Natural oil polyols derived from post-consumer recycle oils

Patent metadata

Field	Value
Publication number	US-2016102166-A1
Application number	US-201414889809-A
Country	US
Kind code	A1
Filing date	May 5, 2014
Priority date	May 7, 2013
Publication date	Apr 14, 2016
Grant date	—

Abstract

Disclosed embodiments include an open cell, molded polyurethane foam comprising the reaction product of a reaction mixture comprising: an isocyanate mixture; and a polyol formulation, comprising a glycerin-initiated, alkylene-oxide capped natural oil polyol having a molecular weight of between 3,000 and 8,000 and a polydispersity index (PDI) of between approximately 1.5 and 2.5, wherein the PDI is defined as the ratio of the weight-average molecular weight, Mw, to the number-average molecular weight, Mn.

First claim

1 . An open cell, molded foam produced by a process, the process comprising:
reacting a polyol formulation with an isocyanate mixture, wherein at least one component of the polyol formulation is produced by a process comprising:
reacting a first polyol with an acid anhydride compound to produce a monol having two or more polycarboxylic acid substituents;
reacting the monol having two or more polycarboxylic acid substituents with an epoxidized fatty acid of a post-consumer recycle oil to produce a polyol branching agent;
reacting the polyol branching agent with a polyol initiator to link at least two molecules of the polyol branching agent together to produce a branched polyol; and
capping the branched polyol with an alkylene oxide to produce a natural oil-based polyol having a molecular weight of between 2,000 and 6,000.

2 . The foam of claim 1 , wherein the process used to produce the foam further comprises extracting the polyol branching agent from a reaction mixture produced from the monol having two or more polycarboxylic acid substituents and the epoxidized fatty acid of a post-consumer recycle oil using one or more solvents.

3 . The foam of claim 2 , wherein the one or more solvents comprise a hydrocarbon solvent having between 2 and 8 carbon atoms.

4 . The foam of claim 2 , wherein the one or more solvents comprise petroleum ether, and the extraction separates the polyol branching agent from saturated fatty acid components of the reaction mixture, and wherein the extraction is performed before the polyol branching agent is reacted with the polyol initiator.

5 . The foam of claim 1 , wherein the first polyol is a glycerin-initiated polyol based on propylene oxide.

6 . The foam of claim 5 , wherein the first polyol has a molecular weight of between 200 and 300.

7 . The foam of claim 1 , wherein the acid anhydride compound comprises an aryl acid anhydride having at least one carboxylic acid.

8 . The foam of claim 1 , wherein reacting the monol having two or more polycarboxylic acid substituents with the epoxidized fatty acid of a post-consumer recycle oil comprises performing a catalyzed ring-opening of the epoxidized fatty acid using the monol having two or more polycarboxylic acid substituents.

9 . The foam of claim 1 , wherein the polyol branching agent has a molecular weight that is between approximately 25% and 50% of a molecular weight of the natural oil-based polyol.

10 . The foam of claim 1 , wherein the natural oil-based polyol has a polydispersity index (PDI) of between approximately 1.5 and 2.5, wherein the PDI is defined as the ratio of the weight-average molecular weight, Mw, to the number-average molecular weight, Mn.

11 . The foam of claim 1 , wherein between approximately 10% by weight and 40% by weight of the foam is from the natural oil-based polyol.

12 . A method, comprising:
reacting a first polyol with an acid anhydride compound to produce a monol having two or more polycarboxylic acid substituents; reacting the monol having two or more polycarboxylic acid substituents with an epoxidized fatty acid of a post-consumer recycle oil to produce a polyol branching agent; extracting the polyol branching agent from a reaction mixture produced from the monol having two or more polycarboxylic acid substituents and the epoxidized fatty acid of a post-consumer recycle oil using one or more solvents; reacting the extracted polyol branching agent with a polyol initiator to link at least two molecules of the polyol branching agent together to produce a branched polyol; and capping the branched polyol with an alkylene oxide to produce a natural oil-based polyol having a molecular weight of between 2,000 and 6,000.

13 . The method of claim 12 , wherein the one or more solvents comprise a hydrocarbon solvent having between 2 and 8 carbon atoms.

14 . The method of claim 12 , wherein the first polyol is a glycerin-initiated triol based on propylene oxide and having a molecular weight between 200 and 300.

15 . The method of claim 12 , wherein the polyol branching agent has a molecular weight of between 1,000 and 2,000.

16 . The method of claim 12 , wherein the polyol branching agent has a molecular weight that is between approximately 25% and 50% of a molecular weight of the natural oil-based polyol.

17 . The method of claim 12 , wherein:
the first polyol comprises a compound having the formula:

and
the acid anhydride is an aryl anhydride having at least one carboxylic acid.

18 . The method of claim 12 , wherein the polyol branching agent is produced in a one-pot synthesis in which the first polyol is reacted with the acid anhydride and the monol having two or more polycarboxylic acid substituents is reacted with the epoxidized fatty acid of a post-consumer recycle oil.

19 . The method of claim 12 , wherein the natural oil-based polyol has a polydispersity index (PDI) of between approximately 1.5 and 2.5, wherein the PDI is defined as the ratio of the weight-average molecular weight, Mw, to the number-average molecular weight, Mn.

20 . An open cell, molded polyurethane foam comprising the reaction product of a reaction mixture comprising:
an isocyanate mixture; and a polyol formulation, comprising a glycerin-initiated, alkylene-oxide capped natural oil polyol having a molecular weight of between 3,000 and 8,000 and a polydispersity index (PDI) of between approximately 1.5 and 2.5, wherein the PDI is defined as the ratio of the weight-average molecular weight, Mw, to the number-average molecular weight, Mn.

21 . A method, comprising:
reacting a plurality of refined oils produced from used oils with an alcohol to generate a plurality of modified oils; oxidizing the plurality of refined oils to generate a plurality of epoxidized oils; and reducing the plurality of epoxidized oils to generate a plurality of polyhydroxylated oils; and producing a plurality of natural oil polyols from the plurality of natural oil polyols, wherein the plurality of natural oil polyols comprise primary alcohols and have a molecular weight of at least 3,000.

22 . The method of claim 21 , wherein the plurality of refined oils comprise a plurality of triglycerides having the formula:

wherein R1, R2, and R3 independently comprise an unsaturated or saturated carbon chain having between 16 and 22 carbon atoms.

23 . The method of claim 22 , wherein R1, R2, and R3 independently comprise a stearic, elaidic, linoleic, α-linolenic, or α-eleostearic substituent.

24 . The method of claim 21 , wherein the alcohol comprises glycerol, sucrose, pentaerythritol, or a combination thereof.

25 . The method of claim 21 , wherein the plurality of modified oils comprise a glyceride having the formula:

wherein R1 and R2 comprise hydroxyl or aliphatic moieties, and the aliphatic moieties comprise stearate, elaidate, linoleate, α-linolenate, α-eleostearate.

26 . The method of claim 25 , wherein R1 or R2 comprise a hydroxyl group.

27 . The method of claim 21 , wherein the plurality of epoxidized oils comprise an epoxidized glyceride.

Assignees

• Johnson Controls Tech Co
• Beijing Johnson Controls Automotive Components Co

Inventors

• Ni Haifeng
• Dong Jenny
• Gu Yao
• Mcevoy James T
• Li William

Classifications

• C08G18/36 Primary

  Hydroxylated esters of higher fatty acids · CPC title

• C07C67/12

  from asymmetrical anhydrides · CPC title

• C07C67/26

  with an oxirane ring · CPC title

• C08G18/4887 Primary

  containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids · CPC title

• C08G18/14

  Manufacture of cellular products · CPC title