Curing composition with improved heat resistance
View Patent ↗The present invention provides a curable composition including: an organic polymer (A) which has on average 1.1 to 50 groups per one molecule thereof each represented by the general formula (1) and has one or more silicon-containing functional groups capable of cross-linking by forming siloxane bonds: —NR 1 —C(═O)— (1) wherein R 1 is a hydrogen atom, or a substituted or unsubstituted monovalent organic group; and a metal carboxylate and/or a carboxylic acid (B), the curable composition giving a cured article excellent in curability and also excellent in heat resistance although a non-organotin catalyst is used.
1. A curable composition comprising:
a polyoxypropylene polymer (A) which has on average 1.1 to 5 groups per one molecule thereof represented by the general formula (1) and has one or more silicon-containing functional groups capable of cross-linking by forming siloxane bonds:
—NR 1 —C(═O)— (1)
wherein R 1 is a hydrogen atom, or a substituted or unsubstituted monovalent organic group;
tin neodecanoate (B),
a primary amine as a component (C),
a filler, and
a plasticizer,
wherein
the plasticizer is phthalate,
an amount of the tin neodecanoate (B) is 0.5 to 10 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A),
an amount of the component (C) is 0.1 to 5 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A),
an amount of the filler is 10 to 200 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A), and
an amount of the plasticizer is 20 to 100 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A).
2. The curable composition according to claim 1 , wherein the polyoxypropylene polymer (A) has on average 1.5 to 2 groups per one molecule thereof represented by the general formula (1).
3. The curable composition according to claim 1 , wherein the polyoxypropylene polymer (A) is produced by following production methods (a) or (b):
the production method (a) in which an excessive amount of a polyisocyanate compound (E) is reacted with a polyoxypropylene polymer (D) having active hydrogen-containing groups at the terminals thereof to convert the polyoxypropylene polymer (D) into a polymer having isocyanate groups at the terminals of the polyurethane main chain thereof, and thereafter, or at the same time, the whole isocyanate groups or a part of the isocyanate groups are reacted with the W group of a silicon compound (F) represented by formula (7) to produce the polyoxypropylene polymer (A):
W—R 5 —SiR 4 3-c X c (7)
wherein R 4 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a triorganosiloxy group represented by (R′) 3 SiO—, and when there are two or more R 4 s, they may be the same or different from each other; R′ represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, and 3 R′s may be the same or different from each other; X represents a hydroxy group or a hydrolyzable group, and when there are two or more Xs, they may be the same or different from each other; c represents an integer of 1 to 3; R 5 is a divalent organic group; and W is an active hydrogen-containing group selected from the group consisting of a hydroxy group, a carboxyl group, a mercapto group and a primary or secondary amino group; or
the production method (b) in which an hydrolyzable silicon group-containing isocyanate compound (G) represented by formula (8) is reacted with the polyoxypropylene polymer (D) having active hydrogen-containing groups at the terminals thereof to produce the polyoxypropylene polymer (A):
O═C═N—R 5 —SiR 4 3-c X c (8)
wherein R 4 , R 5 , X and c are the same as described above.
4. The curable composition according to claim 3 , wherein R 5 is a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms.
5. The curable composition according to claim 1 , wherein the plasticizer is diisodecyl phthalate.
6. The curable composition according to claim 1 , wherein the silicon-containing functional group capable of cross-linking by forming siloxane bonds is a trimethoxysilyl group.
7. A curable composition comprising:
a polyoxypropylene polymer (A) which has on average 1.1 to 5 groups per one molecule thereof represented by the general formula (1) and has one or more silicon-containing functional groups capable of cross-linking by forming siloxane bonds:
—NR 1 —C(═O)— (1)
wherein R 1 is a hydrogen atom, or a substituted or unsubstituted monovalent organic group; and
a component (B) which is a carboxylic acid,
an amine compound as a component (C),
a filler, and
a plasticizer,
wherein the carbon atom adjacent to the carbonyl group of the carboxylic acid is a quaternary carbon atom,
the plasticizer is phthalate,
an amount of component (B) is 0.5 to 10 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A),
an amount of the component (C) is 0.1 to 5 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A),
an amount of the filler is 10 to 200 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A) , and
an amount of the plasticizer is 20 to 100 parts by weight in relation to 100 parts by weight of the polyoxypropylene polymer (A).
8. The curable composition according to claim 7 , wherein the polyoxypropylene polymer (A) has on average 1.5 to 2 groups per one molecule thereof represented by the general formula (1).
9. The curable composition according to claim 7 , wherein the component (B) is neodecanoic acid.
10. The curable composition according to claim 7 , wherein the plasticizer is diisodecyl phthalate.
11. The curable composition according to claim 7 , wherein the silicon-containing functional group capable of cross-linking by forming siloxane bonds is a trimethoxysilyl group.