GB1475081A - Water-soluble anthraquinone dyes - Google Patents
Water-soluble anthraquinone dyesInfo
- Publication number
- GB1475081A GB1475081A GB2302173A GB2302173A GB1475081A GB 1475081 A GB1475081 A GB 1475081A GB 2302173 A GB2302173 A GB 2302173A GB 2302173 A GB2302173 A GB 2302173A GB 1475081 A GB1475081 A GB 1475081A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- nuclei
- alkyl
- alkylene
- dyes
- 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
- 239000001000 anthraquinone dye Substances 0.000 title abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 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 abstract 1
- 150000004056 anthraquinones Chemical class 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 150000004982 aromatic amines Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000000981 basic dye Substances 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/002—Dyes with anthracene nucleus not condensed with any other ring containing onium groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
1475081 Water soluble anthraquinone dyes YORKSHIRE CHEMICALS Ltd 14 May 1974 [15 May 1973] 23021/73 Heading C4P The invention comprises water soluble basic dyes having the general formula wherein the n quaternary alkylamino groups are in α-positions in the anthraquinone nucleus, R<SP>1</SP> is alkylene, R<SP>2</SP> is alkyl, R<SP>3</SP> is alkyl or R<SP>2</SP> and R<SP>3</SP> together with the quaternary N atom represent a heterocyclic ring, R<SP>4</SP> is alkylene, R<SP>5</SP> is a substituted or unsubstituted aryl group with the proviso that R<SP>5</SP> does not represent an unsubstituted phenyl group when R<SP>4</SP> is methylene, X- is an anion which renders the dyestuff soluble in water and n is 1 or 2, and wherein the nuclei A and B, and the alkyl, aryl and alkylene groups may be optionally further substituted, but not by sulphonic or carboxylic acid groups, and in the case of nuclei A and B not by α-positioned branched chain alkylamine residues or α- halogen substituted arylamine residues and when n is 1 and nucleii A and B are further substituted, at least one of the further substituents must be present in the same nucleus as the quaternary alkylamino group and when n is 2, at least one further substituent must be present in nuclei A and/or B. They are prepared by reacting one mole of a compound of the general formula with n moles of an aralkylating agent R<SP>4</SP>R<SP>5</SP>R<SP>6</SP> where A, B, n, 12<SP>1</SP>-12<SP>5</SP> are as above and R<SP>6</SP> is an atom or group replaceable under the reaction conditions, e.g. Cl, Br, I or toluene 4-sulphonic acid ester group. The reaction takes place at 30 -150‹ C. in an organic solvent. The dyes are used to dye or print polyacrylonitrile and its copolymers, tannin-mordanted cotton, cellulose acetate, and acid-modified polyamide and polyesters.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2302173A GB1475081A (en) | 1974-05-14 | 1974-05-14 | Water-soluble anthraquinone dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2302173A GB1475081A (en) | 1974-05-14 | 1974-05-14 | Water-soluble anthraquinone dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1475081A true GB1475081A (en) | 1977-06-01 |
Family
ID=10188823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2302173A Expired GB1475081A (en) | 1974-05-14 | 1974-05-14 | Water-soluble anthraquinone dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1475081A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014899A1 (en) * | 1979-02-17 | 1980-09-03 | Bayer Ag | Process for the preparation of cationic anthraquinone dyes |
| FR2456806A1 (en) * | 1979-05-14 | 1980-12-12 | Ici Ltd | Colouring wet-spun acrylic! fibres in gel condition - using a bis. cationic anthraquinone dyestuff |
| US4456552A (en) * | 1979-08-02 | 1984-06-26 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
| US4614618A (en) * | 1979-08-02 | 1986-09-30 | American Cyanamid Company | 1,4-bis(substituted-amino)-5,8-dihydroxy anthraquinones and leuco bases thereof |
| US4820738A (en) * | 1977-08-15 | 1989-04-11 | American Cyanamid Company | 1,4-bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof |
| US5520707A (en) * | 1995-08-07 | 1996-05-28 | Clairol, Inc. | Methods for dyeing hair with anthraquinone hair dyes having a quaternary ammonium side chain |
| WO2019223015A1 (en) * | 2018-05-25 | 2019-11-28 | 苏州大学张家港工业技术研究院 | Precursor of blue anthraquinone active disperse dye and preparation method therefor |
-
1974
- 1974-05-14 GB GB2302173A patent/GB1475081A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820738A (en) * | 1977-08-15 | 1989-04-11 | American Cyanamid Company | 1,4-bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof |
| EP0014899A1 (en) * | 1979-02-17 | 1980-09-03 | Bayer Ag | Process for the preparation of cationic anthraquinone dyes |
| FR2456806A1 (en) * | 1979-05-14 | 1980-12-12 | Ici Ltd | Colouring wet-spun acrylic! fibres in gel condition - using a bis. cationic anthraquinone dyestuff |
| US4456552A (en) * | 1979-08-02 | 1984-06-26 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
| US4614618A (en) * | 1979-08-02 | 1986-09-30 | American Cyanamid Company | 1,4-bis(substituted-amino)-5,8-dihydroxy anthraquinones and leuco bases thereof |
| US5520707A (en) * | 1995-08-07 | 1996-05-28 | Clairol, Inc. | Methods for dyeing hair with anthraquinone hair dyes having a quaternary ammonium side chain |
| US5891200A (en) * | 1995-08-07 | 1999-04-06 | Lim; Mu-Ill | Hair dye compositions containing anthraquinone dyes having a quaternary ammonium side chain and neutral direct dyes |
| WO2019223015A1 (en) * | 2018-05-25 | 2019-11-28 | 苏州大学张家港工业技术研究院 | Precursor of blue anthraquinone active disperse dye and preparation method therefor |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |