Pressure sensitive adhesive including a 1,1-disubstituted alkene compound

• US 9,969,819 B2
• Filed: 05/08/2017
• Issued: 05/15/2018
• Est. Priority Date: 09/08/2014
• Status: Active Grant

• Current Assignee: Nippon Shokubai Company Limited
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Palsule, Aniruddha, Holzer, Alexander R., Stevenson, Peter Rulon, Parab, Kshitij Kishen, Sullivan, Jeffrey M.
• Primary Examiner(s): Nguyen, Vu A
• Application Number:
  US15/589,364
• Publication Number:
  US 20170253675A1
• Time in Patent Office: 372 Days
• Field of Search: None
• CPC Class Codes: B05D 3/007 After-treatment
• CPC Class Codes: C08F 2/06 Organic solvent
• CPC Class Codes: C08F 2/26 anionic
• CPC Class Codes: C08F 222/14 Esters having no free carboxylic acid groups , e.g. dialkyl maleates or fumarates
• CPC Class Codes: C08F 297/02 using a catalyst of the anionic type
• CPC Class Codes: C09D 135/02 Homopolymers or copolymers of esters C09D135/06, C09D135/08 take precedence
• CPC Class Codes: C09D 153/00 Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09J 135/02 Homopolymers or copolymers of esters C09J135/06, C09J135/08 take precedence
• CPC Class Codes: C09J 153/00 Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers

Abstract

The present teachings show that it is possible to polymerize 1,1-disubstituted alkene compounds in a solution (for example using one or more solvents). Polymerization of 1,1-disubstituted alkene compounds in an solution provides opportunities to better control the polymerization compared with bulk polymerization. The solution polymerization techniques can be employed for preparing homopolymers, copolymers (e.g., random copolymers), and block copolymers.

Claims

1. A pressure sensitive adhesive including a polymer comprising

one or more 1,1-disubstituted alkene compounds, wherein the polymer has a weight average molecular weight of about 3000 daltons or more.

2. The pressure sensitive adhesive of claim 1, wherein the polymer includes about 30 weight percent or more of the 1,1-disubstituted alkene compounds, based on the total weight of the polymer.

3. The pressure sensitive adhesive of claim 2, wherein the polymer is a block copolymer.

4. The pressure sensitive adhesive of claim 3, wherein the polymer partially or entirely coats a substrate.

5. The pressure sensitive adhesive of claim 3, wherein

the one or more monomers includes one or more monomers selected from the group consisting of methyl propyl methylene malonate, dihexyl methylene malonate, di-isopropyl methylene malonate, butyl methyl methylene malonate, ethoxyethyl ethyl methylene malonate, methoxyethyl methyl methylene malonate, hexyl methyl methylene malonate, dipentyl methylene malonate, ethyl pentyl methylene malonate, methyl pentyl methylene malonate, ethyl methoxyethyl methylene malonate, ethoxyethyl methyl methylene malonate, butyl ethyl methylene malonate, dibutyl methylene malonate, diethyl methylene malonate (DEMM), diethoxyethyl methylene malonate, dimethyl methylene malonate, di-n-propyl methylene malonate, ethyl hexyl methylene malonate, fenchyl methyl methylene malonate, menthyl methyl methylene malonate, 2-phenylpropyl ethyl methylene malonate, and dimethoxyethyl methylene malonate.

6. The pressure sensitive adhesive of claim 5, wherein the polymer is substantially free of a melting temperature and is substantially free of a glass transition temperature of about 15°

C. or more.

7. The pressure sensitive adhesive of claim 3, wherein the polymer is substantially free of a melting temperature and is substantially free of a glass transition temperature of about 15°

C. or more.

8. The pressure sensitive adhesive of claim 3, wherein the polymer includes at least one block having a glass transition temperature or melting temperature of about 15°

C. or more and at least one different block having no melting temperature above 15°

C. and having a glass transition temperature about 0°

C. or less.

9. The pressure sensitive adhesive of claim 3, wherein the polymer includes two or more monomers including a first monomer which is a first 1,1-disubstituted alkene compound and a second monomer different from the first monomer.

10. The pressure sensitive adhesive of claim 9, wherein the second monomer is a second 1,1-disubstituted alkene compound.

11. The pressure sensitive adhesive of claim 10, wherein the polymer includes a first polymer block having a first glass transition temperature and a second polymer block having a different glass transition temperature.

12. The pressure sensitive adhesive of claim 11, wherein the second polymer block and the first polymer block have different concentration of monomers.

13. The pressure sensitive adhesive of claim 12, wherein the polymer is a linear polymer.

14. The pressure sensitive adhesive of claim 12, wherein the pressure sensitive adhesive includes a cross-linking agent.

15. The pressure sensitive adhesive of claim 12, wherein the pressure sensitive adhesive includes a plasticizer.

16. The pressure sensitive adhesive of claim 1, wherein the polymer is a random copolymer including two or more monomers including a first monomer that is one of the one or more 1,1-disubstituted alkene compounds and a second monomer, wherein the first monomer is present in an amount of about 30 weight percent or more, based on the total weight of the polymer.

17. The pressure sensitive adhesive of claim 16, wherein the weight ratio of the first monomer to the second monomer is from about 5:

95 to about 95;

5.

18. The pressure sensitive adhesive of claim 17, wherein the polymer includes two or more 1,1-disubstituted alkene compounds.

19. The pressure sensitive adhesive of claim 18, wherein the polymer is substantially free of a melting temperature and is substantially free of a glass transition temperature of about 15°

C. or more.

20. The pressure sensitive adhesive of claim 3, wherein the polymer includes two or more 1,1-disubstituted alkene compounds.