり、成型体としたときの物性の低下が起こるおそれがある。一方、顔料分散剤組成物の配合量が顔料１００質量部に対して０．０１質量部より少ない場合には、十分な顔料分散性が得られないおそれがある。 The blending amount of the pigment dispersant composition with respect to the pigment is preferably 0.01 to 100 parts by weight, more preferably 0.05 to 75 parts by weight, and still more preferably 0.00 to 100 parts by weight of the pigment. 1 to 50 parts by mass. When the blending amount of the pigment dispersant composition is more than 100 parts by mass with respect to 100 parts by mass of the pigment, no further improvement in pigment dispersibility tends to be observed, resulting in a decrease in physical properties when formed into a molded body. There is a fear. On the other hand, when the blending amount of the pigment dispersant composition is less than 0.01 parts by mass with respect to 100 parts by mass of the pigment, there is a possibility that sufficient pigment dispersibility may not be obtained.
（熱可塑性樹脂）
熱可塑性樹脂としては、エチレン、プロピレン、ブテン、オクテン等の重合体やＥＶＡ（エチレンビニルアセテート）、ＥＥＡ（エチレンエチルアクリレート）等の共重合体を含むオレフィン系樹脂、スチレン、アクリル酸エステルの重合体やその共重合体、スチレンアクリロニトリル、スチレンアクリロニトリルブタジエン等の共重合体を含むスチレン系樹脂、ポリカーボネート、ポリオキシメチレン、ポリアミド６や６６等のエンジニアリング樹脂等が挙げられる。
(Thermoplastic resin)
Thermoplastic resins include polymers such as ethylene, propylene, butene, octene, olefin resins including copolymers such as EVA (ethylene vinyl acetate) and EEA (ethylene ethyl acrylate), polymers of styrene and acrylate esters. And styrene resins containing copolymers such as styrene acrylonitrile and styrene acrylonitrile butadiene, engineering resins such as polycarbonate, polyoxymethylene, polyamide 6 and 66, and the like.
顔料及び顔料分散剤組成物を混合して着色剤組成物を製造する際に使用される混合機としては従来公知の機器でよく、例えば、水平円筒型、Ｖ型（攪拌羽根付）、二重円錐型、揺動回転型、単軸リボン型、複軸パドル型、回転鋤型、二軸遊星攪拌型、円錐スクリュー型、高速流動型（ヘンシェルミキサー等）、回転円盤型、ローラー付回転容器型（マラー型）、攪拌付回転容器型、高速楕円ロータ型、気流攪拌型、無攪拌型（重量型）等が挙げられる。また、別の混合方法として、顔料に顔料分散剤組成物の溶液を噴霧し乾燥する、加熱乾燥させた顔料に顔料分散剤組成物を混合する方法がある。しかし、混合方法はこれらに限定されるものではなく、既存の方法を採用することができる。混合時間、混合温度は特に限定されず、既存の混合機に適した公知の方法を採用することができる。 As a mixer used for producing a colorant composition by mixing a pigment and a pigment dispersant composition, a conventionally known apparatus may be used, for example, a horizontal cylindrical type, a V type (with stirring blades), a double Cone type, oscillating rotation type, single axis ribbon type, double axis paddle type, rotary saddle type, biaxial planetary stirring type, conical screw type, high-speed flow type (Henschel mixer, etc.), rotary disk type, rotary container type with roller (Muller type), rotating container type with stirring, high-speed elliptical rotor type, airflow stirring type, non-stirring type (weight type) and the like. Further, as another mixing method, there is a method in which a pigment dispersant composition is mixed with a pigment that has been heat-dried by spraying and drying a pigment dispersant composition solution onto the pigment. However, the mixing method is not limited to these, and an existing method can be adopted. A mixing time and a mixing temperature are not particularly limited, and a known method suitable for an existing mixer can be employed.
着色剤組成物は、ドライカラー、ペーストカラー又はリキッドカラーといった形態をとることができ、それぞれにおいて高い顔料分散性を発揮することができる。また、それら形態を得るために、既存の製造方法を採用することができる。 The colorant composition can take a form such as a dry color, a paste color, or a liquid color, and can exhibit high pigment dispersibility in each. Moreover, in order to obtain these forms, existing manufacturing methods can be employed.
顔料、顔料分散剤組成物及び熱可塑性樹脂（ベース樹脂）を溶融混練して着色剤組成物を製造する際に使用される混練機としては従来公知の機器でよく、一軸押出機、二軸押出機、バンバリーミキサー、ロール、ニーダー等の通常の混練機を使用することができる。混練時間、混練温度は特に限定されず、既存の混練機及び熱可塑性樹脂（ベース樹脂）に適した公知の方法を採用することができる。着色剤組成物はカラーマスターバッチであり、被着色熱可塑性樹脂への顔料分散性やその取り扱い易さからペレット状、フレーク状、ビーズ状の形態にすることが好ましく、その形態を得るために既存の製造方法を採用することができる。 As a kneading machine used for producing a colorant composition by melting and kneading a pigment, a pigment dispersant composition and a thermoplastic resin (base resin), a conventionally known apparatus may be used. Conventional kneaders such as a machine, a Banbury mixer, a roll, and a kneader can be used. The kneading time and kneading temperature are not particularly limited, and a known method suitable for existing kneaders and thermoplastic resins (base resins) can be employed. The colorant composition is a color masterbatch, preferably in the form of pellets, flakes, or beads, from the standpoint of dispersibility of pigment in the thermoplastic resin to be colored and its ease of handling. The manufacturing method can be adopted.
（着色熱可塑性樹脂の製造方法）
着色熱可塑性樹脂の製造方法は、上述の顔料、顔料分散剤及び熱可塑性樹脂を、溶融混練することを特徴とする。本発明の製造方法は、直接添加法であっても、上述の着色剤組成物を作製し使用する製造方法であってもよい。
(Production method of colored thermoplastic resin)
A method for producing a colored thermoplastic resin is characterized by melt-kneading the above-described pigment, pigment dispersant, and thermoplastic resin. The production method of the present invention may be a direct addition method or a production method in which the above-described colorant composition is produced and used.
また、着色熱可塑性樹脂には、上記成分以外に酸化マグネシウム、酸化カルシウム、酸化ストロンチウム、酸化バリウム等のアルカリ土類金属の酸化物；水酸化マグネシウム、水酸化カルシウム、水酸化ストロンチウム、水酸化バリウム等のアルカリ土類金属の水酸化物からなるフォギング防止剤；脂肪酸エステル、脂肪酸アマイド、低分子量ポリオレフィン、スチレン系オリゴマー等の分散剤や滑剤、さらに紫外線吸収剤、光安定剤、熱安定剤等の添加剤を適宜加えることができる。
また、着色熱可塑性樹脂は、顔料以外のタルク、炭酸カルシウム、マイカ、ガラス繊維等で改質複合化されていてもよい。
In addition to the above components, colored thermoplastic resins include oxides of alkaline earth metals such as magnesium oxide, calcium oxide, strontium oxide, barium oxide; magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, etc. Anti-fogging agent consisting of alkaline earth metal hydroxides; dispersants and lubricants such as fatty acid esters, fatty acid amides, low molecular weight polyolefins, styrene oligomers, UV absorbers, light stabilizers, heat stabilizers, etc. Agents can be added as appropriate.
The colored thermoplastic resin may be modified and composited with talc other than the pigment, calcium carbonate, mica, glass fiber, or the like.
本発明の製造方法では、原料を混合せずに直接混練機へ投入して溶融混練してもよいし、原料を混合する種々の工程を経た後に混練機へ投入してもよい。着色熱可塑性樹脂の製造方法としては、例えば、既存の混合機で熱可塑性樹脂、顔料及び顔料分散剤組成物を混合し、顔料及び顔料分散剤組成物を樹脂ペレット上に付着させた熱可塑性樹脂を溶融混練する方法、又は顔料及び顔料分散剤組成物をあらかじめ既存の混合機で混合して、若しくは、顔料、顔料分散剤組成物及び熱可塑性樹脂（ベース樹脂）をあらかじめ既存の混練機で溶融混練して着色剤組成物を得た後、該着色剤組成物と被着色熱可塑性樹脂とを混合し、溶融混練する方法等が挙げられる。 In the production method of the present invention, the raw materials may be directly charged into a kneader without being mixed and melt-kneaded, or may be charged into the kneader after various steps of mixing the raw materials. As a method for producing a colored thermoplastic resin, for example, a thermoplastic resin, a pigment, and a pigment dispersant composition are mixed with an existing mixer, and the pigment and the pigment dispersant composition are adhered to resin pellets. Or kneading the pigment and pigment dispersant composition with an existing mixer in advance, or melting the pigment, pigment dispersant composition and thermoplastic resin (base resin) with an existing kneader in advance Examples of methods include kneading to obtain a colorant composition, mixing the colorant composition and a thermoplastic resin to be colored, and melt-kneading.
着色熱可塑性樹脂は、顔料、顔料分散剤組成物及び熱可塑性樹脂を原料として直接溶融混練して製造され、又はドライカラー、ペーストカラー、リキッドカラー、カラーマスターバッチといった着色剤組成物を使用しても製造される。つまり、着色剤組成物の違いを問わず、顔料分散性を損なうことなく、着色熱可塑性樹脂を製造することができる。 The colored thermoplastic resin is produced by directly melting and kneading a pigment, a pigment dispersant composition and a thermoplastic resin as raw materials, or using a colorant composition such as a dry color, paste color, liquid color, or color master batch. Is also manufactured. That is, regardless of the colorant composition, a colored thermoplastic resin can be produced without impairing pigment dispersibility.
着色熱可塑性樹脂は、通常の方法に従って加熱溶融して製造される。すなわち、一軸押出機、二軸押出機、バンバリーミキサー、ロール、ニーダー等の通常の混練機を用いて製造することができる。 The colored thermoplastic resin is produced by heating and melting according to a normal method. That is, it can be manufactured using a normal kneader such as a single screw extruder, a twin screw extruder, a Banbury mixer, a roll, a kneader.
成型品は、上記着色熱可塑性樹脂を製造した加熱溶融の状態で直接に、若しくは着色ペレットの状態を経て、通常の方法に従って加熱溶融して製造される。すなわち、押出成型、中空成型、射出成型、シート成型、熱成型、回転成型、積層成型等成型法の違いを問わず製造することができる。 The molded product is manufactured by heating and melting in the state of heating and melting in which the colored thermoplastic resin is manufactured or through the state of colored pellets according to a normal method. That is, it can be manufactured regardless of the difference in molding methods such as extrusion molding, hollow molding, injection molding, sheet molding, thermoforming, rotational molding, and lamination molding.
以下、本発明の実施例を示して、本発明をさらに具体的に説明するが、本発明はこれらの実施例に限定されるものではなく、本発明の技術的思想を逸脱しない範囲での種々の変更が可能である。本発明の顔料分散剤組成物を使用して得られた着色熱可塑性樹脂の性能は、その顔料分散性によって以下のように評価される。実施例において使用される数値は特に断りのない限り質量基準である。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples of the present invention. However, the present invention is not limited to these examples, and various modifications can be made without departing from the technical idea of the present invention. Can be changed. The performance of the colored thermoplastic resin obtained by using the pigment dispersant composition of the present invention is evaluated as follows according to the pigment dispersibility. Numerical values used in the examples are based on mass unless otherwise specified.
（顔料分散性の評価）
実施例及び比較例で得られた着色熱可塑性樹脂を熱プレス機によって２００℃で２分間溶融させ、その後同じ温度で１分間１００ｋｇ／ｍ２の圧力でプレスを行い、０．１ｍｍの厚さの着色熱可塑性樹脂の薄膜試料を得た。厚さの調整には、０．１ｍｍの金属型を使用した。次にマイクロスコープで薄膜の拡大画像を撮影し、凝集している顔料を目視にて観察した。マイクロスコープにより倍率４０倍で撮影を行い、１つの試料につき６カ所撮影した。その後、以下の評価基準に従って顔料分散性の評価を行った。
Ａ：凝集物がない
Ｂ：わずかに凝集物がある
Ｃ：部分的に凝集物がある
Ｄ：全体的に凝集物がある
(Evaluation of pigment dispersibility)
The colored thermoplastic resins obtained in the examples and comparative examples were melted at 200 ° C. for 2 minutes by a hot press machine, then pressed at the same temperature for 1 minute at a pressure of 100 kg / m 2 , and the thickness of 0.1 mm A thin film sample of colored thermoplastic resin was obtained. A 0.1 mm metal mold was used to adjust the thickness. Next, an enlarged image of the thin film was taken with a microscope, and the aggregated pigment was visually observed. Images were taken with a microscope at a magnification of 40 times, and 6 images were taken for each sample. Thereafter, the pigment dispersibility was evaluated according to the following evaluation criteria.
A: No aggregate B: Slight aggregate C: Partial aggregate D: Overall aggregate
（顔料分散剤組成物１〜５の調製）
式［１］又は式［２］で表されるスルホコハク酸エステルと１価の金属イオン又は置換基を有していてもよいアンモニウムイオンとの塩と、式［３］で表されるカルボニル基含有芳香族化合物とをそれぞれ表１に示した組成でエタノール中に溶解・分散させ、スプレードライヤーにて噴霧乾燥を行い、嵩密度０．２ｇ／ｃｍ３の粉末状の顔料分散剤組成物を得た。以下で用いられる記号Ｎａ、Ｋ、Ｃａ及びＬｉはそれぞれナトリウム、カリウム、カルシウム及びリチウムを表す。
(Preparation of pigment dispersant compositions 1 to 5)
A salt of a sulfosuccinate represented by the formula [1] or the formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and a carbonyl group containing the formula [3] Aromatic compounds were dissolved and dispersed in ethanol with the compositions shown in Table 1 and spray-dried with a spray dryer to obtain a powdery pigment dispersant composition with a bulk density of 0.2 g / cm 3 . . The symbols Na, K, Ca and Li used below represent sodium, potassium, calcium and lithium, respectively.
（顔料分散剤組成物６、７の調製）
式［１］又は式［２］で表されるスルホコハク酸エステルと１価の金属イオン又は置換基を有していてもよいアンモニウムイオンとの塩と、式［３］で表されるカルボニル基含有芳香族化合物とをそれぞれ表１に示した組成でエタノール中に溶解・分散させた後、エタノールを蒸発させて、ペースト状の顔料分散剤組成物を得た。
(Preparation of pigment dispersant compositions 6 and 7)
A salt of a sulfosuccinate represented by the formula [1] or the formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and a carbonyl group containing the formula [3] The aromatic compounds were dissolved and dispersed in ethanol with the compositions shown in Table 1, respectively, and then the ethanol was evaporated to obtain a paste-like pigment dispersant composition.
（実施例１）
熱可塑性樹脂としてのポリプロピレン（ＰＰ）（メルトフローレート：３０ｇ／１０ｍｉｎ（２３０℃））のペレット１００質量部、顔料としてのカーボンブラック（Ｐｉｇｍｅｎｔ Ｂｌａｃｋ ７）０．６７質量部、及び顔料分散剤組成物１（スルホコハク酸ジ２−エチルヘキシルＮａ塩：９０％、安息香酸：１０％）０．３３質量部を、ヘンシェルミキサーにて混合して、表面に顔料及び顔料分散剤組成物が付着したポリプロピレン樹脂ペレットを作製した。得られたポリプロピレン樹脂ペレットを２軸ニーダーに投入し、２００℃で２分間溶融させ、その後同じ温度で１分間混練を行い、着色熱可塑性樹脂を得た。顔料分散性の評価結果を表２に示した。
Example 1
100 parts by mass of pellets of polypropylene (PP) (melt flow rate: 30 g / 10 min (230 ° C.)) as a thermoplastic resin, 0.67 parts by mass of carbon black (Pigment Black 7) as a pigment, and a pigment dispersant composition Polypropylene resin pellets having 0.33 parts by mass of 1 (di-2-ethylhexyl sulfosuccinate Na salt: 90%, benzoic acid: 10%) mixed with a Henschel mixer, and the pigment and pigment dispersant composition adhered to the surface Was made. The obtained polypropylene resin pellets were put into a biaxial kneader, melted at 200 ° C. for 2 minutes, and then kneaded for 1 minute at the same temperature to obtain a colored thermoplastic resin. The evaluation results of the pigment dispersibility are shown in Table 2.
（実施例２〜１４）
顔料及び顔料分散剤組成物の種類及び量を表２〜４のように変えた以外は、実施例１と同様にして着色熱可塑性樹脂を得た。なお、下記の表中、カーボンブラックとしてはＰｉｇｍｅｎｔ Ｂｌａｃｋ ７を、フタロシアニングリーンとしてはＰｉｇｍｅｎｔ Ｇｒｅｅｎ ７、鉄黒としてはＰｉｇｍｅｎｔ Ｂｌａｃｋ １１を、それぞれ使用している。顔料分散剤性の評価結果を表２〜４に示した。
(Examples 2 to 14)
A colored thermoplastic resin was obtained in the same manner as in Example 1 except that the types and amounts of the pigment and the pigment dispersant composition were changed as shown in Tables 2 to 4. In the table below, Pigment Black 7 is used as carbon black, Pigment Green 7 is used as phthalocyanine green, and Pigment Black 11 is used as iron black. The evaluation results of the pigment dispersant properties are shown in Tables 2 to 4.
（実施例１５）
顔料としてのカーボンブラック（Ｐｉｇｍｅｎｔ Ｂｌａｃｋ ７）６７質量部、及び顔料分散剤組成物１（スルホコハク酸ジ２−エチルヘキシルＮａ塩：９０％、安息香酸：１０％）３３質量部を、水平円筒型混合機で混合し、粉末状の着色剤組成物を得た。
熱可塑性樹脂としてのポリプロピレン（ＰＰ）（メルトフローレート：３０ｇ／１０ｍｉｎ（２３０℃））のペレット１００質量部と、得られた粉末状の着色剤組成物０．７３６質量部とをヘンシェルミキサーにて混合し、表面に顔料及び顔料分散剤組成物が付着したポリプロピレン樹脂ペレットを作製した。得られたポリプロピレン樹脂ペレットを２軸ニーダーに投入し、２００℃で２分間溶融させ、その後同じ温度で１分間混練を行い、着色熱可塑性樹脂を得た。顔料分散性の評価結果を表５に示した。
(Example 15)
67 parts by mass of carbon black (Pigment Black 7) as a pigment and 33 parts by mass of pigment dispersant composition 1 (di-2-ethylhexyl sulfosuccinate Na salt: 90%, benzoic acid: 10%) were mixed in a horizontal cylindrical mixer. To obtain a powdery colorant composition.
In a Henschel mixer, 100 parts by mass of a pellet of polypropylene (PP) (melt flow rate: 30 g / 10 min (230 ° C.)) as a thermoplastic resin and 0.736 parts by mass of the obtained powdery colorant composition Mixing was performed to prepare polypropylene resin pellets having the pigment and pigment dispersant composition attached to the surface. The obtained polypropylene resin pellets were put into a biaxial kneader, melted at 200 ° C. for 2 minutes, and then kneaded for 1 minute at the same temperature to obtain a colored thermoplastic resin. The evaluation results of the pigment dispersibility are shown in Table 5.
（実施例１６〜２８）
顔料及び顔料分散剤組成物の種類及び量を表５〜７のように変えた以外は、実施例１５と同様にして着色熱可塑性樹脂を得た。顔料分散剤性の評価結果を表５〜７に示した。
(Examples 16 to 28)
A colored thermoplastic resin was obtained in the same manner as in Example 15 except that the types and amounts of the pigment and the pigment dispersant composition were changed as shown in Tables 5 to 7. The evaluation results of the pigment dispersant properties are shown in Tables 5-7.
（比較例１）
顔料としてのカーボンブラック（Ｐｉｇｍｅｎｔ Ｂｌａｃｋ ７）９１質量部、及び顔料分散剤としてのスルホコハク酸ジ２−エチルヘキシルＮａ塩９質量部をエタノール１５０質量部に添加し、３０〜６０分攪拌することにより顔料分散液を作製した。その後得られた顔料分散液を連続流動造粒装置内蔵式スプレードライヤで噴霧乾燥し、着色剤組成物を得た。
熱可塑性樹脂としてのポリプロピレン（ＰＰ）（メルトフローレート：３０ｇ／１０ｍｉｎ（２３０℃））のペレット１００質量部と、得られた着色剤組成物０．７３６質量部とをヘンシェルミキサーにて混合し、表面に顔料及び顔料分散剤が付着したポリプロピレン樹脂ペレットを作製した。得られたポリプロピレン樹脂ペレットを２軸ニーダーに投入し、２００℃で２分間溶融させ、その後同じ温度で３分間混練を行い、着色熱可塑性樹脂を得た。顔料分散性の評価結果を表８に示した。
(Comparative Example 1)
91 parts by mass of carbon black (Pigment Black 7) as a pigment and 9 parts by mass of di-2-ethylhexyl sulfosuccinate Na salt as a pigment dispersant are added to 150 parts by mass of ethanol, and the pigment is dispersed by stirring for 30 to 60 minutes. A liquid was prepared. Thereafter, the obtained pigment dispersion was spray-dried with a spray dryer with a built-in continuous flow granulator to obtain a colorant composition.
100 parts by mass of polypropylene (PP) (melt flow rate: 30 g / 10 min (230 ° C.)) as a thermoplastic resin and 0.736 parts by mass of the obtained colorant composition were mixed in a Henschel mixer, Polypropylene resin pellets having a pigment and a pigment dispersant attached to the surface were prepared. The obtained polypropylene resin pellets were put into a biaxial kneader, melted at 200 ° C. for 2 minutes, and then kneaded for 3 minutes at the same temperature to obtain a colored thermoplastic resin. The evaluation results of the pigment dispersibility are shown in Table 8.
（比較例２〜６）
顔料、顔料分散剤の種類を表８のように変えた以外は、比較例１と同様にして着色熱可塑性樹脂を得た。顔料分散性の評価結果を表８に示した。
(Comparative Examples 2-6)
A colored thermoplastic resin was obtained in the same manner as in Comparative Example 1 except that the types of pigment and pigment dispersant were changed as shown in Table 8. The evaluation results of the pigment dispersibility are shown in Table 8.
（比較例７）
熱可塑性樹脂としてのポリプロピレン（ＰＰ）（メルトフローレート：３０ｇ／１０ｍｉｎ（２３０℃））のペレット１００質量部、顔料としてのカーボンブラック（Ｐｉｇｍｅｎｔ Ｂｌａｃｋ ７）０．６７質量部、及びステアリン酸Ｃａ０．０６７質量部を、ヘンシェルミキサーにて混合して、表面に顔料及び顔料分散剤が付着したポリプロピレン樹脂ペレットを作製した。得られたポリプロピレン樹脂ペレットを２軸ニーダーに投入し、２００℃で２分間溶融させ、その後同じ温度で１分間混練を行い、着色熱可塑性樹脂を得た。顔料分散性の評価結果を表９に示した。
(Comparative Example 7)
100 parts by mass of pellets of polypropylene (PP) (melt flow rate: 30 g / 10 min (230 ° C.)) as a thermoplastic resin, 0.67 parts by mass of carbon black (Pigment Black 7) as a pigment, and 0.067 of Ca stearate Mass parts were mixed with a Henschel mixer to produce polypropylene resin pellets having a pigment and a pigment dispersant attached to the surface. The obtained polypropylene resin pellets were put into a biaxial kneader, melted at 200 ° C. for 2 minutes, and then kneaded for 1 minute at the same temperature to obtain a colored thermoplastic resin. The evaluation results of the pigment dispersibility are shown in Table 9.
（比較例８〜９）
顔料の種類を表９のように変えた以外は、比較例７と同様にして着色熱可塑性樹脂を得た。顔料分散性の評価結果を表９に示した。
(Comparative Examples 8-9)
A colored thermoplastic resin was obtained in the same manner as in Comparative Example 7 except that the type of pigment was changed as shown in Table 9. The evaluation results of the pigment dispersibility are shown in Table 9.
（比較例１０）
顔料としてのカーボンブラック（Ｐｉｇｍｅｎｔ Ｂｌａｃｋ ７）９１質量部、及びステアリン酸Ｃａ９質量部を、水平円筒型混合機で混合し、粉末状の着色剤組成物を得た。
熱可塑性樹脂としてのポリプロピレン（ＰＰ）（メルトフローレート：３０ｇ／１０ｍｉｎ（２３０℃））のペレット１００質量部と、得られた粉末状の着色剤組成物０．７３６質量部とをヘンシェルミキサーにて混合し、表面に顔料及び顔料分散剤が付着したポリプロピレン樹脂ペレットを作製した。得られたポリプロピレン樹脂ペレットを２軸ニーダーに投入し、２００℃で２分間溶融させ、その後同じ温度で１分間混練を行い、着色熱可塑性樹脂を得た。顔料分散性の評価結果を表１０に示した。
(Comparative Example 10)
91 parts by mass of carbon black (Pigment Black 7) as a pigment and 9 parts by mass of Ca stearate were mixed with a horizontal cylindrical mixer to obtain a powdery colorant composition.
In a Henschel mixer, 100 parts by mass of a pellet of polypropylene (PP) (melt flow rate: 30 g / 10 min (230 ° C.)) as a thermoplastic resin and 0.736 parts by mass of the obtained powdery colorant composition Mixing was performed to prepare polypropylene resin pellets having pigments and pigment dispersants attached to the surface. The obtained polypropylene resin pellets were put into a biaxial kneader, melted at 200 ° C. for 2 minutes, and then kneaded for 1 minute at the same temperature to obtain a colored thermoplastic resin. The evaluation results of pigment dispersibility are shown in Table 10.
（比較例１１〜１２）
顔料の種類を表１０のように変えた以外は、比較例１０と同様にして着色熱可塑性樹脂を得た。顔料分散性の評価結果を表１０に示した。
(Comparative Examples 11-12)
A colored thermoplastic resin was obtained in the same manner as in Comparative Example 10 except that the pigment type was changed as shown in Table 10. The evaluation results of pigment dispersibility are shown in Table 10.
Claims (5)
（式［１］中、Ｒ１及びＲ２は同一であっても異なっていてもよく、直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２のアリールアルキル基、あるいはこれらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基を表す。）
（式［２］中、Ｒ３は直鎖若しくは分岐鎖状の炭素数２〜２２のアルキル基、炭素数３〜２２のアルケニル基、炭素数６〜２２のアリール基又は炭素数７〜２２のアリールアルキル基、あるいはこれらの基のいずれかが繰り返し数２〜３０のポリオキシアルキレン基の末端に結合した基を表す。）
（式［３］中、Ｒ４は水素原子、直鎖若しくは分岐鎖状の炭素数１〜６のアルキル基、炭素数２〜６のアルケニル基、炭素数７〜１３のアリールアルキル基、又は金属イオン若しくは置換基を有していてもよいアンモニウムイオンを表し、ｎは１〜３の整数を示す。） A salt of a sulfosuccinic acid ester represented by the following formula [1] or the following formula [2] and a monovalent metal ion or an ammonium ion optionally having a substituent, and the following formula [3] A pigment dispersant composition comprising a carbonyl group-containing aromatic compound.
(In the formula [1], R 1 and R 2 may be the same or different and are linear or branched alkyl groups having 2 to 22 carbon atoms, alkenyl groups having 3 to 22 carbon atoms, carbon The aryl group having 6 to 22 or the arylalkyl group having 7 to 22 carbon atoms, or a group in which any one of these groups is bonded to the terminal of the polyoxyalkylene group having 2 to 30 repeating units.
(In the formula [2], R 3 represents a linear or branched alkyl group having 2 to 22 carbon atoms, an alkenyl group having 3 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, or 7 to 22 carbon atoms. An arylalkyl group or a group in which any of these groups is bonded to the end of a polyoxyalkylene group having 2 to 30 repeats.
(In the formula [3], R 4 represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group having 7 to 13 carbon atoms, or a metal. Represents an ammonium ion which may have an ion or a substituent, and n represents an integer of 1 to 3.)
前記カルボニル基含有芳香族化合物と、
を１：０．０５〜１：１の質量比で含む請求項１記載の顔料分散剤組成物。 A salt of the sulfosuccinic acid ester and a monovalent metal ion or an ammonium ion optionally having a substituent;
The carbonyl group-containing aromatic compound;
The pigment dispersant composition according to claim 1, comprising a mass ratio of 1: 0.05 to 1: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010035284A JP2011168724A (en) | 2010-02-19 | 2010-02-19 | Pigment dispersant composition, colorant composition and method for producing colored thermoplastic resin |
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| JP2010035284A JP2011168724A (en) | 2010-02-19 | 2010-02-19 | Pigment dispersant composition, colorant composition and method for producing colored thermoplastic resin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024166690A1 (en) * | 2023-02-07 | 2024-08-15 | Dic株式会社 | Pigment composition and production method for pigment composition |
| JP7805425B1 (en) * | 2024-10-25 | 2026-01-23 | 大日精化工業株式会社 | resin molded products |
-
2010
- 2010-02-19 JP JP2010035284A patent/JP2011168724A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024166690A1 (en) * | 2023-02-07 | 2024-08-15 | Dic株式会社 | Pigment composition and production method for pigment composition |
| JPWO2024166690A1 (en) * | 2023-02-07 | 2024-08-15 | ||
| JP7697595B2 (en) | 2023-02-07 | 2025-06-24 | Dic株式会社 | Pigment composition and method for producing the same |
| JP7805425B1 (en) * | 2024-10-25 | 2026-01-23 | 大日精化工業株式会社 | resin molded products |
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