Microwave-polymerizable isocyanate/epoxy resins for heavy-duty applications
AssigneesEnichem S.p.A., Eniricerche S.p.A.
InventorsFabrizio Parodi, Renata Gerbelli, Mark De Meuse
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Abstract
Crosslinkable liquid composition based on organic isocyanates and epoxy compounds, comprising the following components: (A) an organic polyisocyanate; (B) a polyepoxide or mixture of a polyepoxide and a monoepoxide; and (C) a catalyst constituted by at least one cyanoderivative containing a quaternary nitrogen atom, which composition can be polymerized at temperatures of 40.degree. C. or higher, by a process comprising exposure thereof to a non-ionizing electromagnetic radiation having a frequency comprised in the microwave range of frequencies, to obtain a solid material endowed with an excellent combination of physical, chemical and mechanical properties.
Claims30
A crosslinkable liquid composition based on organic isocyanate and epoxy compounds, polymerizable at temperatures of 40.degree. C. or higher by exposure to non-ionizing electromagnetic radiation having a frequency in the microwave range, to obtain a solid material, said composition comprising:
- (A) at least one organic polyisocyanate;
- (B) at least one polyepoxide or mixture of a polyepoxide and a monoepoxide;
- and
- (C) from 0.05 to 5 parts by weight per 100 parts of the sum of (A) and (B), of a catalyst comprising at least one cyano compound containing a quaternary nitrogen atom and having formula (III) ##STR9## wherein Z is hydrogen, a C.sub.1-10 aliphatic radical, a C.sub.3-10 cycloaliphatic radical, a C.sub.3-10 heterocyclic radical, or a C.sub.6-10 aromatic radical;
- Y is a non-monovalent C.sub.2-16 aliphatic organic radical, a C.sub.5-16 cycloaliphatic radical, a C.sub.5-16 heterocyclic radical, or a C.sub.6-16 aromatic radical;
- R.sub.1 and R.sub.2, which may be the same or different, are independently an aliphatic, cycloaliphatic, aromatic or heterocyclic radical, or R.sub.1 and R.sub.2 are linked together to form a heterocyclic, aliphatic or aromatic ring containing at least 5 ring atoms and containing a quaternary nitrogen atom, wherein R.sub.1 and R.sub.2 contain a total of 2-20 carbon atoms, or
- Y and R.sub.1, or Y, R.sub.1 and R.sub.2, are linked together to form a heterocyclic, monocyclic, bicyclic, aliphatic or aromatic ring containing at least 5 ring atoms and containing a quaternary nitrogen atom;
- R.sub.3 is a C.sub.1-20 aliphatic radical or a C.sub.7-20 aryl-alkyl radical;
- r is 0 or 1;
- and
- X is a halide anion selected from the group consisting of chloride, bromide and iodide.
A crosslinkable liquid composition based on organic isocyanate and epoxy compounds, polymerizable at temperatures of 40.degree. C. or higher by exposure to non-ionizing electromagnetic radiation having a frequency in the microwave range, to obtain a solid material, said composition comprising:
- (A) at least one organic polyisocyanate;
- (B) at least one polyepoxide or mixture of a polyepoxide and a monoepoxide;
- and
- (C) from 0.05 to 5 parts by weight per 100 parts of the sum of (A) and (B), of a catalyst comprising at least one cyano compound containing a quaternary nitrogen atom and having formula (III) ##STR10## wherein Z is hydrogen, a C.sub.1-10 aliphatic radical, a C.sub.3-10 cycloaliphatic radical, a C.sub.3-10 heterocyclic radical, or a C.sub.6-10 aromatic radical;
- Y is a non-monovalent C.sub.2-16 aliphatic organic radical, a C.sub.5-16 cycloaliphatic radical, a C.sub.5-16 heterocyclic radical, or a C.sub.6-16 aromatic radical;
- R.sub.1 and R.sub.2, which may be the same or different, are independently an aliphatic, cycloaliphatic, aromatic or heterocyclic radical, or R.sub.1 and R.sub.2 are linked together to form a heterocyclic, aliphatic or aromatic ring containing at least 5 ring atoms and containing a quaternary nitrogen atom, wherein R.sub.1 and R.sub.2 contain a total of 2-20 carbon atoms, or
- Y and R.sub.1, or Y, R.sub.1 and R.sub.2, are linked together to form a heterocyclic, monocyclic, bicyclic, aliphatic or aromatic ring containing at least 5 ring atoms and containing a quaternary nitrogen atom;
- R.sub.3 is a C.sub.1-20 aliphatic radical or a C.sub.7-20 aryl-alkyl radical;
- r is 0 or 1;
- and
- X is a halide anion selected from the group consisting of chloride, bromide and iodide,
- wherein said catalyst is obtained by a process wherein an .alpha.,.beta.-unsaturated nitrile of formula XXV
- N.tbd.C--CH.dbd.CH(Z) XXV
- wherein Z is as defined above, is reacted with a tertiary hydroxyamino compound of formula XXIV
- HO--Y--NR.sub.1 R.sub.2 XXIV
- wherein Y, R.sub.1 and R.sub.2 are as defined above, or with a mixture of said hydroxyamino compound and with an alkyl monohalide of formula R.sub.3 X, wherein R.sub.3 is as defined above and X is a chlorine, bromine or iodine atom;
- according to the following steps:
- I-a) said .alpha., .beta.-unsaturated nitrile is added to a liquid mixture containing said tertiary hydroxyamino compound, a strong base, and optionally a solvent or mixture of solvents, maintained at a temperature within the range of 0.degree. to 80.degree. C., wherein said strong base is present in an amount of 0.5-5 milliequivalents with respect to 100 g of the reaction mixture including said .alpha.,.beta.-unsaturated nitrile;
- I-b) the reaction mixture obtained in I-a is stirred for 0.5-6 hours at temperatures between 0.degree. and 80.degree. C.;
- II-a) said alkyl monohalide is added to the mixture obtained in step I-b and stirred at a temperature between 0.degree. and 40.degree. C., stirring is continued for an additional 0.5-6 hours between 0.degree. and 40.degree. C.;
- II-b) the mixture obtained in step II-a) is heated with stirring to a temperature between 50.degree. and 120.degree. C. and maintained at this temperature for 6-60 hours;
- and
- II-c) the optional solvent is removed by evaporation.
Dependencies are inferred from the claim text.