GB394312A - New anthraquinone dyestuffs and the application thereof - Google Patents
New anthraquinone dyestuffs and the application thereofInfo
- Publication number
- GB394312A GB394312A GB3144031A GB3144031A GB394312A GB 394312 A GB394312 A GB 394312A GB 3144031 A GB3144031 A GB 3144031A GB 3144031 A GB3144031 A GB 3144031A GB 394312 A GB394312 A GB 394312A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- dihydrobenz
- keto
- thiazine
- acid
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 238000004043 dyeing Methods 0.000 abstract 3
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 abstract 2
- BWVCFRAIWIZNNF-UHFFFAOYSA-N 7-amino-4h-1,4-benzothiazin-3-one Chemical compound N1C(=O)CSC2=CC(N)=CC=C21 BWVCFRAIWIZNNF-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 238000004382 potting Methods 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 2
- FAYAYUOZWYJNBD-UHFFFAOYSA-N 1,3-benzothiazol-6-amine Chemical compound NC1=CC=C2N=CSC2=C1 FAYAYUOZWYJNBD-UHFFFAOYSA-N 0.000 abstract 1
- 150000004434 1-hydroxyanthraquinones Chemical class 0.000 abstract 1
- MFJBNCSJXFYMMJ-UHFFFAOYSA-N 2-amino-4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)C(N)SC2=C1 MFJBNCSJXFYMMJ-UHFFFAOYSA-N 0.000 abstract 1
- JMDVARRGYWIJGZ-UHFFFAOYSA-N 2-chloro-5-methyl-1,3-dinitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 JMDVARRGYWIJGZ-UHFFFAOYSA-N 0.000 abstract 1
- JOPJLJTXWMIJKO-UHFFFAOYSA-N 2h-thiazin-3-amine Chemical class NC1=CC=CSN1 JOPJLJTXWMIJKO-UHFFFAOYSA-N 0.000 abstract 1
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical class C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 abstract 1
- IIIRCTYVTXZKGW-UHFFFAOYSA-N 8-amino-6-methyl-4H-1,4-benzothiazin-3-one Chemical compound NC1=CC(=CC=2NC(CSC21)=O)C IIIRCTYVTXZKGW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 abstract 1
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000010930 lactamization Methods 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- CPDQUIJMRGFOIL-UHFFFAOYSA-N n-(2-aminophenyl)thiohydroxylamine Chemical class NC1=CC=CC=C1NS CPDQUIJMRGFOIL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 abstract 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04R—LOUDSPEAKERS, MICROPHONES, GRAMOPHONE PICK-UPS OR LIKE ACOUSTIC ELECTROMECHANICAL TRANSDUCERS; DEAF-AID SETS; PUBLIC ADDRESS SYSTEMS
- H04R17/00—Piezoelectric transducers; Electrostrictive transducers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Acoustics & Sound (AREA)
- Signal Processing (AREA)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Anthraquinone dyes are prepared by reacting an amino-3-keto-2,3-dihydrobenz-1,4-thiazine with a 1-hydroxyanthraquinone or a leucoderivative thereof, oxidizing, if necessary, and hydrolysing the product to give the substituted thioglycollic acid of which it is the lactam. The 1-hydroxyanthraquinones may carry substituents and may comprise those specified in Specifications 4961/95 and 7538/96, [both in Class 2, Acids and salts, Organic &c.]; they are condensed with the amino-thiazine derivatives by the methods disclosed in these Specifications, the presence of pyridine or dimethylaniline as a diluent being mentioned. In examples (1) leuco-quinizarin is condensed with 7-amino-3-keto-2,3-dihydrobenz-1,4-thiazine in pyridine and in presence of boric acid; saponification by means of aqueous caustic soda yields the thioglycollic acid which dyes wool green shades; the latter on treatment with hot dilute hydrochloric acid are "lactamized" to dyeings fast to potting; (2) the 7-amino derivative may be replaced by the 6-amino or 8-amino-6-methyl-derivatives of 3-keto-2,3-dihydrobenz-1,4-thiazines to give similar products dyeing green shades which may be "lactamized" on the fibre and remained fast to potting; (3) leuco-1,4,5-trihydroxyanthraquinone is similarly condensed with 7-amino-3-keto-2,3-dihydrobenz-1,4-thiazine; the dyeing shade after lactamization is green. The above 6- and 7-aminothiazine derivatives are prepared by first hydrolysing (alkaline) the 5- or 6-aminobenzthiazole according to the process of Specification 355,808, treating the resulting mercaptophenylenediamines with chloracetic acid and ring-closing by means of hot dilute mineral acid. 8-amino-6-methyl-3-keto-2,3-dihydrobenz-1,4-thiazine is prepared by treating 4-chloro-3,5-dinitrotoluene with alcoholic sodium hydrosulphide to give the mercaptan which is then condensed with sodium chloracetate and reduced with zinc and acetic acid.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR745527D FR745527A (en) | 1931-11-13 | ||
| GB3144031A GB394312A (en) | 1931-11-13 | 1931-11-13 | New anthraquinone dyestuffs and the application thereof |
| DEI45752D DE596398C (en) | 1931-11-13 | 1932-11-13 | Process for the preparation of anthraquinone dyes |
| US720593A US2105011A (en) | 1931-11-13 | 1934-04-14 | Piezo-electric apparatus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3144031A GB394312A (en) | 1931-11-13 | 1931-11-13 | New anthraquinone dyestuffs and the application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB394312A true GB394312A (en) | 1933-06-13 |
Family
ID=10323119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3144031A Expired GB394312A (en) | 1931-11-13 | 1931-11-13 | New anthraquinone dyestuffs and the application thereof |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE596398C (en) |
| FR (1) | FR745527A (en) |
| GB (1) | GB394312A (en) |
-
0
- FR FR745527D patent/FR745527A/fr not_active Expired
-
1931
- 1931-11-13 GB GB3144031A patent/GB394312A/en not_active Expired
-
1932
- 1932-11-13 DE DEI45752D patent/DE596398C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE596398C (en) | 1934-05-03 |
| FR745527A (en) | 1933-05-12 |
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