DE1719069A1 - Neue Disazofarbstoffpigmente und Verfahren zu deren Herstellung - Google Patents
Neue Disazofarbstoffpigmente und Verfahren zu deren HerstellungInfo
- Publication number
- DE1719069A1 DE1719069A1 DE19681719069 DE1719069A DE1719069A1 DE 1719069 A1 DE1719069 A1 DE 1719069A1 DE 19681719069 DE19681719069 DE 19681719069 DE 1719069 A DE1719069 A DE 1719069A DE 1719069 A1 DE1719069 A1 DE 1719069A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- alkyl
- amino
- acid
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 17
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 8
- -1 carbonyl- Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 150000004780 naphthols Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 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 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000000485 pigmenting effect Effects 0.000 claims 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 244000172533 Viola sororia Species 0.000 description 8
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 150000003931 anilides Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- XVCKCCODMHCXJD-UHFFFAOYSA-N (4-aminophenyl)urea Chemical compound NC(=O)NC1=CC=C(N)C=C1 XVCKCCODMHCXJD-UHFFFAOYSA-N 0.000 description 3
- NHFKECPTBZZFBC-UHFFFAOYSA-N 4-amino-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N NHFKECPTBZZFBC-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 2
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- KBOFLKMGZJNFES-UHFFFAOYSA-N COC1=C(C=C(C(=O)NC2=CC=C(C=C2)NC(C2=CC(=C(C=C2)OC)N)=O)C=C1)N Chemical compound COC1=C(C=C(C(=O)NC2=CC=C(C=C2)NC(C2=CC(=C(C=C2)OC)N)=O)C=C1)N KBOFLKMGZJNFES-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241001366278 Leptotes marina Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000154870 Viola adunca Species 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- FRDZVVWYFHSMKP-UHFFFAOYSA-N (4-amino-2,5-dichlorophenyl)urea Chemical compound NC1=CC(=C(C=C1Cl)NC(=O)N)Cl FRDZVVWYFHSMKP-UHFFFAOYSA-N 0.000 description 1
- VNSGSGVPSPUXFV-UHFFFAOYSA-N (4-amino-2,5-dimethoxyphenyl)urea Chemical compound NC1=CC(=C(C=C1OC)NC(=O)N)OC VNSGSGVPSPUXFV-UHFFFAOYSA-N 0.000 description 1
- SOWKRIZBBMFWFH-UHFFFAOYSA-N (4-amino-2,5-dimethylphenyl)urea Chemical compound NC1=CC(=C(C=C1C)NC(=O)N)C SOWKRIZBBMFWFH-UHFFFAOYSA-N 0.000 description 1
- WRYXNKICHQLRQN-UHFFFAOYSA-N (4-amino-2-methoxyphenyl)urea Chemical compound COC1=CC(N)=CC=C1NC(N)=O WRYXNKICHQLRQN-UHFFFAOYSA-N 0.000 description 1
- BEQJZHVTOLLYJY-UHFFFAOYSA-N (4-amino-5-chloro-2-methoxyphenyl)urea Chemical compound NC1=CC(=C(C=C1Cl)NC(=O)N)OC BEQJZHVTOLLYJY-UHFFFAOYSA-N 0.000 description 1
- XWSYGQUSQXDRHU-UHFFFAOYSA-N (4-aminophenyl)-(3,4-diaminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C(N)=C1 XWSYGQUSQXDRHU-UHFFFAOYSA-N 0.000 description 1
- CYOPGRYXWQHJKJ-NSCUHMNNSA-N (e)-n-(4-aminophenyl)but-2-enamide Chemical compound C\C=C\C(=O)NC1=CC=C(N)C=C1 CYOPGRYXWQHJKJ-NSCUHMNNSA-N 0.000 description 1
- MAPWYRGGJSHAAU-UHFFFAOYSA-N 1,3-bis(4-aminophenyl)urea Chemical compound C1=CC(N)=CC=C1NC(=O)NC1=CC=C(N)C=C1 MAPWYRGGJSHAAU-UHFFFAOYSA-N 0.000 description 1
- GINUIEXFKFIZSF-UHFFFAOYSA-N 1-(methylamino)ethanesulfonic acid Chemical compound CNC(C)S(O)(=O)=O GINUIEXFKFIZSF-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- RPOHXHHHVSGUMN-UHFFFAOYSA-N 1-n,4-n-bis(4-aminophenyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(N)=CC=2)C=C1 RPOHXHHHVSGUMN-UHFFFAOYSA-N 0.000 description 1
- KHRDFCYMWDXOIX-UHFFFAOYSA-N 2,5-dimethyl-4-N-(pyridin-3-ylmethyl)benzene-1,4-diamine Chemical compound CC1=C(N)C=C(C(=C1)NCC1=CN=CC=C1)C KHRDFCYMWDXOIX-UHFFFAOYSA-N 0.000 description 1
- WQOWBWVMZPPPGX-UHFFFAOYSA-N 2,6-diaminoanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 WQOWBWVMZPPPGX-UHFFFAOYSA-N 0.000 description 1
- KJNHYKBXQOSFJR-UHFFFAOYSA-N 2,7-diaminoanthracene-9,10-dione Chemical compound C1=C(N)C=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 KJNHYKBXQOSFJR-UHFFFAOYSA-N 0.000 description 1
- RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
- JKDBEPYYWWSPKJ-UHFFFAOYSA-N 3-amino-4-chloro-n-phenylbenzamide Chemical compound C1=C(Cl)C(N)=CC(C(=O)NC=2C=CC=CC=2)=C1 JKDBEPYYWWSPKJ-UHFFFAOYSA-N 0.000 description 1
- FDBJTDPSBHSXMV-UHFFFAOYSA-N 3-amino-4-ethoxy-n-phenylbenzamide Chemical compound C1=C(N)C(OCC)=CC=C1C(=O)NC1=CC=CC=C1 FDBJTDPSBHSXMV-UHFFFAOYSA-N 0.000 description 1
- DGILUAOMQWZUKA-UHFFFAOYSA-N 3-amino-4-methyl-n-phenylbenzamide Chemical compound C1=C(N)C(C)=CC=C1C(=O)NC1=CC=CC=C1 DGILUAOMQWZUKA-UHFFFAOYSA-N 0.000 description 1
- QTISFYLEWRMCEY-UHFFFAOYSA-N 3-amino-4-phenoxy-n-phenylbenzamide Chemical compound NC1=CC(C(=O)NC=2C=CC=CC=2)=CC=C1OC1=CC=CC=C1 QTISFYLEWRMCEY-UHFFFAOYSA-N 0.000 description 1
- KPSPULPPMWHXGE-UHFFFAOYSA-N 3-amino-n-phenylbenzamide Chemical compound NC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 KPSPULPPMWHXGE-UHFFFAOYSA-N 0.000 description 1
- KQIKKETXZQDHGE-FOCLMDBBSA-N 4,4'-diaminoazobenzene Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=C(N)C=C1 KQIKKETXZQDHGE-FOCLMDBBSA-N 0.000 description 1
- KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- DNVWHUDIGPWOPP-UHFFFAOYSA-N 4-amino-N-[4-[(4-amino-3-methylbenzoyl)amino]phenyl]-3-methylbenzamide Chemical compound NC1=C(C=C(C(=O)NC2=CC=C(C=C2)NC(C2=CC(=C(C=C2)N)C)=O)C=C1)C DNVWHUDIGPWOPP-UHFFFAOYSA-N 0.000 description 1
- SAXQYTOLSHNBFD-UHFFFAOYSA-N 4-amino-n-[4-[(4-aminobenzoyl)amino]-3-chlorophenyl]benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC(C=C1Cl)=CC=C1NC(=O)C1=CC=C(N)C=C1 SAXQYTOLSHNBFD-UHFFFAOYSA-N 0.000 description 1
- LGTGOCSQAOUUFP-UHFFFAOYSA-N 4-amino-n-[4-[(4-aminobenzoyl)amino]phenyl]benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC(C=C1)=CC=C1NC(=O)C1=CC=C(N)C=C1 LGTGOCSQAOUUFP-UHFFFAOYSA-N 0.000 description 1
- QHWDUJPWCGEBTH-UHFFFAOYSA-N 4-amino-n-phenylbenzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1 QHWDUJPWCGEBTH-UHFFFAOYSA-N 0.000 description 1
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 description 1
- ZZHFNMHFLSLRKU-UHFFFAOYSA-N 5-amino-2,4-dichloro-n-phenylbenzamide Chemical compound C1=C(Cl)C(N)=CC(C(=O)NC=2C=CC=CC=2)=C1Cl ZZHFNMHFLSLRKU-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical class [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- KRFOBCDZBFMKMQ-UHFFFAOYSA-N CC1=CC(NC=O)=C(C)C=C1N Chemical compound CC1=CC(NC=O)=C(C)C=C1N KRFOBCDZBFMKMQ-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
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VNSMYSDAICLZLM-UHFFFAOYSA-N N-(4-amino-2,5-dichlorophenyl)-3-phenylprop-2-enamide Chemical compound ClC1=C(N)C=C(C(=C1)NC(C=CC1=CC=CC=C1)=O)Cl VNSMYSDAICLZLM-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical compound N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 1
- LRUXKCQGGZSNLX-UHFFFAOYSA-N NC1=CC(=C(C=C1C)NC(=O)C1=CC=C(C=C1)C(=O)NC1=C(C=C(C(=C1)C)N)C)C Chemical compound NC1=CC(=C(C=C1C)NC(=O)C1=CC=C(C=C1)C(=O)NC1=C(C=C(C(=C1)C)N)C)C LRUXKCQGGZSNLX-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- RNQDRTJWYRITEA-UHFFFAOYSA-N [4-amino-2-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(N)C=C1C(F)(F)F RNQDRTJWYRITEA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- LOHXYCIOMOANKQ-UHFFFAOYSA-N aniline 2-N-methylbenzene-1,2-diamine Chemical compound CNC1=C(N)C=CC=C1.NC1=CC=CC=C1 LOHXYCIOMOANKQ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 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 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct 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
- 229920002678 cellulose Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KCSDMTDJSBYPJX-UHFFFAOYSA-N ethyl N-(4-amino-2,5-dimethylphenyl)carbamate Chemical compound CC1=C(N)C=C(C(=C1)NC(=O)OCC)C KCSDMTDJSBYPJX-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- UFDGMXHPQNDESO-UHFFFAOYSA-N methyl n-(4-aminophenyl)carbamate Chemical compound COC(=O)NC1=CC=C(N)C=C1 UFDGMXHPQNDESO-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RVDSRPFOMDFFAG-UHFFFAOYSA-N n,n'-bis(4-aminophenyl)oxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C(=O)NC1=CC=C(N)C=C1 RVDSRPFOMDFFAG-UHFFFAOYSA-N 0.000 description 1
- XPKHKHHJLMESEG-UHFFFAOYSA-N n-(4-amino-2,5-diethoxyphenyl)acetamide Chemical compound CCOC1=CC(NC(C)=O)=C(OCC)C=C1N XPKHKHHJLMESEG-UHFFFAOYSA-N 0.000 description 1
- ULWRRNFOVYHBIH-UHFFFAOYSA-N n-(4-amino-2,5-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=CC(C)=C(N)C=C1C ULWRRNFOVYHBIH-UHFFFAOYSA-N 0.000 description 1
- UFZGWYKCLSCGHV-UHFFFAOYSA-N n-(4-amino-3-methoxyphenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1N UFZGWYKCLSCGHV-UHFFFAOYSA-N 0.000 description 1
- NDEZAKJVTYETNC-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(N)C=C1C NDEZAKJVTYETNC-UHFFFAOYSA-N 0.000 description 1
- YRNYPTDHYATPKF-UHFFFAOYSA-N n-(4-aminophenyl)-2,2,2-trichloroacetamide Chemical compound NC1=CC=C(NC(=O)C(Cl)(Cl)Cl)C=C1 YRNYPTDHYATPKF-UHFFFAOYSA-N 0.000 description 1
- LCAGAKXGPVINGX-UHFFFAOYSA-N n-(4-aminophenyl)-2-chloroacetamide Chemical compound NC1=CC=C(NC(=O)CCl)C=C1 LCAGAKXGPVINGX-UHFFFAOYSA-N 0.000 description 1
- BKTOTYLPLPCSKV-UHFFFAOYSA-N n-(4-aminophenyl)-2-phenoxyacetamide Chemical compound C1=CC(N)=CC=C1NC(=O)COC1=CC=CC=C1 BKTOTYLPLPCSKV-UHFFFAOYSA-N 0.000 description 1
- MGYVNHNTBRLDJH-UHFFFAOYSA-N n-(4-aminophenyl)-3-phenylprop-2-enamide Chemical compound C1=CC(N)=CC=C1NC(=O)C=CC1=CC=CC=C1 MGYVNHNTBRLDJH-UHFFFAOYSA-N 0.000 description 1
- LFXCELCZRVHGIJ-UHFFFAOYSA-N n-(4-aminophenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(N)C=C1 LFXCELCZRVHGIJ-UHFFFAOYSA-N 0.000 description 1
- MUQQKIMNQFFGRV-UHFFFAOYSA-N n-(4-aminophenyl)formamide Chemical compound NC1=CC=C(NC=O)C=C1 MUQQKIMNQFFGRV-UHFFFAOYSA-N 0.000 description 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- ZVIDMSBTYRSMAR-UHFFFAOYSA-N p-methylamino-benzoic acid Natural products CNC1=CC=C(C(O)=O)C=C1 ZVIDMSBTYRSMAR-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NLLAHOJDAMQYRU-UHFFFAOYSA-N propan-1-amine;propan-2-amine Chemical compound CCCN.CC(C)N NLLAHOJDAMQYRU-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/033—Disazo dyes characterised by two coupling components of the same type in which the coupling component is an arylamide of an o-hydroxy-carboxylic acid or of a beta-keto-carboxylic acid
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH385967A CH482789A (de) | 1967-03-16 | 1967-03-16 | Verfahren zur Herstellung neuer Disazofarbstoffpigmente |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1719069A1 true DE1719069A1 (de) | 1971-08-12 |
Family
ID=4264994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681719069 Pending DE1719069A1 (de) | 1967-03-16 | 1968-03-07 | Neue Disazofarbstoffpigmente und Verfahren zu deren Herstellung |
Country Status (5)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758847A (fr) * | 1969-11-12 | 1971-04-16 | Bayer Ag | Colorants disazoiques insolubles dans l'eau |
| US3931142A (en) * | 1971-09-23 | 1976-01-06 | Ciba-Geigy Ag | Heterocyclic containing disazo compounds |
| US4100157A (en) * | 1972-09-05 | 1978-07-11 | Ciba-Geigy Corporation | β-Crystalline form of the pigment obtained by coupling diazotized 1-aminobenzene-2-carboxylic acid methyl ester with 2,3-oxynaphthoic acid |
| US4046502A (en) * | 1973-11-23 | 1977-09-06 | Sandoz Ltd. | Basic disazo dyes having two 2-hydroxy-3-substituted carbamoylnaphthyl-1-azophenyl groups for dyeing paper |
| US4204871A (en) * | 1978-04-04 | 1980-05-27 | Sun Chemical Corporation | Printing inks containing nucleated organic pigments |
| US5155175A (en) * | 1989-12-08 | 1992-10-13 | Intellectual Property Law Dept. | Crosslinkable fluorinated polyarylene ether composition |
| US5114780A (en) * | 1990-04-17 | 1992-05-19 | Raychem Corporation | Electronic articles containing a fluorinated poly(arylene ether) dielectric |
| US5270453A (en) * | 1989-12-08 | 1993-12-14 | Raychem Corporation | Aromatic bistriazene compounds |
| WO1991017753A1 (en) * | 1990-05-24 | 1991-11-28 | The United States Of America, As Represented By The Secretary, U.S. Department Of Commerce | Bistriazenes as chemotherapeutic agents |
-
1967
- 1967-03-16 CH CH385967A patent/CH482789A/de not_active IP Right Cessation
-
1968
- 1968-02-26 US US707953A patent/US3555004A/en not_active Expired - Lifetime
- 1968-03-07 DE DE19681719069 patent/DE1719069A1/de active Pending
- 1968-03-14 FR FR1563244D patent/FR1563244A/fr not_active Expired
- 1968-03-14 GB GB02426/68A patent/GB1169841A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3555004A (en) | 1971-01-12 |
| CH482789A (de) | 1969-12-15 |
| GB1169841A (en) | 1969-11-05 |
| FR1563244A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-04-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1768892B2 (de) | Disazopigmente und deren Verwendung | |
| DE1544460C3 (de) | Bis-(acetoacetyl)-arylendiamiddisazopigmente | |
| DE1719069A1 (de) | Neue Disazofarbstoffpigmente und Verfahren zu deren Herstellung | |
| DE2901121C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE943901C (de) | Verfahren zur Herstellung neuer Carbonsaeureamidderivate von Azofarbstoffen | |
| DE2243999A1 (de) | Neue disazopigmente, verfahren zu deren herstellung und verwendung | |
| DE1544453A1 (de) | Verfahren zur Herstellung von Disazopigmenten | |
| DE1817589A1 (de) | Neue wasserunloesliche Azoverbindungen und Verfahren zu deren Herstellung | |
| DE2032601A1 (de) | Neue Disazopigmente und Verfahren zu deren Herstellung | |
| DE1644117A1 (de) | Verfahren zur Herstellung von Disazopigmenten | |
| DE2336915A1 (de) | Neue disazopigmente und verfahren zur herstellung und verwendung | |
| DE1544459A1 (de) | Verfahren zur Herstellung von Disazopigmenten | |
| DE1644127A1 (de) | Verfahren zur Herstellung von Disazopigmenten | |
| DE1278628B (de) | Verfahren zur Herstellung von Carbonsaeureamidazofarbstoffen | |
| CH519007A (de) | Verfahren zur Herstellung neuer wasserunlöslicher Azoverbindungen | |
| DE2002067A1 (de) | Neue Disazopigmente und Verfahren zu deren Herstellung | |
| DE2430197A1 (de) | Neue disazopigmente und verfahren zu deren herstellung | |
| DE1961159A1 (de) | Neue Azofarbstoffpigmente und Verfahren zu deren Herstellung | |
| CH497505A (de) | Verfahren zur Herstellung neuer Azofarbstoffpigmente | |
| DE1903649A1 (de) | Neue wasserunloesliche Azoverbindungen und Verfahren zu deren Herstellung | |
| DE1816990A1 (de) | Neue Azopigmente und Verfahren zu deren Herstellung | |
| CH452749A (de) | Verfahren zur Herstellung neuer Azofarbstoffpigmente | |
| DE1794100A1 (de) | Verfahren zur Herstellung von Disazopigmenten | |
| DE2011043A1 (de) | Neue Polyazopigmente und Verfahren zu deren Herstellung | |
| DE1719067A1 (de) | Neue Monoazofarbstoffpigmente und Verfahren zu deren Herstellung |