Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From reactant having at least one -n=c=x group as well as...
Reexamination Certificate
2000-12-08
2002-12-17
Buttner, David J. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From reactant having at least one -n=c=x group as well as...
C528S293000, C528S370000, C528S377000, C528S406000, C528S407000
Reexamination Certificate
active
06495653
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a curable resin composition and a cured product thereof, and more particularly to a curable composition retaining curability even at a low temperature of, for example, −20 to 5° C., having a low viscosity at low temperature, and capable of curing rapidly at room temperature and a cured product thereof.
PRIOR ART
Epoxy resin has excellent mechanical, electrical, adhesion, chemical resistance and other properties and has been used in a variety of industrial applications such as adhesives, paints, linings and so on. As regards the one-component room temperature-curable system, the present inventors previously proposed a one-component epoxy resin composition containing a special heterocyclic compound as the curing agent and capable of moisture-curing at room temperature at a high cure speed and having good storage stability and workability [Japanese Kokai Publication Hei-9-188744]. However, in spite of the practical utility of the one-component epoxy resin composition disclosed in said Japanese Kokai Publication Hei-9-188744, the market demands a more rapidly-curing, more workable one-component room temperature-curable system.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a curable composition retaining curability even at a low temperature of −20 to 5° C. and having a low viscosity at such low temperature, the cured product of which has excellent water resistance, chemical resistance, mechanical strength and other physical properties. It is a further object of the present invention to provide a one-component curable composition capable of curing rapidly at room temperature and having a low viscosity and good storage stability, the cured product of which has excellent water resistance, chemical resistance, and mechanical and other physical properties. The present inventors did an intensive investigation and arrived at a system conforming to the above objects.
The present invention [1], therefore, is directed to a curable composition
which comprises a hetero ring-containing compound (A) of the following general formula (1), a compound (B) having 2 or more electrophilic groups reactive with thiol or —S— groups per molecule, and a compound (C) having 2 or more nucleophilic groups per molecule:
in the formula (1), n represents an integer of 1 to 10; X
1
, Y
1
and Z
1
each represents an oxygen or sulfur atom; R
1
represents the residue of a cyclic ether group-containing compound (D) or a hydrogen atom; R
2
represents a hydrocarbon group of 2 to 10 carbon atoms.
The present invention [2] is directed to a curing agent for (B) which comprises a reaction product (T1) of said (A) and (C).
The present invention (3) is directed to a cured product as obtainable on curing of said curable composition.
DETAILED DISCLOSURE OF THE INVENTION
[1] Curable composition
[Hetero Ring-containing Compound (A)]
In the present invention [1], the hetero ring-containing compound (A) is represented by the above general formula (1) In the formula, n represents an integer of 1 to 10, preferably 2 to 8; X
1
, Y
1
and Z
1
each represents an oxygen or sulfur atom; preferably, X
1
is a sulfur atom (S) and one of Y
1
and Z
1
represents a sulfur atom (S), and the other represents an oxygen atom (O)
R
2
represents a hydrocarbon group of 2 to 10 carbon atoms and is a trivalent hydrocarbon group of the formula:
(m is an integer of 1 to 9)
or a tetravalent hydrocarbon group of the formula:
(m′ is an integer of 0 to 8). The above-mentioned trivalent hydrocarbon group includes, for example, >CHCH
2
—, >CHCH
2
CH
2
—, >CHCH
2
CH
2
CH
2
— and >CHCH
2
CH
2
CH
2
CH
2
CH
2
—, and said tetravalent hydrocarbon group includes, for example, >CHCH<, >CHCH
2
CH<, >CHCH
2
CH
2
CH< and >CHCH
2
CH
2
CH
2
CH
2
CH<. Preferred is a trivalent hydrocarbon group, and particularly preferred is >CHCH
2
— or >CHCH
2
CH
2
—.
R
1
represents a hydrogen atom or the residue of a cyclic ether group-containing compound (D). The above cyclic ether group-containing compound (D) is represented by the general formula (7):
wherein R
1
, R
2
and n have the same as defined for general formula (1).
Referring to the general formula (7), R
2
means a ring-forming residue of a cyclic ether group, other than the oxygen atom. The cyclic ether group is not particularly restricted as far as it contains one oxygen atom as a ring member. The cyclic ether group-containing compound (D) includes, for example, a compound having 1 to 10 cyclic ether groups per molecule.
The cyclic ether group-containing compound (D) includes an epoxy group-containing compound (D1) and an oxetane compound (D2), which are described hereinafter, and preferred is an epoxy group-containing compound (D1).
The epoxy group-containing compound (D1) includes a monoepoxide (d11) and a polyepoxide (D11) having 2 or more epoxy groups per molecule. The monoepoxide (d11) corresponds to the general formula (7) wherein n is equal to 1, and the polyepoxide (D11) corresponds to the same formula (7) wherein n is 2 or more.
The monoepoxide (d11) is not particularly restricted as far as it contains one epoxy group per molecule and a suitable species can be judiciously selected according to the intended use or purpose. Thus, it includes, for example, C
2-24
hydrocarbon oxides (ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide, C
5-24
&agr;-olefin oxides, styrene oxide, etc.), C
3-10
hydrocarbon glycidyl ethers (n-butyl glycidyl ether, allyl glycidyl ether, 2-ethylhexyl glycidyl ethyl, 2-methyloctyl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, p-sec-butylphenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, etc.), C
3-30
monocarboxylic acid glycidyl esters (glycidyl acrylate, glycidyl methacrylate, etc.), epihalohydrins such as epichlorohydrin, epibromohydrin, etc.; and hydroxyl group-containing oxides such as glycidol. Preferred are C
2-24
hydrocarbon oxides and C
3-10
hydrocarbon glycidyl ethers.
The polyepoxide (D11) is not particularly restricted as far as it contains 2 or more epoxy groups per molecule and a suitable species can be judiciously selected according to the intended use or purpose. Preferred are compounds containing 2 to 6 epoxy groups. The epoxy equivalent (molecular weight per epoxy group) of the polyepoxide (D11) is usually 65 to 1000, preferably 90 to 500. When the epoxy equivalent is not more than 1000, the crosslinked structure is not loose and the physical properties, e.g. water resistance, chemical resistance and mechanical strength, of the cured product are satisfactory. When the epoxy equivalent is not less than 65, the crosslinked structure has good water resistance, chemical resistance and mechanical strength of the cured product.
The polyepoxide (D11) includes the following (D11-1) to (D11-5).
(D11-1) The Glycidyl Ether Type
(i) Diglycidyl Ethers of Dihydric Phenols
Diglycidyl ethers of dihydric phenols containing 6~30 carbon atoms, such as bisphenol F diglycidyl ether, bisphenol A diglycidyl ether, bisphenol B diglycidyl ether, bisphenol AD diglycidyl ether, bisphenol S diglycidyl ether, halogenated bisphenol A diglycidyl ether, tetrachlorobisphenol A diglycidyl ether, catechin diglycidyl ether, resorcinol diglycidyl ether, hydroquinone diglycidyl ether, 1,5-dihydroxynaphthalene diglycidyl ether, dihydroxy-biphenyl diglycidyl ether, octachloro-4,4′-dihydroxy-biphenyl diglycidyl ether, tetramethyl-biphenyl diglycidyl ether, 9,9′-bis(4-hydroxyphenyl)fluorene diglycidyl ether, and the diglycidyl ether as the reaction product of 2 moles of bisphenol A and 3 moles of epichlorohydrin, among others;
(ii) Polyglycidyl Ethers of 3~6 or Higher Functional Polyhydric Phenols
Polyglycidyl ethers of 3~6 or higher functional polyhydric phenols each containing 6 to 50 or more carbon atoms and a molecular weight of 250 to 3000, such as pyrrogallol triglycidyl ether, dihydroxynaphthylcresol triglycidyl ether, tris(hydroxyphenyl)methane trig
Buttner David J.
Sanyo Chemical Industries Ltd.
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