GB986059A - Improvements relating to basic esters of phenylpyrazoline carboxylic acids and theiruse - Google Patents
Improvements relating to basic esters of phenylpyrazoline carboxylic acids and theiruseInfo
- Publication number
- GB986059A GB986059A GB4264261A GB4264261A GB986059A GB 986059 A GB986059 A GB 986059A GB 4264261 A GB4264261 A GB 4264261A GB 4264261 A GB4264261 A GB 4264261A GB 986059 A GB986059 A GB 986059A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- acid
- carbon atoms
- phenyl
- substituted
- 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
- 150000002148 esters Chemical class 0.000 title abstract 3
- KBCFZUVNKKZJOD-UHFFFAOYSA-N 1-phenyl-3H-pyrazole-2-carboxylic acid Chemical class C1(=CC=CC=C1)N1N(CC=C1)C(=O)O KBCFZUVNKKZJOD-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- -1 alkaryl sulphonate Chemical compound 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005282 brightening Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the formulae <FORM:0986059/C2/1> <FORM:0986059/C2/2> where R1 is phenyl, which may be substituted by halogen or alkyl or alkoxy groups having 1 or 2 carbon atoms, R2 is hydrogen or C1- 4 alkyl R3 is hydrogen, C1- 4 alkyl, phenyl, or phenyl substituted by halogen, alkyl, alkoxy, dialkylsulphamyl or alkylsulphonyl, X is alkylene of up to 4 carbon atoms, R4 and R5 are alkyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxyalkyl or cyanoalkyl, each having at most 6 carbon atoms, or R4 and R5 together with the nitrogen make up a heterocyclic ring which may contain oxygen or further nitrogen, R6 is alkyl or aralkyl which may be substituted, and Y is the anion of an inorganic acid or of an organic sulphonic acid; and their production by reacting (i) a functional derivative, e.g. halide or ester, of the phenylpyrazolinobenzoic acid with the alcohol HOXNR4R5 or HOXNR4R5R6.Y; (ii) a sal of said acid with a strong acid ester, e.g. halide or alkaryl sulphonate, of said alcohols; or (iii) HNR4R5 or NR4R5R6 with a phenylpyrazalinobenzoyloxyalkyl halide or sulphonate; and in each case, if necessary or desired, quaternating by reaction with R6Y. Examples and reactants are given. The compounds of the invention are brightening agents (see Division D1). Reference has been directed by the Comptroller to Specifications 669,590 and 832,239.ALSO:Polymeric and copolymeric acrylonitrile fibres are brightened by applying thereto a compound of the formulae <FORM:0986059/D1-D2/1> where R1 is phenyl, which may be substituted by halogen or alkyl or alkoxy groups having 1 or 2 carbon atoms, R2 is hydrogen or C1-4 alkyl, R3 is hydrogen, C1-4 alkyl, phenyl, or phenyl substituted by halogen, alkyl, alkoxy, dialkylsulphamyl or alkyl-sulphonyl, X is alkylene of up to 4 carbon atoms, R4 and R5 are alkyl, hydroxyalkyl, alkoxyalkyl, hydroxy-alkoxyalkyl or cyanoalkyl, each having at most 6 carbon atoms, or R4 and R5 together with the nitrogen make up a heterocyclic ring which may contain oxygen or further nitrogen, R6 is alkyl or aralkyl which may be substituted, and Y is the anion of an inorganic acid or of an organic sulphonic acid (see Division C2). Reference is made to the use of these compounds in aqueous acid baths; examples use aqueous solutions of formic acid, with or without NaHSO4. p Reference has been directed by the Comptroller to Specifications 669,590 and 832,239.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1341660A CH386430A (en) | 1960-11-30 | 1960-11-30 | Process for the preparation of basic esters of phenylpyrazoline carboxylic acids |
CH1289061A CH396917A (en) | 1961-04-08 | 1961-04-08 | Process for the preparation of quaternized nitrogen-containing esters of phenylpyrazoline carboxylic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB986059A true GB986059A (en) | 1965-03-17 |
Family
ID=25711172
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4264261A Expired GB986059A (en) | 1960-11-30 | 1961-11-29 | Improvements relating to basic esters of phenylpyrazoline carboxylic acids and theiruse |
Country Status (2)
Country | Link |
---|---|
BE (1) | BE610946A (en) |
GB (1) | GB986059A (en) |
-
1961
- 1961-11-29 BE BE610946A patent/BE610946A/en unknown
- 1961-11-29 GB GB4264261A patent/GB986059A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE610946A (en) | 1962-05-29 |
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