Polymers including one or more 1,1-disubstituted alkene compounds and polymer compositions thereof

Patent metadata

Field	Value
Publication number	US-10308802-B2
Application number	US-201515509403-A
Country	US
Kind code	B2
Filing date	Sep 8, 2015
Priority date	Sep 8, 2014
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

The disclosure relates to polymers including one or more 1,1-disubstituted alkene monomers. By employing a plurality of monomers and/or tailored chain structure, polymers having improved combinations of properties are achieved. The polymer may be a copolymer, preferably including two or more 1,1-disubstituted alkene monomers. The polymer may be a homopolymer having a tailored chain structure.

First claim

What is claimed is:

1. A copolymer comprising:
i) from about 2 weight percent to about 98 weight percent of a first monomer; and
ii) from about 2 weight percent to about 98 weight percent of a second monomer;
wherein the first monomer is one or more 1,1-disubstituted alkene monomers, wherein the 1,1-disubstituted alkene monomer includes a central carbon atom doubly bonded to another carbon atom and further bonded to two carbonyl groups;
wherein the first monomer has a structure such that homopolymers of the first monomer have a Tg of about 50° C. or more;
the second monomer has a structure such that homopolymers of the second monomer have a Tg of about 15° C. or less; and
wherein the copolymer has a single glass transition temperature of about −100° C. to about 15° C.; and wherein the first monomer corresponds to Formula IIA;

wherein R 1 and R 2 are each hydrocarbyl groups that may be the same or different;
wherein weight percent is based on total weight of the copolymer.

2. The copolymer of claim 1 , wherein the first monomer is present at a concentration of about 20 weight percent or more, based on the total weight of the copolymer and the second monomer is present at a concentration of about 20 weight percent or more, based on the total weight of the copolymer.

3. A copolymer comprising:
i) from about 2 weight percent to about 98 weight percent of a first monomer; and
ii) from about 2 weight percent to about 98 weight percent of a second monomer;
wherein the first monomer is one or more 1,1-disubstituted alkene monomers, wherein the 1,1-disubstituted alkene monomer includes a central carbon atom doubly bonded to another carbon atom and further bonded to two carbonyl groups;
wherein the first monomer has a structure such that homopolymers of the first monomer have a Tg of about 50° C. or more; and
the second monomer has a structure such that homopolymers of the second monomer have a Tg of about 15° C. or less; and

wherein the copolymer has a single glass transition temperature of about −100° C. to about 15° C. and the first monomer is a first 1,1-disubstituted alkene monomer and the second monomer is a second 1,1-disubstituted alkene monomer different from the first monomer; and
the total concentration of the first monomer and the second monomer is about 30 weight percent or more, based on the total weight of the copolymer.

4. The copolymer of claim 2 , wherein the copolymer includes one or more additional monomers different from the first monomer and the second monomer.

5. The copolymer of claim 1 , wherein the first monomer is selected from the group consisting of dimethyl methylene malonate, phenylpropyl methyl methylene malonate, fenchyl methyl methylene malonate, fenchyl ethyl methylene malonate, menthyl ethyl methylene malonate, phenylpropyl ethyl methylene malonate, dicyclohexyl methylene malonate, cyclohexyl ethyl methylene malonate, isobornyl ethyl methylene malonate, benzyl ethyl methylene malonate, benzyl methyl methylene malonate, dibenzyl methylene malonate, and any combination thereof.

6. The copolymer of claim 5 , wherein the second monomer is selected from the group consisting of methylmethoxy ethyl methylene malonate, ethylethoxy ethyl methylene malonate, hexyl methyl methylene malonate, dibutyl methylene malonate, dihexyl methylene malonate, hexyl ethyl methylene malonate, and any combination thereof.

7. The copolymer of claim 1 , wherein the copolymer is a block copolymer including a first polymer block attached to a second polymer block, wherein the first polymer block includes the first monomer.

8. A copolymer comprising:
i) from about 2 weight percent to about 98 weight percent of a first monomer; and
ii) from about 2 weight percent to about 98 weight percent of a second monomer;
wherein the first monomer is one or more 1,1-disubstituted alkene monomers, wherein the 1,1-disubstituted alkene monomer includes a central carbon atom doubly bonded to another carbon atom and further bonded to two carbonyl groups,
wherein the copolymer is a block copolymer including a first polymer block attached to a second polymer block, wherein the first polymer block includes the first monomer,
wherein the copolymer has a first glass transition of about 25° C. to about 250° C., and the copolymer has a second glass transition temperature from about −100° C. to about 15° C.; and
wherein a difference in a melting point of the first polymer block and the second polymer block is about 10° C. or more.

9. The copolymer of claim 7 , wherein
(i) the first polymer block includes about 50 weight percent or more of one or more monomers selected from the group consisting of diethyl methylene malonate, dimethyl methylene malonate, phenylpropyl methyl methylene malonate, phenylpropyl methyl methylene malonate fenchyl methyl methylene malonate, fenchyl ethyl methylene malonate, menthyl ethyl methylene malonate, phenyl propyl ethyl methylene malonate, dicyclohexyl methylene malonate, cyclohexyl ethyl methylene malonate, isobornyl ethyl methylene malonate, benzyl ethyl methylene malonate, benzyl methyl methylene malonate, dibenzyl methylene malonate, and any combination thereof; or
(ii) the second polymer block includes from about 50 weight percent or more of one or more monomers selected from the group consisting of methylmethoxy ethyl methylene malonate, ethylethoxy ethyl methylene malonate, hexyl methyl methylene malonate, dibutyl methylene malonate, dihexyl methylene malonate, hexyl ethyl methylene malonate, and any combination thereof.

10. The copolymer of claim 7 , wherein
(i) the copolymer includes three or more polymer blocks; or
(ii) the copolymer is a diblock copolymer or a triblock copolymer having a structure of A-B-A or A-B-C, wherein A, B, and C are different blocks each having different monomers or a monomer at a different concentration.

11. The copolymer of claim 1 , wherein the copolymer is a random copolymer having a blockiness index of about 0.6 or more.

12. The copolymer of claim 1 , wherein
i) the copolymer has 1 or more long chain branches; or
the copolymer has 5 or more arms; or
the copolymer includes one or more multifunctional monomers.

13. The copolymer of claim 1 , wherein the second monomer is not a 1,1-disubstituted alkene monomer.

Assignees

• Sirrus Inc

Inventors

• Sullivan Jeffrey M
• Palsule Aniruddha Sudhir
• Holzer Alexander R
• Stevenson Peter R
• Parab Kshitij K

Classifications

• C07C69/38

  Malonic acid esters · CPC title

• C08F293/00

  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 title

• C09D135/02

  Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence) · CPC title

• C08L33/04 Primary

  Homopolymers or copolymers of esters {(C08L43/04 takes precedence)} · CPC title

• C08F222/14

  Esters having no free carboxylic acid groups {, e.g. dialkyl maleates or fumarates} · CPC title