Water dispersible, self-crosslinkable prepolymer composition

Patent metadata

Field	Value
Publication number	US-9567311-B2
Application number	US-201314374360-A
Country	US
Kind code	B2
Filing date	Jan 23, 2013
Priority date	Jan 26, 2012
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

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

What is claimed is:

1. A self-crosslinkable prepolymer composition which is comprised of at least one triglyceride oil having appended thereto (1) hydroxyl groups, (2) moieties, which contain at least one aldehyde group or at least one ketone group, and (3) moieties, which contain at least one vinyl and/or substituted vinyl group.

2. The self-crosslinkable prepolymer composition, as specified in claim 1 , wherein the triglyceride oil has epoxy groups appended thereto.

3. The self-crosslinkable prepolymer composition, as specified in claim 1 , further comprising a moiety containing at least one free carboxylic acid group or an ionized carboxylic acid group appended to said at least one triglyceride oil.

4. The self-crosslinkable prepolymer, as specified in claim 1 , wherein the moieties, which contain at least one aldehyde group or at least one ketone group are of the formula:

wherein A represents a hydrocarbyl moiety, containing from 1 to 20 carbon atoms and wherein R represents a hydrogen atom or an alkyl group containing from 1 to 8 carbon atoms.

5. The self-crosslinkable prepolymer, as specified in claim 1 , 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.

6. The self-crosslinkable prepolymer, as specified in claim 5 , wherein n represents 2 and R represents a methyl group.

7. The self-crosslinkable prepolymer, as specified in claim 1 , wherein the moieties, which contain at least one vinyl and/or substituted 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 and wherein said self-crosslinkable prepolymer is water dispersible.

8. The self-crosslinkable prepolymer, as specified in claim 7 , wherein m represents 0.

9. The self-crosslinkable prepolymer composition, as specified in claim 1 , wherein the prepolymer is copolymerized with a monomer(s) selected from
(i) alkyl acrylates of the formula:

wherein R 7 is an alkyl group containing 1 to 15 carbon atoms, an alkoxyalkyl group containing a total of 1 to 10 carbon atoms, a cyanoalkyl group containing 1 to 10 carbon atoms, or a hydroxy alkyl group containing from 1 to 18 carbon atoms;
(ii) alkyl alkacrylates of the formula:

wherein R 8 is an alkyl group containing 1 to 15 carbon atoms, an alkoxyalkyl group containing a total of 1 to 10 carbon atoms, a cyanoalkyl group containing 1 to 10 carbon atoms, or a hydroxy alkyl group containing from 1 to 18 carbon atoms and wherein R 9 is an alkyl containing from 1 to 4 carbon atoms;
(iii) unsaturated acids selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, 2-carboxyethyl acrylate, mono methyl maleate, mono methyl fumarate, and mono methyl itaconate;
(iv) vinyl substituted aromatic compounds selected from styrene, alkyl substituted styrene 1-vinylnaphthalene, 2-vinylnaphthalene, 3-methyl styrene, vinyltoluene, alpha-methylstyrene, 4-n-propyl styrene, 4-t-butyl styrene, 4-dodecyl-styrene, 4-cyclohexylstyrene, 2-ethyl-4-benzylstyrene, 4-methoxy-styrene, 4-dimethylaminostyrene, 3,5-diphenoxystyrene, 4-p-tolyl styrene, 4-phenyl styrene, 4,5-dimethyl-1-vinylnaphthalene, and 3-n-propyl-2-vinyl-naphthalene;
(v) vinyl chloride;
(vi) vinylidene chloride;
(vii) butadiene;
(viii) vinyl esters of the formula:

wherein R 10 is an alkyl group generally having from 1 to 10 or 12 carbon atoms;
(ix) vinyl ethers of the formula:
H 2 C═CH—O—R 4

wherein R 4 is desirably an alkyl having from 1 to 10 carbon atoms;
(x) acrylamide monomers of the formula:

wherein R 5 represents a hydrogen atom or a methyl group and wherein R 6 is represents a hydrogen atom or an alkyl group (straight chained or branched) containing from 1 to 18 carbon atoms;
(xi) functionalized acrylamides selected from 2-acrylamido-2-methylpropanesulfonic acid, and dimethylaminopropyl methacrylamide; and
(xii) acrylonitriles selected from acrylonitrile, methacrylonitrile, and ethacrylonitrile.

10. An aqueous dispersion formed by dispersing the prepolymer described in claim 1 into another waterborne polymer.

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Pajerski Anthony D

Classifications

• C07D303/42 Primary

  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

• C08L2312/00

  Crosslinking · CPC title

• C09D133/068 Primary

  containing glycidyl groups · CPC title