Polymers containing a 1,1-disubstituted alkene compound

• US 10,633,566 B2
• Filed: 01/21/2019
• Issued: 04/28/2020
• 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: Stevenson, Peter Rulon, Holzer, Alexander R., Palsule, Aniruddha Sudhir, Sullivan, Jeffrey M.
• Primary Examiner(s): Nguyen, Vu A
• Application Number:
  US16/253,006
• Publication Number:
  US 20190153272A1
• Time in Patent Office: 463 Days
• Field of Search: None
• CPC Class Codes: B01J 19/10 employing sonic or ultrasonic vibrations
• CPC Class Codes: B01J 19/18 Stationary reactors having moving elements inside B01J19/08, B01J19/26 take precedence
• CPC Class Codes: C07C 69/38 Malonic acid esters
• CPC Class Codes: C08F 122/14 Esters having no free carboxylic acid groups
• CPC Class Codes: C08F 2/22 Emulsion polymerisation
• CPC Class Codes: C08F 2/26 anionic
• CPC Class Codes: C08F 2/30 non-ionic
• CPC Class Codes: C08F 22/10 Esters
• CPC Class Codes: C08F 222/10 Esters
• CPC Class Codes: C08F 222/14 Esters having no free carboxylic acid groups , e.g. dialkyl maleates or fumarates
• CPC Class Codes: C08F 267/06 on to polymers of esters
• CPC Class Codes: C08F 293/00 Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule on to polymers modified by introduction of unsaturated end groups C08F290/02
• CPC Class Codes: C08J 3/07 from polymer solutions
• CPC Class Codes: C08K 5/103 with polyalcohols
• CPC Class Codes: C08K 5/1535 Five-membered rings
• CPC Class Codes: C08K 5/42 Sulfonic acids; Derivatives thereof
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C09D 135/02 Homopolymers or copolymers of esters C09D135/06, C09D135/08 take precedence
• CPC Class Codes: C09D 7/45 Anti-settling agents
• CPC Class Codes: C09D 7/65 macromolecular C09D7/41-C09D7/48 take precedence
• CPC Class Codes: C09J 11/06 : organic
• CPC Class Codes: C09J 11/08 : Macromolecular additives
• CPC Class Codes: C09J 135/02 : Homopolymers or copolymers of esters C09J135/06, C09J135/08 take precedence

Abstract

Disclosed is a block copolymer having a first polymer block including a first primary monomer that is a 1,1-disubstituted alkene compound, wherein the first primary monomer is present at a concentration of about 50 weight percent or more, based on the total weight of the first polymer block, the first polymer block covalently bonded to a second polymer block including a second primary monomer different from the first primary monomer, wherein the second primary monomer is present at a concentration of about 50 weight percent or more, based on the total weight of the second polymer block. Also disclosed is a polymer comprising at least one monomer of a 1,1-disubstituted alkene compound having a weight average molecular weight of about 3000 daltons or more, 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.

Claims

1. A composition comprising:

a block copolymer having a first polymer block including a first primary monomer that is a 1,1-disubstituted alkene compound, wherein the first primary monomer is present at a concentration of about 50 weight percent or more, based on the total weight of the first polymer block, the first polymer block covalently bonded to a second polymer block including a second primary monomer different from the first primary monomer, wherein the second primary monomer is present at a concentration of about 50 weight percent or more, based on the total weight of the second polymer block;

wherein the first polymer block has a first glass transition temperature and the second polymer block has a second glass transition temperature, wherein the first glass transition temperature and the second glass transition temperature differ by about 20°

C. or more and wherein the block copolymer 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.

2. The composition of claim 1, wherein the block copolymer has, the second polymer block and the first polymer block at different concentrations of monomers.

3. The composition of claim 2, wherein the block copolymer has a number average molecular weight of about 28,000 daltons or more.

4. The composition of claim 3, wherein the monomers includes monomers selected from a 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.

5. The composition of claim 1, wherein the block copolymer further having a third polymer block that includes a third primary monomer, wherein the third primary monomer is present at a concentration of about 50 weight percent or more, based on the total weight of the third polymer block, the third polymer block is covalently bonded to the first polymer block or the second polymer block.

6. The composition of claim 5, wherein the third primary monomer consists essentially of the first primary monomer, wherein the third polymer block and the first polymer block have different concentrations of monomers.

7. The composition of claim 1, wherein the block copolymer has a polydispersity index of about 1.5 to about 2.5.

8. The composition of claim 1, wherein the first polymer block is a homopolymer, and the second polymer block is a homopolymer.

9. The composition of claim 1, wherein the first polymer block has a number average molecular weight of about 16,000 daltons or more.

10. The composition of claim 5, wherein the second polymer block and the third polymer block each have monomers that are different than the first primary monomer.

11. The composition of claim 5, wherein the third primary monomer is a 1,1-disubstituted alkene compound, wherein the 1,1-disubstituted alkene compound of the third primary monomer is different than the 1,1-disubstitued alkene compound of the first primary monomer.