CA1080907A - Compositions pigmentaires - Google Patents

Compositions pigmentaires

Info

Publication number: CA1080907A
Authority: CA; Canada
Prior art keywords: parts; phthalocyanine; pigment; formula; groups
Prior art date: 1975-09-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA260,622A

Other languages

English (en)

Inventor

Ian R. Wheeler

George H. Robertson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1975-09-09

Filing date

1976-09-07

Publication date

1980-07-08

1975-09-09 Priority claimed from GB37106/75A external-priority patent/GB1501184A/en

1976-05-07 Priority claimed from GB1873676A external-priority patent/GB1541599A/en

1976-09-07 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1980-07-08 Application granted granted Critical

1980-07-08 Publication of CA1080907A publication Critical patent/CA1080907A/fr

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title claims abstract description 92
239000000203 mixture Substances 0.000 title claims abstract description 65
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 claims abstract description 47
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
125000003118 aryl group Chemical group 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 11
150000003512 tertiary amines Chemical class 0.000 claims abstract description 9
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 8
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 claims abstract description 7
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000002015 acyclic group Chemical group 0.000 claims abstract description 6
125000000129 anionic group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000002091 cationic group Chemical group 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
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 claims description 26
239000000975 dye Substances 0.000 claims description 20
-1 urethane compound Chemical class 0.000 claims description 17
125000003277 amino group Chemical group 0.000 claims description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
229910006069 SO3H Inorganic materials 0.000 claims 1
239000003973 paint Substances 0.000 abstract description 35
239000000976 ink Substances 0.000 abstract description 29
239000000047 product Substances 0.000 description 64
239000006185 dispersion Substances 0.000 description 42
235000013350 formula milk Nutrition 0.000 description 41
150000001875 compounds Chemical class 0.000 description 39
238000000034 method Methods 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 21
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 20
150000001412 amines Chemical class 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
229960004592 isopropanol Drugs 0.000 description 16
206010001497 Agitation Diseases 0.000 description 14
238000013019 agitation Methods 0.000 description 14
239000012530 fluid Substances 0.000 description 14
150000003839 salts Chemical class 0.000 description 13
JVTCNOASZYIKTG-UHFFFAOYSA-N stk329495 Chemical compound [Cu].[N-]1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)[N-]3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 JVTCNOASZYIKTG-UHFFFAOYSA-N 0.000 description 13
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
208000012641 Pigmentation disease Diseases 0.000 description 12
230000019612 pigmentation Effects 0.000 description 12
239000002002 slurry Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 11
239000011230 binding agent Substances 0.000 description 10
230000007935 neutral effect Effects 0.000 description 10
239000002966 varnish Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000020 Nitrocellulose Substances 0.000 description 8
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 8
238000007792 addition Methods 0.000 description 8
238000000498 ball milling Methods 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229940079938 nitrocellulose Drugs 0.000 description 8
238000003756 stirring Methods 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 7
238000001035 drying Methods 0.000 description 7
229920001220 nitrocellulos Polymers 0.000 description 7
239000000843 powder Substances 0.000 description 7
229920005989 resin Polymers 0.000 description 7
239000011347 resin Substances 0.000 description 7
239000003760 tallow Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
229920000180 alkyd Polymers 0.000 description 6
239000001055 blue pigment Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000009775 high-speed stirring Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
238000003801 milling Methods 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
239000004925 Acrylic resin Substances 0.000 description 4
229920000178 Acrylic resin Polymers 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
241001510071 Pyrrhocoridae Species 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
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 4
239000000839 emulsion Substances 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
230000009974 thixotropic effect Effects 0.000 description 4
238000005406 washing Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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 3
239000011324 bead Substances 0.000 description 3
VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
238000005189 flocculation Methods 0.000 description 3
230000016615 flocculation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
229920001983 poloxamer Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
235000012424 soybean oil Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003673 urethanes Chemical class 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
206010013647 Drowning Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
150000001804 chlorine Chemical class 0.000 description 2
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
229960000443 hydrochloric acid Drugs 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000005011 phenolic resin Substances 0.000 description 2
229920001568 phenolic resin Polymers 0.000 description 2
125000000565 sulfonamide group Chemical group 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
101100099490 Alkalihalobacillus halodurans (strain ATCC BAA-125 / DSM 18197 / FERM 7344 / JCM 9153 / C-125) thiY gene Proteins 0.000 description 1
101100256368 Arabidopsis thaliana SBP3 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical group [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
BFAQRUGPWJVQDA-WFBUOHSLSA-N [(1r,4as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine;acetic acid Chemical compound CC(O)=O.NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 BFAQRUGPWJVQDA-WFBUOHSLSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical group 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
DWPDSISGRAWLLV-JHZYRPMRSA-L calcium;(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Ca+2].C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O.C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O DWPDSISGRAWLLV-JHZYRPMRSA-L 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
239000001056 green pigment Substances 0.000 description 1
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 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
UWHRNIXHZAWBMF-UHFFFAOYSA-N n-dodecyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCCCCCCCCCCC UWHRNIXHZAWBMF-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 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
239000002245 particle Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
230000000485 pigmenting effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical class O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
241000894007 species Species 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
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
239000010698 whale oil Substances 0.000 description 1
239000002023 wood Substances 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Compositions Of Macromolecular Compounds (AREA)
Paints Or Removers (AREA)
Coloring (AREA)

CA260,622A 1975-09-09 1976-09-07 Compositions pigmentaires Expired CA1080907A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB37106/75A GB1501184A (en)	1975-09-09	1975-09-09	Phthalocyanine pigment composition
GB1873676A GB1541599A (en)	1976-05-07	1976-05-07	Pigment composition

Publications (1)

Publication Number	Publication Date
CA1080907A true CA1080907A (fr)	1980-07-08

Family

ID=26253579

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA260,622A Expired CA1080907A (fr)	1975-09-09	1976-09-07	Compositions pigmentaires

Country Status (6)

Country	Link
JP (1)	JPS6059264B2 (fr)
CA (1)	CA1080907A (fr)
CH (1)	CH623348A5 (fr)
DE (1)	DE2640063A1 (fr)
DK (1)	DK403976A (fr)
FR (1)	FR2355885A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1575562A (en) *	1977-03-19	1980-09-24	Ciba Geigy Ag	Pigment composition
US4522654A (en) *	1983-12-23	1985-06-11	Inmont Corporation	Continuous method of producing phthalocyanine pigment dispersions in organic solvent
JPH01284867A (ja) *	1988-05-11	1989-11-16	Sharp Corp	電子写真プリンター装置
CH685162A5 (de) *	1991-05-07	1995-04-13	Ciba Geigy Ag	Pigmentzusammensetzungen.
JP2836320B2 (ja) *	1991-10-04	1998-12-14	東洋インキ製造株式会社	塗料組成物
JP3132231B2 (ja) *	1993-04-23	2001-02-05	東洋インキ製造株式会社	顔料組成物および印刷インキもしくは塗料組成物
AU3386195A (en) *	1995-08-18	1997-03-12	Bayer Aktiengesellschaft	Microbicidal formulations
JPH08240945A (ja) *	1996-01-23	1996-09-17	Sanyo Electric Co Ltd	Ｌｅｄプリンタ
CN1281490A (zh) *	1997-12-09	2001-01-24	日本化药株式会社	新的盐类及含有该盐类的光敏性着色树脂组合物
DE102008026584A1 (de) *	2008-06-03	2009-12-10	Clariant International Limited	Verbessertes Cyanfarbmittel
WO2019124050A1 (fr) *	2017-12-22	2019-06-27	Dic株式会社	Composition de pigment phtalocyanine de cuivre et composition d'encre la contenant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4057436A (en) *	1974-09-17	1977-11-08	Imperial Chemical Industries Limited	Dispersion of solids in organic solvents
DE3111052C2 (de) *	1981-03-20	1985-03-07	Ciba-Geigy GmbH, 7867 Wehr	Distanzfolie für den Formen- und Modellbau sowie ihre Verwendung
JPS5916580A (ja) *	1982-07-17	1984-01-27	コンピユ−タ−サ−ビス株式会社	選別装置の通口遮蔽機構

1976
- 1976-09-06 DE DE19762640063 patent/DE2640063A1/de not_active Ceased
- 1976-09-07 CA CA260,622A patent/CA1080907A/fr not_active Expired
- 1976-09-07 CH CH1132876A patent/CH623348A5/de not_active IP Right Cessation
- 1976-09-08 DK DK403976A patent/DK403976A/da not_active Application Discontinuation
- 1976-09-09 FR FR7627101A patent/FR2355885A1/fr active Granted
- 1976-09-09 JP JP51108376A patent/JPS6059264B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2640063A1 (de)	1977-03-17
JPS5233922A (en)	1977-03-15
FR2355885B1 (fr)	1980-10-03
FR2355885A1 (fr)	1978-01-20
JPS6059264B2 (ja)	1985-12-24
CH623348A5 (en)	1981-05-29
DK403976A (da)	1977-03-10

Legal Events

Date	Code	Title	Description
1997-07-08	MKEX	Expiry

Publication	Publication Date	Title
US7077899B2 (en)	2006-07-18	Pigment dispersing agent, pigment composition containing the same and pigment dispersion containing the same
CN1326951C (zh)	2007-07-18	酞菁颜料制剂
US2861005A (en)	1958-11-18	Phthalocyanine pigments
GB2071683A (en)	1981-09-23	Pigment compositions
GB2173812A (en)	1986-10-22	Triazine dyes and pigments for use as pigment dispersants
US4576649A (en)	1986-03-18	Color enhanced permanent pigments from precipitated cationic dyes
CA1073880A (fr)	1980-03-18	Preparation de pigments de phthalocyanine de type a dispersion amelioree
US3764360A (en)	1973-10-09	Process for preparing phthalocyanine pigments
US5024698A (en)	1991-06-18	Monoazo pigment compositions
AU750476B2 (en)	2002-07-18	Production process of copper phthalocyanine in the beta modification
EP0761770B1 (fr)	2000-10-18	Compositions pigmentaires
JPS63305173A (ja)	1988-12-13	顔料分散剤
US4055440A (en)	1977-10-25	Pigment compositions
CN101932659B (zh)	2013-10-16	改进的青色着色剂
US4133695A (en)	1979-01-09	Pigment composition
US3891455A (en)	1975-06-24	Phythlocyanine pigments
JPS6059264B2 (ja)	1985-12-24	フタロシアニン顔料を含有する顔料組成物
US4194921A (en)	1980-03-25	Pigment compositions and process for dust free pigment beads
CA1089450A (fr)	1980-11-11	Traitement de pigments de phtalocyanine
CA2429011C (fr)	2010-01-26	Traitement de pigments haute performance a l'aide de sels dispersant l'etheramine
US4199509A (en)	1980-04-22	Copper phthalocyanine derivatives
US4278601A (en)	1981-07-14	Process for conditioning phthalocyanine pigment
US2823205A (en)	1958-02-11	Oil and spirit-soluble derivatives of phthalocyanines
JPH10245502A (ja)	1998-09-14	顔料組成物およびその製造方法
JPH06336557A (ja)	1994-12-06	顔料組成物及び塗料