GB993055A - Improvements in or relating to optical whitening agents - Google Patents
Improvements in or relating to optical whitening agentsInfo
- Publication number
- GB993055A GB993055A GB3281460A GB3281460A GB993055A GB 993055 A GB993055 A GB 993055A GB 3281460 A GB3281460 A GB 3281460A GB 3281460 A GB3281460 A GB 3281460A GB 993055 A GB993055 A GB 993055A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- pyrazoline
- chlorophenyl
- compound
- sulphonyl
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0993055/C2/1> in which X is -SO2R where R is an alkylene group containing at least two carbon atoms and which may be interrupted by one or more oxygen atoms, Y is hydrogen, halogen, alkoxy, alkylamino, dialkylamino or an acylamino group. The group R is preferably an hydroxyl group which may be esterified for example by mono or dibasic carboxylic acids, sulphuric acid or phosphoric acid. R is preferably CH2CHOH.R1 where R1 is alkyl or (CH2OCH2)n, n=0 or an integer, e.g. 1-5. X and Y are preferably para orientated. The compounds may be prepared by condensing a compound of general formula XC6H4NHNH2 (II) with a compound of the general formula <FORM:0993055/C2/2> where R2 and R3 are alkyl, e.g. CH3 or C2H5 or together form a heterocyclic ring with the adjacent nitrogen atom. Alternatively, instead of III, there may be used p-YC6H4COCH=CH2 or YC6H4COCH2CH2.Hal where Hal is generall C1 or Br. The stannic chloride complex compound of II may be used. This is prepared from the coresponding primary amine which is diazotized and then reduced in the presence of stannic chloride. The reaction between II and III may be effected by heating the reactants in a solvent medium or reacting in an aqueous alkaline solution. Typical examples describe the preparation of:-(1) 1-[41-(211-hydroxyethylsulphonyl)phenyl] - 3 - (41 -chlorophenyl) pyrazoline from the stannic chloride complex of 4 - (21 - hydroxyethylsulphonyl)-phenyl hydrazine and 3-dimethylamino-4-chloro propiophenone hydrochloride; (2) the product of Example (1) from the uncomplexed hydrazine and propiophenone of Example (1); (3) 1 - [41 - (211 - hydroxyethylsulphonyl)-phenyl] - 3 - [41 chlorophenyl] pyrazoline from 4 (21 - hydroxyethylsulphonyl)phenyl hydrazine sulphate and 3,41-dichloropropiophenone; (4) 1 - [4 - (211 - hydroxy propyl sulphonyl)-phenyl] - 3 - (4 - chlorophenyl) pyrazoline from 4-chlorophenyl vinyl ketone and 4-(21 - hydroxy propyl sulphonyl) phenyl hydrazine; (6) 1-[41-(211-hydroxy ethyl sulphonyl)phenyl]-3-(41 dimethyl amino phenyl) pyrazoline from 3,41 bis (dimethylamino)propiohenone hydrochloride and the stannic chloride complex of 4-(21-hydroxyethyl sulphonyl) phenyl hydrazine. The products may be incorporated in detergent compositions and act as optical whitening agents (see Division D1).ALSO:A composition for treating fabrics comprises an optical whitening agent of general formula <FORM:0993055/D1-D2/1> where X is the group SO2R in which R is an alkylene group containing at least two carbon atoms and which may be interrupted by one or more oxygen atoms, said alkylene group containing at least one group (generally OH or esterified OH or CH2CHOHR1 where R1 = (-CH2OCH2-)n n = 0 or integer e.g. 1-5) and Y is hydrogen, halogen, alkoxy, acylamino, alkylamino, or dialkylamino. The compound may be used in admixture with a detergent of the soap or soapless class, washing agent or other textile auxillary in suitable proportion e.g. 0.01-0.5% preferably 0.01-0.2% by weight. In an example (1) nylon fabric was treated for 30 min at 80 DEG C. in baths containing per litre 0.05-0.5 g of 1[41-(211 hydroxy ethyl sulphonyl) phenyl] -3-(41-chlorophenyl) pyrazoline, the fabric-liquor ratio being 1 : 40. The compound was dissolved in dimethylformamide and diluted with water, containing a small quantity of a non-ionic detergent, to the required volume.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3281460A GB993055A (en) | 1960-10-28 | 1960-10-28 | Improvements in or relating to optical whitening agents |
CH1211961A CH405326A (en) | 1960-10-28 | 1961-10-20 | Process for the preparation of 1,3-diaryl-pyrazolines |
BE609589A BE609589A (en) | 1960-10-28 | 1961-10-25 | Improvements to optical brighteners |
DE1961H0043990 DE1237124B (en) | 1960-10-28 | 1961-10-27 | Process for the production of 1,3-diphenylpyrazoline derivatives which can be used as optical brighteners |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3281460A GB993055A (en) | 1960-10-28 | 1960-10-28 | Improvements in or relating to optical whitening agents |
Publications (1)
Publication Number | Publication Date |
---|---|
GB993055A true GB993055A (en) | 1965-05-26 |
Family
ID=10344402
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3281460A Expired GB993055A (en) | 1960-10-28 | 1960-10-28 | Improvements in or relating to optical whitening agents |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE609589A (en) |
CH (1) | CH405326A (en) |
DE (1) | DE1237124B (en) |
GB (1) | GB993055A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7300474B2 (en) | 2002-02-28 | 2007-11-27 | Clariant Produkte (Deutschland) Gmbh | Aqueous liquid formulations of pyrazoline brighteners |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1419329B1 (en) * | 1962-04-21 | 1970-01-15 | Hoechst Ag | 1,3-diaryl-delta-pyrazoline compounds and their use as whitening agents |
DE1469222B1 (en) * | 1964-09-25 | 1972-03-09 | Hoechst Ag | Pyrazoline derivatives and their preparation and use |
US4045169A (en) * | 1971-09-09 | 1977-08-30 | Hoechst Aktiengesellschaft | 3-[3',4'-Dichloro-6'-alkyl-phenyl]-Δ 2-pyrazoline derivatives and their use as optical brighteners |
DE2560051C3 (en) * | 1975-07-31 | 1981-07-23 | Basf Ag, 6700 Ludwigshafen | Pyrazoline compounds |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE919411C (en) * | 1950-06-03 | 1954-10-21 | Ilford Ltd | Process for the preparation of aryl-substituted pyrazoline compounds |
-
1960
- 1960-10-28 GB GB3281460A patent/GB993055A/en not_active Expired
-
1961
- 1961-10-20 CH CH1211961A patent/CH405326A/en unknown
- 1961-10-25 BE BE609589A patent/BE609589A/en unknown
- 1961-10-27 DE DE1961H0043990 patent/DE1237124B/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7300474B2 (en) | 2002-02-28 | 2007-11-27 | Clariant Produkte (Deutschland) Gmbh | Aqueous liquid formulations of pyrazoline brighteners |
Also Published As
Publication number | Publication date |
---|---|
BE609589A (en) | 1962-04-15 |
DE1237124B (en) | 1967-03-23 |
CH405326A (en) | 1966-01-15 |
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