POLYOL MADE FROM PARTIALY HYDROGENATED, FULLY EPOXIDIZED NATURAL OILS

• US 20110065821A1
• Filed: 05/13/2009
• Published: 03/17/2011
• Est. Priority Date: 05/13/2008
• Status: Abandoned Application

• Current Assignee: Cargill, Inc. (Agricultural Services Division)
• Original Assignee: Cargill, Inc. (Agricultural Services Division)
• Inventors: Abraham, Timothy W., Gower, William C.
• Application Number:
  US12/992,518
• Publication Number:
  US 20110065821A1
• Time in Patent Office: Days
• US Class Current: 521/114
• CPC Class Codes: C08G 18/36 Hydroxylated esters of higher fatty acids
• CPC Class Codes: C08G 18/6696 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures
• CPC Class Codes: C08G 2101/00 Manufacture of cellular products
• CPC Class Codes: C08G 2110/0083 prepared using water as the sole blowing agent
• CPC Class Codes: C11C 3/006 by oxidation
• CPC Class Codes: C11C 3/12 by hydrogenation

Abstract

A method is disclosed for making a polyol comprising: fully-epoxidizing a partially hydrogenated vegetable oil to obtain a fully-epoxidized vegetable oil derivative having an iodine value less than 4 g I₂/100 gram, an EOC of from 4.0 to 5.7% and a Gardner color value of 2 or less; and then reacting the fully-epoxidized vegetable oil derivative with a ring opener to form a polyol having a hydroxyl number from 40 to 80 mg KOH/gram, a number average molecular weight of at least 1500 Daltons, a dynamic viscosity less than 10 pascal-seconds, and an EOC below 3.0 wt %.

Claims

1. A method for making a polyol suitable for use in low density, flexible, yellowing resistant, polyurethane foam, the method comprising:

(a) hydrogenating a vegetable oil having an initial iodine value of at least about 101 g I₂/100 gram oil to a final iodine value of from about 70 to 100 g I₂/100 gram oil;

(b) fully epoxidizing the unsaturated carbon-carbon bounds in the hydrogenated vegetable oil from step (a), to obtain a partially-hydrogenated, fully-epoxidized vegetable oil derivative, wherein the vegetable oil derivative exhibits a iodine value of less than 4 g I₂/100 gram vegetable oil derivative, an acid number less than 1 mg KOH/gram, an EOC of from about 4.0 to about 5.7%, and a Gardner Color value of 2 or less; and

(c) reacting the partially-hydrogenated, fully-epoxidized vegetable oil derivative from step (b) with a ring opener to form a polyol having a hydroxyl number of from about 40 to about 80 mg KOH/gram polyol, a number average molecular weight of at least about 1500 Daltons, a dynamic viscosity of less than about 10 pascal-second, an EOC below about 3.0 wt %.

2. The method of claim 1, wherein the hydrogenated vegetable oil (a) has at least 50% monounsaturated fatty acid groups and less than 40% saturated fatty acid groups.

4. The method of claim 1, wherein the polyol has a hydroxyl number of from about 50 to about 70 mg KOH/gram polyol, a number average molecular weight of at least about 1700 Daltons, and a dynamic viscosity of less than about 7 pascalseconds, and an EOC below about 2.8 wt %.

5. The method of claim 4, wherein the polyol has an EOC of less about 2.5 wt %.

6. The method of claim 5, wherein the vegetable oil is selected from the group consisting of sunflower, soybean, canola, cotton seed, rape seed, safflower, linseed, tung, and corn oil.

10. The method of claim 1, wherein the polyol has a number average molecular weight of at least 1700 Daltons.

15. The method of claim 1, wherein the partially-hydrogenated vegetable oil is made by hydrogenating a vegetable oil having an initial iodine value of at least 120 grams I₂/100 grams oil.

16. The method of claim 15, wherein the initial iodine value of the vegetable oil is from about 120 to about 140 grams I₂/100 grams oil.

23. A yellowing resistant flexible foam made from the reaction of a polyisocyanate compound, an active-hydrogen containing composition comprising the polyol of claim 1, and a catalyst, the flexible foam having a density of from about 8 to 97 KG/m3, and exhibits a yellowness index of less than 30 after being exposed to ambient light for 21 days.

24. The flexible foam of claim 23, wherein the active-hydrogen containing composition further comprises a polyether or polyester polyol.

26. The flexible foam of claim 23, wherein the foam maintains a yellowness index of 31.0 or less after to being exposed to ambient light for 18 weeks.

27. The flexible foams of claim 26, wherein the foam has a density of from 8 to 24 KG/m3.

28. The method of claim 1, wherein the ring opener is selected from the group consisting of monofunctional alcohols, polyols, mono-carboxylic acids, di-carboxylic acids, and mixtures thereof.

29. The method of claim 28, wherein the ring opener is selected from the group consisting of monofunctional alcohols, mono-carboxylic acids, and mixtures thereof.

3. (canceled)

7. A method for making a polyol suitable for use in low density, flexible, yellowing resistant, polyurethane foam applications, the method comprising:

(a) fully-epoxidizing the unsaturated carbon-carbon bounds in a partially hydrogenated vegetable oil having an iodine value of from about 85 to about 95 g I₂/100 grams oil to less than 4 g I₂/100 gram vegetable oil, to obtain a fully-epoxidized vegetable oil derivative having an acid number less than 1 mg KOH/gram vegetable oil derivative, an EOC of from about 4.5 to about 5.41 wt %, and a Gardner Color value of 1.5 or less; and

(b) reacting the fully-epoxidized vegetable oil derivative from step (a) with a ring opener to form a polyol having a hydroxyl number of from about 50 to about 70 mg KOH/gram polyol, a number average molecular weight of at least about 1500 Daltons, a dynamic viscosity of less than about 7 pascal-seconds, and an EOC below about 2.8 wt %.

8. The method of claim 7, wherein the ring opener comprises a monofunctional C1-C4 alcohol and wherein the molar ratio of alcohol to epoxy groups present in the fully-epoxidized vegetable oil is from about 0.2/1.0 to about 0.7/1.0.

11. The method of claim 7, wherein the partially hydrogenated vegetable oil is made by hydrogenating a vegetable oil having an iodine value of at least about 110 g I₂/100 grams oil.

12. The method of claim 11, wherein the vegetable oil is selected from the group consisting of:

soybean oil, sunflower oil, canola oil, cottonseed oil, rapeseed oil, safflower oil, linseed oil, tung oil, and corn oil.

13. The method of claim 12, wherein the vegetable oil comprises soybean oil.

9. (canceled)

14. (canceled)

17. A bio-based polyol suitable for low density, flexible, yellowing resistant, polyurethane foam applications having a hydroxyl number from about 50 to 70 mg KOH/gram polyol, a number average molecular weight of at least 1500 Daltons, a viscosity of less than 7 pascalseconds, an EOC of less than about 2.8 wt %, an acid number of less than about 1.5 mg KOH/gram polyol, a Gardner Color value of about 1 or less and an iodine value of less than about 4 grams I₂/100 grams polyol.

18-22. -22. (canceled)

25. (canceled)