GB1114848A - 1-halophenyl pyrazolines,their production and use as optical brightening agents - Google Patents
1-halophenyl pyrazolines,their production and use as optical brightening agentsInfo
- Publication number
- GB1114848A GB1114848A GB2240365A GB2240365A GB1114848A GB 1114848 A GB1114848 A GB 1114848A GB 2240365 A GB2240365 A GB 2240365A GB 2240365 A GB2240365 A GB 2240365A GB 1114848 A GB1114848 A GB 1114848A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen
- alkyl
- compounds
- ionogenic
- unsubstituted
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/40—Dyes ; Pigments
- C11D3/42—Brightening agents ; Blueing agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
Abstract
Polymers of olefinic compounds may be optically brightened with compounds of the general formula <FORM:1114848/C3/1> wherein X is halogen or -CF3, Y is H, halogen, -CF3, C1- 4 alkyl, optionally esterified carboxyl, C1- 4 alkylsulphonyl, C1- 4 hydroxyalkylsulphonyl, -CN, or an optionally N-substituted sulphonic or carboxylic acid amide group, Z is H, halogen or C1- 4 alkyl, R is H, C1- 4 alkyl or a carbocyclic- or heterocyclic-aromatic radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents, and A is a phenyl radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents. In examples: (56) highpressure polyethylene granulate containing 1-(31 - chlorophenyl) - 3 - (411 - chlorophenyl)-pyrazoline is extruded to form a tube; (57) polyvinyl chloride sheet is drawn from a gelatinized mixture of polyvinyl chloride, dioctyl phthalate, sodium pentaoctyl tripolyphosphate and (a) di-n-butyl dilauryl dioxystannate and 1 - (31 - chlorophenyl) - 3 - (411 - chlorophenyl)-pyrazoline; or (b) dibutyl-tin dilaurate and 1-(31 - bromophenyl) - 3 - phenyl - pyrazoline.ALSO:Soap and detergents may be optically brightened by the incorporation of compounds of the formula <FORM:1114848/C4-C5/1> wherein X is halogen or -CF3, Y is H, halogen, -CF3, C1-4 alkyl, optionally esterified carboxyl, C1-4 alkylsulphonyl, C1-4 hydroxyalkylsulphonyl, -CN, or an optionally N-substituted sulphonic or carboxylic acid amide group, Z is H, halogen or C1-4 alkyl, R is H, C1-4 alkyl or a carboxylic- or heterocyclic-aromatic radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents, and A is a phenyl radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents. The usual fillers and auxiliaries for washing agents may be present in addition. The optical brighteners of the above general formula are stated to fluoresce, those having halogen substituents in A fluorescing blue to blue-green and those having no halogen substituents in A fluorescing violet to blue. In general, solutions of the compounds in organic solvents are almost colourless but exhibit vivid violet to blue fluorescence. In Example 56, a tube extruded from high-pressure polyethylene containing 1 - (31 - chlorophenyl) - 3 -(411-chlorophenyl)-pyrazoline exhibits blue-violet fluorescence in daylight.ALSO:The invention comprises compounds of the general formula <FORM:1114848/C2/1> wherein X is halogen or -CF3, Y is H, halogen, -CF3, C1- 4 alkyl, optionally esterified carboxyl, C1- 4 alkylsulphonyl, C1- 4 hydroxyalkylsulphonyl, -CN, or an optionally N-substituted sulphonic or carboxylic acid amide group, Z is H, halogen or C1- 4 alkyl, R is H, C1- 4 alky or a carbocyclic- or heterocyclic-aromatic radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents, and A is a phenyl radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents. The compounds are prepared by reacting a compound of the formula <FORM:1114848/C2/2> with a compound of the formula (II) R-CH = CH-CO-A or of the formula <FORM:1114848/C2/3> wherein W is Cl, Br or tertiary amino, the reaction being conducted in the presence of an acid binding agent when W is Cl or Br. The compounds may be obtained as mixed crystals either by using a mixture of starting materials or by melting or recrystallizing mixtures of the compounds of the invention.ALSO:Textiles are optically brightened with compounds of the general formula <FORM:1114848/D1-D2/1> wherein X is halogen or -CF3, Y is H, halogen, -CF3, C1-4 alkyl, optionally esterfied carboxyl, C1-4 alkyl-sulphonyl, C1-4 hydroxyalkylsulphonyl, -CN, or an optionally N-substituted sulphonic or carboxylic acid amide group, Z is H, halogen or C1-4 alkyl, R is H, C1-4 alkyl or a carbocyclic - or heterocyclice - aromatic radical which is unsubstituted or contains non-ionogenic and non-colour imparting substituents, and A is a phenyl radical which is unsubstituted or contains non-ionogenic and non-colour importing substituents. The brigteners are preferably applied as aqueous dispersions which may also contain dispersing agents and organic acids. Specified materials to be brightened are polyamides such as nylon and polycaprolactum, polyacrlyonitrile, cellulose esters such as cellulose acetate, and cotton.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH691764A CH434273A (en) | 1964-05-27 | 1964-05-27 | Process for the preparation of pyrazoline compounds |
CH1578964A CH437195A (en) | 1964-05-27 | 1964-12-07 | Use of pyrazoline mixtures as optical brightening agents for textile organic material |
CH902165A CH471275A (en) | 1965-06-28 | 1965-06-28 | Use of pyrazoline mixtures as optical brightening agents for textile organic material |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1114848A true GB1114848A (en) | 1968-05-22 |
Family
ID=27175630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2240365A Expired GB1114848A (en) | 1964-05-27 | 1965-05-26 | 1-halophenyl pyrazolines,their production and use as optical brightening agents |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE664574A (en) |
DE (1) | DE1545895C3 (en) |
FR (1) | FR1543174A (en) |
GB (1) | GB1114848A (en) |
NL (1) | NL134416C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114057647A (en) * | 2021-11-26 | 2022-02-18 | 重庆工商大学 | Pyrazoline fluorescent molecule and preparation method thereof |
CN114276296A (en) * | 2021-12-27 | 2022-04-05 | 同济大学 | Photoacid generator containing pyrazoline group, preparation method and application thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6291600A (en) * | 1985-10-08 | 1987-04-27 | モベイ・コ−ポレ−シヨン | Detergent |
-
0
- NL NL134416D patent/NL134416C/xx active
- FR FR1543174D patent/FR1543174A/en active Active
-
1965
- 1965-05-26 BE BE664574A patent/BE664574A/xx unknown
- 1965-05-26 GB GB2240365A patent/GB1114848A/en not_active Expired
- 1965-05-26 DE DE19651545895 patent/DE1545895C3/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114057647A (en) * | 2021-11-26 | 2022-02-18 | 重庆工商大学 | Pyrazoline fluorescent molecule and preparation method thereof |
CN114057647B (en) * | 2021-11-26 | 2023-06-13 | 重庆工商大学 | Pyrazoline fluorescent molecule and preparation method thereof |
CN114276296A (en) * | 2021-12-27 | 2022-04-05 | 同济大学 | Photoacid generator containing pyrazoline group, preparation method and application thereof |
CN114276296B (en) * | 2021-12-27 | 2023-06-02 | 同济大学 | Pyrazoline group-containing photoacid generator, preparation method and application |
Also Published As
Publication number | Publication date |
---|---|
FR1543174A (en) | |
DE1545895A1 (en) | 1969-12-11 |
BE664574A (en) | 1965-11-26 |
DE1545895C3 (en) | 1974-11-21 |
NL134416C (en) | |
DE1545895B2 (en) | 1974-04-11 |
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