GB643681A - Improvements in or relating to dyestuffs and pigments derived from thiazolyl-2 thioglycollic acids - Google Patents
Improvements in or relating to dyestuffs and pigments derived from thiazolyl-2 thioglycollic acidsInfo
- Publication number
- GB643681A GB643681A GB2992047A GB2992047A GB643681A GB 643681 A GB643681 A GB 643681A GB 2992047 A GB2992047 A GB 2992047A GB 2992047 A GB2992047 A GB 2992047A GB 643681 A GB643681 A GB 643681A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thioglycollic
- acid
- benzthiazolyl
- anhydride
- thioglycollic 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
- 239000002253 acid Substances 0.000 title abstract 4
- 150000007513 acids Chemical class 0.000 title abstract 4
- 239000000049 pigment Substances 0.000 title abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 abstract 1
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical compound SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- -1 amino, substituted amino Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- BEQBQOAWTXSRIB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-thiazole Chemical compound C1=CSC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BEQBQOAWTXSRIB-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- FHZUMJAAGNDUKE-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzothiazole Chemical compound C1=CC=C2C=C3C(N=CS4)=C4C=CC3=CC2=C1 FHZUMJAAGNDUKE-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/16—Sulfur atoms
Abstract
Dyes and pigments are made by reacting together a monocarboxylic acid anhydride and a compound of the general structure <FORM:0643681/IV (c)/1> three types of such compounds being specified, viz. S-(thiazolyl or thiazolinyl-2) thioglycollic acids, which may have alkyl, aryl, or aralkyl substituents in the ring, and S-(benzthiazolyl-2) thioglycollic acids, which may be substituted by alkyl, aryl, aralkyl, alkoxy, amino, substituted amino, or halogen, and which may have further rings fused on to the benzene rings, as in naphthathiazole, anthrathiazole, phenanthrathiazole or anthraquinone-thiazole. Preferably the minimum effective quantity of the anhydride, and a small quantity of a base such as pyridine or triethylamine are employed. In examples: (1) S-(benzthiazolyl-2)-thioglycollic acid is heated on the water bath with acetic, propionic, butyric, or benzoic anhydride; (2) S-(6-ethoxy or amino-benzthiazolyl-2)-thioglycollic acid; (3) S-(5-bromo- or methyl-benzthiazolyl-2)-thioglycollic acid; (4) S-(5.6-dimethoxy - benzthiazolyl - 2) - thioglycollic acid; (5) S-(6.7-benzbenzthiazolyl-2)-thioglycollic acid; (6) S-(4-methylthiazolyl-2)-thioglycollic acid; (7) S-(thiazolinyl-2)-thioglycollic acid, are each heated with acetic anhydride. The thioglycollic acids above referred to are prepared from the mercapto thiazole and chloracetic acid in presence of caustic soda.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2992047A GB643681A (en) | 1947-11-10 | 1947-11-10 | Improvements in or relating to dyestuffs and pigments derived from thiazolyl-2 thioglycollic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2992047A GB643681A (en) | 1947-11-10 | 1947-11-10 | Improvements in or relating to dyestuffs and pigments derived from thiazolyl-2 thioglycollic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB643681A true GB643681A (en) | 1950-09-27 |
Family
ID=10299341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2992047A Expired GB643681A (en) | 1947-11-10 | 1947-11-10 | Improvements in or relating to dyestuffs and pigments derived from thiazolyl-2 thioglycollic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB643681A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2156486A1 (en) * | 1971-10-22 | 1973-06-01 | Roussel Uclaf | Oxazolyl oxy or thio acetic acids - analgesics antipyretics and anti-inflammatories |
| US4014864A (en) * | 1975-02-25 | 1977-03-29 | Ciba-Geigy Corporation | Heterocyclic substituted azo dyestuff |
-
1947
- 1947-11-10 GB GB2992047A patent/GB643681A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2156486A1 (en) * | 1971-10-22 | 1973-06-01 | Roussel Uclaf | Oxazolyl oxy or thio acetic acids - analgesics antipyretics and anti-inflammatories |
| US4014864A (en) * | 1975-02-25 | 1977-03-29 | Ciba-Geigy Corporation | Heterocyclic substituted azo dyestuff |
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