Glycidyl (meth)acrylate polymer polyol stabilizers

Patent metadata

Field	Value
Publication number	US-11866543-B2
Application number	US-202117313122-A
Country	US
Kind code	B2
Filing date	May 6, 2021
Priority date	May 6, 2021
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

This invention relates to novel macromers that comprise a polyether polyol having (meth)acrylate unsaturation. These novel macromers are the polymerization product of a glycidyl (meth)acrylate, with a polyether polyol, and optionally, an alkylene oxide, in the presence of a double metal cyanide catalyst. This invention also relates to preformed stabilizers prepared from these macromers, and to polymer polyols prepared from these novel macromers and novel preformed stabilizers. The present invention also relates to processes for preparing these compositions, to polyurethane foams comprising these polymer polyols, and to processes for preparing these polyurethane foams.

First claim

What is claimed is:

1. A polymer polyol comprising the reaction product of:
(A) a base polyol having a functionality of 2 to 5 and a hydroxyl number of 20 to 150,
(B) a preformed stabilizer comprising the free-radical polymerization product of (1) a macromer, with (2) an ethylenically unsaturated monomer, in the presence of (3) a free-radical polymerization initiator, and, optionally, (4) a polymer control agent, and, optionally, (5) a liquid diluent,

and
(C) an ethylenically unsaturated monomer,

in the presence of
(D) a free-radical polymerization initiator,

and, optionally
(E) a polymer control agent,
wherein the macromer comprises a polyether polyol having (meth)acrylate unsaturation and which comprises the polymerization product of a reaction mixture comprising: (a) a glycidyl (meth)acrylate, (b) a polyether polyol having a hydroxyl number of 10 to 300, a functionality of 2 to 8, and an ethylene oxide content of 2 to 25% by weight, based on the weight of the polyether polyol, and (c) a double metal cyanide catalyst.

2. A polymer polyol comprising the reaction product of:
(A) a base polyol having a functionality of 2 to 5 and a hydroxyl number of 20 to 150,
(B) a macromer comprising a polyether polyol having (meth)acrylate unsaturation and which comprises the polymerization product of a reaction mixture comprising: (a) a glycidyl (meth)acrylate, (b) a polyether polyol having a hydroxyl number of 10 to 300, a functionality of 2 to 8, and an ethylene oxide content of 2 to 25% by weight, based on the weight of the polyether polyol, and (c) a double metal cyanide catalyst,

and
(C) an ethylenically unsaturated monomer,

in the presence of
(D) a free-radical polymerization initiator,

and, optionally
(E) a polymer control agent.

3. A process for preparing the polymer polyol of claim 1 , comprising free-radically polymerizing
(A) the base polyol having a functionality of 2 to 5 and a hydroxyl number of 20 to 150,
(B) the preformed stabilizer,

and
(C) the ethylenically unsaturated monomer,

in the presence of
(D) the free-radical polymerization initiator,

and, optionally
(E) the polymer control agent.

4. A process for preparing the polymer polyol of claim 2 , comprising free-radically polymerizing
(A) the base polyol having a functionality of 2 to 5 and a hydroxyl number of 20 to 150,
(B) the macromer,

and
(C) the ethylenically unsaturated monomer,

in the presence of
(D) the free-radical polymerization initiator,

and, optionally
(E) the polymer control agent.

5. The process of preparing a polyurethane foam, comprising reacting (I) the polymer polyol of claim 1 , with (II) a di- and/or polyisocyanate component.

6. The process of preparing a polyurethane foam, comprising reacting (I) the polymer polyol of claim 2 , with (II) a di- and/or a polyisocyanate component.

7. The polymer polyol of claim 1 , wherein the amount of glycidyl (meth)acrylate present in the macromer is such that there are from 0.1 to 1.5 moles of glycidyl (meth)acrylate per mole of (b) polyether polyol present in the macromer.

8. The polymer polyol of claim 2 , wherein the amount of glycidyl (meth)acrylate present in the macromer is such that there are from 0.1 to 1.5 moles of glycidyl (meth)acrylate per mole of (b) polyether polyol present in the macromer.

9. The polymer polyol of claim 1 , wherein (b) the polyether polyol has a hydroxyl number of 15 to 250 and a functionality of 2.5 to 7.

10. The polymer polyol of claim 2 , wherein (b) the polyether polyol has a hydroxyl number of 15 to 250 and a functionality of 2.5 to 7.

11. The polymer polyol of claim 1 , wherein the reaction mixture further comprises (d) an alkylene oxide.

12. The polymer polyol of claim 2 , wherein the reaction mixture further comprises (d) an alkylene oxide.

13. The polymer polyol of claim 11 , wherein (c) the alkylene oxide comprises ethylene oxide, propylene oxide, or a mixture thereof.

14. The polymer polyol of claim 12 , wherein (c) the alkylene oxide comprises ethylene oxide, propylene oxide, or a mixture thereof.

Assignees

• Covestro Llc

Inventors

• Adkins Rick L
• Hayes John E

Classifications

• C08G18/833 Primary

  by nitrogen containing compounds (by azo compounds C08G18/85) · CPC title

• C08F283/06

  on to polyethers, polyoxymethylenes or polyacetals {(C08F283/004 takes precedence)} · CPC title

• C08F285/00

  Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers · CPC title

• C08G18/14

  Manufacture of cellular products · CPC title

• C08G18/632

  onto polyethers · CPC title