# US 10,308,802 B2 · Polymers including one or more 1,1-disubstituted alkene compounds and polymer compositions thereof

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- Number: US 10,308,802 B2
- Document ID: US10308802B2
- Status: Granted
- Kind: B2
- Application number: 15/509,403
- Filed: 2015-09-08
- Published: 2017-09-28
- Granted: 2019-06-04
- Earliest claimed: 2014-09-08
- Assignees: Sirrus, Inc.
- Applicants: Sirrus, Inc.
- Inventors: Jeffrey M. Sullivan; Aniruddha Sudhir Palsule; Alexander R. Holzer; Peter R. Stevenson; Kshitij K. Parab
- Web page: https://patentgrep.com/patent/US10308802B2

## CPC

- C09D 7/45: Anti-settling agents
- B01J 19/10: employing sonic or ultrasonic vibrations
- B01J 19/18: Stationary reactors having moving elements inside (B01J19/08, B01J19/26 take precedence)
- C07C 69/38: Malonic acid esters
- C08F 2/22: Emulsion polymerisation
- C08F 2/26: anionic
- C08F 2/30: non-ionic
- C08F 22/10: Esters
- C08F 122/14: Esters having no free carboxylic acid groups
- C08F 222/10: Esters
- C08F 222/14: Esters having no free carboxylic acid groups {, e.g. dialkyl maleates or fumarates}
- C08F 267/06: on to polymers of esters
- 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)
- C08J 3/07: from polymer solutions
- C08L 33/04: Homopolymers or copolymers of esters {(C08L43/04 takes precedence)}
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- C09J 11/06: organic
- C09J 11/08: Macromolecular additives
- C09J 135/02: Homopolymers or copolymers of esters (C09J135/06, C09J135/08 take precedence)
- C08K 5/103: with polyalcohols
- C08K 5/1535: Five-membered rings
- C08K 5/42: Sulfonic acids; Derivatives thereof
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## 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.

## Claims

### Claim 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 R1 and R2 are each hydrocarbyl groups that may be the same or different;
wherein weight percent is based on total weight of the copolymer.

### Claim 2 (depends on 1)

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.

### Claim 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.

### Claim 4 (depends on 2)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 5)

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.

### Claim 7 (depends on 1)

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.

### Claim 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.

### Claim 9 (depends on 7)

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.

### Claim 10 (depends on 7)

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.

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 1)

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