GB1088580A - Process for improving the adhesion of synthetic fibrous materials to elastomers - Google Patents

Process for improving the adhesion of synthetic fibrous materials to elastomers

Info

Publication number
GB1088580A
GB1088580A GB4955964A GB4955964A GB1088580A GB 1088580 A GB1088580 A GB 1088580A GB 4955964 A GB4955964 A GB 4955964A GB 4955964 A GB4955964 A GB 4955964A GB 1088580 A GB1088580 A GB 1088580A
Authority
GB
United Kingdom
Prior art keywords
polyvinyl
polyisocyanate
latex
molecule
contain
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
GB4955964A
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 GB1088580A publication Critical patent/GB1088580A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/06Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
    • 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
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/77Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78Nitrogen
    • C08G18/79Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2321/00Characterised by the use of unspecified rubbers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

A composition suitable for use in bonding synthetic polymeric fibrous materials to elastomers comprises an aqueous medium which contains a finely divided dimer or polymer of a polyisocyanate having at least one uretidinedione ring in the molecule and a latex of natural rubber or a synthetic elastomer. The dimers or polymers of polyisocyanates which contain uretidinedione rings may be based on monomeric organic compounds containing at least two isocyanate groups in the molecule at least one of which must be capable of undergoing di- or polymerization with another molecule of the polyisocyanate so that a uretidinedione ring forms, e.g. toluylene-2:4-diisocyanate, toluylene - 2:4:6 - triisocyanate, diphenylmethane - 4:41 - diisocyanate and polyisocyanates obtained by polymerization of vinyl isocyanate alone or with other vinyl compounds, by splitting off hydrogen chloride from halogeno-methyl-aryl isocyanates by means of Friedel-Crafts catalysts or by phosgenation of polymeric compounds containing primary amino groups. The dimers or polymers of the polyisocyanate groups whose reactivity has been lowered by steric or mesomeric influence or by electrostatic induction. The composition may also contain a compound having a phenolic hydroxyl group and formaldehyde or a condensate thereof or a condensate of an aldehyde with urea, melamine, a ketone or casein, anionic, cationic or non-ionic wetting agents, water-soluble protective colloids, e.g. cellulose methyl ether, polyvinyl methyl ether, polyethylene glycols, polyvinyl alcohols which may be partially acetylated polyvinyl pyrrolidone, salts of polyacrylic acids or alginic acids, polyacrylamide, proteinic substances or partially desulphurized lignosulphonates, catalysts, e.g. triethyl phosphine, triethyl amine, pyridine or its homologues, zinc adipate, titanium oxychloride or di-n-butyl tin oxide, antioxidants, pigments or dyestuffs and may be adjusted to pH in the acid or basic range by the addition of acetic or hydrochloric acid, ammonia, an alkali metal hydroxide, mono-di or triethanolaminic or am quaternary ammonium base. The latex may be of natural rubber, a terpolymer of vinyl pyridine, butadiene and styrene, hevea rubber, polybutadiene, polyisoprene, butyl rubber, copolymers of butadiene and styrene or acrylonitrile or of ethylene and propylene, polychlorobutadiene, polymeric sulphochlorinated ethylene, fluorine-containing elastomers, silicone rubbers, polysulphide rubbers, cross-linked polyurethanes, polyvinyl chloride, polyvinylidene chloride or polyvinyl acetate.ALSO:The adhesion of synthetic polymeric fibrous materials, e.g polyester fibres, filaments, threads, cables, cords and woven, knitted, braided and non woven fabrics, to elastomers is improved by treating them with a finely divided dimer or polymer of a polyisocyanate having at least one uretidinedione ring in the molecule and a latex of natural rubber or a synthetic elastomer, the treatment being carried out in one or more aqueous baths and drying them. The dimers or polymers of polyisocyanates which contain uretidinedione rings may be based on monomeric organic compounds containing at least two isocyanate groups in the molecule at least one of which must be capable of undergoing di- or polymerisation with another molecule of the polyisocyanate so that a uretidinedione ring forms e.g. toluylene -2:4-diisocyanate, toluylene-2:4:6-triisocyanate, diphenylmethane-4:4\sv-diisocyanate and polyisocyanates obtained by polymerisation of vinyl isocyanate alone or with other vinyl compounds, by splitting off hydrogen chloride from halogeno-methyl-aryl isocyanates by means of Friedel-Crafts' catalysts or by phosgenation of polymeric compounds containing primary amino groups. The dimers or polymers of the polyisocyanates may also contain one or more isocyanate groups whose reactivity has been lowered by steric or mesomeric influence or by electrostatic induction. The treatment bath or baths may also contain a compound having a phenolic hydroxyl group and formaldehyde or a condensate thereof or a condensate of an aldehyde with urea, melamine, a ketone or casein, anionic, cationic or non-ionic wetting agents, water-soluble protective colloids, e.g. cellulose methyl ether, polyvinyl methyl ether, polyethylene glycols, polyvinyl alcohols which may be partially acetylated, polyvinyl pyrrolidone, salts of polyacrylic acids or alginic acids, polyacrylamide, proteinic substances or partially desulphurized lignosulphonates, catalysts, e.g. triethyl phosphine, triethyl amine, pyridine or its homologues, zinc adipate, titanium oxychloride or di-n-butyl tin oxide, antioxidants, pigments or dyestuffs and may be adjusted to a pH in the acid or basic range by the addition of acetic or hydrochloric acid, ammonia, an alkali metal hydroxide, mono-, di- or triethanolamine or a quarternary ammonium base. When the dimer or polymer of the polyisocyanate and the latex are applied separately the polymer of the isocyanate may be applied with or immediately after the spinning preparation, after twisting, before stretching, between the first and second stretching operations, after stretching or after heat-setting and the latex applied subsequently after drying, e.g. after heat-setting or after the filaments have been made up into yarn, cord or fabric. The latex may be of natural rubber, a terpolymer of vinyl pyridine, butadiene and styrene, hevea rubber, polybutadiene, polyisoprene, butyl rubber, copolymers of butadiene and styrene or acrylonitrile or of ethylene and propylene, polychlorobutadiene, polymeric sulphochlorinated ethylene, fluorine-containing elastomers, silicone rubbers, polysulphide rubbers, cross-linked polyurethanes, polyvinyl chloride, polyvinylidene chloride or polyvinyl acetate.ALSO:The adhesion of fabrics made from synthetic fibres e.g polyester fibres, to elastomers is improved by treating them with a finely divided dimer or polymer of a polyisocyanate having at least one uretidinedione ring in the molecule and a latex of natural rubber or a synthetic elastomer, the treatment being carried out in one or more aqueous baths and drying them. The dimers or polymers of polyisocyanates which contain uretidinedione rings may be based on monomeric organic compounds containing at least two isocyanate groups in the molecule at least one of which must be capable of undergoing di- or polymerisation with another molecule of the polyisocyanate so that a uretidinedione ring forms e.g. toluylene -2:4-diisocyanate, toluylene-2:4:6-triisocyanate, diphenylmethane-4:4'-diisocyanate and polyisocyanates obtained by polymerisation of vinyl isocyanate alone or with other vinyl compounds, by splitting off hydrogen chloride from halogeno-methyl-aryl isocyanates by means of Friedel-Crafts' catalysts or by phosgenation of polymeric compounds containing primary amino groups. The dimers or polymers of the polyisocyanates may also contain one or more isocyanate groups whose reactivity has been lowered by steric or mesomeric influence or by electrostatic induction. The treatment bath or baths may also contain a compound having a phenolic hydroxyl group and formaldehyde or a condensate thereof or a condensate of an aldehyde with urea, melamine, a ketone or casein, anionic, cationic or non-ionic wetting agents, water-soluble protective colloids, e.g. cellulose methyl ether, polyvinyl methyl ether, polyethylene glycols, polyvinyl alcohols which may be partially acetylated, polyvinyl pyrrolidone, salts of polyacrylic acids or alginic acids, polyacrylamide, proteinic substances or partially desulphurized lignosulphonates, catalysts, e.g. triethyl phosphine, triethyl amine, pyridine or its homologues, zinc adipate, titanium oxychloride or di-n-butyl tin oxide, antioxidants, pigments or dyestuffs and may be adjusted to a pH in the acid or basic range by the addition of acetic or hydrochloric acid, ammonia, an alkali metal hydroxide, mono-, di- or triethanolamine or a quarternary ammonium base. The latex may be of natural rubber, a terpolymer of vinyl pyridine, butadiene and styrene, hela rubber, polybutadiene, polyisoprene, butyl rubber, copolymers of butadiene and styrene or acrylonitrile or of ethylene and propylene, polychlorobutadiene, polymeric sulphochlorinated ethylene, fluorine-containing elastomers, silicone rubbers, polysulphide rubbers, cross-linked polyurethanes, polyvinyl chloride, polyvinylidene chloride or polyvinyl acetate.
GB4955964A 1963-12-04 1964-12-04 Process for improving the adhesion of synthetic fibrous materials to elastomers Expired GB1088580A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0041463 1963-12-04

Publications (1)

Publication Number Publication Date
GB1088580A true GB1088580A (en) 1967-10-25

Family

ID=7098679

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4955964A Expired GB1088580A (en) 1963-12-04 1964-12-04 Process for improving the adhesion of synthetic fibrous materials to elastomers

Country Status (4)

Country Link
AT (1) AT257148B (en)
BE (1) BE656656A (en)
GB (1) GB1088580A (en)
NL (1) NL6414122A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1085036A1 (en) * 1999-09-13 2001-03-21 Milliken & Company Formaldehyde-free adhesion promotor composition for waistband fabric
EP2065220A1 (en) * 2007-11-30 2009-06-03 The Goodyear Tire & Rubber Company Pneumatic tire
EP2159241A1 (en) * 2009-04-09 2010-03-03 Isochem Kautschuk GmbH Method for producing oligomeric diphenylmethane-4,4' and/or diphenylmethan-2,4'-diisocyanate-uretdione
EP2423247A1 (en) * 2010-08-30 2012-02-29 Rhein Chemie Rheinau GmbH New aqueous resorcinol-formaldehyde-latex dispersions, process for their production and their use

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1085036A1 (en) * 1999-09-13 2001-03-21 Milliken & Company Formaldehyde-free adhesion promotor composition for waistband fabric
EP2065220A1 (en) * 2007-11-30 2009-06-03 The Goodyear Tire & Rubber Company Pneumatic tire
EP2159241A1 (en) * 2009-04-09 2010-03-03 Isochem Kautschuk GmbH Method for producing oligomeric diphenylmethane-4,4' and/or diphenylmethan-2,4'-diisocyanate-uretdione
WO2010115684A1 (en) * 2009-04-09 2010-10-14 Isochem Kautschuk Gmbh Method for producing oligomeric diphenylmethane-4,4'- and/or diphenylmethane-2,4'-diisocyanate-uretdiones
EP2423247A1 (en) * 2010-08-30 2012-02-29 Rhein Chemie Rheinau GmbH New aqueous resorcinol-formaldehyde-latex dispersions, process for their production and their use
RU2573874C2 (en) * 2010-08-30 2016-01-27 Райн Хеми Райнау ГмбХ Water resorcinol-formaldehyde latex dispersions, adhesion promoter composition, fibres with improved adhesion, methods of obtaining and application thereof

Also Published As

Publication number Publication date
NL6414122A (en) 1965-06-07
BE656656A (en) 1965-06-04
AT257148B (en) 1967-09-25

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