Moisture curable polyurethane polymers

• US 4,625,012 A
• Filed: 08/26/1985
• Issued: 11/25/1986
• Est. Priority Date: 08/26/1985
• Status: Expired due to Term

• Current Assignee: Diamond Technology Partnership Company
• Original Assignee: Essex Specialty Products Incorporated
• Inventors: Rizk, Sidky D., Hsieh, Harry W. S.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/769,409
• Time in Patent Office: 456 Days
• Field of Search: 528/28, 528/29, 528/38
• 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 18/302 Water
• CPC Class Codes: C08G 18/809 containing silicon
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints
• CPC Class Codes: C09J 175/04 Polyurethanes

Abstract

Methods for making a moisture curable polyurethane polymer having terminal isocyanate groups and pendant alkoxysilane groups by reacting an isocyanatosilane adduct, having terminal isocyanate groups and at least one hydrolyzable alkoxy group bonded to silicon, with a polyisocyanate and a polyol; moisture curable polymers made by said methods; sealant compositions directly adherent to a non-porous substrate such as glass or metal without the use of a primer, said compositions comprising such a moisture curable polymer in combination with a filler; and methods for curing and using such sealant compositions.

Claims

1. A method for making a moisture curable polyurethane polymer having terminal isocyanate groups and pendant silane groups having at least one hydrolyzable alkoxy group bonded to silicon, which method comprises reacting

(1) an isocyanatosilane adduct having at least two isocyanato groups and

(2) an isocyanate different from (1) and having at least two isocyanato groups with

(3) a polyol,

said isocyanatosilane adduct being the reaction product of an isocyanate having at least three isocyanato groups with an organofunctional alkoxysilane.

2. A method as in claim 1 wherein the number of said pendant silane groups is from 2 to 50 equivalent percent of the total number of isocyanato groups theoretically available in said isocyanate having at least three isocyanato groups and said isocyanate (2) having at least two isocyanato groups.

4. A moisture curable polyurethane polymer made by the method of claim 2.

10. A method as in claim 1 wherein said organofunctional silane is a mercaptoalkoxysilane of the formula

11. A method as in claim 10 wherein said organofunctional silane is

N,N-bis[(3-trimethoxysilyl)propyl]amine.

12. A method as in claim 10 wherein said organofunctional silane is gamma-mercaptopropyl trimethoxy silane.

13. A method as in claim 1 wherein said polyol is a polyether polyol.

14. A method as in claim 1 wherein said polyether polyol is a mixture of a polyether diol and a polyether triol.

15. A method as in claim 14 wherein said polyether diol is a polyoxyalkylene diol and said polyether triol is a polyoxyalkylene triol.

16. A moisture curable polyurethane polymer made by the method of claim 1.

17. A moisture curable sealant composition comprising a polymer as in claim 16 in combination with at least one filler.

18. The method of accelerating the moisture cure of a sealant composition as in claim 17 which comprises mixing said sealant composition with a paste containing filler and sufficient water to react with isocyanate and alkoxysilane groups present in said composition.

3. A method for making a moisture curable polyurethane polymer having terminal isocyanate groups and pendant silane groups having at least one hydrolyzable alkoxy group bonded to silicon, which method comprises reacting

(1) an isocyanatosilane adduct having at least two isocyanato groups and

(2) an isocyanate different from (1) and having at least two isocyanato groups with

(3) a polyether polyol,

said isocyanato adduct being the reaction product of an isocyanate having at least three isocyanato groups with an organofunctional mercaptoalkoxysilane or aminoalkoxysilane, the number of said pendant silane groups being from 2 to 50 equivalent percent of the total number of isocyanato groups theoretically available in said isocyanate having at least three isocyanato groups and said isocyanate (2) having at least two isocyanato groups.

5. A moisture curable polyurethane polymer made by the method of claim 3.

6. A method as in claim 3 wherein said isocyanate having at least three isocyanate groups is an aliphatic triisocyanate made by reacting three moles of hexamethylene diisocyanate with one mole of water.

7. A moisture curable polyurethane polymer made by the method of claim 6.

8. A method as in claim 6 wherein said polyether polyol is a polyoxyalkylene polyol.

9. A moisture curable polyurethane polymer made by the method of claim 8.