US 5,712,331 A · Curable epoxy compositions containing aziridine in supercritical fluid carbon dioxide

Abstract

A curable resin system in supercritical carbon dioxide as diluent includes an epoxy resin, a co-reactant selected from poly N-substituted aziridines, and a catalyst to promote cure at ambient temperature. The system is compatible with various epoxy resins such as bisphenol A epoxy, bisphenol F epoxy, novolac epoxy, cycloaliphatic epoxy, triglycidyl-aminophenol, and triglycidyl isocyanurate. The aziridine co-reactant may be selected from reaction products of NH aziridines with acrylates and methacrylates of trimethylolpropane, ethylene glycol, propylene glycol, bisphenol A, bisphenol F, pentaerythritol, glycerol, and their alkoxylated derivatives; reaction products of NH aziridines with epoxy compounds; and 1-aziridine ethanol and its reaction products with epoxy and isocyanate functional compounds. Suitable catalysts include acid salts and complexes, strong electron accepting compounds, combinations of silicon hydrides and metal complexes, and non-halogen containing boron derivatives. As an option, compounds having active hydrogen, such as mono or multifunctional phenols, alcohols, and carboxylic acids, with or without anhydrides, may be added. The curable resin system provides controlled cure rates at ambient temperature, compatibility with SCF CO.sub.2 spray application systems, and no release of volatile organic compounds during cure.

Claims11

Dependent claims

A curable epoxy composition, comprising:

an epoxy resin;
a co-reactant selected from the group consisting of poly N-substituted aziridines, wherein the aziridine:epoxy ratio is in the range of 1:2 to 3:1;
a catalyst to promote cure at ambient temperature, selected from the group consisting of salts and complexes of acids;
electron accepting compounds;
non-halogen containing boron derivatives;
and combinations of a silicon hydride with a complex of a metal selected from the group consisting of Al, Fe, Pt, Pd, Rh, Ru, Ti, and Zr;
and further comprising;
supercritical fluid carbon dioxide as a diluent for spray application.

5 more elements

A curable epoxy composition, comprising:

an epoxy resin selected from the group consisting of bisphenol A epoxy, bisphenol F epoxy, novolac epoxy, cycloaliphatic epoxy, triglycidyl-aminophenol, and triglycidyl isocyanurate;
a co-reactant selected from the group of poly N-substituted aziridines, wherein the aziridine:epoxy ration is in the range of 1:2 to 3:1, said aziridines consisting of reaction products of an NH aziridine with a member of the group consisting of acrylates and methacrylates of trimethylolpropane ethylene glycol, propylene glycol, bisphenol A, bisphenol F, pentaerythritol, glycerol, and their alkoxylated derivatives;
reaction products of an NH aziridine with an epoxy compound;
and reaction products of 1-aziridine ethanol with a member of the group consisting of epoxy and isocyanate functional compounds;
a catalyst, to promote cure at ambient temperature, selected from the group consisting of salts and complexes of acids, electron accepting compounds, non-halogen containing boron derivatives, and combinations of a silicon hydride with a complex of a metal selected from the group consisting of Al, Fe, Pt, Pd, Rh, Ru, Ti and Zr;
and further comprising;
supercritical fluid carbon dioxide as a diluent for spray application.

4 more elements

A curable epoxy composition, comprising:

an epoxy resin selected from the group consisting of bisphenol A epoxy, bisphenol F epoxy, novolac epoxy, cycloaliphatic epoxy, triglycidyl-aminophenol, and triglycidyl isocyanurate;
a co-reactant selected from the group of poly N-substituted aziridines, wherein the aziridine:epoxy ratio is in the range of 1:2 to 3:1, said aziridines consisting of:
Reaction products of an NH aziridine with a member of the group consisting of acrylates and methacrylates of trimethylolpropane, ethylene glycol, propylene glycol, bisphenol A, bisphenol F, pentaerythritol, glycerol, and their alkoxylated derivatives;
reaction products of an NH aziridine with an epoxy compound;
and
reaction products of 1-aziridine ethanol with the group consisting of epoxy and isocyanate functional compounds;
and
a catalyst, to promote cure at ambient temperature, selected from the group consisting of:
BF.sub.3 -amine complexes, p-toluene sulfonic acid metal salts, cetyltrimethylammonium p-toluene sulfonate, 1-dodecylpyridinum p-toluene sulfonate, tetraethylamine trifluorosulfonate, and ferrocenesulfonic acid ammonium salt;
tetracyanobenzene and tetrachlorobenzoquinone;
a non-halogen containing boron derivative selected from the group consisting of boric acid and alkyl borates;
combinations of a silicon hydride selected from the group consisting of phenylsilane, diphenylsilane, and butylsilane, with a metal complex selected from the group consisting of aluminum acetylacetonate, aluminum trifluoroacetylacetate, 8-hydroxyquinolinol aluminum complex, aluminum isopropoxide aluminum tri-tert-butoxide, aluminum tri-sec-butoxide, acetoalkoxy aluminum diisopropylate, (1-acetylcyclopentadienyl) cyclopentadienyl iron, chloroplatinic acid, platinum dibenzonitrile dichloride, platinum acetylacetonate, tetramethyl-tetravinylcyclotetrasiloxaneplatinum complex, palladium acetate, palladium acetylacetonate, cycopentrdienylruthenium, titanium isopropoxide, and zirconium n-propoxide, and further comprising;
supercritical fluid carbon dioxide as a diluent for spray application of the epoxy composition.

10 more elements

Dependencies are inferred from the claim text.

Curable epoxy compositions containing aziridine in supercritical fluid carbon dioxide

Life of this patent

Curable epoxy compositions containing aziridine in supercritical fluid carbon dioxide

Life of this patent

Abstract

Claims11