Low viscosity polyols for polyurethane applications

Patent metadata

Field	Value
Publication number	US-11208522-B2
Application number	US-202016734911-A
Country	US
Kind code	B2
Filing date	Jan 6, 2020
Priority date	Jul 7, 2017
Publication date	Dec 28, 2021
Grant date	Dec 28, 2021

Abstract

Lactide-based random polyester polyols for use in polyurethane compositions are disclosed. The polyester polyols have an OH value in the range of greater than 400 mg KOH/g up to 1100 mg KOH/g and are the reaction product of at least one polycarboxylic acid, at least one lactide, and one or more polyalcohols. The polyester polyols can be formulated into the B-side of a two part polyurethane composition to obtain a polyurethane having improved hardness and solvent resistance and a low VOC content. The polyurethane composition is particularly suitable for polyurethane coating applications.

First claim

The invention claimed is:

1. A random polyester polyol comprising the reaction product of components forming the random polyester polyol, wherein the components comprise:
from about 10% to about 59% by weight, based on the total weight of the components forming the random polyester polyol, of (a) a polycarboxylic acid component comprising at least one of a polycarboxylic acid and a polycarboxylic acid derivative;
from about 5% to about 40% by weight, based on the total weight of the compounds forming the random polyester polyol, of (b) a lactide component comprising at least one of lactide, lactic acid, and a lactic acid derivative; and
from about 29% to about 80% by weight, based on the total weight of the compounds forming the random polyester polyol, of (c) a polyalcohol component comprising one or more polyalcohols,
wherein the random polyester polyol has an Acid Value of 10.0 mg KOH/g or less, an OH value of greater than 400 up to about 1100 mg KOH/g, an average molecular weight of less than about 900 g/mol, a functionality greater than 2 to about 6, and a viscosity of about 500 cps to less than about 10,000 cps at 25° C.

2. The random polyester polyol of claim 1 , wherein (c) the polyalcohol component comprises one or more of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, butylene glycols, neopentyl glycol, 1,6-hexanediol, 2-methyl-1,3-propanediol, 1,3-propane glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,2-cyclohexandiol, 1,3-cyclohexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, resorcinol, hydroquinone, poly(oxyalkylene) polyols derived by the condensation of ethylene oxide, propylene oxide, or a combination thereof, glycerol, diglycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, ethoxylated trimethylolpropane, propoxylated trimethylolpropane, sucrose, glucose, fructose, sorbitol, and mannitol.

3. The random polyester polyol of claim 1 , wherein (a) the polycarboxylic acid component comprises one or more of straight or branched aliphatic diacids, aromatic diacids, cycloaliphatic diacids, and polycarboxylic acids having a functionality of at least two.

4. The random polyester polyol of claim 1 , wherein (a) the polycarboxylic acid component comprises one or more of glutaric acid, adipic acid, succinic acid, maleic acid, fumaric acid, sebacic acid, pimelic acid, octanedioic acid, dodecanedioic acid, azelaic acid, phthalic acid, terephthalic acid, isophthalic acid, citric acid, isocitric acid, trimellitic acid, pyromellitic acid, trimellitic anhydride, and pyromellitic anhydride.

5. The random polyester polyol of claim 1 , wherein the components forming the random polyester polyol comprise from about 10% to about 55% by weight, based on the total weight of the components forming the random polyester polyol, of (a) the polycarboxylic acid component.

6. The random polyester polyol of claim 1 , wherein the weight ratio of (c) the polyalcohol component to (b) the lactide component is from 10:1 to 1.0:1.

7. The random polyester polyol of claim 1 , wherein the components forming the random polyester polyol further comprise a natural oil.

8. A B-side composition for preparing a polyurethane composition, the B-side composition comprising:
a 100% solids random polyester polyol, wherein the random polyester polyol is the random polyester polyol of claim 1 ;
optionally, at least one oxazolidine in an amount of 0% to 60% by weight, or at least one ketimine resin in an amount of 0% to 60% by weight, based on the weight of the B-side composition; and
optionally, one or more additional components having two or more active hydrogen groups;
wherein the polyurethane composition is a coating, adhesive, sealant, elastomer, or foam.

9. The B-side composition of claim 8 , wherein (c) the polyalcohol component comprises one or more of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, butylene glycols, neopentyl glycol, 1,6-hexanediol, 2-methyl-1,3-propanediol, 1,3-propane glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,2-cyclohexandiol, 1,3-cyclohexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, resorcinol, hydroquinone, poly(oxyalkylene) polyols derived by the condensation of ethylene oxide, propylene oxide, or a combination thereof, glycerol, diglycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, ethoxylated trimethylolpropane, propoxylated trimethylolpropane, sucrose, glucose, fructose, sorbitol and mannitol.

10. The B-side composition of claim 8 , wherein (a) the polycarboxylic acid component comprises one or more of glutaric acid, adipic acid, succinic acid, maleic acid, fumaric acid, sebacic acid, pimelic acid, octanedioic acid, dodecanedioic acid, azelaic acid, phthalic acid, terephthalic acid, isophthalic acid, citric acid, isocitric acid, trimellitic acid, pyromellitic acid, trimellitic anhydride, and pyromellitic anhydride.

11. The B-side composition of claim 8 , wherein the components forming the random polyester polyol comprise from about 10% to about 55% by weight, based on the total weight of the components forming the random polyester polyol, of (a) the polycarboxylic acid component.

12. The B-side composition of claim 8 , wherein the weight ratio of (c) the polyalcohol component to (b) the lactide component is from 10:1 to 1.0:1.

13. The B-side composition of claim 8 , wherein the one or more additional components having two or more active hydrogen groups are selected from polyester polyols, polyether polyols, polyetherester polyols, polycarbonate polyols, acrylic polyols, amine polyols, polycaprolactones, silicones, hydroxyl-containing thioethers, aspartic resins, and ketimine resins.

14. The B-side composition of claim 8 , wherein the 100% solids random polyester polyol is present in an amount of 30% to 95% by weight, based on the weight of the B-side composition.

15. The B-side composition of claim 8 , wherein the at least one oxazolidine is present in an amount of greater than zero to 60% by weight, based on the weight of the B-side composition.

16. The B-side composition of claim 8 , wherein the at least one ketimine resin is present in an amount of greater than zero to 60% by weight, based on the weight of the B-side composition.

17. A 2-part polyurethane coating composition comprising an A-side composition and a B-side composition, wherein the B-side composition comprises:
a 100% solids random polyester polyol, wherein the random polyester polyol is the random polyester polyol of claim 1 ;
optionally, at least one oxazolidine in an amount of 0% to 60% by weight, or at least one ketimine resin in an amount of 0% to 60%, based on the weight of the B-side composition; and
optionally, one or more additional components having two or more active hydrogen groups; and
wherein the A-side composition comprises an isocyanate component comprising at least one polyisocyanate, in an amount to provide a proportion of NCO to OH groups of about 0.9:1 to about 1.3:1.

18. The 2-part polyurethane coating composition of claim 17 , having a VOC content of less than 200 g/liter.

19. The 2-part polyurethane coating composition of claim 17 , wherein the isocyanate component comprises a biuret or isocyanurate of hexamethylene diisocyanate having a nominal functionality of about three and an NCO content of about 23 weight percent.

20. The 2-part polyurethane coating composition of claim 17 , wherein the 100% solids random poly

Assignees

• Stepan Co

Inventors

• O'Brien Michael Edward
• Janos Jeffrey R
• Yin Scott

Classifications

• C08G18/7831

  containing biuret groups · CPC title

• C08G18/244

  tin salts of carboxylic acids · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C09D175/06 Primary

  from polyesters · CPC title

• C08G63/08

  Lactones or lactides · CPC title