GB637093A - Production of quinoneimine and quinone dyestuff images - Google Patents
Production of quinoneimine and quinone dyestuff imagesInfo
- Publication number
- GB637093A GB637093A GB33149/46A GB3314946A GB637093A GB 637093 A GB637093 A GB 637093A GB 33149/46 A GB33149/46 A GB 33149/46A GB 3314946 A GB3314946 A GB 3314946A GB 637093 A GB637093 A GB 637093A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- anthrone
- carboxylic acid
- acid
- anthrones
- 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
Links
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title 2
- 239000000975 dye Substances 0.000 title 1
- 150000004060 quinone imines Chemical class 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 4
- 239000001117 sulphuric acid Substances 0.000 abstract 4
- 235000011149 sulphuric acid Nutrition 0.000 abstract 4
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- DIGYASCXPKODLJ-UHFFFAOYSA-N 2-(4-phenoxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 DIGYASCXPKODLJ-UHFFFAOYSA-N 0.000 abstract 2
- PFXKWHLJTMTMCG-UHFFFAOYSA-N 4-amino-n-(9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O PFXKWHLJTMTMCG-UHFFFAOYSA-N 0.000 abstract 2
- DGJNWQJOASAMHY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)Cl)=CC=C3C(=O)C2=C1 DGJNWQJOASAMHY-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- -1 Anthraquinone-2-carboxylic acid thiobutyl ester Chemical class 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 230000000397 acetylating effect Effects 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 abstract 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- WGHNATLBRRKWMQ-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O WGHNATLBRRKWMQ-UHFFFAOYSA-N 0.000 abstract 2
- POIYYVDACRBGPJ-UHFFFAOYSA-N n-(9-oxo-10h-anthracen-1-yl)acetamide Chemical compound C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C POIYYVDACRBGPJ-UHFFFAOYSA-N 0.000 abstract 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 2
- SJIBPUPVXUKJQQ-UHFFFAOYSA-N 1-(N-acetylanilino)-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1(=CC=CC=C1)N(C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O)C(C)=O SJIBPUPVXUKJQQ-UHFFFAOYSA-N 0.000 abstract 1
- CCTLQSUUBCRKNZ-UHFFFAOYSA-N 1-(N-phenylanilino)-10H-anthracen-9-one Chemical compound O=C1C2=CC=CC=C2CC2=CC=CC(N(C3=CC=CC=C3)C3=CC=CC=C3)=C12 CCTLQSUUBCRKNZ-UHFFFAOYSA-N 0.000 abstract 1
- UVSGJHDAVDKNJW-UHFFFAOYSA-N 1-(benzenesulfonyl)-10H-anthracen-9-one Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=CC=CC=2CC3=CC=CC=C3C(C1=2)=O UVSGJHDAVDKNJW-UHFFFAOYSA-N 0.000 abstract 1
- GEPYVKUBBIVIHJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O GEPYVKUBBIVIHJ-UHFFFAOYSA-N 0.000 abstract 1
- HAKVFTLDTFUSBM-UHFFFAOYSA-N 1-(dimethylamino)-9,10-dioxoanthracene-2-carboxylic acid Chemical compound CN(C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O)C HAKVFTLDTFUSBM-UHFFFAOYSA-N 0.000 abstract 1
- FNTSHBHJZQRXCT-UHFFFAOYSA-N 1-(methylamino)-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(O)=O)=C2NC FNTSHBHJZQRXCT-UHFFFAOYSA-N 0.000 abstract 1
- CKHOEUPAAHONHA-UHFFFAOYSA-N 1-(octadecylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCCCCCCCCCCCCCCCCCC CKHOEUPAAHONHA-UHFFFAOYSA-N 0.000 abstract 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 abstract 1
- MUHKYVRADCWPMM-UHFFFAOYSA-N 1-[acetyl(methyl)amino]-9,10-dioxoanthracene-2-carboxylic acid Chemical compound CN(C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O)C(C)=O MUHKYVRADCWPMM-UHFFFAOYSA-N 0.000 abstract 1
- LDIICGUDBCCVGW-UHFFFAOYSA-N 1-acetamido-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C(C)(=O)NC1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)(=O)O LDIICGUDBCCVGW-UHFFFAOYSA-N 0.000 abstract 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 abstract 1
- ZHLRCPOFSPCJPL-UHFFFAOYSA-N 1-chloro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C(=O)O)=CC=C3C(=O)C2=C1 ZHLRCPOFSPCJPL-UHFFFAOYSA-N 0.000 abstract 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 abstract 1
- SPWQFDDHEPTXOZ-UHFFFAOYSA-N 1-ethylsulfanyl-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C(C)SC1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O SPWQFDDHEPTXOZ-UHFFFAOYSA-N 0.000 abstract 1
- XNJJQOWLFGWEMU-UHFFFAOYSA-N 1-ethylsulfonyl-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C(C)S(=O)(=O)C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O XNJJQOWLFGWEMU-UHFFFAOYSA-N 0.000 abstract 1
- YRDVFHIHPSMINQ-UHFFFAOYSA-N 10-oxo-9H-anthracene-9-sulfonic acid Chemical compound S(=O)(=O)(O)C1C=2C=CC=CC2C(C2=CC=CC=C12)=O YRDVFHIHPSMINQ-UHFFFAOYSA-N 0.000 abstract 1
- ANAIEEBCQKHOKO-UHFFFAOYSA-N 10-oxo-N-phenyl-9H-anthracene-1-carboxamide Chemical class C1(=CC=CC=C1)NC(=O)C1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O ANAIEEBCQKHOKO-UHFFFAOYSA-N 0.000 abstract 1
- POBJIPJUUVDEHD-UHFFFAOYSA-N 2-(10-hydroxyanthracen-9-yl)oxy-2-oxoacetic acid Chemical compound OC=1C2=CC=CC=C2C(=C2C=CC=CC12)OC(C(=O)O)=O POBJIPJUUVDEHD-UHFFFAOYSA-N 0.000 abstract 1
- CMUSFGOGIIXRDU-UHFFFAOYSA-N 2-(benzenesulfonyl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(=C2)S(=O)(=O)C1=CC=CC=C1 CMUSFGOGIIXRDU-UHFFFAOYSA-N 0.000 abstract 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- MCLGWOXRKSRKDE-UHFFFAOYSA-N 2-[(10-oxo-9H-anthracen-1-yl)amino]acetic acid Chemical class C(=O)(O)CNC1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O MCLGWOXRKSRKDE-UHFFFAOYSA-N 0.000 abstract 1
- JRGIOJQESXVHDO-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CC1=CC=CC=C1C(O)=O JRGIOJQESXVHDO-UHFFFAOYSA-N 0.000 abstract 1
- FLFUMDCTNUJMKZ-UHFFFAOYSA-N 2-[(4-phenoxyphenyl)methyl]benzoic acid Chemical compound O(C1=CC=CC=C1)C1=CC=C(CC2=C(C(=O)O)C=CC=C2)C=C1 FLFUMDCTNUJMKZ-UHFFFAOYSA-N 0.000 abstract 1
- CQODGVGHIURXJO-UHFFFAOYSA-N 2-butylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(SCCCC)=CC=C3C(=O)C2=C1 CQODGVGHIURXJO-UHFFFAOYSA-N 0.000 abstract 1
- FPIMRECKIFNQHC-UHFFFAOYSA-N 2-butylsulfonylanthracene-9,10-dione Chemical compound C(CCC)S(=O)(=O)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O FPIMRECKIFNQHC-UHFFFAOYSA-N 0.000 abstract 1
- XNWWJPDGBVFOFX-UHFFFAOYSA-N 2-methoxy-10h-anthracen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(OC)=CC=C3CC2=C1 XNWWJPDGBVFOFX-UHFFFAOYSA-N 0.000 abstract 1
- WUWVLTIKBWZFTM-UHFFFAOYSA-N 2-sulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(S)=CC=C3C(=O)C2=C1 WUWVLTIKBWZFTM-UHFFFAOYSA-N 0.000 abstract 1
- SJLSNORDONFZQK-UHFFFAOYSA-N 3-(benzenesulfonyl)-10H-anthracen-9-one Chemical class C1(=CC=CC=C1)S(=O)(=O)C=1C=CC=2C(C3=CC=CC=C3CC=2C=1)=O SJLSNORDONFZQK-UHFFFAOYSA-N 0.000 abstract 1
- YGAUDUHNXNCKEG-UHFFFAOYSA-N 3-butylsulfonyl-10H-anthracen-9-one Chemical class C(CCC)S(=O)(=O)C=1C=CC=2C(C3=CC=CC=C3CC=2C=1)=O YGAUDUHNXNCKEG-UHFFFAOYSA-N 0.000 abstract 1
- KODNZXLDEAMWAC-UHFFFAOYSA-N 3-methylsulfonyl-10H-anthracen-9-one Chemical class CS(=O)(=O)C=1C=CC=2C(C3=CC=CC=C3CC=2C=1)=O KODNZXLDEAMWAC-UHFFFAOYSA-N 0.000 abstract 1
- JPXAUUAQGUFRDX-UHFFFAOYSA-N 3-sulfanyl-10H-anthracen-9-one Chemical class SC=1C=CC=2C(C3=CC=CC=C3CC2C1)=O JPXAUUAQGUFRDX-UHFFFAOYSA-N 0.000 abstract 1
- YXMBKPBBBCFGBU-UHFFFAOYSA-N 4-(N-phenylanilino)-10H-anthracen-9-one Chemical compound O=C1C2=CC=CC=C2CC2=C(C=CC=C12)N(C1=CC=CC=C1)C1=CC=CC=C1 YXMBKPBBBCFGBU-UHFFFAOYSA-N 0.000 abstract 1
- XRKPYGFTWHONPR-UHFFFAOYSA-N 4-(dimethylamino)-10H-anthracen-9-one Chemical compound CN(C1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O)C XRKPYGFTWHONPR-UHFFFAOYSA-N 0.000 abstract 1
- CWFIHCUGELURMS-UHFFFAOYSA-N 4-(ethylamino)-10H-anthracen-9-one Chemical class C(C)NC1=CC=CC=2C(C3=CC=CC=C3CC12)=O CWFIHCUGELURMS-UHFFFAOYSA-N 0.000 abstract 1
- JDLMJXBQXXFQAK-UHFFFAOYSA-N 4-amino-10h-anthracen-9-one Chemical compound O=C1C2=CC=CC=C2CC2=C1C=CC=C2N JDLMJXBQXXFQAK-UHFFFAOYSA-N 0.000 abstract 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 abstract 1
- HZVGOSXOSYFHOI-UHFFFAOYSA-N 4-anilino-10H-anthracen-9-one Chemical class C1(=CC=CC=C1)NC1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O HZVGOSXOSYFHOI-UHFFFAOYSA-N 0.000 abstract 1
- LGSDXCKCSRNZRX-UHFFFAOYSA-N 4-ethylsulfanyl-10H-anthracen-9-one Chemical class C(C)SC1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O LGSDXCKCSRNZRX-UHFFFAOYSA-N 0.000 abstract 1
- LUCNBNWPAVQPKZ-UHFFFAOYSA-N 4-ethylsulfonyl-10H-anthracen-9-one Chemical compound C(C)S(=O)(=O)C1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O LUCNBNWPAVQPKZ-UHFFFAOYSA-N 0.000 abstract 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- APXUOLUXAYLREJ-UHFFFAOYSA-N 9,10-dioxo-1-(N-phenylanilino)anthracene-2-carboxylic acid Chemical compound C1(=CC=CC=C1)N(C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C(=O)O)C1=CC=CC=C1 APXUOLUXAYLREJ-UHFFFAOYSA-N 0.000 abstract 1
- QPKWSXCYFGQKJU-UHFFFAOYSA-N 9,10-dioxo-N-phenylanthracene-1-carboxamide Chemical compound C1(=CC=CC=C1)NC(=O)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O QPKWSXCYFGQKJU-UHFFFAOYSA-N 0.000 abstract 1
- LLSVGXGSYBLMNY-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)Cl LLSVGXGSYBLMNY-UHFFFAOYSA-N 0.000 abstract 1
- POLMYHOPWZVMTE-UHFFFAOYSA-N 9-(diethylamino)anthracene-2-carboxylic acid Chemical compound C(C)N(C=1C2=CC=CC=C2C=C2C=CC(=CC12)C(=O)O)CC POLMYHOPWZVMTE-UHFFFAOYSA-N 0.000 abstract 1
- IPDULFXVESNAFO-UHFFFAOYSA-N 9-acetyloxyanthracene-2-carboxylic acid Chemical compound C(C)(=O)OC=1C2=CC=CC=C2C=C2C=CC(=CC12)C(=O)O IPDULFXVESNAFO-UHFFFAOYSA-N 0.000 abstract 1
- XFWUYBJFDCKWEH-UHFFFAOYSA-N 9-propylsulfonyloxyanthracene-2-carboxylic acid Chemical compound C(CC)S(=O)(=O)OC=1C2=CC=CC=C2C=C2C=CC(=CC12)C(=O)O XFWUYBJFDCKWEH-UHFFFAOYSA-N 0.000 abstract 1
- ASDLSKCKYGVMAI-UHFFFAOYSA-N AQC Natural products C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- XSYCFBUQTWYSCL-UHFFFAOYSA-N C1(=CC=CC=C1)SC1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O Chemical class C1(=CC=CC=C1)SC1=CC=CC=2C(C3=CC=CC=C3CC1=2)=O XSYCFBUQTWYSCL-UHFFFAOYSA-N 0.000 abstract 1
- WMMTWLGDQVQANR-UHFFFAOYSA-N CSC1=CC=2CC3=CC=CC=C3C(C2C=C1)=O Chemical class CSC1=CC=2CC3=CC=CC=C3C(C2C=C1)=O WMMTWLGDQVQANR-UHFFFAOYSA-N 0.000 abstract 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 abstract 1
- YQMMVVPCZSTLFL-UHFFFAOYSA-N N-(10-aminoanthracen-1-yl)acetamide Chemical class C(C)(=O)NC1=CC=CC2=C(C3=CC=CC=C3C=C12)N YQMMVVPCZSTLFL-UHFFFAOYSA-N 0.000 abstract 1
- JFHYRNULRSCSCP-UHFFFAOYSA-N N-(10-oxo-9H-anthracen-1-yl)-N-phenylacetamide Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=2C(C3=CC=CC=C3CC12)=O)C(C)=O JFHYRNULRSCSCP-UHFFFAOYSA-N 0.000 abstract 1
- CMPDOPFAGJDLAQ-UHFFFAOYSA-N N-[10-(methylamino)anthracen-1-yl]octadecanamide Chemical class C(CCCCCCCCCCCCCCCCC)(=O)NC1=CC=CC2=C(C3=CC=CC=C3C=C12)NC CMPDOPFAGJDLAQ-UHFFFAOYSA-N 0.000 abstract 1
- XHQOQCJNTUYEJT-UHFFFAOYSA-N N-ethyl-10-oxo-9H-anthracene-2-carboxamide Chemical class C(C)NC(=O)C=1C=CC=2C(C3=CC=CC=C3CC=2C=1)=O XHQOQCJNTUYEJT-UHFFFAOYSA-N 0.000 abstract 1
- LYURDFXBEJNNEC-UHFFFAOYSA-N N-methyl-N-(10-oxo-9H-anthracen-1-yl)acetamide Chemical compound CN(C1=CC=CC=2C(C3=CC=CC=C3CC12)=O)C(C)=O LYURDFXBEJNNEC-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- WDCWDDUSXCJQKY-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=2C(C3=CC=CC=C3CC2C=C1)=O Chemical compound O(C1=CC=CC=C1)C1=CC=2C(C3=CC=CC=C3CC2C=C1)=O WDCWDDUSXCJQKY-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- QRIJEPHXWKXBDD-UHFFFAOYSA-N n-anthracen-1-ylacetamide Chemical compound C1=CC=C2C=C3C(NC(=O)C)=CC=CC3=CC2=C1 QRIJEPHXWKXBDD-UHFFFAOYSA-N 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 229950000244 sulfanilic acid Drugs 0.000 abstract 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000004862 thiobutyl group Chemical group 0.000 abstract 1
- FZWSEGZCDCMETR-UHFFFAOYSA-N thiophen-2-yl 9,10-dioxoanthracene-2-carboxylate Chemical compound S1C(=CC=C1)OC(=O)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O FZWSEGZCDCMETR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 229940007718 zinc hydroxide Drugs 0.000 abstract 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US637093XA | 1945-11-20 | 1945-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB637093A true GB637093A (en) | 1950-05-10 |
Family
ID=22050971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33149/46A Expired GB637093A (en) | 1945-11-20 | 1946-11-07 | Production of quinoneimine and quinone dyestuff images |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE469264A (enrdf_load_stackoverflow) |
| FR (1) | FR941876A (enrdf_load_stackoverflow) |
| GB (1) | GB637093A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3835167A (en) * | 1972-12-18 | 1974-09-10 | Syntex Inc | Anthrone carboxylic acids and derivatives |
| US4288608A (en) * | 1978-06-01 | 1981-09-08 | Research Corporation | Synthesis of anthracyclines |
| US4472495A (en) * | 1983-01-20 | 1984-09-18 | Edward Degginger | Reduction of color intensity of Kodachrome color film |
-
0
- BE BE469264D patent/BE469264A/xx unknown
-
1946
- 1946-11-07 GB GB33149/46A patent/GB637093A/en not_active Expired
- 1946-11-20 FR FR941876D patent/FR941876A/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3835167A (en) * | 1972-12-18 | 1974-09-10 | Syntex Inc | Anthrone carboxylic acids and derivatives |
| US4288608A (en) * | 1978-06-01 | 1981-09-08 | Research Corporation | Synthesis of anthracyclines |
| US4472495A (en) * | 1983-01-20 | 1984-09-18 | Edward Degginger | Reduction of color intensity of Kodachrome color film |
Also Published As
| Publication number | Publication date |
|---|---|
| BE469264A (enrdf_load_stackoverflow) | |
| FR941876A (fr) | 1949-01-24 |
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