GB965908A - Use of 4-benzoyl-1-hydroxynaphthalene-2-carboxylic acid,its esters and amides as ultra-violet light absorbents - Google Patents

Use of 4-benzoyl-1-hydroxynaphthalene-2-carboxylic acid,its esters and amides as ultra-violet light absorbents

Info

Publication number
GB965908A
GB965908A GB29563/60A GB2956360A GB965908A GB 965908 A GB965908 A GB 965908A GB 29563/60 A GB29563/60 A GB 29563/60A GB 2956360 A GB2956360 A GB 2956360A GB 965908 A GB965908 A GB 965908A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
benzoyl
naphthol
ester
ultra
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
GB29563/60A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB965908A publication Critical patent/GB965908A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/06—Coating with compositions not containing macromolecular substances
    • C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/132—Phenols containing keto groups, e.g. benzophenones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety

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)
  • Textile Engineering (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds of formula: <FORM:0965908/C1/1> wherein R is a carboxylic acid ester or a substituted or unsubstituted carboxylic acid amide group are used as ultra-violet light absorbents (see Divisions C3 and D1). They are prepared by reacting 4-benzoyl-1-naphthol-2-carboxylic acid or an alkali metal salt or halide thereof with ammonia or an amine, an alcohol or a phenol. In examples: (1) 4-benzoyl-1-naphthol-2-carboxylic acid sodium is reacted in an aqueous alkaline medium with dimethyl sulphate to yield the methyl ester; (2) 4-benzoyl-1-naphthol-2-carboxylic acid chloride dissolved in carbon tetrachloride is reacted with a solution of phenol in carbon tetrachloride and pyridine to give the phenyl ester; (3) a solution of 4-benzoyl-1-naphthol-2-carboxylic acid in toluene and o-anisidine is treated with phosphorus trichloride to give the 21-methoxy-phenylamide. Further compounds of the above formula are specified.ALSO:The invention comprises a synthetic plastic, a synthetic resin, a lacquer, a cellulose derivative, or a natural rubber-like material having incorporated therein an agent which absorbs ultra-violet rays and is of formula: <FORM:0965908/C3/1> wherein R is a carboxylic acid, carboxylic ester or substituted or unsubstituted carboxylic acid amide group (see Division C2). The ultra-violet absorbent is incorporated in a proportion of 0.001 to 5% by weight e.g. by dissolving in a lacquer, adding to a synthetic resin before working up, mixing with a monomer before polymerization or polycondensation, spraying or mixing granules, powders, foils &c. with a solution of the absorbent in a solvent and drying or steeping a finished article in such a solution, possibly at elevated temperature and then drying. Specified substances which may be treated in this way include acetyl-cellulose, cellulose propionate, cellulose butyrate, nitrocellulose, polyvinyl acetate, polyvinyl alcohol, polyvinyl chloride, copolymers of vinyl chloride and vinylidene chloride, polyethylene, polypropylene, polyisobutylene, polyurethanes, polyamides, polyacrylonitriles, polyesters, polymethacrylates, epoxide resins, polystyrene, alkyd resins, melamine, urea and phenol-aldehyde resins and natural and synthetic rubbers, e.g. polychloroprene, polybutadiene or butadiene-styrene copolymers. In Examples: (4) a polyvinyl chloride foil containing 2% by weight of 4-benzoyl-1-naphthol-2-carboxylic acid 21-methoxy-phenylamide is specified; (5) a foil is obtained by mixing polyvinyl chloride, dibutyl phthalate and 4-benzoyl-1-naphthol-2-carboxylic acid 21-methylphenyl ester and working up the mass; (6) polyethylene powder is mixed with 0.05% of 4-benzoyl-1-naphthol-2-carboxylic acid or the corresponding methyl ester, rolled to form a sheet and then compressed to form plates; (7) a polyethyleneglycol terephthalate foil is immersed in a solution of 4-benzoyl-1-naphthol-2-carboxylic acid in acetone, rinsed with alcohol and dried; (8) a polyethylene foil is treated as in (7); (9) a lacquer is prepared from collodion cotton, butylacetate butyl alcohol, toluene, dibutyl phthalate a 4-benzoyl-1-naphthol-2-carboxylic acid methyl ester.ALSO:The invention comprises textile materials having incorporated therein an ultra-violet light absorbent of formula:- <FORM:0965908/D1-D2/1> p wherein R is a carboxylic acid, carboxylic ester or substituted or unsubstituted carboxylic acid amide group. Specified textile materials are fibres, yarns, filaments or fabrics of cotton, wool, silk, viscose rayon, acetate or cuprammonium rayon, regenerated cellulose, cellulose acetate, polyacrylonitrile, polyesters, polyamides, polyurethanes or polyvinyl alcohol. The material may be sprayed with or steeped in a solution of the absorbent in a solvent and subsequently dried.
GB29563/60A 1959-08-26 1960-08-26 Use of 4-benzoyl-1-hydroxynaphthalene-2-carboxylic acid,its esters and amides as ultra-violet light absorbents Expired GB965908A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF29243A DE1144726B (en) 1959-08-26 1959-08-26 Ultraviolet absorber for plastics, synthetic resin compounds, varnishes and paints

Publications (1)

Publication Number Publication Date
GB965908A true GB965908A (en) 1964-08-06

Family

ID=7093219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29563/60A Expired GB965908A (en) 1959-08-26 1960-08-26 Use of 4-benzoyl-1-hydroxynaphthalene-2-carboxylic acid,its esters and amides as ultra-violet light absorbents

Country Status (6)

Country Link
BE (1) BE594450A (en)
CH (2) CH415038A (en)
DE (1) DE1144726B (en)
FR (1) FR1266782A (en)
GB (1) GB965908A (en)
NL (2) NL125570C (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1021981B (en) * 1956-12-20 1958-01-02 Hoffmann La Roche Protective agent against ultraviolet radiation

Also Published As

Publication number Publication date
BE594450A (en) 1961-02-27
CH958460A4 (en) 1962-09-14
NL125570C (en)
CH415038A (en) 1966-06-15
FR1266782A (en) 1961-07-17
NL255233A (en)
DE1144726B (en) 1963-03-07
CH366262A (en) 1963-02-15

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