Compounds containing alkoxysilane groups and hydantoin groups

• US 5,756,751 A
• Filed: 05/13/1997
• Issued: 05/26/1998
• Est. Priority Date: 05/15/1996
• Status: Expired due to Fees

• Current Assignee: Bayer AG, Bayer Corporation (Bayer AG)
• Original Assignee: Bayer AG, Bayer Corporation (Bayer AG)
• Inventors: Rettig, Rainer, Limbeck, Gotz, Roesler, Richard R., Squiller, Edward P., Schmalstieg, Lutz, Yeske, Philip E., Siranovich, Stanley F.
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/855,423
• Time in Patent Office: 378 Days
• Field of Search: 548/110, 106/14.05, 106/14.16, 106/14.44, 528/17, 528/18
• US Class Current: 548/110
• 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 18/3893 containing silicon
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints
• CPC Class Codes: C09K 3/1021 Polyurethanes or derivatives thereof

Abstract

The present invention relates to compounds containing alkoxysilane and hydantoin groups and corresponding to the formula ##STR1## wherein X represents identical or different organic groups which are inert to isocyanate groups below 100° C., provided that at least one of these groups is an alkoxy group,

Z represents COOR₁ or an aromatic ring,

R represents the residue obtained by removing the isocyanate groups from an organic monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer,

R₁ represents an organic group which is inert to isocyanate groups at a temperature of 100° C. or less,

R₃ and R₄ are identical or different and represent hydrogen or organic groups which are inert to isocyanate groups at a temperature of 100° C. or less,

n is an integer from 1 to 8 and

m has an average value of 1.5 to 6.

The present invention also relates to the use of these compounds for the preparation coatings, sealants and adhesives.

Claims

1. A compound containing alkoxysilane and hydantoin groups and corresponding to the formula ##STR6## wherein X represents identical or different organic groups which are inert to isocyanate groups below 100°

C., provided that at least one of these groups is an alkoxy group,

Z represents COOR₁ or an aromatic ring,

R represents the residue obtained by removing the isocyanate groups from an organic monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer,

R₁ represents an organic group which is inert to isocyanate groups at a temperature of 100°

C. or less,

R₃ and R₄ are identical or different and represent hydrogen or organic groups which are inert to isocyanate groups at a temperature of 100°

C. or less,

n is an integer from 1 to 8 and

m has an average value of 1.5 to 6.

2. The compound of claim 1 wherein

X represents identical or different alkyl or alkoxy groups having 1 to 4 carbon atoms,

Z represents COOR₁,

R₁ is an alkyl group having 1 to 8 carbon atoms,

R₃ and R₄ represent hydrogen and

n is an integer from 2 to 4.

3. The compound of claim 1 wherein

X represents identical or different alkoxy groups having 1 to 4 carbon atoms,

Z represents COOR₁,

R₁ is methyl, ethyl or butyl,

R₃ and R₄ represent hydrogen and

n is 3.

4. The compound of claim 1 wherein R represents the residue obtained by removing the isocyanate groups from an organic monomeric polyisocyanate.

5. The compound of claim 2 wherein R represents the residue obtained by removing the isocyanate groups from an organic monomeric polyisocyanate.

6. The compound of claim 3 wherein R represents the residue obtained by removing the isocyanate groups from an organic monomeric polyisocyanate.

7. The compound of claim 1 wherein R represents the residue obtained by removing the isocyanate groups from a polyisocyanate adduct.

8. The compound of claim 2 wherein R represents the residue obtained by removing the isocyanate groups from a polyisocyanate adduct.

9. The compound of claim 3 wherein R represents the residue obtained by removing the isocyanate groups from a polyisocyanate adduct.

10. The compound of claim 1 wherein R represents the residue obtained by removing the isocyanate groups from a polyisocyanate adduct containing isocyanurate groups, biuret groups, allophanate groups and/or uretdione groups.

11. The compound of claim 2 wherein R represents the residue obtained by removing the isocyanate groups from a polyisocyanate adduct containing isocyanurate groups, biuret groups, allophanate groups and/or uretdione groups.

12. The compound of claim 3 wherein R represents the residue obtained by removing the isocyanate groups from a polyisocyanate adduct containing isocyanurate groups, biuret groups, allophanate groups and/or uretdione groups.

13. The compound of claim 1 wherein R represents the residue obtained by removing the isocyanate groups from an NCO prepolymer.

14. The compound of claim 2 wherein R represents the residue obtained by removing the isocyanate groups from an NCO prepolymer.

15. The compound of claim 3 wherein R represents the residue obtained by removing the isocyanate groups from an NCO prepolymer.

20. A coating, sealant or adhesive prepared from the compound of claim 1.

16. A compound containing alkoxysilane and hydantoin groups and corresponding to the formula ##STR7## wherein X represents identical or different alkyl or alkoxy groups having 1 to 4 carbon atoms, provided that at least one of these groups is an alkoxy group,

Z represents COOR₁,

R represents the residue obtained by removing the isocyanate groups from an NCO prepolymer having an NCO content of 0.4 to 5% by weight,

R₁ represents a an alkyl group having 1 to 8 carbon atoms,

R₃ and R₄ represent hydrogen,

n is 3 and

m has an average value of 1.5 to 4.

17. The compound of claim 16 wherein said NCO prepolymer is based on a polyether polyol.

18. The compound of claim 16 wherein m has an average value of 1.8 to 2.2.

19. The compound of claim 17 wherein m has an average value of 1.8 to 2.2.

21. A moisture-curable composition containing the compound of claim 16.