GB2031927A - Dyestuffs - Google Patents
Dyestuffs Download PDFInfo
- Publication number
- GB2031927A GB2031927A GB7927357A GB7927357A GB2031927A GB 2031927 A GB2031927 A GB 2031927A GB 7927357 A GB7927357 A GB 7927357A GB 7927357 A GB7927357 A GB 7927357A GB 2031927 A GB2031927 A GB 2031927A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- hydrogen atom
- halogen atom
- cyano group
- alkyl
- 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.)
- Withdrawn
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 11
- 239000004758 synthetic textile Substances 0.000 claims abstract description 11
- 239000000975 dye Substances 0.000 claims abstract description 10
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 7
- 229920000728 polyester Polymers 0.000 claims abstract description 6
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 5
- 239000004753 textile Substances 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 238000012505 colouration Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229920002301 cellulose acetate Polymers 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- -1 n-butyl isobutyl Chemical group 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910015850 Be—Ba Inorganic materials 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- QLRBNEZOQPLERN-UHFFFAOYSA-N (sulfonylamino)benzene Chemical compound O=S(=O)=NC1=CC=CC=C1 QLRBNEZOQPLERN-UHFFFAOYSA-N 0.000 description 1
- NKXGCKWWAUWPEM-UHFFFAOYSA-N 1-[3-(2-methylpropylamino)phenyl]ethanone Chemical compound CC(C)CNC1=CC=CC(C(C)=O)=C1 NKXGCKWWAUWPEM-UHFFFAOYSA-N 0.000 description 1
- IATFESHWEQUTKA-UHFFFAOYSA-N 2,5-dimethyl-n-octylaniline Chemical compound CCCCCCCCNC1=CC(C)=CC=C1C IATFESHWEQUTKA-UHFFFAOYSA-N 0.000 description 1
- YPZJMNUEDVDMFI-UHFFFAOYSA-N 2,5-dimethyl-n-pentylaniline Chemical compound CCCCCNC1=CC(C)=CC=C1C YPZJMNUEDVDMFI-UHFFFAOYSA-N 0.000 description 1
- UUUCNDYWOCRNPT-UHFFFAOYSA-N 2,5-dimethyl-n-propylaniline Chemical compound CCCNC1=CC(C)=CC=C1C UUUCNDYWOCRNPT-UHFFFAOYSA-N 0.000 description 1
- JCRMYLUIMGTZSR-UHFFFAOYSA-N 2-chloro-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1Cl JCRMYLUIMGTZSR-UHFFFAOYSA-N 0.000 description 1
- WFQXGJMHCGBRQJ-UHFFFAOYSA-N 2-methoxy-n-propan-2-ylaniline Chemical compound COC1=CC=CC=C1NC(C)C WFQXGJMHCGBRQJ-UHFFFAOYSA-N 0.000 description 1
- PEVQARAUCAKBFU-UHFFFAOYSA-N 2-methyl-N-[3-(pentan-2-ylamino)phenyl]benzamide Chemical compound C=1(C(=CC=CC1)C(=O)NC=1C=C(NC(C)CCC)C=CC1)C PEVQARAUCAKBFU-UHFFFAOYSA-N 0.000 description 1
- OUJCYMJDHPYQHZ-UHFFFAOYSA-N 3-(2-methylpropylamino)benzonitrile Chemical compound CC(C)CNC1=CC=CC(C#N)=C1 OUJCYMJDHPYQHZ-UHFFFAOYSA-N 0.000 description 1
- JWCZFFVZNIDFIM-UHFFFAOYSA-N 3-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CNC1=CC=CC(C)=C1 JWCZFFVZNIDFIM-UHFFFAOYSA-N 0.000 description 1
- LOUBHADNEPMWMA-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1Cl LOUBHADNEPMWMA-UHFFFAOYSA-N 0.000 description 1
- TVAZCWJQAKRQPS-UHFFFAOYSA-N 4-amino-2,5-dicyano-N-ethylbenzenesulfonamide Chemical compound C(#N)C1=C(N)C=C(C(=C1)S(=O)(=O)NCC)C#N TVAZCWJQAKRQPS-UHFFFAOYSA-N 0.000 description 1
- QAFHAHOUPBVOKB-UHFFFAOYSA-N 4-amino-3,5-dibromo-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC(Br)=C(N)C(Br)=C1 QAFHAHOUPBVOKB-UHFFFAOYSA-N 0.000 description 1
- XBNCYNPBBJJYBN-UHFFFAOYSA-N 4-amino-3,5-dichloro-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC(Cl)=C(N)C(Cl)=C1 XBNCYNPBBJJYBN-UHFFFAOYSA-N 0.000 description 1
- LTFVELCIFWEGGA-UHFFFAOYSA-N 4-amino-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(N)C=C1 LTFVELCIFWEGGA-UHFFFAOYSA-N 0.000 description 1
- VNBAGPGLMFYJKB-UHFFFAOYSA-N 4-amino-n-(2-methylphenyl)benzenesulfonamide Chemical compound CC1=CC=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VNBAGPGLMFYJKB-UHFFFAOYSA-N 0.000 description 1
- RDQKWPXWHYYREU-UHFFFAOYSA-N 4-amino-n-butyl-2,5-dichlorobenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl RDQKWPXWHYYREU-UHFFFAOYSA-N 0.000 description 1
- 101000912181 Arabidopsis thaliana Cysteine synthase, mitochondrial Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IBQMRTOSIDYBGY-UHFFFAOYSA-N N-(3-aminophenyl)-N-pentan-3-ylacetamide Chemical compound C(C)C(CC)N(C1=CC(=CC=C1)N)C(C)=O IBQMRTOSIDYBGY-UHFFFAOYSA-N 0.000 description 1
- HBAVSAHQZFGICR-UHFFFAOYSA-N N-[3-(pentan-2-ylamino)phenyl]-2-phenylacetamide Chemical compound C1(=CC=CC=C1)CC(=O)NC=1C=C(NC(C)CCC)C=CC1 HBAVSAHQZFGICR-UHFFFAOYSA-N 0.000 description 1
- TYGJXDVBFMMVCZ-UHFFFAOYSA-N N-[3-(pentan-2-ylamino)phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC=1C=C(NC(C)CCC)C=CC=1 TYGJXDVBFMMVCZ-UHFFFAOYSA-N 0.000 description 1
- QTXSKOUTHSQRDE-UHFFFAOYSA-N N-[3-(pentan-2-ylamino)phenyl]butanamide Chemical compound C(CCC)(=O)NC=1C=C(NC(C)CCC)C=CC1 QTXSKOUTHSQRDE-UHFFFAOYSA-N 0.000 description 1
- TVFPOXCOLUAGNQ-UHFFFAOYSA-N N-[3-(pentan-2-ylamino)phenyl]formamide Chemical compound C(=O)NC=1C=C(NC(C)CCC)C=CC1 TVFPOXCOLUAGNQ-UHFFFAOYSA-N 0.000 description 1
- DNCARGPSYUBXHH-UHFFFAOYSA-N N-[3-(pentan-2-ylamino)phenyl]hexanamide Chemical compound C(CCCCC)(=O)NC=1C=C(NC(C)CCC)C=CC=1 DNCARGPSYUBXHH-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- LWYVBYCZGZSFRJ-UHFFFAOYSA-N [3-(pentan-2-ylamino)phenyl]urea Chemical compound CCCC(C)NC1=CC=CC(NC(N)=O)=C1 LWYVBYCZGZSFRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- VYKUPVHEQKWXSQ-UHFFFAOYSA-N ethyl 3-(2-methylpropylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC(NCC(C)C)=C1 VYKUPVHEQKWXSQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UKYIRVIOSWMROO-UHFFFAOYSA-N methyl 3-(2-methylpropylamino)benzoate Chemical compound COC(=O)C1=CC=CC(NCC(C)C)=C1 UKYIRVIOSWMROO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KHRPZGKVYFQHDF-UHFFFAOYSA-N methyl n-[3-(pentan-2-ylamino)phenyl]carbamate Chemical compound CCCC(C)NC1=CC=CC(NC(=O)OC)=C1 KHRPZGKVYFQHDF-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- FLLXIDNFXBLBMT-UHFFFAOYSA-N n,2,5-trimethylaniline Chemical compound CNC1=CC(C)=CC=C1C FLLXIDNFXBLBMT-UHFFFAOYSA-N 0.000 description 1
- GGARKJIWYNVMBF-UHFFFAOYSA-N n-(2-methylpropyl)aniline Chemical compound CC(C)CNC1=CC=CC=C1 GGARKJIWYNVMBF-UHFFFAOYSA-N 0.000 description 1
- ZVKGOCKADDESLH-UHFFFAOYSA-N n-(3-aminophenyl)-n-propan-2-ylacetamide Chemical compound CC(C)N(C(C)=O)C1=CC=CC(N)=C1 ZVKGOCKADDESLH-UHFFFAOYSA-N 0.000 description 1
- UKTXCPBHCDRRGS-UHFFFAOYSA-N n-[3-(pentan-2-ylamino)phenyl]methanesulfonamide Chemical compound CCCC(C)NC1=CC=CC(NS(C)(=O)=O)=C1 UKTXCPBHCDRRGS-UHFFFAOYSA-N 0.000 description 1
- GQJLNLFMPBSORR-UHFFFAOYSA-N n-butyl-2,5-dimethylaniline Chemical compound CCCCNC1=CC(C)=CC=C1C GQJLNLFMPBSORR-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFKFTGZBQNLFCC-UHFFFAOYSA-N n-hexyl-2,5-dimethylaniline Chemical compound CCCCCCNC1=CC(C)=CC=C1C OFKFTGZBQNLFCC-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Disperse monoazo dyestuffs having the general formula: <IMAGE> wherein R represents a hydrogen atom or an alkyl group, R<1> represents a hydrogen atom or a hydrocarbyl group, R<2> represents a hydrocarbyl group, V represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R<2>, W represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R<2>, X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or a group -CO2R<2>, Y represents a hydrogen atom, a halogen atom or an alkyl, alkoxy or alkoxycarbonyl group, and Z represents an acyl, acylamino or cyano group or the group Y, and wherein at least one of V and X is hydrogen. The dyes are applicable to synthetic textile materials for example cellulose acetates, polyamides and especially aromatic polyester textile materials
Description
SPECIFICATION
Dyestuffs
This invention relates to dyestuffs and more particularly to disperse monoazo dyestuffs based on secondary amine coupling components.
According to the present invention there are provided disperse monoazo dyestuffs having the generai formula:
wherein R represents a hydrogen atom or an alkyl group, which may be further substituted,
R1 represents a hydrogen atom or a hydrocarbyl group,
R2 represents a hydrocarbyl group,
V represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2,
W represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or a group -CO2R2,
Y represents a hydrogen atom, a halogen atom or an alkyl, alkoxy or alkoxycarbonyl group, and
Z represents an acyl, acylamino, or cyano group or the group y, and wherein at least one of V and X is a hydrogen atom.
The hydrocarbyl groups represented by R1 and R2 may be alkyl, alkenyl, cycloalkyl, aralkyl or optionally substituted aryl groups.
Examples of alkyl groups represented by R, 131,132 and Y are methyl, ethyl, n-propyl, isopropyl, n-butyl isobutyl, n-pentyl, sec-pentyl, n-hexyl, 2-ethylhexyl and n-octyl.
An example of a cycloalkyl group represented by R' and R2 is cyclohexyl.
Examples of aralkyl groups represented by R' and R2 are benzyl and ss-phenylethyl.
Examples of aryl and substituted aryl groups represented by R1 and R2 are phenyl, tolyl and chlorophenyl.
Examples of alkoxy groups represented by y are methoxy and ethoxy, and examples of alkoxycarbonyl groups represented by Y are methoxycarbonyl, ethoxycarbonyl and n-butoxycarbonyl.
Examples of halogen atoms represented by V, W, X and Y are chlorine and bromine.
Examples of acyl groups; represented by Z are acetyl and propionyl. The acylamino groups which may be represented by Z include formylamino, alkylcarbonylamino, substituted alkylcarbonylamino, alkenylcarbonylamino, arylcarbonylamino, aralkylcarbonylamino, cycloalkylcarbonylamino, alkylsulphonylamino, arylsulphonylamino, alkoxycarbonylamino, alkoxyalkoxycarbonylamino, aminocarbonylmino and alkylaminocarbonylamino groups.
Examples of such groups include acetylamino, propionylamino, butyrylamino, pivaloylamino, hexanoyla minx, benzoylamino, toluoylamino, phenylacetylamino, cyclo hexylcarbonylamino, methylsulphonylamino, p-toluenesulphonylamino, methoxycarbonylamino and t3-methoxyethoxycarbonylamino.
It is preferred that the alkyl and alkoxy groups represented by Y and the various alkyl and alkoxy radicals present in the acylamino groups are lower alkyl and lower alkoxy groups.
In this specification the terms "lower alkyl" and "lower alkoxy" mean alkyl and alkoxy groups respectively which contain from 1 to 4 carbon atoms.
According to a further feature of the invention there is provided a processforthe manufactureofdisperse monoazo dyestuffs having the above-defined formula (I) which comprises diazotising an arylamine having the formula:
and coupling the diazonium compound so obtained on to a coupling component having the formula:
wherein R, R', R2, V, W, X, Y and Z have the meanings stated above.
Examples of the arylamines of formula (II) which may be used in the process are 2,5.dichlorn-4- sulphonylanil ine, 2,5-dichloro-4-(N-n-butylaminosulphonyl)aniline, 2-chloro-4-(Nethylaminosulphonyl)aniline, 2,6-dichloro-4-(N-ethyl-aminosulphonyl)aniline, 2-bromo4-(Nethylanimosulphonyl)anilihe, 2,6-dibromo-4-(N-ethylaminosulphonyl)aniline, 2-cyano4-(Nethylaminosulphonyl)aniline, 2-(methoxycarbonyl)-4-N-(ethylaminosulphonyl)aniline, 2,5-dicyano4-(N- ethylaminosulphonyl)aniline, 2,5-di(methoxycarbonyl)-4-N-(ethylaminosulphonyl)aniline, 2-nitro4-N- (ethylaminosulphonyl)aniline, 4-2-methylaminosulphonyIaniline4-prnpylaminosulphonylaniIine, 4octylaminosulphonylaniline, 4-('-ethylhexyl)aminosulphonylaniline, 4-diethylaminosulphonylaniline, 4-(Nmethyl-N-phenylamino)sulphonylaniline, 4-(o-tolylamino)sulphonylaniline, 4-(m-tolylamino)sulphonyl, 4 (p-tolylamine)sulphonylaniline, 4-(N-methyl-N-o-chlorophenylamino)sulphonylaniline, 4-(N-methyl-N-Mchlorophenylamino(sulphonylaniline, 4-(N-methyl-N-p-chlorophenylamin)sulphonylaniline, 4 (phenylaminosulponyl)aniline, 4-(benzylaminosulponyl)aniline, 4-[(phenylethyl)aminosulponyl]aniline and 4-cyclohexaminosulphonylaniline.
Examples of the coupling components of formula (III) which may be used are N-sec-pentyl-maminoacetanilide, N-isopropyl-m-aminoacetanilide, 2,5-dimethyl-N-methylaniline, 2,5-dimethyl-Nethylaniline, 2,5-dimethyl-N-n-propylaniline, 2,5-dimethyl-N-butylaniline, 2,5-dimethyl-N-pentylaniline, 2,5dimethyl-N-hexylaniline, 2,5-dimethyl-N-octylaniline, N-isobutylaniline, N-isobutyl-m-toluidine, N-ethyl-otoluidine, 2-chloro-N-isopropyl-aniline, 2-methyi-N-isopropylaniline, 2-methoxy-N-isopropylaniline, 2methoxycarbonyl-N-isopropylaniline, 3-cyano-N-isobutylaniline, 3-acetyl-N-isobutylaniline, 3-propionyl-Nisobutylaniline, 3-methoxycarbonyl-N-isobutylaniline, 3-ethoxycarbonyl-N-isobutyl-aniline, m-formylamino
N-sec-pentylaniline, m-pripionylamino-N-sec-pentylaniline, m-butyrylamino-N-sec-pentylaniline, mpivaloylamino-N-sec-pentylaniline, m-hexanoylamino-N-sec-pentylaniline, m-benzoylamino-N-secpentylaniline, m-toluoylamino-N-sec-pentylaniline, m-phenylacetylamino-N-sec-pentylaniline, mcyclohexylcarbonylamino-N-sec-pentylaniline, m-methylsulphonylamino-N-sec-pentylaniline m-(ptoluenesulphonylamino)-N-sec-pentylaniline, m-methoxycarbonylamino-N-sec-pentylaniline, m-(ss- methoxyethoxycarbonylamino)-N-sec-pentylaniline, m-aminocarbonylamino-N-sec-pentylaniline and methylaminocarbonyl-N-sec-pentylaniline.
In the above coupling components, "sec-pentyl" refers to the radical having the structure (C2H5)2CH-.
The diazotisation and coupling may be carried out by known method for these reactions. For example, the process may be carried out by adding sodium nitrate to a solution or dispersion of the arylamine in hydrochloric acid, sulphuric acid, an aqueous solution of sulphuric acid or a mixture of hydrochloric acid or sulphuric acid with an organic acid such as acetic and/or propionic acid, or by stirring the arylamine with nitrosylsulphuric acid, followed by addition of the resulting solution or dispersion of the diazonium compound thus obtained to a solution of the coupling component in water or in a mixture of water and a water-miscible organic liquid, if necessary adjusting the pH of the mixture to facilitate the coupling reaction, and final!y isolating the resulting dyestuff by conventional methods.
According to a yet further feature of the invention there is provided a method for the colouration of synthetic textile materials which comprises applying to the said synthetic textile materials from an aqueous medium a monoazo dyestuff as hereinbefore defined.
The dyestuffs of the present invention may be applied to synthetic textile materials by dyeing, padding or printing methods in the form of aqueous dispersions which are prepared by conventional methods, for example, by milling the dyestuffs with water and a suitable dispersing agent such as the sodium salt of a naphthalene-2-sulponic acid/formaldehyde condensate.
Examples of synthetic textile materials to which the dyestuffs may be applied are textile materials fabricated from secondary cellulose acetate, cellulose triacetate, polyamides such as poly(hexamethylene adipamide) and above all aromatic polyesters such as polyethylene terephthalate.
The dyestuffs may also be applied to synthetic textile materials by known methods of transfer colour printing such as sublimation transfer printing, optionally under reduced pressure, and wet transfer printing.
The dyestuffs also find application for the melt colouration of polymers such as aromatic polyesters.
When applied to synthetic textile materials as indicated above, the dyestuffs of the present invention provide scarlet shades having good fastness to the tests conventionally applied to coloured synthetic textile materials, and in particular good dyeing properties and tinctorial strength.
The invention is illustrated but not limited by the following Examples in which parts and percentages are by weight.
Example 1
2,5-Dichloro-4-sulphamoylaniline (4.82 parts) is dissolved in a mixture of glacial acetic acid (40 parts) and concentrated hydrochloric acid (6 parts) and diazotised at 0-5"C by addition of 2N-aqueous sodium nitrate solution (10 parts). The solution of the diazonium compound so obtained is added to a mixture of N-(1-ethylpropyl)-m-aminoacetanilide (4.4 parts) in acetic acid (50 parts) and ice water (200 parts). The mixture is stirred for 3 hours, after which time the precipitated dyestuff is collected, washed well with water and recrystallised from aqueous acetone.
When applied in the form of an aqueous dispersion to aromatic polyester textile material a bright scarlet shade is obtained.
The following table gives further Examples of dyes of the invention which may be obtained by diazotising the amines listed in the second column and coupling with the secondary amines listed in the third column.
The fourth column gives the shades obtained on aromatic polyester textile material.
Diazo D5aw Component Goupling Co po ent shade Cl 2 ew 2 c2a5 'harlot 3 C4, CS?- Cl a CE5 CL 4 'sCs(CS3)2 I c ! a=?1, x," ce, p S:e | cOvplk6 Coo,ooet 3 . , .
5 e2llSwIw2 -(c3), scubt d CL 3 6 c,2=2 vNs Cg3) 49 2 CL 32 CL 7 Ca'C HI a pia m.:o | Coapl:.=g Cossent suac CL 8 (al3)zw z tcE3)2 CL 9 Ca)oc.C,2q.ao tO 2 2vY2
DIrD Ca.inacot I | Coupl5ng I 9ud+ CL 11 Ct 2 N - (Z(CS3)2 aa1at 12 2M2 MR,aIC2u3 Or n C,3 13 oupl ) =o Co-ponese coupling Coopcsent 14 Oa2ND2 FCHC2115 Or nv "3 15 (CS31 2NHI2 (c|92 se-rlee CL 16 a ms Hadd 'a H'=plc Dia Cemcnt Coupliq "oaocat Cl 17 (Ca3)1O MCS3 1at CL 18 -C17 Sn1at HI(D(z3 19 a ,arlet
. Exu=ple Diam C03pnnent Coupling Component HIC,,, Cl 3 20 cc"r'r"z- 2 bN15{9 HIM Scarlet C1 N COCa3 Z1 6 NE Crana' 22 wE 2 'BIa2e5 Scarlet "3 jfra-e aro bo.mt Coupling Cacpe3cnt I SuedC Br OC83 23 CzaTDza""fs Scarlet Br 24 Ha\coc3lj ,Bc2H5 cm "3 25 ("3)?sDa " Reddian orange . C.;rrinant ç 'flede a"2"5 .3 N'dM 26 tC15 I SO w, cag5 dand1gdhe "3 27 ("3)?SO2NH2.2 HICOdE 28 n 9 )LC4!9 orange
z,aopl. CWEne COpdOe.t Coupli Cccent Be-Ba 2, (eE3)21150 42 W2. 5 Bed RBX:H 30 a nc Bla'eh red 31 " T N CE(CE3)2 ROE4d6X1 laaople D{.W Iro CoJolmr Col:ponent Be-Ba 32 (CE3)zNX26g2 t}- ezX5 sCrçe LrrW 4 1 I '(a@~m"Hs CS CL HICOC B13 3W cg3ES)z b GN~Cl5(CD3)2 .
Cl 1apple rte coRrDD.e Cncot I Coupitag panant ) Shade Cl 35 3 2 SN)6C;5(CS3)2 L Xt 2Cl2 32 36 'B(a(cr5)a a 7"3)2 MCC 37 a McH("3)2
Zrepl Di w Btane E | een6 cO:p=auent Be-Be el NrdOOOQ3 38 tt bt no - it - ":i"-"H Scarlet . CS C HICOOC B 39 gShCg(CE3)2 40 CaCc52 a i=ple t Diana Co~ponent | Coupling Cospoúent Be-Be MC2B5 i1 "31?22 2 bX N'dCd(C=-3)2 Scarlet I I Q a 5 cE3 n 43 Ca(C)2 Cm-a 4 h=ple Dluo Corpnnest Cnuplin6 Coespanest shady Cl 0' 4i ("3)2wEo2 M2 MCB(C)2 CL "3 45 CM cLw HIcH-C Beddiak- CL "3I orange Ca 46 fl'BC
aapla Cespme e Coapanent c-pltq Cne203ent 47 Cg9NNsD2 p2 OCb Ca CCS *8 t (:1MCa Brarlat 49 T C* Baddiek OEBR3 3 Impla Di w cnepDnent Cop1Iag Cceponent I Be-Be P "z"c" 30 C42 ap.-p 2 g - C* Scarlet Cl Nldmlrd - ca2 51 aICCCS Sd 3 Reddleh BBCa2CS Impla Bt ',op=t Coupling Canpoot Be-Be MEBE C B 53 e5'dE22 ea CS2CS(Ca3)2 Scarlet
Claims (8)
1. A disperse monoazo dyestuff having the general formula:
wherein R represents a hydrogen atom or an alkyl group which may be further substituted,
R' represents a hydrogen atom or a hydrocarbyl group,
R2 represents a hydrocarbyl group,
V represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, W represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or a group -CO2R2, Y represents a hydrogen atom, a halogen atom or an alkyl, alkoxy or alkoxycarbonyl group, and
Z represents an acyl, acylamino or cyano group or the group Y, and wherein at least one of V and X is hydrogen.
2. A disperse monoazo dyestuff as claimed in claim 1 and specifically identified herein.
3. A process for the manufacture of a disperse monoazo dyestuff as defined in claim 1 which comprises diazotising an arylamine having the formula:
and coupling the diazonium compound so obtained with a coupling component having the formula:
wherein R, R1, R2, V, W, X, Y and Z have the meanings stated in claim 1,
4. A process as claimed in claim 3 conducted substantially as hereinbefore described with reference to any one of the foregoing Examples.
5. A disperse monoazo dyestuff whenever manufactured by a method claimed in claim 3 or claim 4.
6. A process for the colouration of synthetic textile materials which comprises applying thereto a disperse monoazo dyestuff as claimed in any one of claims 1, 2 and 5.
7. A process as claimed in claim 6 wherein the synthetic textile material is an aromatic polyester textile material.
8. Synthetic textile materials whenever coloured by the process claimed in claim 6 or claim 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7836177 | 1978-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2031927A true GB2031927A (en) | 1980-04-30 |
Family
ID=10499552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7927357A Withdrawn GB2031927A (en) | 1978-09-08 | 1979-08-06 | Dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5538878A (en) |
| DE (1) | DE2935034A1 (en) |
| FR (1) | FR2435504A1 (en) |
| GB (1) | GB2031927A (en) |
| IT (1) | IT1207231B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4424156A (en) | 1979-09-25 | 1984-01-03 | Bayer Aktiengesellschaft | Halo-substituted amino-and substituted-sulphonamido-containing azo dyestuffs |
| USD948633S1 (en) * | 2019-09-19 | 2022-04-12 | Ao Jie Plastic Toys Factory Ltd. | Toy projectile launcher |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5922964A (en) * | 1982-07-30 | 1984-02-06 | Hitachi Ltd | Azo-based polychroic dyestuff and liquid crystal composition containing the same |
| SE533765C2 (en) * | 2009-05-05 | 2010-12-28 | Tetra Laval Holdings & Finance | Method of controlling a process |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR966775A (en) * | 1941-12-05 | 1950-10-18 | Cie Nat Matieres Colorantes | Yellow monoazo dyes for rayon based? cellulose ethers or other plastics |
| FR1009445A (en) * | 1949-01-20 | 1952-05-29 | Yorkshire Dyeware And Chemical | Manufacture of azo dyes for dyeing thermoplastic materials |
| GB862269A (en) * | 1957-10-04 | 1961-03-08 | Ici Ltd | New azo dyestuffs |
| DE1644052A1 (en) * | 1967-01-26 | 1971-03-25 | Basf Ag | Process for the production of new, water-insoluble azo dyes |
| CH517185A (en) * | 1969-02-20 | 1971-12-31 | Ciba Geigy Ag | Process for dyeing cellulose esters in the spinning mass |
-
1979
- 1979-08-06 GB GB7927357A patent/GB2031927A/en not_active Withdrawn
- 1979-08-28 IT IT7925316A patent/IT1207231B/en active
- 1979-08-30 DE DE19792935034 patent/DE2935034A1/en not_active Withdrawn
- 1979-09-05 JP JP11301379A patent/JPS5538878A/en active Pending
- 1979-09-07 FR FR7922376A patent/FR2435504A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4424156A (en) | 1979-09-25 | 1984-01-03 | Bayer Aktiengesellschaft | Halo-substituted amino-and substituted-sulphonamido-containing azo dyestuffs |
| USD948633S1 (en) * | 2019-09-19 | 2022-04-12 | Ao Jie Plastic Toys Factory Ltd. | Toy projectile launcher |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1207231B (en) | 1989-05-17 |
| DE2935034A1 (en) | 1980-03-20 |
| FR2435504A1 (en) | 1980-04-04 |
| JPS5538878A (en) | 1980-03-18 |
| IT7925316A0 (en) | 1979-08-28 |
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Legal Events
| Date | Code | Title | Description |
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| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |