Polyhydroxy urethanes formed by reaction of reduced sugars and organic diisocyanates

• US 5,218,073 A
• Filed: 10/15/1990
• Issued: 06/08/1993
• Est. Priority Date: 10/15/1990
• Status: Expired due to Fees

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Evans, William L.
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): COONEY, JOHN M
• Application Number:
  US07/597,405
• Time in Patent Office: 967 Days
• Field of Search: 528/73, 528/75, 528/76, 528/85, 528/26, 524/27, 525/456, 525/458, 525/453, 568/704, 568/705
• US Class Current: 528/73
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08K 5/205 Compounds containing groups, e.g. carbamates
• CPC Class Codes: C08L 75/04 Polyurethanes

Abstract

Polyhydroxy urethanes prepared from reduced sugars of the formula C_x H₂(x+1) O_x where x is 4, 5 and 6 and diisocyanates are disclosed. There is a molar excess of 1.5 and preferably 2.0 of the reduced sugar in the polyhydroxy urethane product and the molecular weight of the product is generally less than 1,500 and preferably less than 1,000.

Claims

1. Low molecular weight polyhydroxy urethanes having a molecular weight of less than about 1,500 consisting essentially of the reaction product of the hydroxyl groups of at least about a 1.5 molar excess of a reduced sugar of the formula C_x H₂(x+1) O_x where x is 4, 5 or 6 and the isocyanate groups of a diisocyanate.

2. The low molecular weight polyhydroxy urethane of claim 1 wherein the reduced sugar is selected from the group consisting of sorbitol, xylitol and mannitol.

3. The low molecular weight polyhydroxy urethane of claim 2 wherein the diisocyanate is selected from the group consisting of hexamethylene diisocyanate, diphenylmethane 4,4'"'"'-diisocyanate 4,4'"'"'-methylene-bis-(cyclohexylisocyanate), isophorone diisocyanate, and 1,3-bis(l-isocyanatol-1-methylethyl)benzene.

4. The low molecular weight polyhydroxy urethane of claim 3 wherein at least about a 2.0 molar excess of reduced sugar is present.

5. The low molecular weight polyhydroxy urethane of claim 4 wherein the molecular weight is less than about 1,000.

6. The low molecular weight polyhydroxy urethane of claim 5 wherein the reduced sugar is mannitol.

7. The low molecular weight polyhydroxy urethane of claim 6 wherein the diisocyanate is 4,4'"'"'-methylene-bis-(cyclohexylisocyanate).

8. The low molecular weight polyhydroxy urethane of claim 5 wherein the reduced sugar is sorbitol.

9. The low molecular weight polyhydroxy urethane of claim 8 wherein the diisocyanate is 4,4'"'"'-methylene-bis-(cyclohexylisocyanate).

10. The low molecular weight polyhydroxy urethane of claim 8 wherein the diisocyanate is isophoronediisocyanate.

11. The low molecular weight polyhydroxy urethane of claim 8 wherein the diisocyanate is 1,3-bis(1-isocyanato-1-methylethyl)benzene.

12. The low molecular weight polyhydroxyl urethane of claim 8 wherein the diisocyanate is toluene diisocyanate.

13. The low molecular weight polyhydroxy urethane of claim 8 wherein the diisocyanate is a mixture of 4,4'"'"'-methylene-bis-(cyclohexylisocyanate) and 1,3-bis(1-isocyanato-1-methylethyl)benzene.

14. The low molecular weight polyhydroxy urethane of claim 5 wherein the reduced sugar is xylitol.

15. The low molecular weight polyhydroxy urethane of claim 14 wherein the diisocyanate is 4,4'"'"'-methylene-bis-(cyclohexylisocyanate).

16. The low molecular weight polyhydroxy urethane of claim 14 wherein the diisocyanate is 1,3-bis(1-isocyanato-1-methylethyl)benzene.

17. The low molecular weight polyhydroxy urethane of claim 14 wherein the diisocyanate is a mixture of 4,4'"'"'-methylene -bis(cyclohexylisocyanate) and 1,3-bis(1-isoctanato-1-methylethyl)benzene.