GB1086999A - Improvements in or relating to a paint composition for rubber - Google Patents

Improvements in or relating to a paint composition for rubber

Info

Publication number
GB1086999A
GB1086999A GB4608065A GB4608065A GB1086999A GB 1086999 A GB1086999 A GB 1086999A GB 4608065 A GB4608065 A GB 4608065A GB 4608065 A GB4608065 A GB 4608065A GB 1086999 A GB1086999 A GB 1086999A
Authority
GB
United Kingdom
Prior art keywords
acid
polyester
diisocyanate
sulphur
mol
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
GB4608065A
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.)
Toyo Tire Corp
Original Assignee
Toyo Tire and Rubber Co Ltd
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 Toyo Tire and Rubber Co Ltd filed Critical Toyo Tire and Rubber Co Ltd
Publication of GB1086999A publication Critical patent/GB1086999A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91Polymers modified by chemical after-treatment
    • C08G63/914Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/918Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67Unsaturated compounds having active hydrogen
    • C08G18/68Unsaturated polyesters
    • C08G18/683Unsaturated polyesters containing cyclic groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/83Chemically modified polymers
    • C08G18/87Chemically modified polymers by sulfur
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08Lactones or lactides
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66Polyesters containing oxygen in the form of ether groups
    • C08G63/668Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/676Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Paints Or Removers (AREA)

Abstract

A coating composition for rubber comprises a polyester derived from (a) at least one aliphatic dicarboxylic acid and at least one aromatic dicarboxylic acid amounting to 5-30 mol. per cent of the total acid, and (b) a mixture of di-and/or tri-functional alcohols of which 10-80 mol. per cent is a di- or tri-functional alcohol containing a b ,g -alkenyloxy group or an equivalent glycidyl compound, the overall ratio of OH:COOH being 1-1.17:1, or a polyurethane derived from said polyester when component (b) is used in excess by reaction with a diisocyanate equivalent to the excess OH groups, together with sulphur, a vulcanization accelerator, a pigment and a diluent solvent. Suitable components for the polyester are (a) adipic, succinic and sebacic acids; phthalic anhydride, isophthalic and terephthalic acids; carboxyl-ended polyesters and polylactones, and (b) ethylene glycol, di- and tri-ethylene glycols, propylene glycol, trimethylolethane, trimethylolpropane, hexane triol and glycerol or unsaturated fatty acid monoglycerides, hydroxy -terminated polyesters, polyethers or polylacton diols, and hydroxy-terminated diisocyanate prepolymers of these; a - and b -allyloxypropane diol, trimethylolpropane monoallyl ether and allyl glycidyl ether. Suitable diisocyanates include toluene diisocyanate, diphenylmethane diisocyanate and NCO-terminated prepolymer of these with hydroxy-polymers, e.g. e -caprolactone polyester of M.W. 600-1200 or a polyether glycol of M.W. 400-1200, using 1.5-2 moles diisocyanate per mole of polymer. The sulphur may amount to 2-15 wt. per cent of the polymer vehicle, and the preferred accelerator is mercaptobenzthiazole. In Examples diethylene glycol and a -allyloxypropane diol or trimethylolpropane monoallyl ether or allyl glycidyl ether and, optionally, dehydrated castor oil monoglyceride are heated with adipic acid and phthalic anhydride or isophthalic acid to give polyesters. In Example 4, the diethylene glycol is pre-reacted with some diphenylmethane diisocyanate. In Examples 1, 3, 5 and 6, the polyester is further reacted with toluene diisocyanate, diphenylmethane diisocyanate or prepolymer from 2 mols. of the latter with 1 mol. of poly-e -caprolactone. Coating compositions contain solutions of these polymers in ethyl acetate or ethoxyethyl acetate mixed with ethyl and/or butyl acetate and/or butoxyethanol and sulphur, mercaptobenzthiazole, stearic acid, zinc white, rutile or anatase TiO2 or carbon black and, optionally, dehydrated silicic acid or zinc diethyl dithiocarbamate.ALSO:A coating composition for rubber comprises a polyester derived from (a) at least one aliphatic dicarboxylic acid and at least one aromatic dicarboxylic acid, the latter amounting to 5-30 mol % of the total acid, and (b) a mixture of diols and/or triols of which 10-80 mol % is a diol or triol (or equivalent glycidyl compound) containing a b :g -alkenyloxy group, the overal ratio of OH:COOH being 1.0-1.7:1, or a polyurethane derived from a polyisocyanate and said polyester when excess OH is present, together with sulphur (e.g. 2-15 wt % of the polymer), a vulcanization accelerator (e.g. mercaptobenzthiazole) a pigment and a diluent solvent. (see Division C3). In Examples polyesters are derived from diethylene glycol, a -allyloxypropane diol or trimethylolpropane monoallyl ether or glycidyl allyl ether, and, optionally, dehydrated castor oil monoglyceride, with adipic acid and phthalic anhydride or isophthalic acid. These may further be reacted with toluene diisocyanate, diphenylmethane diisocyanate or prepolymers thereof. The product polyesters and polyurethanes are dissolved in ether alcohols and acetates and mixed with sulphur, mercaptobenzthiazole, stearic acid, zinc white, rutile or anatase TiO2 or C black and, optionally, dehydrated silicic acid or zinc diethyl dithiocarbamate. The coating compositions are coated onto vulcanized rubber and cured.
GB4608065A 1964-11-14 1965-11-01 Improvements in or relating to a paint composition for rubber Expired GB1086999A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6445664 1964-11-14

Publications (1)

Publication Number Publication Date
GB1086999A true GB1086999A (en) 1967-10-11

Family

ID=13258748

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4608065A Expired GB1086999A (en) 1964-11-14 1965-11-01 Improvements in or relating to a paint composition for rubber

Country Status (2)

Country Link
DE (1) DE1595851A1 (en)
GB (1) GB1086999A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10752811B2 (en) 2015-08-18 2020-08-25 3M Innovative Properties Company Polyester compositions
EP3337869B1 (en) * 2015-08-18 2021-01-06 3M Innovative Properties Company Chemical-resistant polyester pressure-sensitive adhesive

Also Published As

Publication number Publication date
DE1595851A1 (en) 1969-09-18

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