Impact-resistant glass-polyesterurethane laminates

• US 4,010,311 A
• Filed: 09/14/1973
• Issued: 03/01/1977
• Est. Priority Date: 09/14/1973
• Status: Expired due to Term

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Lewis, Charles W., Parker, Earl E.
• Primary Examiner(s): Lesmes, George F.
• Assistant Examiner(s): Roche, R. J.
• Application Number:
  US05/397,507
• Time in Patent Office: 1,264 Days
• Field of Search: 161/190, 117/124 E, 117/161 KP, 117/126 GR, 260/77.5 AM, 260/75 NP, 260/75 NT, 260/75 NK, 428/423, 428/425
• US Class Current: 428/412
• CPC Class Codes: B32B 17/10018 comprising only one glass sheet
• CPC Class Codes: B32B 17/10036 comprising two outer glass sheets
• CPC Class Codes: B32B 17/10688 Adjustment of the adherence to the glass layers
• CPC Class Codes: B32B 17/1077 containing polyurethane
• CPC Class Codes: B32B 17/10779 containing polyester
• CPC Class Codes: B32B 2307/412 Transparent
• CPC Class Codes: B32B 2367/00 Polyesters, e.g. PET, i.e. polyethylene terephthalate
• CPC Class Codes: B32B 2369/00 Polycarbonates
• CPC Class Codes: B32B 2375/00 Polyureas; Polyurethanes
• CPC Class Codes: B32B 2605/006 Transparent parts other than made from inorganic glass, e.g. polycarbonate glazings
• CPC Class Codes: B32B 27/08 of synthetic resin
• CPC Class Codes: B32B 27/308 comprising acrylic (co)polymers
• CPC Class Codes: B32B 27/36 comprising polyesters
• CPC Class Codes: B32B 27/365 comprising polycarbonates
• CPC Class Codes: B32B 27/40 comprising polyurethanes
• CPC Class Codes: C08G 18/4238 derived from dicarboxylic acids and dialcohols
• CPC Class Codes: C08G 18/75 cycloaliphatic
• CPC Class Codes: C09J 175/06 from polyesters
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31565 : Next to polyester [polyethylene terephthalate, etc.]
• CPC Class Codes: Y10T 428/31573 : Next to addition polymer of ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/31601 : Quartz or glass

Abstract

Laminated articles of at least one sheet of relatively rigid, transparent material, e.g., glass, and polyesterurethane sheet are described. Such laminates, e.g., a bilayer assembly of one glass sheet with an adhered sheet of polyesterurethane or a trilayer assembly of two glass sheets with an interlayer of polyesterurethane sheet, are useful in safety glass applications, e.g., automobile windshields, and automobile side and rear windows. The polyesterurethane is preferably the reaction product of a cycloaliphatic diisocyanate and a relatively low molecular weight hydroxy-terminated aliphatic polyester, e.g., the esterification product of an aliphatic dibasic acid and an aliphatic diol.

Claims

1. An optically clear laminate, comprising a sheet of relatively rigid, transparent material bonded to a sheet of thermoplastic, transparent polyesterurethane consisting essentially of the reaction product of (a) hydroxy-terminated polyester composition that is the esterification reaction product of an aliphatic dicarboxylic acid containing from 4 to 10 carbon atoms and an aliphatic diol containing from 4 to 8 carbon atoms, said polyester composition having a number average molecular weight of between about 500 and about 800 and containing no more than about 7 percent by weight residual, unreacted aliphatic diol, and (b) dinuclear cycloaliphatic diisocyanate, the mole ratio of diisocyanate to polyester being such that said polyesterurethane is substantially free of unreacted isocyanate groups.

2. The laminate of claim 1 wherein the dicarboxylic acid contains from 6 to 9 carbon atoms and the aliphatic diol contains 4 carbon atoms.

3. The laminate of claim 2 wherein the dicarboxylic acid contains 6 carbon atoms.

4. The laminate of claim 2 wherein the dicarboxylic acid contains 7 carbon atoms.

5. The laminate of claim 1 wherein the polyester has a number average molecular weight of from about 520 to about 585.

6. The laminate of claim 5 wherein the polyester contains no more than about 5.5 weight percent residual, unreacted aliphatic diol.

7. The laminate of claim 1 wherein the diisocyanate is 4,4'"'"'-methylene-bis-(cyclohexyl isocyanate).

8. The laminate of claim 7 wherein the diisocyanate has a stereoisomer content of about 55 percent trans and about 45 percent cis.

9. The laminate of claim 7 wherein the polyesterurethane sheet is an interlayer between two sheets of glass.

10. The laminate of claim 1 wherein the rigid, transparent material is glass.

11. The laminate of claim 1 wherein the relatively rigid transparent sheet is selected from the group of polycarbonate, polyester, acrylic or glass.

12. The laminate of claim 11 wherein the relatively rigid transparent sheet is glass and the polyesterurethane is bonded to and between two sheets of glass.

13. The laminate of claim 1 wherein the laminate comprises a glass sheet bonded to a sheet of the polyesterurethane which has on its exposed surface a thin abrasion resistant protective coating.

19. The laminate of claim 10 wherein the cycloaliphatic diisocyanate is 4,4'"'"'-methylene-bis-(cyclohexyl isocyanate).

20. The laminate of claim 19 wherein the dicarboxylic acid is adipic acid.

21. The laminate of claim 20 wherein the polyurethane sheet is an interlayer between two sheets of glass.

14. An optically clear glass laminate, comprising a glass sheet bonded to a sheet of thermoplastic, transparent polyesterurethane consisting essentially of the reaction product of (a) hydroxy-terminated polyester composition that is the esterification reaction product of an aliphatic dicarboxylic acid containing from 4 to 10 carbon atoms and an aliphatic diol containing from 4 to 8 carbon atoms, said polyester composition having a number average molecular weight of from about 500 to about 650 and containing no more than 6 percent by weight of residual, unreacted aliphatic diol, and (b) dinuclear cycloaliphatic diisocyanate, the mole ratio of diisocyanate to polyester being such that the polyesterurethane is substantially free of unreacted diisocyanate groups.

15. The laminate of claim 14 wherein the mole ratio of diisocyanate to polyester is from about 0.9:

1 to about 1.1;

1.

16. The laminate of claim 14 wherein the aliphatic diol is hydroxy-terminated.

17. The laminate of claim 14 wherein the aliphatic dicarboxylic acid contains from 6 to 9 carbon atoms and the aliphatic diol is 1,4-butanediol.

18. The laminate of claim 17 wherein the polyester has a number average molecular weight of from about 520 to about 585.