GB905725A - Improvements in or relating to an epoxy resin composition - Google Patents

Improvements in or relating to an epoxy resin composition

Info

Publication number
GB905725A
GB905725A GB4409459A GB4409459A GB905725A GB 905725 A GB905725 A GB 905725A GB 4409459 A GB4409459 A GB 4409459A GB 4409459 A GB4409459 A GB 4409459A GB 905725 A GB905725 A GB 905725A
Authority
GB
United Kingdom
Prior art keywords
diamine
methyl
pentanediamine
butylidene
bis
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
GB4409459A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB905725A publication Critical patent/GB905725A/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
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50Amines
    • 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
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014Nitrogen containing compounds
    • C08G59/4042Imines; Imides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

Compositions which are curable by exposure to moisture comprise a polyepoxide and a ketimine. Long lists of a wide variety of suitable polyepoxides are given, bisphenol A/epichlorhydrin condensates being used in the examples. Similarly long lists are given of suitable ketones and primary amines are given, ketimines prepared from the following being used in the examples:-methyl ethyl, methyl isobutyl and diisobutyl ketones and methyl levulinate; ethylene diamine, diethylene triamine, tetramethylene diamine, and m-xylene diamine. The preferred method of curing is to expose the composition to an atmosphere of at least 20% relative humidity. There may also be added to the composition conventional solvents, e.g. ketones, esters, monoether alcohols, chlorinated hydrocarbons, with or without aromatic hydrocarbons and/or alcohols (lists are given), a mixture of methyl isobutyl ketone, ethylene glycol and xylene being used in the examples. Other additives mentioned are diethylphthalate, allyl glycidyl ether, phenyl glycidyl ether, styrene oxide, acetonitrile, BF3-amine complexes, unspecified anhydrides, and in the examples a polysiloxane. Uses: Coating: laminates (see Group VIII).ALSO:Ketimines which are used for curing poly epoxides (see Group IV(a)) are prepared by reacting a ketone with an amine containing at least one primary amine group. The ketimines may be aliphatic, cycloaliphatic, aromatic or heterocyclic; saturated or unsaturated; and may be substituted by chlorine, ether, ester, keto or amide groups. The following ketimines are specified:-N,N1-di(2-propylidene)-1,5-pentanediamine, N1,N5-di(2-propylidene)-3-aza-1,5-pentanediamine, N,N1-di(2 - butylidene) - 1,4-cyclohexanediamine, N1,N8-di(2-butylidene)-3,6-diaza-1,8-octanediamine, p N,N1 - di(2 - propylidene)-1,4-benzenediamine, N,N1 - di(2-proplidene)-2,2-bis(4-aminophenyl)propane, N,N1-di (2 - butylidene) - bis(4 - aminophenyl sulphone, N,N1 - di(2 - butylidene) - bis(4-aminophenyl) methane, N,N1-di(4-methoxy-2-hexylidene)-2,2-bis(4-aminophenyl) propane, N,N1-di(4-chloro-2-hexylidene)-2,2-bis(4-aminophenyl) propane, N,N1-di(4-chloro-2-hexylidene)-1,5 - pentanediamine, N,N1 - di(2 - methoxy-4-hexylidene)-1,5-pentanediamine, N,N1-di(3-allyl-6-octylidene)-1,5-pentanediamine, N1,N5-di(4-methyl-2-pentylidene)-3-aza-1, 5-pentanediamine, N,N1-di (4-methyl - 2 - pentylidene) - 1,2 - ethane diamine, N1,N5-di(2 - butylidene) - 3-aza-1,5-pentane diamine, N,N1-di(2,6-dimethyl-4-heptylidene)-m-xylylene diamine, N,N1 - di(4-methyl-2-pentylidene)-1,4-butanediamine, and N1,N5-di(1-carboxy - 3 - butylidene)-aza-1,5-pentane diamine. And an example is given of the preparation of N,N1-di(4-methyl-2-pentylidene)-m-xylylene diamine from m-xylylene diamine and methyl isobutyl ketone in benzene. Other suitable ketones and amines are listed.
GB4409459A 1958-12-31 1959-12-29 Improvements in or relating to an epoxy resin composition Expired GB905725A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US78404258A 1958-12-31 1958-12-31

Publications (1)

Publication Number Publication Date
GB905725A true GB905725A (en) 1962-09-12

Family

ID=25131170

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4409459A Expired GB905725A (en) 1958-12-31 1959-12-29 Improvements in or relating to an epoxy resin composition

Country Status (4)

Country Link
CH (1) CH431965A (en)
FR (1) FR1243743A (en)
GB (1) GB905725A (en)
NL (2) NL246904A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468830A (en) * 1966-08-26 1969-09-23 Pall Corp Curing of epoxide resins with the reaction product of an organic amine and an aldehyde,and curing and resin compositions and process
EP0234047A2 (en) * 1986-01-29 1987-09-02 Sika AG, vorm. Kaspar Winkler & Co. Composition curable by the influence of humidity
EP2133381A1 (en) * 2008-06-13 2009-12-16 Sika Technology AG Water soluble amine and its application
CN103524716A (en) * 2013-08-31 2014-01-22 苏州保力瑞生物材料科技开发有限公司 Ketimine and preparation method thereof
CN111253834A (en) * 2020-03-19 2020-06-09 滨州学院 Moisture-curing epoxy coating and preparation method thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1236194B (en) * 1962-03-01 1967-03-09 Basf Ag Process for the production of molded articles on the basis of polyadducts
DE2418041C3 (en) * 1974-04-13 1982-04-29 Schering Ag, 1000 Berlin Und 4619 Bergkamen Process for the production of elasticized molded parts according to flat structures

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468830A (en) * 1966-08-26 1969-09-23 Pall Corp Curing of epoxide resins with the reaction product of an organic amine and an aldehyde,and curing and resin compositions and process
EP0234047A2 (en) * 1986-01-29 1987-09-02 Sika AG, vorm. Kaspar Winkler & Co. Composition curable by the influence of humidity
US4748083A (en) * 1986-01-29 1988-05-31 Sika Ag, Vorm. Kaspar Winkler & Co. Moisture curable composition
EP0234047A3 (en) * 1986-01-29 1988-11-09 Sika AG, vorm. Kaspar Winkler & Co. Composition curable by the influence of humidity
EP2133381A1 (en) * 2008-06-13 2009-12-16 Sika Technology AG Water soluble amine and its application
WO2009150212A1 (en) * 2008-06-13 2009-12-17 Sika Technology Ag Water-soluble amine and uses thereof
US8524807B2 (en) 2008-06-13 2013-09-03 Sika Technology Ag Water soluble amine and uses thereof
CN102037051B (en) * 2008-06-13 2014-12-24 Sika技术股份公司 Water-soluble amine and uses thereof
CN103524716A (en) * 2013-08-31 2014-01-22 苏州保力瑞生物材料科技开发有限公司 Ketimine and preparation method thereof
CN103524716B (en) * 2013-08-31 2016-02-03 苏州保力瑞生物材料科技开发有限公司 A kind of ketoimine and preparation method thereof
CN111253834A (en) * 2020-03-19 2020-06-09 滨州学院 Moisture-curing epoxy coating and preparation method thereof
CN111253834B (en) * 2020-03-19 2022-05-24 滨州学院 Moisture-cured epoxy coating and preparation method thereof

Also Published As

Publication number Publication date
NL128837C (en)
CH431965A (en) 1967-03-15
FR1243743A (en) 1960-10-14
NL246904A (en)

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