GB928619A - New anthraquinone dyestuffs and their manufacture and use - Google Patents
New anthraquinone dyestuffs and their manufacture and useInfo
- Publication number
- GB928619A GB928619A GB1984861A GB1984861A GB928619A GB 928619 A GB928619 A GB 928619A GB 1984861 A GB1984861 A GB 1984861A GB 1984861 A GB1984861 A GB 1984861A GB 928619 A GB928619 A GB 928619A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- amino
- sulphonic acid
- dyes
- aromatic
- 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
- 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 title 1
- 150000004056 anthraquinones Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- 239000000975 dye Substances 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- -1 aromatic sulphonyl halide Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 abstract 1
- 229940081735 acetylcellulose Drugs 0.000 abstract 1
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000001993 wax Substances 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
- C09B6/00—Anthracene dyes not provided for above
-
- 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
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl 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
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/06—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
In an example (4), 1-amino-4-(41-(p-toluene-sulphonylamino) phenylamino]-anthraquinone is dissolved in acetone and the solution is mixed with a solution of commercial acetylcellulose in acetone and spun to give reddish-blue threads.ALSO:The invention comprises anthraquinone dyes free from carboxylic acid and sulphonic acid groups and which contain a primary or secondary amino group in the 1-position and a phenylamino group in the 4-position of which the phenyl nucleus contains a substituent of the formula:- -X-SO2-R where R is an aromatic group and X is an oxygen, nitrogen or sulphonic acid -N-(aminoethyl) amide bridge. The dyes are made by acylating a 1-amino-4-phenylaminoanthraquino amino or hydroxy group in the phenyl nucleus, with an aromatic sulphonyl halide, splitting off the 2-sulphonic acid group by reduction and, if necessary, re-oxidizing the dye. The nitrogen atom of the sulphonylamino group may be subsequently methylated. The aromatic group R may be a substituted or unsubstituted benzene or a naphthalene radical. Examples are given. The dyes dye natural or synthetic resins, waxes, lacquers and plastics giving blue shades.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH640360A CH394441A (en) | 1960-06-03 | 1960-06-03 | Process for the production of new anthraquinone dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB928619A true GB928619A (en) | 1963-06-12 |
Family
ID=4309015
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1819461A Expired GB934727A (en) | 1960-06-03 | 1961-05-18 | New anthraquinone dyestuffs and their manufacture and use |
| GB1984861A Expired GB928619A (en) | 1960-06-03 | 1961-06-01 | New anthraquinone dyestuffs and their manufacture and use |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1819461A Expired GB934727A (en) | 1960-06-03 | 1961-05-18 | New anthraquinone dyestuffs and their manufacture and use |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE604568A (en) |
| CH (1) | CH394441A (en) |
| DE (1) | DE1214346B (en) |
| ES (1) | ES267873A1 (en) |
| GB (2) | GB934727A (en) |
| NL (1) | NL265502A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3421828A (en) * | 1963-07-19 | 1969-01-14 | Geigy Ag J R | Sulfuric acid ester derivatives of 1-anilino - 4 - hydroxy - anthraquinone and mixtures |
| US4188187A (en) | 1977-04-06 | 1980-02-12 | Sandoz Ltd. | Dyeing of polyamide textiles and anthraquinone dyestuffs therefor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2392663A (en) * | 1941-10-15 | 1946-01-08 | Chem Ind Basel | Aminoanthraquinone derivatives |
| US2876061A (en) * | 1954-08-05 | 1959-03-03 | Gen Aniline & Film Corp | Solubilization of pigments |
-
0
- BE BE604568D patent/BE604568A/xx unknown
- NL NL265502D patent/NL265502A/xx unknown
-
1960
- 1960-06-03 CH CH640360A patent/CH394441A/en unknown
-
1961
- 1961-05-18 GB GB1819461A patent/GB934727A/en not_active Expired
- 1961-06-01 GB GB1984861A patent/GB928619A/en not_active Expired
- 1961-06-02 DE DEC24280A patent/DE1214346B/en active Pending
- 1961-06-02 ES ES0267873A patent/ES267873A1/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3421828A (en) * | 1963-07-19 | 1969-01-14 | Geigy Ag J R | Sulfuric acid ester derivatives of 1-anilino - 4 - hydroxy - anthraquinone and mixtures |
| US4188187A (en) | 1977-04-06 | 1980-02-12 | Sandoz Ltd. | Dyeing of polyamide textiles and anthraquinone dyestuffs therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| ES267873A1 (en) | 1961-11-16 |
| NL265502A (en) | |
| CH394441A (en) | 1965-06-30 |
| GB934727A (en) | 1963-08-21 |
| DE1214346B (en) | 1966-04-14 |
| BE604568A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB965006A (en) | Anthraquinone dyestuffs free from acid groups imparting water-solubility and a process for their manufacture | |
| GB867571A (en) | New dyestuffs of the anthraquinone series containing a halogenated triazine radical, their manufacture and use | |
| GB928619A (en) | New anthraquinone dyestuffs and their manufacture and use | |
| GB1102789A (en) | Improvements relating to acid anthraquinone dyestuffs and their use | |
| GB830876A (en) | New acid anthraquinone dyestuffs | |
| US2434765A (en) | 1-amino-2-hydroxyalkylthio-4-arylamino-anthraquinones | |
| US2506025A (en) | Anthraquinone vat dyestuffs | |
| GB781930A (en) | New anthraquinonoid dyestuffs | |
| GB873617A (en) | Anthraquinone vat dyestuffs and process for their manufacture | |
| GB819956A (en) | Dyestuffs of the anthraquinone series | |
| GB1230668A (en) | ||
| GB895399A (en) | Triazinylamino anthraquinone dyestuffs and process for their manufacture | |
| GB1048882A (en) | Anthraquinone dyestuffs | |
| ES269798A2 (en) | Disazo dyestuffs containing a trisulfonate diazo component | |
| US3522264A (en) | Anthraquinone dyestuffs | |
| US2193151A (en) | Acid wool dyestuffs of the anthraquinone series | |
| GB772030A (en) | New anthraquinonoid dyestuffs | |
| ES274470A1 (en) | Anthraquinone vat dyestuffs containing sulfohalide groups | |
| GB891774A (en) | Hydroxyanthraquinone dyestuffs | |
| GB958924A (en) | Alkylated dihydroxy-diaminoanthraquinones and process for their manufacture | |
| GB926327A (en) | New dyestuffs of the azostilbene series containing halopyrimidyl residues | |
| US1855278A (en) | Process of dyeing acetate silk | |
| GB507206A (en) | Manufacture of compounds of the anthraquinone series | |
| GB736187A (en) | Improvements relating to acid dyestuffs of the anthraquinone series and their use | |
| GB1043520A (en) | Anthraquinone-2-carboxamides and process for their manufacture and use |