GB885814A - Water-soluble dyestuffs containing unsaturated carboxylic acid residues - Google Patents
Water-soluble dyestuffs containing unsaturated carboxylic acid residuesInfo
- Publication number
- GB885814A GB885814A GB7312/58A GB731258A GB885814A GB 885814 A GB885814 A GB 885814A GB 7312/58 A GB7312/58 A GB 7312/58A GB 731258 A GB731258 A GB 731258A GB 885814 A GB885814 A GB 885814A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyes
- acid
- amino
- sulphonic acid
- anthraquinone
- 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
- 150000001732 carboxylic acid derivatives Chemical group 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 6
- 239000000987 azo dye Substances 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 2
- 150000004056 anthraquinones Chemical class 0.000 abstract 2
- -1 methylsulphonyl Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- DZXNARMBWJFBGD-UHFFFAOYSA-N 1,4-diamino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2N DZXNARMBWJFBGD-UHFFFAOYSA-N 0.000 abstract 1
- JILYTRJVXLAMCE-UHFFFAOYSA-N 2-(4-aminophenyl)-4h-pyrazol-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)CC=N1 JILYTRJVXLAMCE-UHFFFAOYSA-N 0.000 abstract 1
- VZMULMSIWMLZLC-UHFFFAOYSA-N 2-aminoanthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=C(N)C=C3C3=CC=C4C1=C32 VZMULMSIWMLZLC-UHFFFAOYSA-N 0.000 abstract 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 abstract 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract 1
- SPHQXPPVJCWUGX-UHFFFAOYSA-N 4,8-diamino-1,5-dihydroxy-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=C(N)C=C(S(O)(=O)=O)C(O)=C2C(=O)C2=C1C(O)=CC=C2N SPHQXPPVJCWUGX-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- QQKUVYODQWWIHQ-UHFFFAOYSA-N N-(8-amino-9,10-dioxoanthracen-1-yl)prop-2-enamide Chemical compound NC=1C=CC=C2C(C=3C=CC=C(C3C(C12)=O)NC(=O)C=C)=O QQKUVYODQWWIHQ-UHFFFAOYSA-N 0.000 abstract 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000009435 amidation Effects 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 150000004984 aromatic diamines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001844 chromium Chemical class 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000004040 coloring Methods 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
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000002657 fibrous material Substances 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
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001007 phthalocyanine dye Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract 1
- 235000021286 stilbenes Nutrition 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises water-soluble organic dyes which contain at least one group imparting solubility in water and the residue of an a ,b -unsaturated aliphatic carboxylic acid which has three carbon atoms and is bound to an aromatic nucleus through an amino bridge of formula <FORM:0885814/IV (c)/1> where n is an integer, preferably 1. The dyes may be made by conventional methods by condensation or by diazotisation and coupling of appropriate components or by acylation of appropriate dyes. Indicated are stilbene, acid phthalocyanine, acid anthraquinone, oxazine and especially mono- and poly-azo dyes which may be metallized, copper, cobalt and chromium complexes being mentioned. Indicated unsaturated residues are CH2CH-CO, which may contain an a - or b -negative substituent such as a halogen atom, HC-C-CO and especially -N(C(n-1)H(2n-1)CO-C(X)=CH-X where n is an integer, preferably 1, and one X is H and the other H or Cl. Indicated water-solubilising groups are sulphonamide, which may be acylated, methylsulphonyl, carboxy or sulphonic acid. Other substituents indicated are halogen, nitro, acylamino, alkyl and alkoxy. Indicative of starting dyes to be acylated are amino-azo-dyes obtained by hydrolysing acylamino-azo or reducing nitro-azo dyes, dyes made by coupling diazotised aromatic amines with acylatable coupling components such as 1-amino-3-alkyl-and -acylamino-benzenes, b -ketocarboxylic acid arylides, m- or p-aminophenyl-5-pyrazolone and aminonaphthol sulphonic acids, 1-amino-4-(31-or 41 - aminophenylamino) - anthraquinone - 2 - sulphonic acid, 1-amino-4-(41-aminophenylamino)-anthraquinone-2, 21-di- and 2,31,8-tri-sulphonic acids, 1,5-dihydroxy-4,8-diaminoanthraquinone-2-sulphonic acid, 1,4-diaminoanthraquinone-2-sulphonic acid, 8-amino-1-acrylaminoanthraquinone, aminodibenzanthrone sulphonic acid ands dyes obtained by the partial amidation of 1 mol proportion of a tri- or tetra-sulphonic acid chloride of an anthraquinone or phthalocyanine dye with 1 mol proportion of an aromatic diamine, or a monoacyl derivative thereof, with subsequent hydrolysis of unreacted sulphonic acid chloride groups, and the acylamino group, if present. The dyes are used especially to colour polyhydroxylated fibrous materials, e.g. regenerated cellulose, cotton and linen, and are preferably used in conjunction with a treatment with an alkali and heat. The dyes also colour nitrogenous materials, e.g. leather, silk, wool and superpolyamide and -urethane fibres, from a weakly alkaline to acid bath. Examples are provided of the preparation of the dyes and their use in colouring processes various shades of red, blue, yellow and green being obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH885814X | 1957-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB885814A true GB885814A (en) | 1961-12-28 |
Family
ID=4545260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7312/58A Expired GB885814A (en) | 1957-03-06 | 1958-03-06 | Water-soluble dyestuffs containing unsaturated carboxylic acid residues |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB885814A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234205A (en) * | 1962-02-08 | 1966-02-08 | Hoechst Ag | Metal complex compounds of monoazo-dyestuffs |
| DE1221384B (en) * | 1962-01-29 | 1966-07-21 | Ici Ltd | Process for the production of azo dyes |
| DE1275233B (en) * | 1961-05-24 | 1969-03-20 | Ici Ltd | Process for the preparation of disazo dyes |
| CN106349747A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Blue active dye with high alkali resistance and preparation method of blue active dye |
-
1958
- 1958-03-06 GB GB7312/58A patent/GB885814A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1275233B (en) * | 1961-05-24 | 1969-03-20 | Ici Ltd | Process for the preparation of disazo dyes |
| DE1221384B (en) * | 1962-01-29 | 1966-07-21 | Ici Ltd | Process for the production of azo dyes |
| US3234205A (en) * | 1962-02-08 | 1966-02-08 | Hoechst Ag | Metal complex compounds of monoazo-dyestuffs |
| CN106349747A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Blue active dye with high alkali resistance and preparation method of blue active dye |
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