Polyols derived from farnesene for polyurethanes

Patent metadata

Field	Value
Publication number	US-10323117-B2
Application number	US-201815978897-A
Country	US
Kind code	B2
Filing date	May 14, 2018
Priority date	Jan 6, 2016
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

A composition is provided for making a polyurethane that may be incorporated in various products, such as a sealant, a coating, a caulk, an electric potting compound, a membrane, a sponge, a foam, an adhesives, and a propellant binder. The composition includes one or more polyols, one or more isocyanate-group containing compounds having an isocyanate group functionality of at least two, and optionally one or more chain extenders. At least one of the polyols is a farnesene-based polyol having a number average molecular weight less than or equal to 100,000 g/mol and a viscosity at 25° C. less than 10,000 cP. The farnesene-based polyol may be a homopolymer or a copolymer of farnesene. The composition may also comprise additional polyols, such as a polyol of a homopolymer or copolymer of a polydiene. Methods of preparing a polyurethane are also provided.

First claim

What is claimed:

1. A method of preparing a polyurethane comprising:
combining one or more polyols with one or more isocyanate-containing compounds having a isocyanate functionality of at least two to form a reaction mixture, and
curing the reaction mixture to produce a polyurethane which has a backbone derived from monomers comprising farnesene,
wherein at least one of the one or more polyols is a farnesene-based polyol which is a polyol of a farnesene homopolymer or a polyol of a copolymer of farnesene and a comonomer selected from the group consisting of dienes, vinyl aromatics, and combinations thereof, the farnesene-based polyol being a polymer having a backbone derived from monomers comprising farnesene and at least one terminal end comprising a hydroxyl group.

2. The method of claim 1 , further comprising combining the one or more polyols and one or more isocyanate-containing compounds with a chain extender.

3. The method of claim 1 , wherein the chain extender is selected from the group consisting of monomeric polyols and polyamines.

4. The method of claim 1 , wherein the chain extender is selected from the group consisting of 1,4-butanediol, 1,6-hexanediol, ethylene glycol, 2-ethyl-1,3-hexanediol (EHD), 2-butyl-2-ethyl-1,3-propanediol (BEPG), 2,2,4-trimethyl-1,3-pentanediol (TMPD), 2,4-deithyl-1,5-pentanediol (PD-9), N,N-diisopropanol aniline, dimethylolpropionic acid, hydroquinone dihydroxyethyl ether (HQEE), diethylene glycol, propylene glycol, trimethylolpropane, glycerol, diethyltoluenediamine (DETDA), 4,4′-methylene bis(2-chloroaniline) (MBCA), ethylenediamine (EDA), dimethylthiotoluene-diamine (DMTTDA), 4,4′-methylenedianiline (MDA), complex of methylenediamine with NaCI (MDA complex), trimethyleneglycol di-p-aminobenzoate (TMGDAB), 4,4′-methylene-bis(3-chloro-2,6-diethylaniline) (M-CDEA), N,N′-bis(sec-butyl)methylene-dianiline (SBMDA), and mixtures thereof.

5. The method of claim 1 , wherein the farnesene-based polyol is a polyol of a copolymer of farnesene and one or more monomers selected from the group consisting of dienes, vinyl aromatics, and combinations thereof.

6. The method of claim 5 , wherein the dienes are selected from the group consisting of butadiene and isoprene.

7. The method of claim 5 , wherein the vinyl aromatics are selected from the group consisting of styrene and alpha methyl styrene.

8. The method of claim 1 , wherein the one or more isocyanate-containing compounds are selected from the group consisting of 4,4′-diphenylmethane diisocyanate (MDI), cyclohexanediisocyanate, p-phenylene diisocyanate, 1,5-naphthalene diisocyanate, toluene diisocyanate (TDI), p-xylene diisocyanate, hexamethylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,4-bis(isocyanomethyl)- cyclohexane, p-tetramethylxylene diisocyanate, m-tetramethylxylene diisocyanate, isophorone diisocyanate, and combinations thereof.

9. The method of claim 1 , wherein the farnesene-based polyol has been hydrogenated to have a degree of unsaturation less than or equal to 50% of the degree of unsaturation of the farnesene-based polyol prior to hydrogenation.

10. The method of claim 1 , wherein the farnesene-based polyol has been hydrogenated to have a degree of unsaturation less than or equal to 10% of the degree of unsaturation of the farnesene-based polyol prior to hydrogenation.

11. The method of claim 1 , wherein the method comprises forming a prepolymer by reacting the one or more polyols with the one or more isocyanate-containing compounds.

12. The method of claim 11 , additionally comprising chain-extending the prepolymer with one or more chain extenders.

13. The method of claim 12 , wherein the method comprises combining the one or more polyols, the one or more isocyanate-containing compounds, and, optionally, one or more chain extenders generally simultaneously into a common reaction vessel to form the reaction mixture.

14. The method of claim 1 , wherein the curing comprises a hot air post-cure for up to twenty-four hours at 25° C. to about 200° C.

15. The method of claim 1 , wherein curing is accelerated using a catalyst.

Assignees

• Fina Technology

Inventors

• Tian Nan
• Chao Herbert

Classifications

• C09J175/14

  Polyurethanes having carbon-to-carbon unsaturated bonds · CPC title

• C08G18/6208

  Hydrogenated polymers of conjugated dienes · CPC title

• C08G18/6588

  with compounds of group C08G18/3203 · CPC title

• C08F236/22

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F36/22 Primary

  the radical having three or more carbon-to-carbon double bonds · CPC title