Methods and compositions for making water-borne dispersions

• US 20020183443A1
• Filed: 01/30/2002
• Published: 12/05/2002
• Est. Priority Date: 01/30/2001
• Status: Abandoned Application

• Current Assignee: Inolex Investment Corporation (Inolex Group, Inc.)
• Original Assignee: Inolex Investment Corporation (Inolex Group, Inc.)
• Inventors: Gleason, Glenn, Housel, Tyler
• Application Number:
  US10/062,890
• Publication Number:
  US 20020183443A1
• Time in Patent Office: Days
• US Class Current: 524/591
• CPC Class Codes: A61K 8/85 Polyesters
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/06 Preparations for styling the hair, e.g. by temporary shaping or colouring
• CPC Class Codes: C08G 18/4211 derived from aromatic dicarboxylic acids and dialcohols
• CPC Class Codes: C08G 63/123 the acids or hydroxy compounds containing carbocyclic rings
• CPC Class Codes: C08G 63/18 the acids or hydroxy compounds containing carbocyclic rings
• CPC Class Codes: C08G 63/668 derived from polycarboxylic acids and polyhydroxy compounds

Abstract

Dispersion-stable polymeric acid functional polyols and dispersions of such materials, a method for improving the long term storage dispersibility and hydrolytic resistance of an acid functional polyol and a method for making a water-borne polyurethane, as well as personal care and industrial lubricants, using such improved acid functional polymeric polyols are provided. The polymeric acid functional polyols are reaction products of reaction mixtures including a base polyol having at least one of a terminal secondary and/or tertiary hydroxyl group and an aromatic anhydride.

Claims

1. A dispersion-stable polymeric acid functional polyol that is a reaction product of a reaction mixture comprising

a base polyol having at least one of a terminal secondary or tertiary hydroxyl group, and

an aromatic anhydride, wherein the polymeric acid functional polyol exhibits improved dispersion stability and is resistant to hydrolysis.

2. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the base polyol has a terminal secondary hydroxyl group.

3. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the base polyol has the formula:

HO—

C(R¹)_n(R²)_mR³OH 

 

(I)

wherein R¹ is a hydrogen atom;

R² is selected from the group consisting of substituted and unsubstituted branched and straight chain aliphatic alkyl and alkoxy groups of from 1 to 20 carbon atoms, substituted and unsubstituted cycloaliphatic groups, substituted and unsubstituted aryl groups, and substituted and unsubstituted aralkyl groups;

R³ is selected from the group consisting of substituted and unsubstituted aliphatic alkyl or alkoxy groups of from 1 to 20 carbon atoms, cycloaliphatic groups, polymeric ethers, polymeric esters, polycarbonate, and polymeric ether esters;

n is 0 or 1;

m is 1 or 2.

4. The dispersion-stable polymeric acid functional polyol according to claim 3, wherein substituted R² or R³ may be substituted with at least one moiety selected from the group consisting halogen, carbamate, amine, lower alkyl, carboxylic acid, and hydroxyl.

5. The dispersion-stable polymeric acid functional polyol according to claim 3, wherein the base polyol is selected from the group consisting of propylene glycol, polypropylene glycol, 1,3-butanediol, 2,2,4-trimethyl-1,3-pentanediol, and ester polyols that are a reaction product of at least one polyol having a terminal secondary or tertiary hydroxyl group and a primary polyol, and/or at least one of a mono- or polycarboxylic acid and a mono- and polycarboxylic anhydride.

6. The dispersion-stable polymeric acid functional polyol according to claim 5, wherein the at least one mono- or polycarboxylic acid or mono- or polycarboxylic anhydride is hexanedioic acid.

7. The dispersion-stable polymeric acid functional polyol according to claim 6, wherein the at least one polyol is selected from the group consisting of propylene glycol, dipropylene glycol, 1,3 butanediol, and 2,2,4- trimethyl-1,3 pentanediol.

8. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the base polyol is a polyester polyol formed from a reaction of at least one diacid and at least one monomeric or oligomeric diol.

9. The dispersion-stable polymeric acid functional polyol according to claim 8, wherein the at least one diacid is a cycloaliphatic diacid.

10. The dispersion-stable polymeric acid functional polyol according to claim 8, wherein the at least one diacid is hexanedioic acid.

11. The dispersion-stable polymeric acid functional polyol according to claim 8, wherein the at least one monomeric or oligomeric diol is selected from the group consisting of propylene glycol, dipropylene glycol, 1,3 butanediol, and 2,2,4-trimethyl-1,3 pentanediol.

12. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the base polyol has a hydroxyl number of about 50 to about 1000 and a hydroxyl functionality of about 1 to about 5.

13. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the base polyol has a hydroxyl number of about 60 to about 200 and a hydroxyl functionality of about 2.

14. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the aromatic anhydride is a polyanhydride.

15. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the aromatic anhydride is selected from the group consisting of trimellitic anhydride, pyromellitic dianhydride, and phthalic anhydride.

16. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the dispersion-stable polymeric acid functional polyol has an acid number of about 5 to about 200 and a hydroxyl number of about 10 to about 300.

17. The dispersion-stable polymeric acid functional polyol according to claim 1, wherein the dispersion-stable polymeric acid functional polyol has an acid number of about 10 to about 100 and a hydroxyl number of about 10 to about 200.

19. The storage stable acid functional polyol dispersion according to claim 18, wherein the aromatic anhydride is a polyanhydride.

20. The storage stable acid functional polyol dispersion according to claim 18, wherein the pendant carboxylic acid functional group is neutralized by an organic or an inorganic amine.

21. The storage stable acid functional polyol dispersion according to claim 20, wherein the amine is ammonia.

22. The storage stable acid functional polyol dispersion according to claim 18, further comprising at least one additive selected from the group consisting of catalysts, UV curing agents, colorants, thixotropic agents, pigments, leveling agents, corrosion inhibitors, emollients, odorants, dyes, biocides, fungicides, surfactants, monomers, oligomers, and UV stabilizers.

24. The solid polymeric material according to claim 23, wherein the curing reaction is a radiation cure or a reaction of the acid functional polyol and a curative, wherein the curative is at least one selected from the group consisting of an isocyanate and an amine.

25. The solid polymeric material according to claim 23, wherein the aromatic anhydride is a polyanhydride.

27. The method according to claim 26, wherein the aromatic anhydride is a polyanhydride.

29. The method according to claim 28, wherein the aromatic anhydride is a polyanhydride.

18. A storage stable acid functional polyol dispersion, comprising an acid functional polymeric polyol which is a reaction product of a reaction mixture comprising a base polyol having at least one of a terminal secondary or tertiary hydroxyl group and an aromatic anhydride, wherein the acid functional polymeric polyol is dispersed by neutralizing at least one pendant carboxylic acid functional group on the acid functional polymeric polyol.

23. A solid polymeric material formed from a curing reaction of an acid functional polymeric polyol, wherein the acid functional polyol is the reaction product of a reaction mixture comprising a base polyol having at least one of a terminal secondary or tertiary hydroxyl group and an aromatic anhydride.

26. A method for improving the long term storage dispersibility and hydrolytic resistance of an acid functional polyol, the method comprising forming the acid functional polyol from the reaction of a base polyol having at least one of a terminal secondary or tertiary hydroxyl group and an aromatic anhydride.

28. A method for making a water-borne polyurethane comprising reacting of a polyisocyanate and an acid functional polyol dispersion, wherein the dispersion comprises an acid functional polyol formed from the reaction of a base polyol having at least one of a terminal secondary or tertiary hydroxyl group with an aromatic anhydride.

30. A formulation comprising a dispersion-stable polymeric acid functional polyol, wherein the dispersion-stable polymeric acid functional polyol is formed from a reaction of a base polyol having at least one of a terminal secondary or tertiary hydroxyl group and an aromatic anhydride.

31. The formulation of claim 30, wherein the base polyol has a terminal secondary hydroxyl group.

32. The formulation according to claim 30, wherein the aromatic anhydride is a polyanhydride.

33. The formulation of claim 30, wherein the formulation further comprises an additive selected from the group consisting of water, amines or other neutralizing agents, acids, performance additives, antioxidants, and biocides.

34. The formulation of claim 30, wherein the formulation further comprises an additive selected from the group consisting of fungicides, colorants, odorants, lubricant oils, silicones, emulsifiers, and defoamers.

35. The formulation of claim 30, wherein the formulation is a personal care formulation.

36. The formulation of claim 30, wherein the formulation is a lubricant formulation.

37. The formulation according to claim 36, wherein the lubricant formulation is adapted for use in a machining process, wherein the machining process is selected from the group consisting of a metal machining process, a ceramic machining process, a glass machining process, a wood machining process, and a polymer machining process.

38. The formulation according to claim 37, wherein the metal machining process is selected from the group consisting of an aluminum machining processes and a ferrous metal machining process.