Moisture-curable resin composition

• US 5,068,304 A
• Filed: 12/06/1989
• Issued: 11/26/1991
• Est. Priority Date: 12/09/1988
• Status: Expired due to Fees

• Current Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Nakano, Yasuhiko, Yamaguchi, Yoshiyuki, Higuchi, Toshihiko, Kozawa, Shigeyuki, Kunii, Nobuaki
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US07/446,661
• Time in Patent Office: 720 Days
• Field of Search: 528/28, 528/29, 528/25, 528/38, 528/31
• US Class Current: 528/28
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08G 18/4837 and other oxyalkylene units
• CPC Class Codes: C08G 18/4866 having a low unsaturation value
• CPC Class Codes: C08G 18/718 containing silicon
• CPC Class Codes: C08G 18/809 containing silicon
• CPC Class Codes: C08G 18/8108 having only one isocyanate or isothiocyanate group
• CPC Class Codes: C08G 18/832 by water acting as hydrolizing agent reaction of isocyanates with water C08G18/302; reaction of isocyanate prepolymers with water C08G18/10 + C08G18/302
• CPC Class Codes: C08G 18/837 by silicon containing compounds
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints

Abstract

A moisture-curable resin composition containing a hydrolyzable silyl group-containing polyether compound as a curable component, said polyether compound comprising polyoxyalkylene chains derived from a polyoxyalkylene polyol having a hydroxyl value (x mgKOH/g) of from 5 to 35, a total degree of unsaturation (y meq/g) of not higher than 0.07 meq/g and y≦0.9/(x-10), from 2 to 8 hydroxyl groups, and a content of oxyalkylene groups having at least 3 carbon atoms, of at least 60% by weight, and a hydrolyzable silyl group-containing terminal group present at least 1.3 terminals on the average of said polyoxyalkylene chains, said terminal group having a urethane bond linked to the polyoxyalkylene chain.

Claims

1. A moisture-curable resin composition containing a hydrolyzable silyl group-containing polyether compound as a curable component, said polyether compound comprising polyoxyalkylene chains derived from a polyoxyalkylene polyol having a hydroxyl value, x mgKOH/G, wherein x ranges from to 5 to 35, a total degree of unsaturation, y meq/g, wherein y is not higher than 0.07 meq/g and h≦

0.9/(x-10), from 2 to 8 hydroxyl groups, and a content of oxyalkylene groups having at least 3 carbon atoms, of at least 60% by weight, and a hydrolyzable silyl group-containing terminal group present at least 1.3 terminals on the average of said polyoxyalkylene chains, said terminal group having a urethane bond linked to the polyoxyalkylene chain.

2. The moisture-curable resin composition according to claim 1, wherein the polyoxyalkylene polyol is a polyoxyalkylene polyol consisting essentially of a polymer obtained by ring-opening addition polymerization of a monoepoxide by a polyvalent initiation.

3. The moisture-curable resin composition according to claim 1, wherein the polyoxyalkylene polyol is a polyoxyalkylene polyol obtained by ring-opening addition polymerization of an alkylene oxide having 3 or 4 carbon atoms, above or with ethylene oxide.

4. The moisture-curable resin composition according to claim 3, wherein the ring-opening addition polymerization reaction is conducted in the presence of a composite metal cyanide complex catalyst.

5. The moisture-curable resin composition according to claim 1, wherein the hydrolyzable silyl group is a silyl group having from 1 to 3 functional groups selected from the group consisting of a halogen atom, an alkoxy group, an acyloxy group, an amide group, an amino group, an aminooxy group and a ketoximate group.

6. The moisture-curable resin composition according to claim 1, wherein the hydroxyzable silyl group-containing terminal group is a terminal group derived from a compound having a hydrolyzable silyl group and an isocyanate group.

7. The moisture-curable resin composition according to claim 6, wherein the compound having a hydrolyzable silyl group and an isocyanate group is a silane having an isocyanate alkyl group and a hydrolyzable group.

8. The moisture-curable resin composition according to claim 1, which contains from 0.001 to 5% by weight, based on the hydrolyzable silyl group-containing polyether compound, of a curing catalyst.

9. The moisture-curable resin composition according to claim 1, wherein the hydrolyzable silyl group-containing polyoxyalkylene compound is obtained by reacting a polyoxalkylene polyol having a hydroxyl value, x mgKOH/g, wherein x ranges from 5 to 35, a total degree of unsaturation, y mgq/g, wherein y is not greater than 0.07 meq/g and y≦

0.9/(x-10), from 2 to 8 hydroxyl groups and a content of oxyalkylene groups having at least 3 carbon atoms of at least 60% by weight with a compound having a hydrolyzable silyl group and an isocyanate group in amounts of at least 1.3 molecules of hydrolyzable silyl group-isocyanate group containing compound per molecule of said polyoxyalkylene polyol.

10. The moisture-curable resin composition according to claim 1, wherein the hydrolyzable silyl group-containing terminal group of the polyether compound is formed by the reaction of a compound which contains a hydrolyzable silyl group and an active hydrogen atom with a compound having at least two isocyanate groups, one of which reacts with said active hydrogen atom while the other reacts with the hydroxyl group of said polyoxyalkylene polyol.

11. The moisture-curable resin composition according to claim 1, wherein the hydrolyzable silyl group-containing polyoxyalkylene compound is obtained by reacting an (A) isocyanate group-containing prepolymer obtained by reacting a polyoxyalkylene polyol having a hydroxyl value, x mgKOH/g, wherein x ranges from 5 to 35, a total degree of unsaturation, y meq/g, wherein y is not greater than 0.07 meq/g and y≦

0.9/(x-10), from 2 to 8 hydroxyl groups and a content of oxyalkylene groups having at least 3 carbon atoms, of at least 60% by weight, with a stoichiometrically excess amount of a polyisocyanate compound, and a (B) compound having a hydrolyzable silyl group and an active hydrogen-containing group reactive with an isocyanate group in amounts on average of at least 1.3 molecules of said compound (B) per molecule of compound (A).

12. The moisture-curable resin composition according to claim 1, wherein the hydrolyzable silyl group-containing polyoxyalkylene compound is obtained by reacting said polyoxyalkylene polyol having a hydroxyl value, x mgKOH/g, wherein x ranges from 5 to 35, a total degree of unsaturation, y meq/g, wherein y is not greater than 0.07 meq/g, and y≦

0.9/(x-10), from 2 to 8 hydroxyl groups, and a content of oxyalkylene groups having at least 3 carbon atoms, of at least 60% by weight and a compound having an isocyanate group and an α

,β

-unsaturated group in amounts of at least 1.3 molecules of said isocyanate group-unsaturated group containing compound per molecule of said polyoxalkylene polyol, followed by reacting said hydrolyzable silyl group-containing polyoxyalkylene compound with a hydrolyzable group-containing hydrosilane.

13. The moisture-curable resin composition according to claim 12, wherein the compound having an isocyanate group and an α

,β

-unsaturated group is allyl isocyanate.

14. The moisture-curable resin composition according to claim 10, wherein the compound containing a hydrolyzable silyl group and an active hydrogen-containing group reactive with an isocyanate group, is a silane having a hydrolyzable group and an alkyl group having an active hydrogen-containing group selected from the group consisting of a hydroxyl group, a primary amino group and a secondary amino group.