Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures

• US 9,790,295 B2
• Filed: 04/01/2016
• Issued: 10/17/2017
• Est. Priority Date: 09/08/2014
• Status: Active Grant

• Current Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Sullivan, Jeffrey M., Palsule, Aniruddha, Holzer, Alexander R., Parab, Kshitij K., Doshi, Ami
• Primary Examiner(s): NGUYEN, VU ANH
• Application Number:
  US15/088,340
• Publication Number:
  US 20160215078A1
• Time in Patent Office: 564 Days
• Field of Search: None
• CPC Class Codes: C07C 69/593 Dicarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C08F 2/06 Organic solvent
• CPC Class Codes: C08F 22/10 Esters
• CPC Class Codes: C08F 222/145 the ester chains containing seven or more carbon atoms
• CPC Class Codes: C09J 135/02 Homopolymers or copolymers of esters C09J135/06, C09J135/08 take precedence

Abstract

The disclosure relates to compositions containing 1,1-disubstituted alkene compounds capable of preparing polymers having glass transition temperatures above room temperature. The present teaching also relates to polymers prepared 1,1-disubstituted alkene compounds which exhibit glass transition temperatures of 60° C. The disclosure also relate to methods for enhancing the glass transition temperatures of polymers prepared from 1,1-disubstituted alkene compounds.

Claims

1. A composition comprising one or more multifunctional 1,1-disubstituted alkene compounds which correspond to the formula:

2. A composition according to claim 1 wherein R³ is C_4-20 aralkylene or C_4-20 alkarylene groups.

3. A composition according to claim 1 wherein R³ is the residue of 4,4′

-(propane-2,2-diyl) diphenyl or 2,2′

-methylenediphenyl.

14. A composition according to claim 1 wherein the composition when polymerized prepares a polymer having a glass transition temperature of about 60°

C. or greater.

15. A composition according to claim 1 wherein the composition when polymerized prepares a polymer having a glass transition temperature of about 80°

C. or greater.

16. A composition according to claim 1 wherein the composition when polymerized prepares a polymer having a glass transition temperature of about 100°

C. or greater.

4. A composition comprising about 10 weight percent or greater of one or more first 1,1-disubstituted alkene compounds wherein each carbonyl group independently has a hydrocarbyl group bonded to the carbonyl groups by a direct bond, an oxygen atom, a nitrogen atom or a sulfur atom wherein one or more of the hydrocarbyl groups comprise an aryl group, aralkyl group, alkaryl group with the aryl group bonded to the 1 or 2 carbon atom, a cycloalkyl group, an alkyl group with a cycloalkyl group on the 1 or 2 carbon atom, or a branched alkyl group wherein the 1 carbon atom is a tertiary or the 1 and 2 carbon atoms are secondary;

and about 10 weight percent or greater of one or more second 1,1-disubstituted alkene compounds wherein each carbonyl group independently has a hydrocarbyl group bonded to the carbonyl groups by a direct bond, or a heteroatom, and the hydrocarbyl groups are selected such that homopolymers prepared from the second 1,1-disubstituted alkenes exhibit glass transition temperatures of less than 60°

C.;

wherein the composition further comprises one or more multifunctional 1,1-disubstituted alkene compounds which correspond to the formula;

5. A composition according to claim 4 wherein b is 1 or more.

6. A composition according to claim 4 which comprises about 1 percent by weight or greater of one or more multifunctional 1,1-disubstituted alkene compounds.

7. A composition according to claim 4 which comprises about 1 percent by weight to about 30 percent by weight of one or more multifunctional 1,1-disubstituted alkene compounds.

8. A composition according to claim 4 which comprises about 5 percent by weight to about 15 percent by weight of the one or more multifunctional 1,1-disubstituted alkene compounds.

9. A composition comprising about 10 weight percent or greater of one or more first 1,1-disubstituted alkene compounds wherein each carbonyl group independently has a hydrocarbyl group bonded to the carbonyl groups by a direct bond, an oxygen atom, a nitrogen atom or a sulfur atom wherein one or more of the hydrocarbyl groups comprise an aryl group, aralkyl group, alkaryl group with the aryl group bonded to the 1 or 2 carbon atom, a cycloalkyl group, an alkyl group with a cycloalkyl group on the 1 or 2 carbon atom, or a branched alkyl group wherein the 1 carbon atom is a tertiary or the 1 and 2 carbon atoms are secondary;

or about 10 weight percent or greater of one or more second 1,1-disubstituted alkene compounds wherein each carbonyl group independently has a hydrocarbyl group bonded to the carbonyl groups by a direct bond, a heteroatom, and the hydrocarbyl groups are selected such that homopolymers prepared from the second 1,1-disubstituted alkenes exhibit glass transition temperatures of less than 60°

C.;

wherein the composition further comprises one or more multifunctional 1,1-disubstituted alkene compounds which correspond to the formula;

10. A composition according to claim 9 wherein b is 1 or more.

11. A composition according to claim 9 which comprises about 1 percent by weight or greater of one or more multifunctional 1,1-disubstituted alkene compounds.

12. A composition according to claim 9 which comprises about 1 percent by weight to about 30 percent by weight of one or more multifunctional 1,1-disubstituted alkene compounds.

13. A composition according to claim 9 which comprises about 5 percent by weight to about 15 percent by weight of one or more multifunctional 1,1-disubstituted alkene compounds.

17. A composition according to claim 9 wherein the composition when polymerized prepares a polymer having a glass transition temperature of about 60°

C. or greater.

18. A composition according to claim 9 wherein the composition when polymerized prepares a polymer having a glass transition temperature of about 80°

C. or greater.

19. A composition according to claim 9 wherein the composition when polymerized prepares a polymer having a glass transition temperature of about 100°

C. or greater.