US 7,176,269 B2 · Curable composition and its use

Abstract

The curable composition of the present invention contains (A1) a silyl-containing ethylene/α-olefin/non-conjugated polyene random copolymer rubber which has a structural unit derived from a norbornene compound as the non-conjugated polyene with at least one specific vinyl group at the terminal and contains a specific hydrolyzable silyl group, and (B) a compound, other than the rubber (A1), having a hydroxyl group and/or a hydrolyzable group, e.g., (B1) a compound having a silanol group and/or a compound which can react with moisture to form a compound having a silanol group in the molecule. This compound improves elongation of the cured product and residual surface tackiness, and, at the same time, is high in curing speed and capable of giving the cured product of high resistance to weather. It is suitable for, e.g., adhesives, tackifiers, paints, sealants, waterproof materials, spray materials, shaping materials and casting rubber materials.

Claims40

Dependent claims

A curable composition comprising a silyl-containing ethylene/α-olefin/non-conjugated polyene random copolymer rubber (A1) which has a structural unit derived from a norbomene compound, represented by the following general formula [I] or [II], as the non-conjugated polyene with at least one specific vinyl group at the terminal, and containing a hydrolyzable silyl group, represented by general formula [III], and

wherein, “n” is an integer of 0 to 10;
R1 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms;
and
R2 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms,
wherein, R3 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
wherein, R is a monovalent hydrocarbon group of 1 to 12 carbon atoms;
X is a hydrolyzable group selected from the group consisting of hydride, halogen, alkoxyl, acyloxy, ketoximate, amide, acid amide, aminoxy, mercapto, alkenyloxy, thioalkoxy and amino group;
and “a” is an integer of 0 to 2, wherein the rubber (A1) is produced by hydrosilylation, whereby said ethylene/α-olefin/non-conjugated polyene random copolymer rubber is reacted with a silicon compound represented by the following general formula [IV] in the presence of a transition metal complex catalyst:
where R and “a” are as defined above;
and
a compound (B), other than the rubber (A1), having a hydroxyl group and/or a hydrolyzable group.

8 more elements

A curable rubber composition comprising

a silyl-containing ethylene/α-olefin/non-conjugated polyene random copolymer rubber (A1) which has a structural unit derived from a norbomene compound, represented by the following general formula [I] or [II], as the non-conjugated polyene with at least one specific vinyl group at the terminal, and containing a hydrolyzable silyl group, represented by the following general formula [III],
wherein, “n” is an integer of 0 to 10;
R1 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms;
and
R2 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms,
wherein, R3 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
wherein, R is a monovalent hydrocarbon group of 1 to 12 carbon atoms;
X is a hydrolyzable group selected from the group consisting of hydride, halogen, alkoxyl, acyloxy, ketoximate, amide, acid amide, aminoxy, mercapto, alkenyloxy, thioalkoxy and amino group;
and “a” is an integer of 0 to 2, wherein the rubber (A1) is produced by hydrosilylation, whereby said ethylene/α-olefin/non-conjugated polyene random copolymer rubber is reacted with a silicon compound represented by the following general formula [IV] in the presence of a transition metal complex catalyst:
wherein R and “a” are as defined above;
a tetravalent tin compound (C), and
a silicon compound (B2) represented by the following general formula [V]:
R4aSi(OR5)4-a [V]
wherein, R4 and R5 are each a substituted or unsubstituted hydrocarbon group of 1 to 20 carbon atoms, and “a” is 0, 1, 2, or 3.

11 more elements

A rubber composition curable at an ordinary temperature and comprising

a silyl-containing ethylene/α-olefin/non-conjugated polyene random copolymer rubber (A1) which has a structural unit derived from a norbornene compound, represented by the following general formula [I] or [II], as the non-conjugated polyene with at least one specific vinyl group at the tenninal, and containing a hydrolyzable silyl group, represented by the following general formula [III],
wherein, “n” is an integer of 0 to 10;
R1 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms;
and
R2 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms,
wherein, R3 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
wherein, R is a monovalent hydrocarbon group of 1 to 12 carbon atoms;
X is a hydrolyzable group selected from the group consisting of hydride, halogen, alkoxyl, acyloxy, ketoximate, amide, acid amide, aminoxy, mercapto, alkenyloxy, thioalkoxy and amino group;
and “a” is an integer of 0 to 2, and
a silane compound (B5) represented by one of the following general formulae [VII-1] to [VII-6]:
wherein, R4 is a monovalent hydrocarbon group of 1 to 10 carbon atoms, selected from the group consisting of alkyl, aralkyl and aryl;
X is a group selected from the group consisting of halogen, hydroxy, alkoxyl, acyloxy, aminoxy, phenoxy, thioalkoxy, amino, ketoximate, mercapto and alkenyloxy;
R5 is an alkylene or arylene group of 8 to 200 carbon atoms;
R6 is a monovalent alkyl group of 8 to 200 carbon atoms;
and “n” is an integer of 0 to 2.

12 more elements

A curable rubber composition comprising, as the active components,

(A1) a silyl-containing ethylene/α-olefin/non-conjugated polyene random copolymer rubber which has a structural unit derived from a norbomene compound, represented by the following general formula [I] or [II], as the non-conjugated polyene with at least one specific vinyl group at the terminal, and containing a hydrolyzable silyl group, represented by the following general formula [III],
wherein, “n” is an integer of 0 to 10;
R1 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms;
and
R2 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, the following general formula [I] or [II], as the non-conjugated polyene with at least one specific vinyl group at the terminal, and containing a hydrolyzable silyl group, represented by the following general formula [III],
wherein, “n” is an integer of 0 to 10;
R1 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms;
and
R2 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms,
wherein, R3 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
wherein, R is a monovalent hydrocarbon group of 1 to 12 carbon atoms;
X is a hydrolyzable group selected from the group consisting of hydride, halogen, mercapto, alkenyloxy, alkoxyl, acyloxy, ketoximate, amide, acid amide, aminoxy, thioalkoxy and amino
wherein, R3 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
wherein, R is a monovalent hydrocarbon group of 1 to 12 carbon atoms;
X is a hydrolyzable group selected from the group consisting of hydride, halogen, alkoxyl, acyloxy, ketoximate, amide, acid amide, aminoxy, mercapto, alkenyloxy, thioalkoxy and amino group;
and “a” is an integer of 0 to 2,
(D) amines selected from the group consisting of aliphatic amines, alicyclic amines, modified cycloaliphatic polyamines and ethanolamines,
(B6) a silane coupling agent represented by the general formula Y3(Si)Z, wherein Y is an alkoxyl group;
and Z is an alkyl group containing a functional group selected from the group consisting of amino group, which may be substituted with an aminoalkyl group or not, and mercapto group, and
(E) a resin composed of a lacquer-based paint, an acrylic lacquer-based paint, an acrylic resin-based paint, a thermosetting acrylic paint, an alkyd paint, a melamine paint, an epoxy paint or organopolysiloxane.

17 more elements

A curable rubber composition comprising,

a silyl-containing ethylene/α-olefin/non-conjugated polyene random copolymer rubber (A1) which has a structural unit derived from a norbomene compound, represented by the following general formula [I] or [II], as the non-conjugated polyene with at least one specific vinyl group at the terminal, and containing a hydrolyzable silyl group, represented by the following general formula [III],
wherein, “n” is an integer of 0 to 10;
R1 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms;
and
R2 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms,
wherein, R3 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
wherein, R is a monovalent hydrocarbon group of 1 to 12 carbon atoms;
X is a hydrolyzable group selected from the group consisting of hydride, halogen, alkoxyl, acyloxy, ketoximate, amide, acid amide, aminoxy, mercapto, alkenyloxy, thioalkoxy and amino group;
and “a” is an integer of 0 to 2, wherein the rubber (A1) is produced by hydrosilylation, whereby said ethylene/α-olefin/non-conjugated polyene random copolymer rubber is reacted with a silicon compound represented by the following general formula [IV] in the presence of a transition metal complex catalyst:
wherein R and “a” are as defined above;
alcohols (B9) and/or a hydrolyzable ester (I) (except the hydrolyzable organosilicon compound (B10), and
a hydrolyzable organosilicon compound (B10) other than the rubber (A1).

9 more elements