GB786929A - Improvements relating to quaternary ammonium salts of thiazole monazo dyestuffs - Google Patents
Improvements relating to quaternary ammonium salts of thiazole monazo dyestuffsInfo
- Publication number
- GB786929A GB786929A GB35890/55A GB3589055A GB786929A GB 786929 A GB786929 A GB 786929A GB 35890/55 A GB35890/55 A GB 35890/55A GB 3589055 A GB3589055 A GB 3589055A GB 786929 A GB786929 A GB 786929A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- amino
- ethyl
- phenyl
- dimethyl
- 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 title 1
- -1 phenyl- Chemical group 0.000 abstract 10
- 239000000975 dye Substances 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 7
- 125000003277 amino group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 239000002168 alkylating agent Substances 0.000 abstract 3
- 229940100198 alkylating agent Drugs 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical group C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 abstract 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 abstract 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical group C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 abstract 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 abstract 1
- ZDWPBMJZDNXTPG-UHFFFAOYSA-N 2h-benzotriazol-4-amine Chemical group NC1=CC=CC2=C1NN=N2 ZDWPBMJZDNXTPG-UHFFFAOYSA-N 0.000 abstract 1
- USPVTJCHQHJFBQ-UHFFFAOYSA-N 3-chloro-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC(Cl)=C1 USPVTJCHQHJFBQ-UHFFFAOYSA-N 0.000 abstract 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical class OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 abstract 1
- FMKMKBLHMONXJM-UHFFFAOYSA-N 5-methyl-2-phenylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC=C1 FMKMKBLHMONXJM-UHFFFAOYSA-N 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 208000006558 Dental Calculus Diseases 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 150000001348 alkyl chlorides Chemical class 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 abstract 1
- 150000001649 bromium compounds Chemical class 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical class CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 abstract 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 239000002895 emetic Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical class CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical class C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 abstract 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical class COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 abstract 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical class C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000005181 nitrobenzenes Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 238000005185 salting out Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000001256 steam distillation Methods 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 235000018553 tannin Nutrition 0.000 abstract 1
- 229920001864 tannin Polymers 0.000 abstract 1
- 239000001648 tannin Substances 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyestuffs of formula <FORM:0786929/IV (b)/1> where the cation is free of acid dissociating, salt forming groups, R1 is an alkyl radicle which may be substituted, A is an alkene radicle, the two adjacent doubly bound C atoms of which are connected to the N and S atoms of the hetero nucleus, B is the residue of an azo component and X1 is an anion equivalent to the cyclammonium cation. They may be made by alkylating appropriate dyestuffs. A is indicated as an ethene, propene, D 1- or D 2-butene or D 3-hexene radicle or a phenyl-, cycloalkyl-, halogen-, alkoxy-, nitro- or acylamino-alkene radicle. Methyl, ethyl, propyl, butyl, hydroxyethyl and benzyl groups are specified as substituents for the alkyl group of R1. The azo component may be of the aliphatic, cycloaliphatic, or isocyclic- or heterocyclic-aromatic series, e.g. acyloacetyl compounds, and compounds containing dihydroresorcinol, phenylnaphthyl, pyrrole or pyrazole rings which may contain amino, hydroxy, amido, acylamino, alkyl, aralkyl groups as substituents or may be fused with other rings. Amino groups in the starting dyestuff may be acylated. Thus, B may comprise acetoacetyl - phenylamide, hydroxy- and amino- and acylamino-phenyl and -naphthyl, 3-indolyl and 5-hydroxy- and -amino-pyrazole residues. The starting dyestuffs may be obtained by the usual processes of diazotization and coupling or by the alkaline condensation of p-nitro-phenols or -aminophenyl compounds with 2-aminothiazoles. Preferred coupling components are isocyclicaromatic amino and hydroxy compounds, especially those coupling in the p-position to these groups. The isocyclic-aromatic compound may contain fused hetero rings such as 4-aminobenztriazole, aminobenzimidazole or aminoindazole compounds. The amino group may be primary, secondary or tertiary in character. The substituents of the amino group may be aliphatic, araliphatic, alicyclic, aromatic or heterocyclic and may be oxalkyl, fluoralkyl, cyanalkyl, alkoxy- and phenoxyalkyl, and alkyl-, alkoxy- and halogen-phenyl and -benzyl residues. Aliphatic substituents of the amino group may form, optionally with an ether oxygen atom or with the aromatic radicle having the amino group, hydrogenated hetero cyclics such as the piperidino, morpholino, 1,2,3,4 - tetrahydroquinolino, lilolidino, julolidino and perimidino compounds. The preferred p-aminophenyl radicle may contain halogen, alkyl, alkoxy, nitro, acylamino or alkylsulphonyl groups. Indicated as alkylating agents are esters of strong mineral and organic sulphonic acids, i.e. those of pK at most 4, with preferably low alcohols. Alkyl chlorides and bromides, aralkyl halides, dialkyl sulphates and alkyl-p-methylbenzene sulphonates may be used. Other specified anions being metho-and etho-sulphate and bisulphate. Quaternary ammonium compounds of formic, acetic, oxalic and lactic acid may be obtained and also the dye bases themselves, i.e. X1 is OH. Further, double salts with inorganic salts, especially those with zinc chloride, may be obtained. When alkylation is effected in inert organic solvents the dye salts may be precipitated. Solvents mentioned are benzene hydrocarbons, halogen- and nitro-benzenes, cycloaliphatic hydrocarbons and excess of alkylating agent. An excess of alkylating agent is desirably used, any amino groups being subsequently alkylated if desired. In some cases alkylation may be performed in aqueous or alcoholic solution. The dye salts may be recovered by salting-out after removal of inert solvent by steam distillation, or they may be isolated by any other conventional method. The dye salts may be further altered, e.g. acylated. The dyestuffs are basic and dye cotton mordanted with tartar emetic and tannin, silk, leather and polyacrylonitrile fibres. Examples are provided illustrating the preparation of the dye salts and their use in dyeing processes the diazo components used being 2-amino-thiazole and its 4-methyl, -acetyl, -methoxy, -n-butyl, -phenyl, 4,5-dimethyl and -diphenyl, 4-methyl-5-ethyl and -(b -oxyethyl), 4-ethyl-5-methyl, 4-carbethoxy-5-methyl and 4-bromo-5-phenyl derivatives; the azo components being 1- and 2-naphthylamine, 1-amino-2-methoxy-, 1-N-phenylamino- and 1-(N,N-dimethyl)aminonaphthalenes, 1,2,3,4 - tetrahydro - 3 - hydroxy-and -5,6-dihydroxy-7,8-benzquinoline, phenol, diphenyl - N - methylamine, 4 - methyl - and -amyl-phenols, 2,5-dimethoxy-aniline, N,N-dimethyl-, -di-(b -oxyethyl)-, -diethyl, -dibenzyl, N-methyl, N,b -oxy- and -cyan-ethyl- and N-ethyl - N - benzyl - anilines, N - methyldiphenylamine, N - phenyl - morpholine, N,N-dimethyl - amino - 3 - nitro -, - methoxy -, methyl- and -carbethoxy-, -2,5-dimethyl- and -dimethoxy- and -2-methoxy-5-methyl-benzenes, N,N - diethylamino - 3 - chloro - benzene, 1 - phenyl - 3 - methyl - 5 - aminopyrazole, pyrrole, indole, 2,5-dimethyl-, 2-methoxy-5-methyl-, 3-chloro- and -methyl- and 2-methoxy-5-acetamino-anilines, N-ethyl-, benzyl- and-phenyl-anilines and 3-methyl- and -chloro-N-ethyl-anilines, and quaternating agents being dimethyl and diethyl sulphate, methyl chloride, methyl and ethyl bromides and iodides, butyl iodide, benzyl bromide and methyl and ethyl p-toluenesulphonates, the dyestuffs yielding blue, orange and red colours on the materials mentioned above.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH786929X | 1954-12-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB786929A true GB786929A (en) | 1957-11-27 |
Family
ID=4536653
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB35890/55A Expired GB786929A (en) | 1954-12-15 | 1955-12-14 | Improvements relating to quaternary ammonium salts of thiazole monazo dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB786929A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3977827A (en) | 1974-02-25 | 1976-08-31 | Sumitomo Chemical Company, Limited | Process for dyeing acid-modified polyester fibers |
-
1955
- 1955-12-14 GB GB35890/55A patent/GB786929A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3977827A (en) | 1974-02-25 | 1976-08-31 | Sumitomo Chemical Company, Limited | Process for dyeing acid-modified polyester fibers |
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