Water dispersible, self-crosslinkable prepolymer composition

Patent metadata

Field	Value
Publication number	US-2017145245-A1
Application number	US-201615361925-A
Country	US
Kind code	A1
Filing date	Nov 28, 2016
Priority date	Jan 26, 2012
Publication date	May 25, 2017
Grant date	—

Abstract

The present invention provides an economical route to environmentally friendly polymeric coatings with a high content of raw materials from renewable resources. These polymeric coatings offer performance characteristics that are competitive with conventional coating systems. The unique polymers on which this invention is based are copolymers of triglyceride oils, such as soybean oil, linseed oil, or another natural oil, with a vinyl compound, such as an acrylate or methacrylate, or a vinyl aromatic monomer. The present invention more specifically discloses a water dispersible, self-crosslinkable prepolymer composition which is comprised of a triglyceride oil having appended thereto (1) hydroxyl groups, (2) epoxy groups, (3) moieties which contain at least one aldehyde group or at least one ketone group, and (4) moieties which contain at least one vinyl and/or substituted vinyl group. In one embodiment of this invention the moiety which contains at least one vinyl group is derived from maleic anhydride.

First claim

1 . (canceled)

2 . (canceled)

3 . (canceled)

4 . (canceled)

5 . (canceled)

6 . (canceled)

7 . (canceled)

8 . (canceled)

9 . (canceled)

10 . (canceled)

11 . An aqueous self-crosslinkable prepolymer dispersion which is comprised of water and a dispersed triglyceride oil having appended thereto (1) hydroxyl groups, (2) epoxy groups, (3) moieties, which contain at least one aldehyde group or at least one ketone group, and (4) moieties, which contain at least one carboxyl group or salt thereof.

12 . (canceled)

13 . (canceled)

14 . The aqueous self-crosslinkable prepolymer dispersion, as specified in claim 11 , wherein the triglyceride oil additionally has moieties which contain at least one vinyl and/or substituted vinyl group appended thereto.

15 . The aqueous self-crosslinkable prepolymer dispersion, as specified in claim 11 , wherein the moieties which contain at least one aldehyde group or at least one ketone group are of the formula:

wherein n represents an integer from 1 to 8 and wherein R represents a hydrogen atom or a methyl group.

16 . The aqueous self-crosslinkable prepolymer dispersion, as specified in claim 15 , wherein n represents 2 and R represents a methyl group.

17 . (canceled)

18 . The aqueous self-crosslinkable prepolymer dispersion, as specified in claim 11 , wherein the moieties, which contain at least one vinyl group, are of a formula selected from the group consisting of:

or are a mixture of such moieties, wherein m represents an integer from 0 to 8, and wherein R 1 , R 2 , and R 3 can be the same or different and represents hydrogen atoms or alkyl groups containing from 1 to 8 carbon atoms.

19 . The aqueous self-crosslinkable prepolymer dispersion, as specified in claim 18 , wherein m represents 0.

20 . (canceled)

21 . The aqueous self-crosslinkable prepolymer dispersion, according to claim 11 , further comprising additional free radically polymerizable monomer or monomers

22 . (canceled)

23 . (canceled)

24 . (canceled)

25 . (canceled)

26 . A coated substrate, which is comprised of a substrate having the self-crosslinkable prepolymer dispersion, according to claim 11 , on the surface thereof.

27 . A process for making a water dispersible, self-crosslinking prepolymer composition which comprises reacting (1) an epoxidized triglyceride oil with, (2) a ketone functionalized carboxylic acid or an aldehyde functionalized carboxylic acid forming a epoxidized triglyceride oil reaction product with pendant aldehyde group or ketone group, wherein said process further comprises reacting the epoxidized triglyceride oil with a vinyl functionalized carboxylic acid or which further comprises reacting the epoxidized triglyceride reaction product with the vinyl functionalized carboxylic acid, and wherein said process further comprises a dispersing agent from a) reacting an anhydride of a di or polycarboxylic acid with said epoxidized triglyceride reaction product or b) adding to said epoxidized triglyceride oil reaction product a dispersing agent of less than 400 Dalton molecular weight.

28 . (canceled)

29 . A process for making a water dispersible, self-crosslinking prepolymer composition, as specified in claim 27 , wherein said process further comprises reacting said epoxidized triglyceride reaction product with a vinyl functionalized carboxylic acid.

30 . A process for making a water dispersible, self-crosslinking prepolymer composition, as specified in claim 27 , wherein said process further comprises reacting an additional organic carboxylic acid with said epoxidized triglyceride reaction product.

31 . A process for making a water dispersible, self-crosslinking prepolymer composition, as specified in claim 30 , wherein the additional organic carboxylic acid is a fatty acid.

32 . The process for making a water dispersible, self-crosslinking prepolymer composition, as specified in claim 27 , wherein a diluent is added to facilitate processing of the prepolymer.

33 . The process for making a water dispersible, self-crosslinking prepolymer composition, as specified in claim 32 , wherein the diluent contains ethylenically unsaturated double bonds.

34 . A process for making a water dispersible, self-crosslinking prepolymer composition, as specified in claim 28 , wherein the anhydride comprises maleic anhydride or itaconic anhydride.

35 . A process for making the water dispersible, self-crosslinking prepolymer composition, specified in claim 34 , which comprises adding an ionizing base directly to the prepolymer composition or an aqueous medium in which the prepolymer composition is dispersed and subsequently polymerizing the prepolymer with a vinyl monomer diluent in an aqueous medium to form a copolymer.

36 . (canceled)

37 . A process for making the water dispersible, self-crosslinking prepolymer composition, specified in claim 27 , further comprising a) adding vinyl monomer or monomers to the waterborne dispersion and b) initiating a free radical copolymerization of said self-crosslinking prepolymer and said vinyl monomer or monomers.

38 . (canceled)

39 . The aqueous self-crosslinkable prepolymer dispersion, as specified in claim 11 , further comprising a hydrazine containing moiety.

40 . An aqueous self-crosslinkable prepolymer dispersion, as specified in claim 11 , wherein said dispersion is further comprised of at least one member sulfite or bisulfite selected from the group consisting of sodium sulfite, potassium sulfite, ammonium sulfite, calcium sulfite, magnesium sulfite, zinc sulfite, sodium bisulfite, potassium bisulfite, ammonium bisulfite, calcium bisulfite, magnesium bisulfite, and zinc bisulfite.

41 . (canceled)

42 . (canceled)

43 . (canceled)

44 . (canceled)

45 . (canceled)

46 . An aqueous dispersion formed by dispersing a polyurethane prepolymer into an aqueous dispersion comprising a composition of claim 11 .

47 . An aqueous self-crosslinkable prepolymer dispersion, as specified in claim 11 , which is further comprised of an acrylic emulsion or a polyurethane dispersion.

Assignees

• Pajerski Anthony D
• Lubrizol Advanced Mat Inc

Inventors

• Pajerski Anthony D

Classifications

• C08G59/1461

  Unsaturated monoacids · CPC title

• C07D303/42

  Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats · CPC title

• C08G59/186

  with acids · CPC title

• C08L2201/54

  Aqueous solutions or dispersions · CPC title

• C09D191/00

  Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof (polishing compositions, ski waxes C09G) · CPC title