GB1595554A - Antraquinoid dyes - Google Patents

Antraquinoid dyes Download PDF

Info

Publication number: GB1595554A
Authority: GB; United Kingdom
Prior art keywords: carbon atoms; alkyl; phenyl; formula; dye
Prior art date: 1977-02-11
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

Application number

GB5417/78A

Other languages

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-02-11

Filing date

1978-02-10

Publication date

1981-08-12

1978-02-10 Application filed by BASF SE filed Critical BASF SE

1981-08-12 Publication of GB1595554A publication Critical patent/GB1595554A/en

Status Expired legal-status Critical Current

Links

239000000975 dye Substances 0.000 title abstract description 32
-1 methoxy, ethoxy Chemical group 0.000 claims abstract description 143
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 81
125000000217 alkyl group Chemical group 0.000 claims abstract description 46
239000000460 chlorine Substances 0.000 claims abstract description 26
229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 19
229910052794 bromium Inorganic materials 0.000 claims abstract description 19
239000003795 chemical substances by application Substances 0.000 claims abstract description 17
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 15
239000000835 fiber Substances 0.000 claims abstract description 14
125000001424 substituent group Chemical group 0.000 claims abstract description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 12
229920002678 cellulose Polymers 0.000 claims abstract description 11
239000001913 cellulose Substances 0.000 claims abstract description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
239000000463 material Substances 0.000 claims abstract description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 7
230000008961 swelling Effects 0.000 claims abstract description 6
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
229920000742 Cotton Polymers 0.000 claims description 20
238000000034 method Methods 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 12
229920000728 polyester Polymers 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
238000004043 dyeing Methods 0.000 claims description 10
239000002270 dispersing agent Substances 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
239000000645 desinfectant Substances 0.000 claims description 3
125000006353 oxyethylene group Chemical group 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
239000004753 textile Substances 0.000 claims description 3
239000002657 fibrous material Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000012209 synthetic fiber Substances 0.000 claims 2
229920002994 synthetic fiber Polymers 0.000 claims 2
238000005108 dry cleaning Methods 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
238000000859 sublimation Methods 0.000 claims 1
230000008022 sublimation Effects 0.000 claims 1
238000005406 washing Methods 0.000 claims 1
WUPLYDUVSCMDJI-UHFFFAOYSA-N 3-methylideneoxane Chemical compound C=C1CCCOC1 WUPLYDUVSCMDJI-UHFFFAOYSA-N 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
229920006395 saturated elastomer Polymers 0.000 abstract 1
239000010981 turquoise Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
230000010933 acylation Effects 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007859 condensation product Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UPTDJEHQSNYQKC-UHFFFAOYSA-N 1,4,5-triamino-8-hydroxyanthracene-9,10-dione Chemical class O=C1C2=C(O)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N UPTDJEHQSNYQKC-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000004744 fabric Substances 0.000 description 3
150000002828 nitro derivatives Chemical class 0.000 description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
239000013011 aqueous formulation Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000000986 disperse dye Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 1
UVFJFPGRSPOHNB-UHFFFAOYSA-N 1,4-diamino-5-hydroxy-8-nitroanthracene-9,10-dione Chemical class O=C1C(C(=CC=C2O)[N+]([O-])=O)=C2C(=O)C2=C1C(N)=CC=C2N UVFJFPGRSPOHNB-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
GCQZRSVHYPEACN-UHFFFAOYSA-N 2-methylideneoxolane Chemical compound C=C1CCCO1 GCQZRSVHYPEACN-UHFFFAOYSA-N 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
TXBFKXDFIPFHAV-UHFFFAOYSA-N 3-methylideneoxolane Chemical compound C=C1CCOC1 TXBFKXDFIPFHAV-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AXVKYVSAXLKIKJ-UHFFFAOYSA-N 4-methyl-3-methylideneoxane Chemical compound C=C1COCCC1C AXVKYVSAXLKIKJ-UHFFFAOYSA-N 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 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 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229920005556 chlorobutyl Polymers 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000002245 particle Substances 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000011282 treatment Methods 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/516—N-acylated derivatives
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/20—Anthraquinone dyes
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6033—Natural or regenerated cellulose using dispersed dyes
- D06P3/6041—Natural or regenerated cellulose using dispersed dyes using specified dyes

Landscapes

Chemical & Material Sciences (AREA)
Dispersion Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Cosmetics (AREA)
Luminescent Compositions (AREA)

GB5417/78A 1977-02-11 1978-02-10 Antraquinoid dyes Expired GB1595554A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2705716A DE2705716C2 (de)	1977-02-11	1977-02-11	Anthrachinoide Farbstoffe und deren Verwendung

Publications (1)

Publication Number	Publication Date
GB1595554A true GB1595554A (en)	1981-08-12

Family

ID=6000889

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
GB5417/78A Expired GB1595554A (en)	1977-02-11	1978-02-10	Antraquinoid dyes

Country Status (6)

Country	Link
JP (1)	JPS5399229A (it)
CH (1)	CH631731A5 (it)
DE (1)	DE2705716C2 (it)
FR (1)	FR2380369A1 (it)
GB (1)	GB1595554A (it)
IT (1)	IT1093403B (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3233948A1 (de) *	1982-09-14	1984-03-15	Basf Ag, 6700 Ludwigshafen	Anthrachinoide farbstoffe
DE3240036A1 (de) *	1982-10-28	1984-05-10	Lev Michajlovi&ccaron; Moskva Blinov	Anthrachinonderivate, verfahren zu ihrer herstellung und ihre verwendung in fluesigkristallmaterialien fuer elektrooptische vorrichtungen
DE59408909D1 (de) *	1993-10-13	1999-12-16	Ciba Sc Holding Ag	Neue Fluoreszenzfarbstoffe
JPH0928436A (ja) *	1995-05-15	1997-02-04	Ikeda Takahiro	傘袋

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2191029A (en) *		1940-02-20		Anthraqbinone compounds and proc-
NL127417C (it) *	1960-01-19
GB1284932A (en) *	1969-06-17	1972-08-09	Ici Ltd	Anthraquinone dyestuffs
DE2116555A1 (en) *	1971-04-05	1972-10-12	Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen	Blue anthraquinoid dispersion dyes - with improved colour and thermofixing props
DE2500237C2 (de) *	1975-01-04	1977-01-13	Basf Ag	Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendung
DE2536536A1 (de) *	1975-08-16	1977-02-24	Basf Ag	Dispersionsfarbstoffe der anthrachinonreihe

1977
- 1977-02-11 DE DE2705716A patent/DE2705716C2/de not_active Expired
1978
- 1978-01-26 IT IT19682/78A patent/IT1093403B/it active
- 1978-02-08 CH CH141678A patent/CH631731A5/de not_active IP Right Cessation
- 1978-02-09 FR FR7803614A patent/FR2380369A1/fr active Granted
- 1978-02-10 GB GB5417/78A patent/GB1595554A/en not_active Expired
- 1978-02-13 JP JP1421378A patent/JPS5399229A/ja active Granted

Also Published As

Publication number	Publication date
JPS641510B2 (it)	1989-01-11
DE2705716C2 (de)	1986-07-24
IT7819682A0 (it)	1978-01-26
FR2380369B1 (it)	1981-04-30
JPS5399229A (en)	1978-08-30
FR2380369A1 (fr)	1978-09-08
CH631731A5 (en)	1982-08-31
DE2705716A1 (de)	1978-08-17
IT1093403B (it)	1985-07-19

Legal Events

Date	Code	Title	Description
1981-10-28	PS	Patent sealed [section 19, patents act 1949]
1991-10-09	PCNP	Patent ceased through non-payment of renewal fee

Publication	Publication Date	Title
US3558670A (en)	1971-01-26	Tetra-alpha-substituted anthraquinones
GB1595554A (en)	1981-08-12	Antraquinoid dyes
DE2644731A1 (de)	1978-04-06	Anthrachinoide farbstoffe
US3649645A (en)	1972-03-14	Naphthostyril type disperse dyes
US3836549A (en)	1974-09-17	Anthraquinone compounds
US3458537A (en)	1969-07-29	1-(p-benzyloxyanilino)-4-hydroxyanthraquinones
US3821200A (en)	1974-06-28	Nitrodiphenylamine dyestuffs
US3989450A (en)	1976-11-02	Nitroanthraquinones
US4221911A (en)	1980-09-09	Naphtholactam dyestuffs
US3636065A (en)	1972-01-18	Water-insoluble anthraquinone dyestuffs
US4096139A (en)	1978-06-20	Azocoumarinic-type dyes for the disperse dyeing of textile fabrics
US3759957A (en)	1973-09-18	Anthraquinoid dyestuffs
GB1583605A (en)	1981-01-28	Naphtholactam dyestuffs
US4507476A (en)	1985-03-26	Anthraquinone dyestuffs for cellulose-containing fibers
US4056544A (en)	1977-11-01	Anthraquinone compounds
US3867406A (en)	1975-02-18	Anthraquinoid disperse dyes
US3862967A (en)	1975-01-28	Tetra-{60 -substituted anthraquinone derivatives
US3549311A (en)	1970-12-22	Nitrodiphenylamine disperse dyes
JPS59138266A (ja)	1984-08-08	マリンブル−色の染料混合物
EP0147938A2 (en)	1985-07-10	Disperse dyestuffs
EP0103278B1 (de)	1988-06-29	Anthrachinoide Farbstoffe und deren Verwendung
US3493587A (en)	1970-02-03	Water-insoluble benzofuran-substituted anthraquinone dyestuffs
US4104284A (en)	1978-08-01	Nitroanthraquinones
US3455958A (en)	1969-07-15	Water-soluble anthraquinone dyestuffs
US4170600A (en)	1979-10-09	Thiocyanomethyl substituted anthraquinone disperse dyes