DE69917897T2 - Gelbes pteridin mit einem farbton-winkel von mindestens 98 - Google Patents
Gelbes pteridin mit einem farbton-winkel von mindestens 98 Download PDFInfo
- Publication number
- DE69917897T2 DE69917897T2 DE69917897T DE69917897T DE69917897T2 DE 69917897 T2 DE69917897 T2 DE 69917897T2 DE 69917897 T DE69917897 T DE 69917897T DE 69917897 T DE69917897 T DE 69917897T DE 69917897 T2 DE69917897 T2 DE 69917897T2
- Authority
- DE
- Germany
- Prior art keywords
- pteridine
- salt
- base
- insoluble
- treated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 title claims description 48
- 239000000203 mixture Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 32
- MPKYQFNZHLRKID-UHFFFAOYSA-N pyrimido[5,4-g]pteridine-2,4,5,7-tetramine Chemical compound NC1=NC(N)=C2N(N)C3=CN(N)C=NC3=NC2=N1 MPKYQFNZHLRKID-UHFFFAOYSA-N 0.000 claims description 29
- 150000003195 pteridines Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 18
- 238000007639 printing Methods 0.000 claims description 17
- 239000012043 crude product Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000000976 ink Substances 0.000 claims description 14
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical class NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 9
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- MQEFDQWUCTUJCP-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=NC(N)=C(N)C(N)=N1 MQEFDQWUCTUJCP-UHFFFAOYSA-N 0.000 claims description 7
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 5
- XLQQJSWJHHKLOK-UHFFFAOYSA-N 5-nitrosopyrimidine-2,4,6-triamine Chemical compound NC1=NC(N)=C(N=O)C(N)=N1 XLQQJSWJHHKLOK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000010186 staining Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 61
- 239000002585 base Substances 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- 235000011121 sodium hydroxide Nutrition 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 17
- 239000012362 glacial acetic acid Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- -1 NaOH or KOH Chemical class 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
- 229920000180 alkyd Polymers 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 8
- 239000003365 glass fiber Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000020 Nitrocellulose Substances 0.000 description 5
- 238000010908 decantation Methods 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 229920001220 nitrocellulos Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- UYAANOHGMOPJEE-UHFFFAOYSA-N Nc1nc(N)nc2nc(nc(N)nc3N)c3nc12 Chemical compound Nc1nc(N)nc2nc(nc(N)nc3N)c3nc12 UYAANOHGMOPJEE-UHFFFAOYSA-N 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
- 238000010306 acid treatment Methods 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 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
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- WZEYZMKZKQPXSX-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1.CC1=CC(C)=CC(C)=C1 WZEYZMKZKQPXSX-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000282461 Canis lupus Species 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
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000004202 carbamide Substances 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
- 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
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [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
- 239000005445 natural material 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 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
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- 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
- C09B17/00—Azine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH93898 | 1998-04-24 | ||
| CH93898 | 1998-04-24 | ||
| PCT/EP1999/002509 WO1999055707A1 (en) | 1998-04-24 | 1999-04-14 | Yellow pteridine having a hue-angle of at least 98 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69917897D1 DE69917897D1 (de) | 2004-07-15 |
| DE69917897T2 true DE69917897T2 (de) | 2005-07-28 |
Family
ID=4198677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69917897T Expired - Lifetime DE69917897T2 (de) | 1998-04-24 | 1999-04-14 | Gelbes pteridin mit einem farbton-winkel von mindestens 98 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6120956A (enExample) |
| EP (1) | EP1073660B1 (enExample) |
| JP (1) | JP2002513046A (enExample) |
| KR (1) | KR100542964B1 (enExample) |
| CN (1) | CN1298405A (enExample) |
| AU (1) | AU3707699A (enExample) |
| CA (1) | CA2313634A1 (enExample) |
| DE (1) | DE69917897T2 (enExample) |
| WO (1) | WO1999055707A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2834401A (en) * | 1999-10-21 | 2001-04-30 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of pyrimido(5,4-g)pteridine derivatives |
| BRPI0512724A (pt) * | 2004-06-30 | 2008-04-01 | Ciba Sc Holding Ag | preparação de pigmentos de pteridina |
| CN101031620B (zh) * | 2004-10-01 | 2011-03-23 | 西巴特殊化学品控股有限公司 | 嘧啶并[5,4-g]蝶啶作为遮光组分在滤色器着色剂组合物中的应用 |
| JP7371121B2 (ja) * | 2019-12-10 | 2023-10-30 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子及び画像表示装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641134A (ja) * | 1992-07-21 | 1994-02-15 | Nippon Soda Co Ltd | ピリミドプテリジン誘導体及びその製造方法 |
| JPH07278456A (ja) * | 1994-04-12 | 1995-10-24 | Nippon Soda Co Ltd | 蛍光着色剤 |
| DE4415656A1 (de) * | 1994-05-04 | 1995-11-09 | Bayer Ag | Neue Pigmentsalze und deren Verwendung zum Färben und Pigmentieren |
| GB9517565D0 (en) * | 1995-08-26 | 1995-10-25 | Ciba Geigy Ag | Pigment compositions |
| US6001167A (en) * | 1996-08-06 | 1999-12-14 | Engelhard Corporation | Pigment compositions |
| AU5050798A (en) * | 1996-10-25 | 1998-05-22 | Ciba Specialty Chemicals Holding Inc. | Process for colouring high molecular weight organic material and polycyclic pigments |
-
1999
- 1999-04-14 JP JP2000545866A patent/JP2002513046A/ja active Pending
- 1999-04-14 CN CN99805344A patent/CN1298405A/zh active Pending
- 1999-04-14 AU AU37076/99A patent/AU3707699A/en not_active Abandoned
- 1999-04-14 CA CA002313634A patent/CA2313634A1/en not_active Abandoned
- 1999-04-14 WO PCT/EP1999/002509 patent/WO1999055707A1/en not_active Ceased
- 1999-04-14 DE DE69917897T patent/DE69917897T2/de not_active Expired - Lifetime
- 1999-04-14 KR KR1020007011776A patent/KR100542964B1/ko not_active Expired - Fee Related
- 1999-04-14 EP EP99919232A patent/EP1073660B1/en not_active Expired - Lifetime
- 1999-04-20 US US09/294,482 patent/US6120956A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69917897D1 (de) | 2004-07-15 |
| AU3707699A (en) | 1999-11-16 |
| EP1073660B1 (en) | 2004-06-09 |
| WO1999055707A1 (en) | 1999-11-04 |
| KR100542964B1 (ko) | 2006-01-20 |
| US6120956A (en) | 2000-09-19 |
| EP1073660A1 (en) | 2001-02-07 |
| KR20010042951A (ko) | 2001-05-25 |
| JP2002513046A (ja) | 2002-05-08 |
| CN1298405A (zh) | 2001-06-06 |
| CA2313634A1 (en) | 1999-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69228280T2 (de) | Oxidationsverfahren zur Herstellung von Chinacridonpigmenten | |
| EP0061426B1 (de) | Verfahren zum Färben von hochmolekularem organischem Material und neue polycyclische Pigmente | |
| DE69213368T2 (de) | Verfahren zur Konditionierung organischer Pigmente | |
| EP0296111B1 (de) | Mit Metalloxiden beschichtete organische Pigmente | |
| DE69416220T2 (de) | Synthese von festen Lösungen von Chinacridonpigmenten | |
| EP0348347A2 (de) | Verfahren zur Herstellung fester Lösungen von Chinacridonen | |
| EP0024702A2 (de) | Disazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel | |
| DE1914271C3 (de) | Verfahren zur Herstellung farbstarker transparenter Pigmente der Isoindolinreihe | |
| DE69416219T2 (de) | Herstellung von pigmentärem 2,9-Dichlorchinacridon | |
| EP0254681A2 (de) | Neue Stoffzusammensetzungen auf der Basis von Indanthronblau-Pigmenten | |
| DE69517277T2 (de) | Verfahren zur Herstellung von Diaryldiketopyrrolopyrrolpigmenten | |
| DE69217295T2 (de) | Modifiziertes Gamma-Chinacridonpigment | |
| DE69520295T2 (de) | Mit Harz behandeltes 2,9-Dimethylchinacridone | |
| EP0029007A1 (de) | Isoindolinpigmente, Verfahren zu deren Herstellung und Verwendung | |
| DE69917897T2 (de) | Gelbes pteridin mit einem farbton-winkel von mindestens 98 | |
| DE69705770T2 (de) | Oxidationsverfahren zur Herstellung von Chinacridonpigmenten | |
| EP0489421A2 (de) | Pigmentzubereitungen | |
| EP1163294B1 (de) | Purpurfarbene pigmentzusammensetzung und deren verwendung | |
| DE60207548T2 (de) | Neue kristallmodifikation einer festen lösung von einem diketopyrrolopyrrolpigment | |
| DE3742388A1 (de) | Neue stoffzusammensetzungen auf der basis von isoindolinpigmenten | |
| DE69708905T2 (de) | Verfahren zum färben von hochmolekularem organischem material und polycyclische pigmente | |
| DE60007700T2 (de) | Gamma-Chinacridonpigment | |
| EP0349489A2 (de) | Hochmolekulares organisches Material enthaltend ein Metallkomplexpigment auf Hydrazonbasis | |
| EP0763538B1 (de) | Verfahren zum Färben von hochmolekularem Material mit polycyclischen Verbindungen | |
| CH620702A5 (en) | Process for conditioning yellow disazo diimide dyestuffs |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CIBA HOLDING INC., BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC |