GB883370A - Ultra-violet light stabilized organic polymers - Google Patents

Ultra-violet light stabilized organic polymers

Info

Publication number
GB883370A
GB883370A GB34790/59A GB3479059A GB883370A GB 883370 A GB883370 A GB 883370A GB 34790/59 A GB34790/59 A GB 34790/59A GB 3479059 A GB3479059 A GB 3479059A GB 883370 A GB883370 A GB 883370A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
carboxybenzophenone
methoxy
dihydroxy
ortho
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
GB34790/59A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB883370A publication Critical patent/GB883370A/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
    • D06M13/152—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 having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • 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
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L89/00—Compositions of proteins; Compositions of derivatives thereof
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/66—Substances characterised by their function in the composition
    • C08L2666/78—Stabilisers against oxidation, heat, light or ozone

Abstract

A composition stabilized against ultraviolet light comprises a polymeric organic material and from 0,05 to 5,0% by weight of a compound of the structure:- <FORM:0883370/IV (a)/1> where X is an ortho-hydroxyphenyl radical and Y is an ortho carboxyphenyl radical, any other substituents in X and Y being alkyl, alkoxy, halogen or hydroxyl groups. Specified ultraviolet light absorbers are 2-hydroxy-5-chloro-21-carboxy-benzophenone, 2-hydroxy-4-methoxy-21-carboxybenzophenone, 2-hydroxy-21-carboxybenzophenone, 2, 4-dihydroxy-21-carboxybenzophenone, 2-hydroxy-4-methoxy-31, 4, 51, 61-tetra chloro-2-carboxybenzophenone, 2-hydroxy-4-butyl-21-carboxybenzophenone, 21-hydroxy-4-bromo-21-carboxybenzophenone and 2-hydroxy -5-methyl-21-carboxybenzophenone. Specified organic polymers are polyhexamethylene adipate, poly-o -armino caproamide, polyacrylamides, nitrogen substituted polyacrylamides, urea-, thiourea- and ethylene urea-formaldehyde resins, melamine-formaldehydes, polyesters, polyvinyl chlorides, polyvinyl acetate, polyalkyl acrylates, glyceride oil modified alkyds, polyacrylonitrile, polystyrene, polyethylene, polypropylene and epoxy resins, many U.S.A. Specifications disclosing suitable polymers being cited. The ultra-violet absorbers may be incorporated with the monomers prior to polymerization or incorporated with the formed polymers. In the Examples:-(1) 2-hydroxy-21-carboxy-4-methoxy benzophenone and 2, 21-dihydroxy-4 methoxybenzophenone are added to an alcohol-water solution of a polyamide, dried films of the stabilized polyamide then being formed; (5) a copolymer of a maleic anhydride-diethylene glycol polyester with vinyl acetate in the presence of benzoyl peroxide, a -cellulose flock and 2-hydroxy-4-methoxy-21-carboxyphenone, the product being formed into pellets and moulded; (6) a vinylidene chloride-vinyl chloride copolymer is extruded with 2-hydroxy-4-methoxy-21-carboxybenzo-phenone to form a thin transparent sheet, and (7) a mixture of o-m- and p-methyl styrenes is polymerized in the presence of 2-hydroxy-4-methoxy-31, 41, 51, 61-tetrachloro -21-carboxybenzophenone, the product being milled with titanium dioxide, granulated and injection moulded.ALSO:Natural and synthetic fibres containing recurring trivalent nitrogen atoms in their molecular chains are stabilised against ultra violet light by agitating in an aqueous dispersion of a compound of the structure <FORM:0883370/IV (c)/1> where X is an ortho-hydroxyphenyl radical and Y is an ortho-carboxyphenyl radical, any other substituents in X and Y being alkyl, alkoxy, halogen or hydroxyl groups, at a pH below and whilst heating the dispersion above 150 DEG F. Specified ultra violet light stabilisers are 2-hydroxy-5-chloro-21-carboxybenzophenone, 2-hydroxy - 21 - carboxybenzophenone, 2 - hydroxy - 4 - methoxy - 21 - carboxybenzophenone, 2,4 - dihydroxy - 21 - carboxybenzophenone, 2 - hydroxy - 4 - methoxy - 31,41,51,61 - tetrachloro - 21 - carboxybenzophenone, 2 - hydroxy - 4 - butyl - 21 - carboxybenzophenone, 2 - hydroxy - 4 - bromo - 21 - carboxybenzophenone and 2 - hydroxy - 5 - methyl - 21 - carboxybenzophenone. Specified fibres are wool, silk and nylon. In the examples nylon and wool fibres are agitated in aqueous alcoholic solutions of 2 - hydroxy - 4 - methoxy - 21 - carboxybenzophenone, 2,4 - dihydroxy - 21 - carboxybenzophenone; 21 - hydroxy - 41 - methoxy - 2 - carboxy; 3,4,5,6 - tetrachlorobenzophenone; 2 - hydroxy - 4 - methoxy - benzophenone and 2,2-dihydroxy-41-benzophenone.
GB34790/59A 1958-10-20 1959-10-14 Ultra-violet light stabilized organic polymers Expired GB883370A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76802158A 1958-10-20 1958-10-20

Publications (1)

Publication Number Publication Date
GB883370A true GB883370A (en) 1961-11-29

Family

ID=25081290

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34790/59A Expired GB883370A (en) 1958-10-20 1959-10-14 Ultra-violet light stabilized organic polymers

Country Status (4)

Country Link
CH (2) CH373732A (en)
DE (1) DE1290720B (en)
FR (2) FR1239049A (en)
GB (1) GB883370A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1170143B (en) * 1961-08-24 1964-05-14 Ruetgerswerke Ag Process for the production of unsaturated polyester

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2818401A (en) * 1955-08-02 1957-12-31 American Cyanamid Co Polyvinyl chloride stabilized with 2-hydroxy-5-salicylylbenzophenone

Also Published As

Publication number Publication date
CH373732A (en) 1964-01-31
DE1290720B (en) 1969-03-13
CH7963459A4 (en) 1963-08-30
FR1239049A (en) 1960-08-19
FR81768E (en) 1963-11-08
CH407542A (en) 1966-02-15

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