ZA200305149B - Single-phase mixed crystals of laked monoazo dyes. - Google Patents

Single-phase mixed crystals of laked monoazo dyes. Download PDF

Info

Publication number: ZA200305149B
Authority: ZA; South Africa
Prior art keywords: pigment; sub; formula; methyl; chlorine
Prior art date: 2001-01-24

Application number

ZA200305149A

Other languages

English (en)

Inventor

Philippe Bugnon

Caroline Sansonnens

Greig Chisholm

Original Assignee

Ciba Sc Holding 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.)

2001-01-24

Filing date

2003-07-02

Publication date

2004-04-20

2003-07-02 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

2004-04-20 Publication of ZA200305149B publication Critical patent/ZA200305149B/en

Links

239000013078 crystal Substances 0.000 title claims abstract description 25
239000000975 dye Substances 0.000 title abstract description 8
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 title abstract description 6
239000000049 pigment Substances 0.000 claims abstract description 68
-1 alkaline earth metal cations Chemical class 0.000 claims abstract description 37
238000000034 method Methods 0.000 claims abstract description 31
230000008569 process Effects 0.000 claims abstract description 16
150000001768 cations Chemical class 0.000 claims abstract description 15
238000002425 crystallisation Methods 0.000 claims abstract description 13
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 12
229910052791 calcium Inorganic materials 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 5
229910052712 strontium Inorganic materials 0.000 claims abstract description 5
239000007788 liquid Substances 0.000 claims abstract description 4
229910052749 magnesium Inorganic materials 0.000 claims abstract 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
239000000460 chlorine Chemical group 0.000 claims description 17
229910052801 chlorine Chemical group 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 16
239000011368 organic material Substances 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
150000008054 sulfonate salts Chemical class 0.000 claims description 8
239000000725 suspension Substances 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
239000000463 material Substances 0.000 claims description 5
239000003495 polar organic solvent Substances 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 3
239000012065 filter cake Substances 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
238000006149 azo coupling reaction Methods 0.000 claims description 2
238000004040 coloring Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000012546 transfer Methods 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
239000010419 fine particle Substances 0.000 abstract description 3
239000000047 product Substances 0.000 description 22
239000012071 phase Substances 0.000 description 17
239000011575 calcium Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000001052 yellow pigment Substances 0.000 description 7
VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
159000000007 calcium salts Chemical class 0.000 description 6
238000000576 coating method Methods 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
238000001816 cooling Methods 0.000 description 5
FHXUYFKYRBLZJU-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(S(O)(=O)=O)=C1 FHXUYFKYRBLZJU-UHFFFAOYSA-N 0.000 description 4
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
229910001424 calcium ion Inorganic materials 0.000 description 4
239000000976 ink Substances 0.000 description 4
239000002245 particle Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000004014 plasticizer Substances 0.000 description 4
238000007639 printing Methods 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004594 Masterbatch (MB) Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
229920000180 alkyd Polymers 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229920000098 polyolefin Polymers 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 2
239000000020 Nitrocellulose Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000002605 large molecules Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229920001220 nitrocellulos Polymers 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000006069 physical mixture Substances 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
239000005060 rubber Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
MWSSFCQDYPYAMQ-UHFFFAOYSA-N 2,4-dichloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(Cl)C=C1Cl MWSSFCQDYPYAMQ-UHFFFAOYSA-N 0.000 description 1
KCEIVWKDBLAQKL-UHFFFAOYSA-N 2,5-dichloro-4-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl KCEIVWKDBLAQKL-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
DJOIZOKQHNHZPN-UHFFFAOYSA-N 2-amino-5-chloro-4-ethylbenzenesulfonic acid Chemical compound CCC1=CC(N)=C(S(O)(=O)=O)C=C1Cl DJOIZOKQHNHZPN-UHFFFAOYSA-N 0.000 description 1
AKLDPNVZTZIVFA-UHFFFAOYSA-N 2-azaniumyl-4,5-dichlorobenzenesulfonate Chemical compound NC1=CC(Cl)=C(Cl)C=C1S(O)(=O)=O AKLDPNVZTZIVFA-UHFFFAOYSA-N 0.000 description 1
MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
101100496858 Mus musculus Colec12 gene Proteins 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
239000001639 calcium acetate Substances 0.000 description 1
235000011092 calcium acetate Nutrition 0.000 description 1
229960005147 calcium acetate Drugs 0.000 description 1
229940061587 calcium behenate Drugs 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
SMBKCSPGKDEPFO-UHFFFAOYSA-L calcium;docosanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O SMBKCSPGKDEPFO-UHFFFAOYSA-L 0.000 description 1
238000003490 calendering Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
229920006218 cellulose propionate Polymers 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
238000012505 colouration Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910001437 manganese ion Inorganic materials 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000005445 natural material Substances 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
230000000485 pigmenting effect Effects 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920005613 synthetic organic polymer Polymers 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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
- 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
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
- 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Compositions Of Macromolecular Compounds (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paints Or Removers (AREA)
Thermal Transfer Or Thermal Recording In General (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Developing Agents For Electrophotography (AREA)
Coloring (AREA)
Glass Compositions (AREA)

ZA200305149A 2001-01-24 2003-07-02 Single-phase mixed crystals of laked monoazo dyes. ZA200305149B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1192001		2001-01-24

Publications (1)

Publication Number	Publication Date
ZA200305149B true ZA200305149B (en)	2004-04-20

Family

ID=4378166

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200305149A ZA200305149B (en)	2001-01-24	2003-07-02	Single-phase mixed crystals of laked monoazo dyes.

Country Status (14)

Country	Link
US (1)	US6913640B2 (ja)
EP (1)	EP1354007B1 (ja)
JP (1)	JP4245922B2 (ja)
KR (1)	KR100824927B1 (ja)
CN (1)	CN1230470C (ja)
AT (1)	ATE353938T1 (ja)
BR (1)	BR0206651A (ja)
CA (1)	CA2434407A1 (ja)
DE (1)	DE60218131T2 (ja)
MX (1)	MXPA03006518A (ja)
PL (1)	PL365025A1 (ja)
RU (1)	RU2003124074A (ja)
WO (1)	WO2002059217A1 (ja)
ZA (1)	ZA200305149B (ja)

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DE102007008218A1 (de) *	2007-02-20	2008-08-21	Clariant International Ltd.	Pigmentzusammensetzung auf Basis von C.I. Pigment Yellow 191
JP6211717B2 (ja) *	2014-09-30	2017-10-11	富士フイルム株式会社	アゾ色素の製造方法、有機アミン塩及びその製造方法、並びに、アゾ化合物及びその製造方法
CN104962101B (zh) *	2015-06-26	2017-08-29	嘉兴科隆化工有限公司	一种食品塑料包装用安全环保型红光黄颜料py191:1的工业化生产方法

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DE2616981C2 (de)	1976-04-17	1983-12-08	Basf Ag, 6700 Ludwigshafen	Pyrazolon-Azofarbstoffe ihre Herstellung und Verwendung
DE3133404A1 (de)	1981-08-24	1983-03-10	Basf Ag, 6700 Ludwigshafen	Sulfonsaeuregruppenhaltige verlackte azofarbstoffe
DE3318073A1 (de)	1983-05-18	1984-11-22	Basf Ag, 6700 Ludwigshafen	Pyrazolonazofarbstoffe
DE3543512A1 (de) *	1985-12-10	1987-06-11	Bayer Ag	Azofarblacke
DE3784362D1 (de) *	1986-03-10	1993-04-08	Ciba Geigy Ag	Neue aminsalze von azoverbindungen.
EP0263074B1 (de) *	1986-10-03	1994-03-02	Ciba-Geigy Ag	Mischkristalle aus verlackten Azofarbstoffen
DE3833226A1 (de)	1988-09-30	1990-04-05	Hoechst Ag	Monoazopigment, verfahren zu seiner herstellung und seine verwendung
GB9201951D0 (en) *	1992-01-30	1992-03-18	Ici Plc	Pigment
US5396970A (en) *	1992-10-09	1995-03-14	Tokyo R&D Co., Ltd.	Electromotive scooter
US6235100B1 (en)	1999-06-24	2001-05-22	Engelhard Corporation	Metallized azo yellow pigments

2002
- 2002-01-15 DE DE60218131T patent/DE60218131T2/de not_active Expired - Lifetime
- 2002-01-15 WO PCT/EP2002/000339 patent/WO2002059217A1/en active IP Right Grant
- 2002-01-15 PL PL02365025A patent/PL365025A1/xx unknown
- 2002-01-15 US US10/466,724 patent/US6913640B2/en not_active Expired - Lifetime
- 2002-01-15 KR KR1020037009834A patent/KR100824927B1/ko not_active Expired - Lifetime
- 2002-01-15 JP JP2002559507A patent/JP4245922B2/ja not_active Expired - Lifetime
- 2002-01-15 CA CA002434407A patent/CA2434407A1/en not_active Abandoned
- 2002-01-15 MX MXPA03006518A patent/MXPA03006518A/es unknown
- 2002-01-15 BR BR0206651-3A patent/BR0206651A/pt not_active Application Discontinuation
- 2002-01-15 AT AT02702270T patent/ATE353938T1/de not_active IP Right Cessation
- 2002-01-15 EP EP02702270A patent/EP1354007B1/en not_active Expired - Lifetime
- 2002-01-15 CN CNB028040821A patent/CN1230470C/zh not_active Expired - Lifetime
- 2002-01-15 RU RU2003124074/04A patent/RU2003124074A/ru not_active Application Discontinuation
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Also Published As

Publication number	Publication date
CN1487980A (zh)	2004-04-07
CA2434407A1 (en)	2002-08-01
EP1354007B1 (en)	2007-02-14
DE60218131D1 (de)	2007-03-29
US6913640B2 (en)	2005-07-05
KR20030072389A (ko)	2003-09-13
RU2003124074A (ru)	2005-03-10
DE60218131T2 (de)	2007-11-22
JP4245922B2 (ja)	2009-04-02
EP1354007A1 (en)	2003-10-22
JP2004534864A (ja)	2004-11-18
MXPA03006518A (es)	2003-09-22
US20040087781A1 (en)	2004-05-06
ATE353938T1 (de)	2007-03-15
WO2002059217A1 (en)	2002-08-01
PL365025A1 (en)	2004-12-27
BR0206651A (pt)	2004-02-25
CN1230470C (zh)	2005-12-07
KR100824927B1 (ko)	2008-04-28

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CA2545210A1 (en)	2005-06-02	Pigment compositions consisting of a yellow disazo pigment and an organic pigment
CZ20012449A3 (cs)	2002-03-13	Nové krystalové modifikace C. I. Pigment Yellow 191 a způsob jejich výroby
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US7387670B2 (en)	2008-06-17	Pigment preparations based on phthalocyanine pigments
EP1354007B1 (en)	2007-02-14	Single-phase mixed crystals of laked monoazo dyes
EP1387870B1 (en)	2005-11-23	New crystal modification of diketopyrrolpyrrole solid solution pigment
US6235100B1 (en)	2001-05-22	Metallized azo yellow pigments
AU2002235840A1 (en)	2002-08-06	Single-phase mixed crystals of laked monoazo dyes
US20040139880A1 (en)	2004-07-22	Laked monoazo pigments based on naphtholsulfonic acids
JP6698636B2 (ja)	2020-05-27	Ｃ．Ｉ．ＰｉｇｍｅｎｔＹｅｌｌｏｗ１３９の安定化
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AU748261B2 (en)	2002-05-30	Solid solutions of monoazo pigments
US20070226920A1 (en)	2007-10-04	Salts of Laked Monoazo Compounds