Ethylenically unsaturated macromers produced from a residue of isocyanate manufacturing, related preformed stabilizers, polymer polyols, foam-forming compositions and foams

Patent metadata

Field	Value
Publication number	US-10851239-B2
Application number	US-201816182705-A
Country	US
Kind code	B2
Filing date	Nov 7, 2018
Priority date	Nov 7, 2018
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

Disclosed are ethylenically unsaturated macromers produced using a residue of an isocyanate manufacturing process. Also disclosed are preformed stabilizers produced using such macromers, polymer polyols produced using such preformed stabilizers, foam-forming compositions produced using such polymer polyols, and foam produced using such compositions.

First claim

What is claimed is:

1. An ethylenically unsaturated macromer comprising the reaction product of a reaction mixture comprising:
(a) an isocyanate residue that is an organic particulate having a content of bound isocyanate that is 0.1 to 10% by weight, based on the total weight of the organic particulate;
(b) a polyol having a hydroxyl number of 20 to 75 and a hydroxyl functionality of 2 to 8; and
(c) a hydroxyl-reactive compound containing reactive ethylenic unsaturation.

2. The macromer of claim 1 , wherein the isocyanate residue is a phosgenation product of toluene diamine containing less than 0.5% by weight of ortho-toluenediamine isomers, based on the total weight of toluene diamine.

3. The macromer of claim 1 , wherein the isocyanate residue is an organic particulate comprising: (i) a crosslinked polymer comprising aromatic groups, biuret groups, urea groups, and carbodiimide groups; and (ii) a high-boiling hydrocarbon.

4. The macromer of claim 3 , wherein the organic particulate is a product of a process for the production of a distilled aromatic polyisocyanate by (1) the reaction of the corresponding amine with phosgene in a suitable solvent and multi-stage distillative work-up of the isocyanate solution obtained, and (2) continuously feeding the residue obtained from the distillation process and from 2 to 50 weight % of a high-boiling hydrocarbon which is inert under the distillation conditions to a heated, product-agitating vacuum drier with a horizontal shaft.

5. The macromer of claim 3 , wherein the organic particulate is a residue from synthesis of 2,6-toluene diisocyanate and/or 2,4-toluene diisocyanate.

6. The macromer of claim 3 , wherein the organic particulate is present in the reaction mixture in an amount of at least 1% and up to 4% by weight, based on the total combined weight of reactants used to produce the macromer.

7. The macromer of claim 1 , wherein the polyol comprises a polyether polyol that is a reaction product of sorbitol and an alkylene oxide comprising propylene oxide and ethylene oxide, wherein the ethylene oxide comprises from 1 to 40% by weight, based on the total weight of the polyol.

8. The macromer of claim 1 , wherein the hydroxyl-reactive compound that contains reactive ethylenic unsaturation comprises isopropenyl dimethyl benzyl isocyanate.

9. The macromer of claim 1 , wherein the reaction mixture further comprises a diisocyanate.

10. An ethylenically unsaturated macromer comprising the reaction product of a reaction mixture comprising:
(a) an organic particulate comprising:
(i) a crosslinked polymer comprising aromatic groups, biuret groups, urea groups, and carbodiimide groups; and
(ii) a high-boiling hydrocarbon;

(b) a polyol having a hydroxyl number of 20 to 75 and a hydroxyl functionality of 2 to 8; and
(c) a hydroxyl-reactive compound containing reactive ethylenic unsaturation.

11. The macromer of claim 10 , wherein the organic particulate that has a content of bound isocyanate that is 0.1 to 10% by weight, based on the total weight of the organic particulate.

12. The macromer of claim 11 , wherein the organic particulate is an isocyanate residue that is a phosgenation product of toluene diamine containing less than 0.5% by weight of ortho-toluenediamine isomers, based on the total weight of toluene diamine.

13. The macromer of claim 10 , wherein the organic particulate is a residue from synthesis of 2,6-toluene diisocyanate and/or 2,4-toluene diisocyanate.

14. The macromer of claim 10 , wherein the organic particulate is present in the reaction mixture in an amount of at least 1% and up to 4% by weight, based on the total combined weight of reactants used to produce the macromer.

15. The macromer of claim 10 , wherein the polyol comprises a polyether polyol that is a reaction product of sorbitol and an alkylene oxide comprising propylene oxide and ethylene oxide, wherein the ethylene oxide comprises from 1 to 40% by weight, based on the total weight of the polyol.

16. The macromer of claim 10 , wherein the reaction mixture further comprises a diisocyanate.

17. An ethylenically unsaturated macromer comprising the reaction product of a reaction mixture comprising:
(a) an isocyanate residue that is an organic particulate having a mean particle size of 0.1 to 100 micron;
(b) a polyol having a hydroxyl number of 20 to 75 and a hydroxyl functionality of 2 to 8; and
(c) a hydroxyl-reactive compound containing reactive ethylenic unsaturation.

18. The macromer of claim 17 , wherein the organic particulate has a content of bound isocyanate that is 0.1 to 10% by weight, based on the total weight of the organic particulate.

19. The macromer of claim 17 , wherein the isocyanate residue is a phosgenation product of toluene diamine containing less than 0.5% by weight of ortho-toluenediamine isomers, based on the total weight of toluene diamine.

20. The macromer of claim 17 , wherein the isocyanate residue is an organic particulate comprising: (i) a crosslinked polymer comprising aromatic groups, biuret groups, urea groups, and carbodiimide groups; and (ii) a high-boiling hydrocarbon.

21. The macromer of claim 20 , wherein the organic particulate is a product of a process for the production of a distilled aromatic polyisocyanate by (1) the reaction of the corresponding amine with phosgene in a suitable solvent and multi-stage distillative work-up of the isocyanate solution obtained, and (2) continuously feeding the residue obtained from the distillation process and from 2 to 50 weight % of a high-boiling hydrocarbon which is inert under the distillation conditions to a heated, product-agitating vacuum drier with a horizontal shaft.

22. The macromer of claim 21 , wherein the organic particulate is a residue from synthesis of 2,6-toluene diisocyanate and/or 2,4-toluene diisocyanate.

23. The macromer of claim 17 , wherein the organic particulate is present in the reaction mixture in an amount of at least 1% and up to 4% by weight, based on the total combined weight of reactants used to produce the macromer.

24. The macromer of claim 17 , wherein the polyol comprises a polyether polyol that is a reaction product of sorbitol and an alkylene oxide comprising propylene oxide and ethylene oxide, wherein the ethylene oxide comprises from 1 to 40% by weight, based on the total weight of the polyol.

25. The macromer of claim 17 , wherein the hydroxyl-reactive compound that contains reactive ethylenic unsaturation comprises isopropenyl dimethyl benzyl isocyanate.

26. The macromer of claim 17 , wherein the reaction mixture further comprises a diisocyanate.

Assignees

• Covestro Llc

Inventors

• Adkins Rick L
• Wardius Don S

Classifications

• C08G2110/0008

  flexible · CPC title

• C08G18/227

  of antimony, bismuth or arsenic · CPC title

• C08G18/4841

  containing oxyethylene end groups · CPC title

• C08L2203/14

  used for foams · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title