GB1010562A - Coumarin derivatives and their use as optical brightening agents - Google Patents
Coumarin derivatives and their use as optical brightening agentsInfo
- Publication number
- GB1010562A GB1010562A GB30650/62A GB3065062A GB1010562A GB 1010562 A GB1010562 A GB 1010562A GB 30650/62 A GB30650/62 A GB 30650/62A GB 3065062 A GB3065062 A GB 3065062A GB 1010562 A GB1010562 A GB 1010562A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thienyl
- coumarin
- group
- carbamyloxy
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
Abstract
Thienyl coumarins of the general formula <FORM:1010562/C2/1> where R is hydrogen or methyl, R1 is halogen or alkyl, which may be substituted by hydroxyl, amino, ammonium or sulphonic groups, a sulphonic acid or carboxylic acid group, which may be esterified, a carboxylic acid amide, an acyloxy or a carbamyloxy group, m is 0, 1 or 2, n is 0, 1 or 2 and R2 is chlorine or bromine or methyl when n is 1 or -CH=CH-CH=CH- when n is 2, and two R1 substitutents may represent a fused ring, and especially the following-coumarins, 3 - thienyl - (21)-; 3 - [51-bromothienyl] - (21)-; 7 - phenyl - carbamyloxy - 3 - thienyl - (21)-; 5,7 - dichloro - 3 - thienyl-(21)-; 7 - acetoxy - 3 - thienyl - (21)-; 5,7 - dimethyl - 3 - thienyl - (21)-, are made by heating the appropriately substituted 2-hydroxy benzaldehyde or acetophenone, with the alkali metal salt of the appropriately substituted thienyl acetic acid in the presence of a lower aliphatic acid anhydride, especially acetic anhydride, or by using thienyl acetonitrile to give the cyanomethine intermediate which is then hydrolysed and cyclized.ALSO:Natural and synthetic fibres such as cellulose acetate, polyacrylonitrile, polyethylene terephthalate, polyamides, polymethanes, polystyrene or wool are brightened by treatment in aqueous or organic solution with a thienyl coumarin of the formula. <FORM:1010562/D1-D2/1> where R is H or Me1R1 is halogen or alkyl, optionally substituted by hydroxyl, amino, ammonium or sulphonic acid groups, a sulphonic acid group, a carboxylic acid group, which may be esterfied, a carboxylic amide group, an acyloxy or a carbamyloxy group, m is 0, 1, or 2, n is 0, 1, or 2, and R2 is chlorine or bromine or methyl when n = 1 or -CH=CH-CH=CH- when n is 2 and two R1 substituents may represent a fused ring in m particular 3-thienyl-(21)-coumarins, 3-[51-bromo thienyl-(21)-]-coumarin, 7-phenyl-carbamyloxy-3-thienyl-(21)-coumarin 7-acetoxy-3-thienyl-(21)-coumarin, 517-dichloro-3-thienyl-(21)-coumarin, 517-dimethyl-3-thienyl-(21)-coumarin optionally in the presence of formaldehyde naphthalene sulphonic acid condensation products, oleyl alcohol or paraffin sulphonates, or formic acid, followed by squeezing, drying and heating for a short time to above 100 DEG C. The fibres may be subsequently treated in a chlorite-containing bleach.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF34734A DE1262206B (en) | 1961-08-19 | 1961-08-19 | Optical brighteners |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1010562A true GB1010562A (en) | 1965-11-17 |
Family
ID=7095685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30650/62A Expired GB1010562A (en) | 1961-08-19 | 1962-08-09 | Coumarin derivatives and their use as optical brightening agents |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE621380A (en) |
| CH (1) | CH378844A (en) |
| DE (1) | DE1262206B (en) |
| GB (1) | GB1010562A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014153533A1 (en) * | 2013-03-21 | 2014-09-25 | The Curators Of The University Of Missouri | A fluorescent chemical sensor for biological amines |
| US10222390B2 (en) | 2015-08-05 | 2019-03-05 | The Curators Of The University Of Missouri | Near-infrared fluorescent sensors for biological amines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2950291A1 (en) * | 1979-12-14 | 1981-06-19 | Basf Ag, 6700 Ludwigshafen | NEW CUMARINE COMPOUNDS AND METHOD FOR PRODUCING CUMARINE COMPOUNDS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1090624B (en) * | 1955-09-28 | 1960-10-13 | Bayer Ag | Optical brighteners |
-
0
- BE BE621380D patent/BE621380A/xx unknown
-
1961
- 1961-08-19 DE DEF34734A patent/DE1262206B/en active Pending
-
1962
- 1962-07-09 CH CH822062A patent/CH378844A/en unknown
- 1962-08-09 GB GB30650/62A patent/GB1010562A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014153533A1 (en) * | 2013-03-21 | 2014-09-25 | The Curators Of The University Of Missouri | A fluorescent chemical sensor for biological amines |
| US10330673B2 (en) | 2013-03-21 | 2019-06-25 | The Curators Of The University Of Missouri | Fluorescent chemical sensor for biological amines |
| US10222390B2 (en) | 2015-08-05 | 2019-03-05 | The Curators Of The University Of Missouri | Near-infrared fluorescent sensors for biological amines |
Also Published As
| Publication number | Publication date |
|---|---|
| CH378844A (en) | 1964-08-14 |
| BE621380A (en) | |
| CH822062A4 (en) | 1964-03-13 |
| DE1262206B (en) | 1968-03-07 |
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