CA2465291A1 - Pigment compositions with modified atrp copolymer dispersants - Google Patents
Pigment compositions with modified atrp copolymer dispersants Download PDFInfo
- Publication number
- CA2465291A1 CA2465291A1 CA002465291A CA2465291A CA2465291A1 CA 2465291 A1 CA2465291 A1 CA 2465291A1 CA 002465291 A CA002465291 A CA 002465291A CA 2465291 A CA2465291 A CA 2465291A CA 2465291 A1 CA2465291 A1 CA 2465291A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- acid
- c4alkyl
- esters
- substituted
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 239000000049 pigment Substances 0.000 title claims abstract description 69
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 24
- 229920001577 copolymer Polymers 0.000 title claims description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 229920001400 block copolymer Polymers 0.000 claims abstract description 34
- 239000008199 coating composition Substances 0.000 claims abstract description 22
- 239000000976 ink Substances 0.000 claims abstract description 10
- 238000012546 transfer Methods 0.000 claims abstract description 10
- 239000012860 organic pigment Substances 0.000 claims abstract description 9
- 239000001023 inorganic pigment Substances 0.000 claims abstract description 8
- 239000004922 lacquer Substances 0.000 claims abstract description 4
- -1 sulphonic acid ester Chemical class 0.000 claims description 98
- 229920000642 polymer Polymers 0.000 claims description 90
- 239000003999 initiator Substances 0.000 claims description 74
- 239000000178 monomer Substances 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 56
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 53
- 150000002148 esters Chemical class 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- 239000006185 dispersion Substances 0.000 claims description 38
- 125000002950 monocyclic group Chemical group 0.000 claims description 35
- 125000003367 polycyclic group Chemical group 0.000 claims description 32
- 235000013350 formula milk Nutrition 0.000 claims description 25
- 239000011230 binding agent Substances 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 239000000654 additive Substances 0.000 claims description 20
- 150000004820 halides Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 15
- 125000004185 ester group Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 150000003009 phosphonic acids Chemical class 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 150000003440 styrenes Chemical class 0.000 claims description 12
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 239000012634 fragment Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000006096 absorbing agent Substances 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 108010069898 fibrinogen fragment X Proteins 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 7
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical group C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 6
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical group C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 5
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004611 light stabiliser Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 238000010669 acid-base reaction Methods 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000006229 carbon black Chemical group 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical group [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- 239000010439 graphite Chemical group 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 150000004760 silicates Chemical class 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical group [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 claims description 2
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 2
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 claims description 2
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims description 2
- GQWAOUOHRMHSHL-UHFFFAOYSA-N 4-ethenyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C=C)C=C1 GQWAOUOHRMHSHL-UHFFFAOYSA-N 0.000 claims description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005083 Zinc sulfide Substances 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002521 alkyl halide group Chemical group 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical group [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 claims description 2
- 150000001716 carbazoles Chemical class 0.000 claims description 2
- 239000004568 cement Substances 0.000 claims description 2
- 239000004035 construction material Substances 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 239000013078 crystal Chemical group 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 claims description 2
- 229940097275 indigo Drugs 0.000 claims description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 2
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical class C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical group 0.000 claims description 2
- 239000011505 plaster Substances 0.000 claims description 2
- 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 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical group [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 claims description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims description 2
- 235000010215 titanium dioxide Nutrition 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 2
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- QSRGACHICDDOHY-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C(=O)N)C.CN(C)CCCC=C(C(=O)N)C QSRGACHICDDOHY-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 150000002979 perylenes Chemical class 0.000 claims 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims 1
- 239000000306 component Substances 0.000 description 32
- 238000009740 moulding (composite fabrication) Methods 0.000 description 32
- 238000000576 coating method Methods 0.000 description 24
- 239000003973 paint Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 11
- 229940048053 acrylate Drugs 0.000 description 11
- 230000000875 corresponding effect Effects 0.000 description 11
- 239000003446 ligand Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 229960005419 nitrogen Drugs 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229910052723 transition metal Inorganic materials 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 8
- 229940043232 butyl acetate Drugs 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003624 transition metals Chemical class 0.000 description 8
- 229920000877 Melamine resin Polymers 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 238000000227 grinding Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 description 6
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
- 229940117913 acrylamide Drugs 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
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- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical group [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 1
- ZJFPXDGPJMHQMW-UHFFFAOYSA-N n,n'-bis[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(=O)NCCCN(C)C ZJFPXDGPJMHQMW-UHFFFAOYSA-N 0.000 description 1
- KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical class 0.000 description 1
- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AYEFIAVHMUFQPZ-UHFFFAOYSA-N propane-1,2-diol;prop-2-enoic acid Chemical compound CC(O)CO.OC(=O)C=C AYEFIAVHMUFQPZ-UHFFFAOYSA-N 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 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 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 125000001174 sulfone group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- SXXSKPVWWYLLQG-UHFFFAOYSA-N trimethyl-[2-methyl-1-(2-methylpropoxy)prop-1-enoxy]silane Chemical compound CC(C)COC(=C(C)C)O[Si](C)(C)C SXXSKPVWWYLLQG-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
- C09B3/10—Amino derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01811158.3 | 2001-11-29 | ||
| EP01811158 | 2001-11-29 | ||
| PCT/EP2002/013064 WO2003046029A1 (en) | 2001-11-29 | 2002-11-21 | Pigment compositions with modified atrp copolymer dispersants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2465291A1 true CA2465291A1 (en) | 2003-06-05 |
Family
ID=8184277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002465291A Abandoned CA2465291A1 (en) | 2001-11-29 | 2002-11-21 | Pigment compositions with modified atrp copolymer dispersants |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20050004317A1 (enExample) |
| EP (1) | EP1465935B1 (enExample) |
| JP (1) | JP4541702B2 (enExample) |
| KR (1) | KR100918576B1 (enExample) |
| CN (1) | CN100408606C (enExample) |
| AU (1) | AU2002352086A1 (enExample) |
| BR (1) | BR0214616B1 (enExample) |
| CA (1) | CA2465291A1 (enExample) |
| MX (1) | MXPA04004693A (enExample) |
| TW (1) | TW200407363A (enExample) |
| WO (1) | WO2003046029A1 (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1802409A (zh) * | 2003-04-08 | 2006-07-12 | 西巴特殊化学品控股有限公司 | 颜料分散体中的光稳定聚合物分散剂 |
| JP2006526678A (ja) * | 2003-06-03 | 2006-11-24 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 放射線硬化性コーティングにおいて用いるための顔料濃厚物の製造方法 |
| TW200604223A (en) * | 2004-01-19 | 2006-02-01 | Dainichiseika Color Chem | Graft copolymers having excellent pigment-dispersing ability, production process of the graft copolymers, production method of emulsions by use of the graft copolymers, and pigment dispersions making use of the graft copolymers or emulsions |
| US7402624B2 (en) | 2004-11-08 | 2008-07-22 | E.I. Du Pont De Nemours & Company | Graft copolymers with segmented arms and their preparation and use |
| JP2006167674A (ja) * | 2004-12-20 | 2006-06-29 | Toyo Ink Mfg Co Ltd | 顔料分散剤 |
| FR2885367B1 (fr) * | 2005-05-03 | 2007-07-27 | Rhodia Chimie Sa | Organosol stabilise par des polymeres sequences amphiphiles |
| TW200730547A (en) * | 2006-01-03 | 2007-08-16 | Byk Chemie Gmbh | Copolymers comprising three segments of different ion density, processes for preparing them and use thereof |
| CN101421360A (zh) * | 2006-04-11 | 2009-04-29 | 西巴控股有限公司 | 制造金属氧化物薄片的方法 |
| CN101426861B (zh) * | 2006-04-21 | 2011-12-28 | 日本板硝子株式会社 | 光辉性颜料及其制造方法以及含有该光辉性颜料的水性树脂组合物 |
| EP2038701B1 (en) | 2006-07-06 | 2017-04-12 | Basf Se | Encapsulated dispersions comprising electrophoretically mobile organic colorants |
| EP2038704B9 (en) * | 2006-07-11 | 2019-03-27 | Basf Se | Color filter composition |
| DE102006035726A1 (de) * | 2006-07-28 | 2008-01-31 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren auf (Meth)acrylatbasis |
| JP5123189B2 (ja) * | 2006-08-29 | 2013-01-16 | 日本板硝子株式会社 | 真珠光沢顔料 |
| DE102006048144A1 (de) * | 2006-10-10 | 2008-04-17 | Byk-Chemie Gmbh | Netz- und Dispergiermittel basierend auf Mischungen von strukturierten Copolymeren |
| DE102006062441A1 (de) | 2006-12-27 | 2008-07-03 | Byk-Chemie Gmbh | Modifizierte Kammcopolymere |
| US8519026B2 (en) * | 2006-12-28 | 2013-08-27 | Nuplex Resins B.V. | Waterborne polymeric dispersions |
| CN101675120B (zh) * | 2007-04-18 | 2012-12-05 | 日本板硝子株式会社 | 光辉性颜料以及使用了该颜料的化妆用组合物 |
| US20080264303A1 (en) | 2007-04-24 | 2008-10-30 | The Diller Corporation | Solid surface product containing oriented reflective particles and method of making same |
| WO2008136471A1 (ja) * | 2007-04-27 | 2008-11-13 | Nippon Sheet Glass Company, Limited | 光輝性顔料と、それを含有する光輝性塗料組成物および自動車外板コート物 |
| ZA200804693B (en) * | 2007-05-30 | 2009-02-25 | Oreal | Cosmetic hair compositions containing metal-oxide layered pigments and functionalized metal-oxide layered pigments and methods of use |
| JP5479343B2 (ja) | 2007-09-07 | 2014-04-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 電気泳動型移動性有機着色剤を含むカプセル化分散液 |
| CN101827898B (zh) * | 2007-10-18 | 2013-03-27 | 日本板硝子株式会社 | 发光性颜料 |
| JP5104478B2 (ja) * | 2008-03-31 | 2012-12-19 | 大日本印刷株式会社 | ナノ微粒子複合体の製造方法 |
| JP5374903B2 (ja) * | 2008-03-31 | 2013-12-25 | 大日本印刷株式会社 | カラーフィルタ用ネガ型レジスト組成物、カラーフィルタ及び液晶表示装置 |
| US8664324B2 (en) | 2008-06-23 | 2014-03-04 | Basf Se | Pigment dispersants with modified copolymers |
| US20090137172A1 (en) * | 2008-12-04 | 2009-05-28 | Lei Huang | Colorant media and articles having photo-stable and surface-functionalizable colorant particles |
| WO2010089295A1 (de) * | 2009-02-03 | 2010-08-12 | Bühler PARTEC GmbH | Mit phosphonocarbonsäure modifizierte zinkoxid-partikel und verwendung von zinkoxid-partikeln |
| EP2241602A1 (de) * | 2009-04-17 | 2010-10-20 | Bühler PARTEC GmbH | Mit Phosphonocarbonsäure modifizierte Zinkoxid-Partikel und Verwendung von Zinkoxid-Partikeln |
| ES2423054T3 (es) | 2009-03-25 | 2013-09-17 | Byk-Chemie Gmbh | Composición que comprende mezclas estables de polioles |
| JP5463712B2 (ja) * | 2009-03-31 | 2014-04-09 | 大日本印刷株式会社 | カラーフィルタ用顔料分散液及びその製造方法、カラーフィルタ用ネガ型レジスト組成物及びその製造方法、カラーフィルタ、並びに、液晶表示装置 |
| US8753708B2 (en) * | 2009-09-02 | 2014-06-17 | Cardiac Pacemakers, Inc. | Solventless method for forming a coating on a medical electrical lead body |
| EP2516495B1 (de) | 2009-12-22 | 2015-07-29 | BYK-Chemie GmbH | Zusammensetzung umfassend stabile polyolmischungen |
| CN103080248B (zh) * | 2010-09-27 | 2014-12-24 | 巴斯夫应用化工有限公司 | 水性白色色浆及其制备方法 |
| DE102011014250A1 (de) * | 2011-03-17 | 2012-09-20 | Clariant International Ltd. | Pulverlackzusammensetzung zum Strukturieren und Texturieren von Lackoberflächen |
| JP5779072B2 (ja) * | 2011-10-20 | 2015-09-16 | 理想科学工業株式会社 | 非水系顔料インク及び非水系顔料インク用顔料分散剤 |
| KR101127959B1 (ko) | 2011-11-18 | 2012-04-04 | (재)한국섬유소재연구소 | 분산제 및 그 제조방법 |
| EP2817358B1 (en) | 2012-02-24 | 2019-08-21 | Basf Se | Novel polymer dispersants |
| WO2013191707A1 (en) * | 2012-06-22 | 2013-12-27 | Hewlett-Packard Development Company, L.P. | Inks including colorant particles with covalently attached dispersants |
| CN103205202A (zh) * | 2013-04-03 | 2013-07-17 | 中山职业技术学院 | 一种表面张力梯度性变化的梯度功能涂料及其制备方法 |
| JP2016523290A (ja) | 2013-06-07 | 2016-08-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 新規のポリマー分散剤 |
| JP2016525154A (ja) | 2013-06-24 | 2016-08-22 | ベーイプシロンカー ヘミー ゲゼルシャフト ミット ベシュレンクター ハフトゥング | 接着強化添加剤およびそれを含むコーティング組成物 |
| EP3024874B1 (en) | 2013-07-22 | 2017-09-06 | Basf Se | Novel polymers and use of these as dispersants |
| EP3052701B1 (en) * | 2013-10-04 | 2017-06-28 | Basf Se | High gloss metal effect papers |
| CN103924459A (zh) * | 2014-04-30 | 2014-07-16 | 江南大学 | 用于纺织品涂料染色的双亲性核壳乳液粘合剂及其制备方法 |
| TWI516520B (zh) | 2014-10-31 | 2016-01-11 | 財團法人工業技術研究院 | 波長轉換聚合物、其製法及包含其之波長轉換裝置 |
| WO2016071386A1 (en) | 2014-11-05 | 2016-05-12 | Basf Se | Novel polymer compositions and use of these polymer compositions as dispersants |
| MX2019008010A (es) | 2017-01-03 | 2019-08-29 | Byk Chemie Gmbh | Copolimeros (met)acrilicos como aditivos reologicos en fluidos de perforacion y fluidos de perforacion que comprenden dichos copolimeros. |
| WO2020035300A1 (en) | 2018-08-16 | 2020-02-20 | Basf Se | Polymer composition |
| US12365762B2 (en) | 2018-08-16 | 2025-07-22 | Basf Se | Dispersant for coating system |
| MX2021002384A (es) | 2018-08-29 | 2021-04-29 | Basf Coatings Gmbh | Dispersante de pigmentos. |
| WO2021009351A1 (en) | 2019-07-18 | 2021-01-21 | Basf Se | Allophanate based dispersing agent |
| CN111039270B (zh) * | 2019-12-27 | 2021-10-08 | 天津科技大学 | 一种花状磷酸锌纳米颗粒抑菌材料及其制备方法与用途 |
| CN114369212B (zh) * | 2021-12-10 | 2024-06-28 | 复旦大学 | 颜料用高分子分散剂及其一锅多步合成方法和应用 |
| EP4457261A1 (en) | 2021-12-28 | 2024-11-06 | BASF Coatings GmbH | Dispersant |
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| US4656226A (en) * | 1985-09-30 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Acrylic pigment dispersants made by group transfer polymerization |
| DE3875105T2 (de) * | 1988-02-23 | 1993-03-18 | Du Pont | Blockmischpolymerisat-dispergiermittel. |
| US5763548A (en) * | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5859113A (en) * | 1997-07-17 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Pigment dispersions containing hydroxylated AB-block polymer dispersant |
| US6265489B1 (en) * | 1998-08-31 | 2001-07-24 | Ppg Industries Ohio, Inc. | Thermosetting compositions containing carboxylic acid functional polymers prepared by atom transfer radical polymerization |
| CN1333790A (zh) * | 1998-12-31 | 2002-01-30 | 西巴特殊化学品控股有限公司 | 含atrp聚合物的颜料组合物 |
| FR2791987A1 (fr) * | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| FR2791989A1 (fr) * | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| US6462125B1 (en) * | 1999-12-16 | 2002-10-08 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants prepared by controlled radical polymerization having hydrophilic and hydrophobic segments |
| US6376597B1 (en) * | 1999-12-16 | 2002-04-23 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants having pendent hydrophilic polymeric segments prepared by controlled radical polymerization |
| EP1254185A1 (en) * | 2000-01-11 | 2002-11-06 | Ciba SC Holding AG | Comb polymers from atrp macromonomers |
| AU6744401A (en) * | 2000-05-31 | 2001-12-11 | Creavis Gesellschaft Fur Technologie Und Innovation Mbh | Polymerically micro-encapsulated pigments |
| US6849679B2 (en) * | 2001-05-21 | 2005-02-01 | Ciba Specialty Chemicals Corporation | Pigment compositions with modified block copolymer dispersants |
-
2002
- 2002-11-13 TW TW091133302A patent/TW200407363A/zh unknown
- 2002-11-21 CN CNB028237803A patent/CN100408606C/zh not_active Expired - Lifetime
- 2002-11-21 AU AU2002352086A patent/AU2002352086A1/en not_active Abandoned
- 2002-11-21 US US10/495,519 patent/US20050004317A1/en not_active Abandoned
- 2002-11-21 CA CA002465291A patent/CA2465291A1/en not_active Abandoned
- 2002-11-21 MX MXPA04004693A patent/MXPA04004693A/es unknown
- 2002-11-21 WO PCT/EP2002/013064 patent/WO2003046029A1/en not_active Ceased
- 2002-11-21 BR BRPI0214616-9A patent/BR0214616B1/pt not_active IP Right Cessation
- 2002-11-21 EP EP02787760.4A patent/EP1465935B1/en not_active Expired - Lifetime
- 2002-11-21 KR KR1020047008249A patent/KR100918576B1/ko not_active Expired - Fee Related
- 2002-11-21 JP JP2003547476A patent/JP4541702B2/ja not_active Expired - Fee Related
-
2006
- 2006-03-21 US US11/387,020 patent/US7723425B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1465935B1 (en) | 2016-09-07 |
| BR0214616B1 (pt) | 2012-08-07 |
| US20060160950A1 (en) | 2006-07-20 |
| US7723425B2 (en) | 2010-05-25 |
| US20050004317A1 (en) | 2005-01-06 |
| CN100408606C (zh) | 2008-08-06 |
| CN1639216A (zh) | 2005-07-13 |
| KR20040070197A (ko) | 2004-08-06 |
| JP4541702B2 (ja) | 2010-09-08 |
| WO2003046029A1 (en) | 2003-06-05 |
| KR100918576B1 (ko) | 2009-09-24 |
| AU2002352086A1 (en) | 2003-06-10 |
| EP1465935A1 (en) | 2004-10-13 |
| TW200407363A (en) | 2004-05-16 |
| MXPA04004693A (es) | 2004-08-19 |
| BR0214616A (pt) | 2004-09-14 |
| JP2005510595A (ja) | 2005-04-21 |
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