Fluoroacrylate-multifunctional acrylate copolymer compositions

• US 7,851,387 B2
• Filed: 02/08/2008
• Issued: 12/14/2010
• Est. Priority Date: 12/28/2004
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Kumar, Ramesh C., Moore, George G. I., Qiu, Zai-Ming, Clark, John C.
• Primary Examiner(s): Salvatore; Lynda
• Application Number:
  US12/028,589
• Publication Number:
  US 20080132132A1
• Time in Patent Office: 1,040 Days
• Field of Search: 442/97, 442/98
• US Class Current: 442/97
• CPC Class Codes: C08F 220/38 Esters containing sulfur
• CPC Class Codes: C08F 220/387 and containing nitrogen and oxygen
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 442/2311 Coating or impregnation is a lubricant or a surface friction reducing agent other than specified as improving the "hand" of the fabric or increasing the softness thereof
• CPC Class Codes: Y10T 442/232 Fluorocarbon containing
• CPC Class Codes: Y10T 442/2754 Pressure-sensitive adhesive

Abstract

A composition comprises a copolymer comprising repeating units derived from at least one co-reactant comprising two or more acrylate groups and repeating units derived from a fluoroacrylate comprising the reaction product of:

• • (a) at least one fluorochemical alcohol represented by the formula:
    C₄F₉—X—OH
  • wherein:

• • • R=hydrogen or an alkyl group of 1 to 4 carbon atoms,
    • m=2 to 8,
    • R_f═C_nF_2n+1,
    • n=1 to 5,
    • y=0 to 6, and
    • q=1 to 8;
  • (b) at least one unbranched symmetric diisocyanate; and
  • (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoroacrylate monomer having 2 to about 30 carbon atoms in its alkylene portion;
    wherein the composition is coatable.

Claims

1. A composition comprising a copolymer comprising the reaction product of

(a) a fluoroacrylate represented by the following general formula:

C₄F₉—

X—

OC(O)NH-A-HNC(O)O—

(C_pH_2p)(O)COC(R′

)═

CH₂

wherein;

2. The composition of claim 1 wherein the weight ratio of co-reactant to fluoroacrylate is about 35:

65 or less.

3. The composition of claim 2 wherein the weight ratio of co-reactant to fluoroacrylate is about 20:

80 or less.

4. The composition of claim 1 wherein the co-reactant is a tri(meth)acrylate or a di(meth)acrylate.

5. The composition of claim 4 wherein the co-reactant is a di(meth)acrylate.

6. The composition of claim 5 wherein the co-reactant is a fluorinated di(meth)acrylate.

7. The composition of claim 1 wherein the copolymer comprises the reaction product of (a), (b), and at least one chain transfer agent.

8. The composition of claim 7 wherein the chain transfer agent is selected from the group consisting of thiols, secondary alcohols, and polyhalocarbons.

9. The composition of claim 1 wherein the copolymer comprises the reaction product of (a), (b), and at least one comonomer.

10. The composition of claim 1 further comprising water or an organic solvent.

11. The composition of claim 10 wherein the composition is a release coating composition.

12. An article comprising a substrate having one or more surfaces coated with the composition of claim 1.

13. The article of claim 12 wherein the substrate comprises a material selected from the group consisting of polyethylene terephthalate, polyolefins, and polyolefin coated paper.

14. The article of claim 12 wherein the substrate is a fibrous substrate.

15. The article of claim 12 wherein the substrate is a non-woven substrate.

16. An article comprising a substrate having one or more surfaces coated with the composition of claim 11.

17. The article of claim 16 wherein the article is a release liner.

18. A method of making a coatable composition comprising reacting a fluoroacrylate with at least one co-reactant comprising two or more acrylate groups, and optionally at least one chain transfer agent, in a reaction solvent to form a copolymer;

wherein the fluoroacrylate, co-reactant, and chain transfer agent are present in an amount up to about 35 weight percent, the weight percent being based upon the total weight of the monomers and the solvent; and

wherein the fluoroacrylate is represented by the following general formula;

C₄F₉—

X—

OC(O)NH-A-HNC(O)O—

(C_pH_2p)(O)COC(R′

)═

CH₂

wherein;

19. The method of claim 18 wherein the co-reactant is present in the copolymer in an amount between about 5 and about 25 weight percent.

20. The method of claim 18 wherein the weight ratio of co-reactant to fluoroacrylate is about 20:

80 or less.

21. A method of making a coatable composition comprising:

reacting at least one co-reactant comprising two or more acrylate groups with a fluoroacrylate comprising the reaction product of;

(a) at least one fluorochemical alcohol represented by the formula;

C₄F₉—

X—

OH

wherein;

22. The method of claim 21 wherein component (c) comprises at least one hydroxy-terminated alkyl (meth)acrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.

23. The method of claim 21 wherein component (c) comprises at least one hydroxy-terminated 2-fluoroacrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.