Polymers of 3-butene esters, their preparation and use

• US 6,160,057 A
• Filed: 04/03/2000
• Issued: 12/12/2000
• Est. Priority Date: 10/23/1997
• Status: Expired due to Fees

• Current Assignee: Eastman Chemical Company
• Original Assignee: Eastman Chemical Company
• Inventors: Crain, Allen Lynn, Webster, Dean Charles, Marlow, Chadwick Edward
• Primary Examiner(s): Zitomer, Fred
• Application Number:
  US09/541,989
• Time in Patent Office: 253 Days
• Field of Search: 525/379, 525/378, 525/374, 525/328.9
• US Class Current: 525/379
• CPC Class Codes: C08F 16/04 Acyclic compounds
• CPC Class Codes: C08F 16/26 Monomers containing oxygen atoms in addition to the ether oxygen
• CPC Class Codes: C08F 18/12 with unsaturated alcohols containing three or more carbon atoms
• CPC Class Codes: C08F 8/32 by reaction with amines
• CPC Class Codes: C09D 129/10 Homopolymers or copolymers of unsaturated ethers C09D135/08 takes precedence
• CPC Class Codes: C09D 131/04 Homopolymers or copolymers of vinyl acetate

Abstract

The specification describes various polymers having monomer of formula (I): ##STR1## In formula (I), R1 and R2 are, independently, hydrogen, a C₁ -C₂₄ alkyl group, an aromatic or heteroaromatic group, a C₃ -C₈ cycloalkyl or C₂ -C₇ heterocycloalkyl group, or a --C(O)R3 group. Preferably R1 and R2 are both a a --C(O)R3 group where R3 which can the same of different is selected from the group consisting of a C₁ -C₂₄ alkyl group, an aromatic or heteroaromatic group, a C₃ -C₈ cycloalkyl or C₂ -C₇ heterocyclic group; or a --CH₂ --C(O)--R4 group in which R4 is a C₁ -C₆ alkyl group. At lease one of R1 and R2 is a --C(O)R3 group. The polymer may be a homopolymer or a copolymer containing other ethylenically unsaturated monomers. The polymer may be used in a variety of coating compositions such as inks, adhesives, paints and films. Unique monomers where both R1 and R2 are acetoacetyl groups and novel monomers where R2 is an acetoacetyl group are also described.

Claims

1. An enamine functional polymer comprising the reaction product of an acetoacetoxy functionalized polymer and an amine selected from the group consisting of ammonia, a primary amine, and a secondary amine, wherein said acetoacetoxy polymer comprises the free-radical polymerization product of:

a monomer of formula (I);

##STR7## where R1 and R2 are both a --C(O)R3 group;

R3, which can be the same or different, is selected from the group consisting of a C₁ -C₂₄ alkyl group, an aromatic or heteroaromatic group, a C₃ -C₈ cycloalkyl or C₂ -C₇ heterocyclic group, and a --CH₂ --C(O)--R4 group;

R4 is a C₁ -C₆ alkyl group;

wherein at least one of R1 and R2 is an acetoacetoxy group;

and an ethylenically unsaturated monomer.

2. A polymer of claim 1, wherein the ethylenically unsaturated monomer is at least one selected from the group consisting of an allylic compound, a vinylic compound, a styrenic compound, an α

,β

-unsaturated compound, an acrylic compound, and an alkene.

3. A coating composition comprising the polymer of claim 1, water, a solvent, a pigment and, optionally, an additive or a filler.

4. A coating composition of claim 3, wherein said coating composition is a paint, an architectural coating, a maintenance coating, an industrial coating, an automotive coating, a textile coating, an ink, an adhesive, or a coating for paper, wood, or plastic.

5. A method of preparing the enamine functional polymer of claim 1, comprising the step of reacting an amine selected from the group consisting of ammonia, a primary amine and a secondary amine, and the free-radical polymerization product of:

a monomer of formula (I);

##STR8## where R1 and R2 are both a --C(O)R3 group;

R3, which can be the same or different, is selected from the group consisting of a C₁ -C₂₄ alkyl group, an aromatic or heteroaromatic group, a C₃ -C₈ cycloalkyl or C₂ -C₇ heterocyclic group, and a --CH₂ --C(O)--R4 group;

R4 is a C₁ -C₆ alkyl group;

wherein at least one of R1 and R2 is an acetoacetoxy group; and

an ethylenically unsaturated monomer.

6. A coated article comprising a substrate coated with a coating composition of claim 3.

7. A coated article of claim 6, wherein said substrate is selected from the group consisting of paper, plastic, steel, aluminum, wood, gypsum board, and primed or unprimed galvanized sheeting.