CH555874A - Verfahren zur herstellung sulfonsaeuregruppenfreier anthrachinonfarbstoffe. - Google Patents
Verfahren zur herstellung sulfonsaeuregruppenfreier anthrachinonfarbstoffe.Info
- Publication number
- CH555874A CH555874A CH1354967A CH1354967A CH555874A CH 555874 A CH555874 A CH 555874A CH 1354967 A CH1354967 A CH 1354967A CH 1354967 A CH1354967 A CH 1354967A CH 555874 A CH555874 A CH 555874A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dependent
- formula
- dye
- alkylene
- Prior art date
Links
- 239000001000 anthraquinone dye Substances 0.000 title claims abstract description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title abstract 2
- -1 sulphonic acid ester Chemical class 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 24
- 150000004056 anthraquinones Chemical class 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- SMGLHFBQMBVRCP-UHFFFAOYSA-N 3-hydroxypropanamide Chemical compound NC(=O)CCO SMGLHFBQMBVRCP-UHFFFAOYSA-N 0.000 claims description 6
- PUMHTFXHONFKOH-UHFFFAOYSA-N ethyl n-(3-hydroxypropyl)carbamate Chemical compound CCOC(=O)NCCCO PUMHTFXHONFKOH-UHFFFAOYSA-N 0.000 claims description 6
- QGGFJIALGORYME-UHFFFAOYSA-N 4-(hydroxymethyl)isoindole-1,3-dione Chemical compound OCC1=CC=CC2=C1C(=O)NC2=O QGGFJIALGORYME-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 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 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- IDWDPUULTDNNBY-UHFFFAOYSA-N ethyl n-(2-hydroxyethyl)carbamate Chemical compound CCOC(=O)NCCO IDWDPUULTDNNBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 19
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004185 ester group Chemical group 0.000 claims 3
- 235000013877 carbamide Nutrition 0.000 claims 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 150000003673 urethanes Chemical class 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract description 22
- 238000000859 sublimation Methods 0.000 abstract description 16
- 230000008022 sublimation Effects 0.000 abstract description 16
- 238000004043 dyeing Methods 0.000 abstract description 6
- 125000003368 amide group Chemical group 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 22
- 230000007935 neutral effect Effects 0.000 description 17
- 238000001035 drying Methods 0.000 description 12
- 239000004744 fabric Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 4
- HJYNGRZUBXMFGB-UHFFFAOYSA-N methoxymethylurea Chemical compound COCNC(N)=O HJYNGRZUBXMFGB-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- YWVVRPJWXVQJNX-UHFFFAOYSA-N 1,4-dihydroxy-2-phenoxyanthracene-9,10-dione Chemical compound OC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=1OC1=CC=CC=C1 YWVVRPJWXVQJNX-UHFFFAOYSA-N 0.000 description 2
- SZJTWEXYILOSJU-UHFFFAOYSA-N 1,4-dihydroxy-2-phenylsulfanylanthracene-9,10-dione Chemical compound OC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=1SC1=CC=CC=C1 SZJTWEXYILOSJU-UHFFFAOYSA-N 0.000 description 2
- VRKMYKBYPQNBDR-UHFFFAOYSA-N 4-(hydroxymethylamino)-4-oxobutanoic acid Chemical compound OCNC(=O)CCC(O)=O VRKMYKBYPQNBDR-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- WFQULOPDYANOIS-IWQZZHSRSA-N (z)-4-amino-3-(hydroxymethyl)-4-oxobut-2-enoic acid Chemical compound NC(=O)C(\CO)=C/C(O)=O WFQULOPDYANOIS-IWQZZHSRSA-N 0.000 description 1
- VHZOXMYERLPGLD-UHFFFAOYSA-N 1,4,5,8-tetrahydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C=1C(O)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C(O)C=1OC1=CC=CC=C1 VHZOXMYERLPGLD-UHFFFAOYSA-N 0.000 description 1
- FEPKIJLKVQKZTO-UHFFFAOYSA-N 1,4-diamino-1,3-diphenoxy-2h-anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(OC=1C=CC=CC=1)CC2(N)OC1=CC=CC=C1 FEPKIJLKVQKZTO-UHFFFAOYSA-N 0.000 description 1
- NZTGGRGGJFCKGG-UHFFFAOYSA-N 1,4-diamino-2,3-diphenoxyanthracene-9,10-dione Chemical compound C=1C=CC=CC=1OC1=C(N)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 NZTGGRGGJFCKGG-UHFFFAOYSA-N 0.000 description 1
- ZKGFMJJJFRNICM-UHFFFAOYSA-N 1,4-diamino-2-(2-hydroxyethylsulfanyl)-3-phenoxyanthracene-9,10-dione Chemical compound OCCSC1=C(N)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 ZKGFMJJJFRNICM-UHFFFAOYSA-N 0.000 description 1
- ZXXTZESOEUNHQC-UHFFFAOYSA-N 1,4-diamino-2-(3-methoxyphenyl)sulfonylanthracene-9,10-dione Chemical compound COC1=CC=CC(S(=O)(=O)C=2C(=C3C(=O)C4=CC=CC=C4C(=O)C3=C(N)C=2)N)=C1 ZXXTZESOEUNHQC-UHFFFAOYSA-N 0.000 description 1
- FLXXQVRPKSNQGJ-UHFFFAOYSA-N 1,4-diamino-2-(4-methylphenoxy)-3-phenoxyanthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1OC(C(=C1N)OC=2C=CC=CC=2)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O FLXXQVRPKSNQGJ-UHFFFAOYSA-N 0.000 description 1
- CBAZXQCRCLPTAU-UHFFFAOYSA-N 1,4-diamino-2-chloro-3-phenoxyanthracene-9,10-dione Chemical compound NC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(Cl)C=1OC1=CC=CC=C1 CBAZXQCRCLPTAU-UHFFFAOYSA-N 0.000 description 1
- MHWWHNUOEQRRLF-UHFFFAOYSA-N 1,4-diamino-5,8-dihydroxy-2-phenoxyanthracene-9,10-dione Chemical compound NC=1C=2C(=O)C3=C(O)C=CC(O)=C3C(=O)C=2C(N)=CC=1OC1=CC=CC=C1 MHWWHNUOEQRRLF-UHFFFAOYSA-N 0.000 description 1
- FPEDFHGLJLFDNU-UHFFFAOYSA-N 1,4-diamino-5-nitro-2-phenoxyanthracene-9,10-dione Chemical compound NC=1C=2C(=O)C3=CC=CC([N+]([O-])=O)=C3C(=O)C=2C(N)=CC=1OC1=CC=CC=C1 FPEDFHGLJLFDNU-UHFFFAOYSA-N 0.000 description 1
- KXIIZFMPAJPCRR-UHFFFAOYSA-N 1,5-diamino-3-chloro-4,8-dihydroxy-2-phenoxyanthracene-9,10-dione Chemical compound ClC=1C(O)=C2C(=O)C=3C(N)=CC=C(O)C=3C(=O)C2=C(N)C=1OC1=CC=CC=C1 KXIIZFMPAJPCRR-UHFFFAOYSA-N 0.000 description 1
- XDWMUDQKNPIWDS-UHFFFAOYSA-N 1,5-diamino-4,8-dihydroxy-2-(4-methoxyphenyl)anthracene-9,10-dione Chemical compound C1=CC(OC)=CC=C1C1=CC(O)=C(C(=O)C=2C(=C(O)C=CC=2N)C2=O)C2=C1N XDWMUDQKNPIWDS-UHFFFAOYSA-N 0.000 description 1
- UJUJZCVBECKVGA-UHFFFAOYSA-N 1,5-diamino-4,8-dihydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C=1C(O)=C2C(=O)C=3C(N)=CC=C(O)C=3C(=O)C2=C(N)C=1OC1=CC=CC=C1 UJUJZCVBECKVGA-UHFFFAOYSA-N 0.000 description 1
- ATXDYXRWYJWMKW-UHFFFAOYSA-N 1,8-dihydroxy-4,5-dinitro-2-phenylsulfanylanthracene-9,10-dione Chemical compound O=C1C=2C(O)=CC=C([N+]([O-])=O)C=2C(=O)C(C(=C2)[N+]([O-])=O)=C1C(O)=C2SC1=CC=CC=C1 ATXDYXRWYJWMKW-UHFFFAOYSA-N 0.000 description 1
- KDFGKZLPSJEZKY-UHFFFAOYSA-N 1-(1-amino-2-phenoxyethoxy)-4-hydroxyanthracene-9,10-dione Chemical compound C=1C=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C=1OC(N)COC1=CC=CC=C1 KDFGKZLPSJEZKY-UHFFFAOYSA-N 0.000 description 1
- PDBDVSDFJDLDPM-UHFFFAOYSA-N 1-(1-amino-2-phenylsulfanylethoxy)-4-hydroxyanthracene-9,10-dione Chemical compound NC(CSC1=CC=CC=C1)OC1=CC=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)O PDBDVSDFJDLDPM-UHFFFAOYSA-N 0.000 description 1
- MOKWUFJFSRNAFE-UHFFFAOYSA-N 1-(1-amino-4-ethoxy-4-hydroxycyclohexa-2,5-dien-1-yl)anthracene-9,10-dione Chemical compound C1=CC(OCC)(O)C=CC1(N)C1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O MOKWUFJFSRNAFE-UHFFFAOYSA-N 0.000 description 1
- LMRWYDAOJRALSX-UHFFFAOYSA-N 1-(1-amino-6-sulfanylcyclohexa-2,4-dien-1-yl)-4-hydroxyanthracene-9,10-dione Chemical compound C=1C=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C=1C1(N)C=CC=CC1S LMRWYDAOJRALSX-UHFFFAOYSA-N 0.000 description 1
- XUIVJNRXWOVWNB-UHFFFAOYSA-N 1-(methoxymethyl)-1,3-dimethylurea Chemical compound CNC(=O)N(C)COC XUIVJNRXWOVWNB-UHFFFAOYSA-N 0.000 description 1
- OLFPBXRQLNFJQR-UHFFFAOYSA-N 1-[(1,4-dihydroxy-6-sulfanylcyclohexa-2,4-dien-1-yl)methyl]anthracene-9,10-dione Chemical compound C1=CC(O)=CC(S)C1(O)CC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O OLFPBXRQLNFJQR-UHFFFAOYSA-N 0.000 description 1
- PHZDDNRFLBMCNJ-UHFFFAOYSA-N 1-amino-2-(2,4-dimethylphenoxy)-4-hydroxyanthracene-9,10-dione Chemical compound CC1=CC(C)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N PHZDDNRFLBMCNJ-UHFFFAOYSA-N 0.000 description 1
- ATUCJTYOKYDSAH-UHFFFAOYSA-N 1-amino-2-(2-anilinoethoxy)-4-hydroxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCCNC1=CC=CC=C1 ATUCJTYOKYDSAH-UHFFFAOYSA-N 0.000 description 1
- HXIOVXBUAPXXEU-UHFFFAOYSA-N 1-amino-2-(2-chlorophenoxy)-4-hydroxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1Cl HXIOVXBUAPXXEU-UHFFFAOYSA-N 0.000 description 1
- JDUOTGBRXCXJLM-UHFFFAOYSA-N 1-amino-2-(benzylamino)-4-hydroxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1NCC1=CC=CC=C1 JDUOTGBRXCXJLM-UHFFFAOYSA-N 0.000 description 1
- HGXIQMXDGVVJDA-UHFFFAOYSA-N 1-amino-2-anilino-4-hydroxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1NC1=CC=CC=C1 HGXIQMXDGVVJDA-UHFFFAOYSA-N 0.000 description 1
- CAGMRPBJBPDUIJ-UHFFFAOYSA-N 1-amino-2-benzylsulfanyl-4-hydroxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1SCC1=CC=CC=C1 CAGMRPBJBPDUIJ-UHFFFAOYSA-N 0.000 description 1
- LOMQMQPZVOYJBN-UHFFFAOYSA-N 1-amino-4-anilino-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(NC=2C=CC=CC=2)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 LOMQMQPZVOYJBN-UHFFFAOYSA-N 0.000 description 1
- QIQBPLFYOLFHTB-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(2-phenoxyethoxy)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCCOC1=CC=CC=C1 QIQBPLFYOLFHTB-UHFFFAOYSA-N 0.000 description 1
- ZUNLYCYGYIWJQS-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(2-phenoxyethylsulfanyl)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1SCCOC1=CC=CC=C1 ZUNLYCYGYIWJQS-UHFFFAOYSA-N 0.000 description 1
- DZOOLKFVBAJJGQ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(2-phenylethoxy)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCCC1=CC=CC=C1 DZOOLKFVBAJJGQ-UHFFFAOYSA-N 0.000 description 1
- JYHMEQDEORLBAZ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(3-methylphenoxy)anthracene-9,10-dione Chemical compound CC1=CC=CC(OC=2C(=C3C(=O)C4=CC=CC=C4C(=O)C3=C(O)C=2)N)=C1 JYHMEQDEORLBAZ-UHFFFAOYSA-N 0.000 description 1
- JBUBYUZDOUATKW-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-hydroxyphenoxy)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=C(O)C=C1 JBUBYUZDOUATKW-UHFFFAOYSA-N 0.000 description 1
- BBGAWQASSKMVOH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-hydroxyphenyl)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1C1=CC=C(O)C=C1 BBGAWQASSKMVOH-UHFFFAOYSA-N 0.000 description 1
- BGIJPDMVGSTDDJ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-methoxyphenoxy)anthracene-9,10-dione Chemical compound C1=CC(OC)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N BGIJPDMVGSTDDJ-UHFFFAOYSA-N 0.000 description 1
- SRQFPTQDOWAIFK-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-methylphenoxy)anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N SRQFPTQDOWAIFK-UHFFFAOYSA-N 0.000 description 1
- WXOSHVARKGGGQM-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-methylsulfanylphenoxy)anthracene-9,10-dione Chemical compound C1=CC(SC)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N WXOSHVARKGGGQM-UHFFFAOYSA-N 0.000 description 1
- DNIGXAQMJSGHCD-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-phenoxybutoxy)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCCCCOC1=CC=CC=C1 DNIGXAQMJSGHCD-UHFFFAOYSA-N 0.000 description 1
- MUPFNTCMAXTLNZ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-phenylphenoxy)anthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC(C=C1)=CC=C1C1=CC=CC=C1 MUPFNTCMAXTLNZ-UHFFFAOYSA-N 0.000 description 1
- UTCJSUIDCBZSAD-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(4-propan-2-ylphenoxy)anthracene-9,10-dione Chemical compound C1=CC(C(C)C)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N UTCJSUIDCBZSAD-UHFFFAOYSA-N 0.000 description 1
- UZHMMSBDIXSBOW-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenylmethoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OCC1=CC=CC=C1 UZHMMSBDIXSBOW-UHFFFAOYSA-N 0.000 description 1
- KBLRWVXBAOMMNQ-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenylsulfanylanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1SC1=CC=CC=C1 KBLRWVXBAOMMNQ-UHFFFAOYSA-N 0.000 description 1
- RULWBFLPUAFFGY-UHFFFAOYSA-N 2-(hydroxymethyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1CO RULWBFLPUAFFGY-UHFFFAOYSA-N 0.000 description 1
- IUQLVHINRWUEGT-UHFFFAOYSA-N 3-(hydroxymethyl)azepan-2-one Chemical compound OCC1CCCCNC1=O IUQLVHINRWUEGT-UHFFFAOYSA-N 0.000 description 1
- OVPZEFAFTQSEJB-UHFFFAOYSA-N 4,8-diamino-1,5-dihydroxy-2-(4-methoxyphenyl)anthracene-9,10-dione Chemical compound C1=CC(OC)=CC=C1C1=CC(N)=C(C(=O)C=2C(=C(N)C=CC=2O)C2=O)C2=C1O OVPZEFAFTQSEJB-UHFFFAOYSA-N 0.000 description 1
- YYBSEGBOVVQCAU-UHFFFAOYSA-N 4,8-diamino-2-(4-ethoxyphenyl)-1,5-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(OCC)=CC=C1C1=CC(N)=C(C(=O)C=2C(=C(N)C=CC=2O)C2=O)C2=C1O YYBSEGBOVVQCAU-UHFFFAOYSA-N 0.000 description 1
- BNFONHJTWQFZPT-UHFFFAOYSA-N 4-amino-1,5-dihydroxy-2-(4-methoxyphenyl)-8-nitroanthracene-9,10-dione Chemical compound C1=CC(OC)=CC=C1C1=CC(N)=C(C(=O)C=2C(=C(C=CC=2O)[N+]([O-])=O)C2=O)C2=C1O BNFONHJTWQFZPT-UHFFFAOYSA-N 0.000 description 1
- PBMWEQHOZPTUQQ-UHFFFAOYSA-N 4-hydroxy-2-methylbut-2-enamide Chemical compound NC(=O)C(C)=CCO PBMWEQHOZPTUQQ-UHFFFAOYSA-N 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BEQYLBDBIZXMIC-UHFFFAOYSA-N Hydroxymethylsuccinic acid Chemical compound OCC(C(O)=O)CC(O)=O BEQYLBDBIZXMIC-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 description 1
- HHUSGXQQESDUMC-UHFFFAOYSA-N ethyl n-ethyl-n-(hydroxymethyl)carbamate Chemical compound CCOC(=O)N(CC)CO HHUSGXQQESDUMC-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- OMLKPIIYNUNCMY-UHFFFAOYSA-N formic acid;sulfuric acid Chemical compound OC=O.OS(O)(=O)=O OMLKPIIYNUNCMY-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical class OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- HWJHZLJIIWOTGZ-UHFFFAOYSA-N n-(hydroxymethyl)acetamide Chemical compound CC(=O)NCO HWJHZLJIIWOTGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/542—Anthraquinones with aliphatic, cycloaliphatic, araliphatic or aromatic ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0048003 | 1965-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH555874A true CH555874A (de) | 1974-11-15 |
Family
ID=7101972
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1627266D CH1627266D (enrdf_load_stackoverflow) | 1965-12-24 | ||
| CH1354967A CH555874A (de) | 1965-12-24 | 1966-11-11 | Verfahren zur herstellung sulfonsaeuregruppenfreier anthrachinonfarbstoffe. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1627266D CH1627266D (enrdf_load_stackoverflow) | 1965-12-24 |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT268480B (enrdf_load_stackoverflow) |
| BE (1) | BE691657A (enrdf_load_stackoverflow) |
| CH (2) | CH555874A (enrdf_load_stackoverflow) |
| DE (1) | DE1644598C3 (enrdf_load_stackoverflow) |
| FR (1) | FR1503492A (enrdf_load_stackoverflow) |
| GB (1) | GB1163956A (enrdf_load_stackoverflow) |
| NL (1) | NL6618137A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2033410B1 (enrdf_load_stackoverflow) * | 1969-02-27 | 1973-07-13 | Sumitomo Chemical Co | |
| US3758505A (en) * | 1971-04-16 | 1973-09-11 | Gaf Corp | Anthraquinone dyes containing n methylenelactam |
| AR203095A1 (es) | 1973-01-08 | 1975-08-14 | Bayer Ag | Colorantes 1-fenilamino-nitroantraquinonas de aplicacion para el tenido y estampado de fibras sinteticas y procedimiento para prepararlos |
-
0
- CH CH1627266D patent/CH1627266D/xx unknown
-
1965
- 1965-12-24 DE DE19651644598 patent/DE1644598C3/de not_active Expired
-
1966
- 1966-11-11 CH CH1354967A patent/CH555874A/de not_active IP Right Cessation
- 1966-12-12 FR FR87103A patent/FR1503492A/fr not_active Expired
- 1966-12-13 GB GB5572166A patent/GB1163956A/en not_active Expired
- 1966-12-22 BE BE691657D patent/BE691657A/xx unknown
- 1966-12-22 AT AT1179366A patent/AT268480B/de active
- 1966-12-23 NL NL6618137A patent/NL6618137A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1163956A (en) | 1969-09-10 |
| AT268480B (de) | 1969-02-10 |
| DE1644598A1 (de) | 1971-05-06 |
| DE1644598C3 (de) | 1974-08-22 |
| DE1644598B2 (de) | 1974-01-31 |
| CH1627266D (enrdf_load_stackoverflow) | |
| BE691657A (enrdf_load_stackoverflow) | 1967-06-22 |
| FR1503492A (fr) | 1967-11-24 |
| NL6618137A (enrdf_load_stackoverflow) | 1967-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |