GB1023384A - Improvements in or relating to nitrile compounds - Google Patents

Improvements in or relating to nitrile compounds

Info

Publication number
GB1023384A
GB1023384A GB5114463A GB5114463A GB1023384A GB 1023384 A GB1023384 A GB 1023384A GB 5114463 A GB5114463 A GB 5114463A GB 5114463 A GB5114463 A GB 5114463A GB 1023384 A GB1023384 A GB 1023384A
Authority
GB
United Kingdom
Prior art keywords
oxide
carbon atoms
butylene
compounds
dioxide
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
Application number
GB5114463A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB1023384A publication Critical patent/GB1023384A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/20Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)

Abstract

As ultra-violet absorbers for waxes, use is made of compounds of the formula <FORM:1023384/C4-C5/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2). Many radicals which R, R1, R2 and R3 may denote are specified. The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof. An example is given of the use of one of the products in a furniture polish based on carnauba wax.ALSO:As ultra-violet absorbers for polymeric materials, use is made of compounds of the formula <FORM:1023384/C3/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2). Many radicals which R, R1, R2 and R3 may denote are specified The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexene oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof. Specified polymeric materials which may be treated include natural or regenerated cellulose, cellulose acetate, nitrocellulose, cellulose ethers, epoxy resins, polyethylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polystyrene, acrylate and methacrylate polymers, polyvinyl ethers and ketones, polytetrafluoroethylene, polyoxymethylene and ester polymers. Comparative examples are given of the use of one of the products in nitrocellulose lacquer, a polyester resin comprising styrene and glyceryl phthalate-maleate.ALSO:The invention comprises compounds of the formula <FORM:1023384/C2/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2. Many radicals which R, R1, R2 and R3 may denote are specified. The compounds may be prepared by condensing an appropriate aromatic ketone with malononitrile under dehydrating conditions, preferably in a solvent. Alternatively, the ketone may be condensed with cyanoacetamide and the amido group then converted into a nitrile group by dehydration, preferably with phosphorus oxychloride. Many ketones which may be used in the reaction are specified. Typical examples describe the manufacture of products from (a) 4-hydroxy-3,5-dimethylacetophenone, (b) 3-butyl-4-ethoxy-acetophenone, (c) 3-methyl-4-phenoxybutyrophenone, (d) 3 - ethyl - 4 - (p - chlorobenzyloxy) butyrophenone, (e) 3-methyl-4-allyloxybutyrophenone and 3 - allyl - 4 - methoxyacetophenone. The invention includes also polyoxalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexene oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof, and examples of such reactions are given. The products are useful as absorbers for ultra-violet light (see Divisions A5, B2, B5, C3, C5, D1 and D2).ALSO:As ultra-violet absorbers in the treatment of dyed textile materials and opaque papers, use is made of compounds of the formula <FORM:1023384/D1-D2/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2). Many radicals which R, R1, R2 and R3 may denote are specified. The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.ALSO:As ultra-violet absorbers for incorporation into transparent coatings or backings e.g. of pressure-sensitive tapes, use is made of compounds of the formula <FORM:1023384/B1-B2/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2). Many radicals which R, R1, R3 and R2 may denote are specified. Specified backings are regenerated cellulose films which may contain the absorber or may be coated with a nitrocellulose lacquer containing the absorber. The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.ALSO:As ultra-violet absorbers in sun-tan preparations, use is made of compounds of the formula <FORM:1023384/A5-A6/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2). Many radicals which R, R1, R2 and R3 may denote are specified. The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexene oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.
GB5114463A 1963-01-08 1963-12-30 Improvements in or relating to nitrile compounds Expired GB1023384A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US25001463A 1963-01-08 1963-01-08

Publications (1)

Publication Number Publication Date
GB1023384A true GB1023384A (en) 1966-03-23

Family

ID=22945952

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5114463A Expired GB1023384A (en) 1963-01-08 1963-12-30 Improvements in or relating to nitrile compounds

Country Status (4)

Country Link
BE (1) BE642224A (en)
CH (1) CH440273A (en)
DE (1) DE1223385B (en)
GB (1) GB1023384A (en)

Also Published As

Publication number Publication date
DE1223385B (en) 1966-08-25
CH440273A (en) 1967-07-31
BE642224A (en) 1964-05-04

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