GB654331A - Adhesives - Google Patents

Adhesives

Info

Publication number
GB654331A
GB654331A GB2919048A GB2919048A GB654331A GB 654331 A GB654331 A GB 654331A GB 2919048 A GB2919048 A GB 2919048A GB 2919048 A GB2919048 A GB 2919048A GB 654331 A GB654331 A GB 654331A
Authority
GB
United Kingdom
Prior art keywords
bis
aliphatic
alpha
aromatic
carbethoxyacetoacetyl
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
GB2919048A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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
Priority to BE492139D priority Critical patent/BE492139A/xx
Priority to NL72389D priority patent/NL72389C/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2919048A priority patent/GB654331A/en
Priority to FR1002666D priority patent/FR1002666A/en
Publication of GB654331A publication Critical patent/GB654331A/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
    • 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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds for use in preparing adhesives (see Group V), having the general formula R(NH COCR1R11COR111)n wherein R is an n-valent, aliphatic, including cyclo-aliphatic, aromatic, or aliphatic-aromatic or aliphatic-aromatic hydrocarbon radical, saturated or unsaturated, unsubstituted or substituted with a group or groups free from active hydrogen, R1 and R11 are hydrogen, X, COX1, or COOX11, the same or different, R111 is X111 or OX1111, wherein X, X1, X11, X111 and X1111 are monovalent aliphatic, including cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon radicals, saturated or unsaturated, substituted or unsubstituted, the same or different, and n is an integer from 2 to 5, are prepared by the interaction of compounds containing reactive methylene groups with polyisocyanates, or by the interaction of polyamines with ketenes, diketenes, substituted or unsubstituted acetacetic esters and homologues The compounds containing methylene groups may be acetoacetic esters, ethyl alpha-acetobutyrate, acetylacetone and malonic esters. The polyisocyanates may be ethylene diisocyanates, butylene diisocyanates, hexamethylene diisocyanates, benzene di- and tri-isocyanates, toluene di- and tri-isocyanates, diphenyl-methane p : p1-diisocyanates, dicyclohexylmethane diisocyanates, chlorobenzene di- and tri-isocyanates, naphthalene di- and tri-isocyanates, stilbene diisocyanate, ditolylmethane p : p1-diisocyanates, dixylyl methane diisocyanates, diphenyl propane p : p1-diisocyanates, diphenylmethane 2 : 4 : 21 : 41-tetraisocyanate, trimethyl benzene triisocyanates, phenyltolylmethane triisocyanates, ditolylmethane triisocyanates and triphenylmethane triisocyanates. Specified compounds are N : N1-bis - (acetoacetyl)-, N : N1 - bis - (carbethoxyacetobutyryl)-, N : N1 - bis - (alpha - (carbo - 2 - chloroethoxy) - acetoacetyl)-, N : N1 - bis - (alpha : alpha-dicarbethoxyacetyl)-, N : N1-bis-(diacetoacetyl) -, N : N1 - bis - (carbethoxyaceto, butyryl) -, N : N1 - bis - (carbethoxyacetyl) - N : N1 - bis - (carballyloxyacetoacetyl) -, N : N1-bis - (alpha - benzoylacetoacetyl) -, N : N1 - bis-(benzyloxyacetoacetyl)-, -hexamethylene diamines or -cyclohexyl diamines, or -diamino cyclohexylmethanes, or -chlorophenylene diamines, or toluylene diamines or -diamino diphenyl methanes; and similar N : N1 : N11-tris-(acetoacetyl)-, toluylene triamines or triaminophenylmethanes; and also N2 : N4 : N6-tris-(alpha-carbethoxyacetoacetyl)-toluene triamine, N : N - bis - (alpha - carbethoxyacetoacetyl) - 4 - chloro - m - phenylene diamine, N : N1 - bis - (alpha - carbethoxyacetoacetyl) - 1 : 6 - hexamethylene diamine, and N : N1-bis-(alpha - carbethoxyacetoacetyl) - 4 : 41 diamino dicyclohexylmethane.ALSO:An adhesive composition comprises, either in solution in a volatile organic liquid, or in aqueous dispersion, or admixed with a natural or synthetic rubber, a compound of the formula R(NHCOCR1R11COR111)n, wherein R is an n-valent, aliphatic, including cyclo-aliphatic, aromatic or aliphatic-aromatic hydrocarbon radical, saturated or unsaturated, unsubstituted or substituted with a group or groups free from active hydrogen, R1 and R11 are hydrogen, X, COX1, or COOX11, the same or different, R111 is X111 or X1111, wherein X, X1, X11, X111 and X1111 are monovalent, aliphatic, including cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon radicals, saturated or unsaturated, substituted or unsubstituted, the same or different, and n is an integer from 2-5. Compounds of this formula may be prepared by reacting compounds containing reactive methylene groups such as aceto-acetic esters, ethyl a -aceto-butyrate, acetyl acetone and malonic esters with polyisocyanates as described in Group IV (b). For bonding rubber to cellulose or to regenerated cellulose compounds in which R contains not more than 8n carbon atoms, R1 is hydrogen, and the hydrocarbon radicals in R11 and R111 each contain not more than 7 carbon atoms are preferred. Specified compounds are N : N1-bis-(acetoacetyl)-, N : N1-bis - (carbethoxyacetoacetyl)-, N : N1 - bis - (a - (carbo - 2 - chlorethoxy) - acetoacetyl)-, N : N1 - bis - (a : a - dicarbethoxyacetyl)-N : N1 - bis - (diacetoacetyl)-, N : N1 - bis - (carbethoxyacetobutyryl)-, N : N1 - bis - (carbethoxyacetyl)-, N : N1 - bis - (carballyloxyacetoacetyl)-, N : N1 - bis - (carbethoxybenzoylacetyl)-, N : N1 - bis - (a - benzoylacetoacetyl)-, N : N1 - bis - (benzyloxyacetoacetyl)-, -hexamethylene diamines, or -cyclohexyl diamines, or -diamino-cyclohexylmethanes, or -chlorophenylene diamines, or -toluylene diamines, or -diamino diphenyl - methanes; and similar N : N1 : N11 - tris - (acetoacetyl)-, toluylene triamines or triaminotriphenylmethanes. Many examples are given in which in addition to some of the above compounds the following compounds are also used: N2 : N4 : N6 - tris - (a - carbethoxyacetoacetyl) - toluene triamine, N : N1 - bis - (a - carbethoxyacetoacetyl) - 4, chloro - m - phenylene diamine, N : N1 - bis - (a - arbethoxyacetoacetyl) - 1 : 6 - hexamethylenediamine, N : N1 - bis - (a - carbethoxyacetoacetyl) - 4 : 41 - diamino-dicyclohexyl-methane. The materials which may be bonded by the process include natural and synthetic rubbers such as polychloroprene, butadiene polymers and interpolymers, and olefine polysulphide rubbers; cellulose derivatives containing hydroxyl, amino or other active-hydrogen containing groups including acetate, propionate, butyrate or nitrate; cellulose ethers such as methyl or ethyl cellulose; carboxylated cellulose polyvinyl alcohol, or polyvinyl halides, polystyrene, polytetrafluoromethylene, polyethylene, alkyd resins; condensate of formaldehyde with phenols, amides, aldehydes, ketones, aromatic ethers, aromatic hydrocarbons, carbamates and amines; polyester amides, polyamides, ether resins, and polymeric derivatives of acrylic, methacrylic or fumaric acid. These materials may be bonded to fibrous materials consisting of yarns, filaments, cords, and fabrics having a basis of regenerated cellulose, cellulose ethers, cellulose esters, cotton, linen, wool, nylon, or polyesters such as polyethylene terephthalate.
GB2919048A 1948-11-10 1948-11-10 Adhesives Expired GB654331A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE492139D BE492139A (en) 1948-11-10
NL72389D NL72389C (en) 1948-11-10
GB2919048A GB654331A (en) 1948-11-10 1948-11-10 Adhesives
FR1002666D FR1002666A (en) 1948-11-10 1949-11-09 Adhesive compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2919048A GB654331A (en) 1948-11-10 1948-11-10 Adhesives

Publications (1)

Publication Number Publication Date
GB654331A true GB654331A (en) 1951-06-13

Family

ID=10287594

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2919048A Expired GB654331A (en) 1948-11-10 1948-11-10 Adhesives

Country Status (4)

Country Link
BE (1) BE492139A (en)
FR (1) FR1002666A (en)
GB (1) GB654331A (en)
NL (1) NL72389C (en)

Also Published As

Publication number Publication date
FR1002666A (en) 1952-03-10
NL72389C (en)
BE492139A (en)

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