Graft polyol and method of forming the same

Patent metadata

Field	Value
Publication number	US-9260346-B2
Application number	US-201214343902-A
Country	US
Kind code	B2
Filing date	Sep 11, 2012
Priority date	Sep 12, 2011
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

A graft polyol includes a natural oil including at least 50% by weight of a natural oil polyol. Particles are dispersed in the natural oil and comprise the reaction product of a macromer polyol, a polymerizable monomer, a chain transfer agent, and a free radical initiator. The macromer polyol and the polymerizable monomer react in the presence of the natural oil. The graft polyol is formed by providing the natural oil and providing the macromer polyol, the chain transfer agent, the free radical initiator, and the polymerizable monomer. The natural oil, the polymerizable monomer, the macromer polyol, the chain transfer agent, and the free radical initiator are combined, and the polymerizable monomer, the macromer polyol, the chain transfer agent, and the free radical initiator react to form particles dispersed in the natural oil.

First claim

What is claimed is:

1. A graft polyol comprising:
A) a natural oil comprising at least 50% by weight of a natural oil polyol represented by formula (I);

 and
B) particles dispersed in said natural oil A) and comprising the reaction product of;
i) a reactor charge comprising a macromer polyol and a portion of said natural oil,
ii) a polymerizable monomer,
iii) a chain transfer agent, and
iv) a free radical initiator, and
v) a macromer charge different from said reactor charge and also comprising said macromer polyol;

wherein said reactor charge, said polymerizable monomer, said chain transfer agent, and said free radical initiator react in the presence of said natural oil to form a reaction intermediary, and said reaction intermediary reacts with said macromer in said macromer charge in the presence of said natural oil to form particles B) dispersed in the natural oil A).

2. The graft polyol as set forth in claim 1 , having a solids content of at least 25% by weight of said graft polyol.

3. The graft polyol as set forth in claim 1 , having a viscosity of less than 30,000 cP measured at 25° C.

4. The graft polyol as set forth in claim 1 , wherein said macromer polyol comprises;
i) the reaction product of a sorbitol initiated polyol and an ethylenically unsaturated compound, in the presence of a catalyst, or
ii) a fumarate.

5. The graft polyol as set forth in claim 4 , wherein said macromer polyol comprises the reaction product i) and the ethylenically unsaturated compound is α,α-dimethyl-meta-isopropenylbenzyl isocyanate.

6. The graft polyol as set forth in claim 1 , wherein said particles have a volume weighted mean particle diameter of at least 2 μm and/or at least 10% of said particles have a volume weighted mean particle diameter of at least 10 μm.

7. The graft polyol as set forth in claim 1 , wherein said chain transfer agent is a thiol.

8. A method of forming a graft polyol, said method comprising the steps of:
providing A) a natural oil comprising at least 50% by weight of a natural oil polyol represented by the formula (I);

providing each of a macromer polyol, a chain transfer agent, a free radical initiator, and a polymerizable monomer;
combining the natural oil A), the macromer polyol, the chain transfer agent, the free radical initiator, and the polymerizable monomer wherein a first portion of the natural oil A) is combined with the macromer polyol to form a reactor charge prior to combining a remaining portion of the natural oil A), the chain transfer agent, the free radical initiator, and the polymerizable monomer; and
reacting the polymerizable monomer, the macromer polyol, and the free radical initiator wherein the polymerizable monomer, the reactor charge, and the free radical initiator are reacted to form a reaction intermediary and the reaction intermediary is further reacted with a macromer charge different from the reactor charge and also comprising the macromer polyol to form B) particles dispersed in the natural oil A).

9. The method as set forth in claim 8 , wherein the graft polyol has a solids content of at least 25% by weight of the graft polyol.

10. The method as set forth in claim 8 , wherein the graft polyol has a viscosity of less than 30,000 cP measured at 25° C.

11. The method as set forth in claim 8 , wherein the macromer polyol comprises;
i) the reaction product of a sorbitol initiated polyol and an ethylenically unsaturated compound, in the presence of a catalyst, or
ii) a fumarate.

12. The method as set forth in claim 11 , wherein the macromer polyol comprises the reaction product i) and the ethylenically unsaturated compound is α,α-dimethyl-meta-isopropenylbenzyl isocyanate.

13. The method as set forth in claim 8 , wherein the particles have a volume weighted mean particle diameter of at least 2 μm and/or at least 10% of the particles have a volume weighted mean particle diameter of at least 10 μm.

14. A polyurethane article comprising the reaction product of a di- and/or poly-isocyanate and a graft polyol comprising:
A) a natural oil comprising at least 50% by weight of a natural oil polyol represented by formula (I);

 and
B) particles dispersed in said natural oil A) and comprising the reaction product of;
i) a reactor charge comprising a macromer polyol and a portion of said natural oil,
ii) a polymerizable monomer,
iii) a chain transfer agent, and
iv) a free radical initiator, and
v) a macromer charge different from said reactor charge and also comprising said macromer polyol;

wherein said reactor charge, said polymerizable monomer, said chain transfer agent, and said free radical initiator react in the presence of said natural oil to form a reaction intermediary, and said reaction intermediary reacts with said macromer in said macromer charge in the presence of said natural oil to form particles B) dispersed in the natural oil A).

15. The polyurethane article as set forth in claim 14 , wherein said graft polyol has a solids content of at least 25% by weight of said graft polyol.

16. The polyurethane article as set forth in claim 14 , having;
i) a tensile hardness of less than 20 psi (137.9 kPa), and/or
ii) an indentation force deflection value at 25% of from 5 to 45 lbs/50in 2 (0.69 to 6.2 kPa), and/or
iii) an indentation force deflection value at 65% of from 20 to 90 lbs/50in 2 (2.7 to 12.4 kPa).

17. The polyurethane article as set forth in claim 14 , wherein the reaction product includes the macromer charge v).

18. The polyurethane article as set forth in claim 16 , having;
i) a tensile hardness of less than 20 psi (137.9 kPa),
ii) an indentation force deflection value at 25% of from 5 to 45 lbs/50in 2 (0.69 to 6.2 kPa), and
iii) an indentation force deflection value at 65% of from 20 to 90 lbs/50in 2 2.7 to 12.4 kPa).

Assignees

• Borst Joseph P
• Ternyayeva Irina
• Wujcik Steven E
• Bower David K
• Kunst Andreas
• Basf Se

Inventors

• Borst Joseph P
• Ternyayeva Irina
• Wujcik Steven E
• Bower David K
• Kunst Andreas

Classifications

• C08G18/4072

  Mixtures of compounds of group C08G18/63 with other macromolecular compounds · CPC title

• C08G18/3275

  containing two hydroxy groups · CPC title

• C04B26/16 Primary

  Polyurethanes · CPC title

• C08G18/631

  onto polyesters and/or polycarbonates · CPC title

• C04B2111/60

  Flooring materials · CPC title