Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed thereform

Patent metadata

Field	Value
Publication number	US-10611861-B2
Application number	US-201815978923-A
Country	US
Kind code	B2
Filing date	May 14, 2018
Priority date	Oct 19, 2011
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

The present invention provides multifunctional monomers, including, but not limited to include multifunctional methylene malonate and methylene beta-ketoester monomers; methods for producing the same; and compositions and products formed therefrom. The multifunctional monomers of the invention may be produced by transesterification or by direct synthesis from monofunctional methylene malonate monomers or methylene beta-ketoester monomers. The present invention further compositions and products formed from methylene beta-ketoester monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).

First claim

What is claimed is:

1. A multifunctional monomer having the formula:

wherein:
each instance of R 1 and R 2 are independently C 3 -C 6 cycloalkyl;
[A] is independently selected from a polyether linking group; and
each instance of Q is —O— or a direct bond.

2. The multifunctional monomer according to claim 1 , wherein [A] is independently selected from a polyethylene glycol linking group or a polytetrahydrofuran linking group wherein the linking group corresponds to the formula [—(CH 2 CH 2 —O) n ] or [(CH 2 CH 2 CH 2 CH 2 —O] n wherein n is from 1 to 6.

3. The multifunctional monomer according to claim 1 , wherein [A] is independently selected from a polyethylene glycol linking group or a polytetrahydrofuran linking group wherein the linking group corresponds to the formula [—(CH 2 CH 2 —O) n —] or [CH 2 CH 2 CH 2 —O] n wherein n is from 3 to 6.

4. The multifunctional monomer according to claim 1 , wherein each instance Q is —O—.

5. A multifunctional monomer according to claim 1 , having the formula:

wherein n is an integer from 1-6.

6. The multifunctional monomer according to claim 5 , wherein n is 3 to 6.

7. The multifunctional monomer according to claim 5 , wherein n is 3.

8. The multifunctional monomer according to claim 1 , wherein A is polytetrahydrofuran.

9. The multifunctional monomer according to claim 1 , wherein R 1 and R 2 are cyclohexyl.

10. A multifunctional monomer according to the formula:

wherein:
each instance of R 1 and R 2 are independently C 1 -C 15 alkyl, C 2 -C 15 alkenyl, or C 3 -C 6 cycloalkyl,
-[A]- is —(CR A R B ) n —;
each instance of R A or R B is independently H, C 1 -C 15 alkyl, C 2 -C 15 alkenyl, or a moiety corresponding to the formula:

-L- is a linking group selected from the group consisting of alkylene, alkenylene, or alkoxy-(alkylene), each of which may be optionally branched and each of which may be optionally substituted by alkyl or C 1 -C 15 alkoxy each of which may be optionally branched;
R 3 is independently selected from the group defined in R 2 above; and
each instance of n is independently an integer from 3 to 6; and

each instance of Q is —O— or a direct bond.

11. The multifunctional monomer according to claim 10 , wherein each instance of R 1 and R 2 are independently C 1 -C 15 alkyl or C 3 -C 6 cycloalkyl,
-[A]- is (CR A R B ) n —;
each instance of R A or R B is independently H, C 1 -C 15 alkyl, or a moiety corresponding to the formula:

-L- is a linking group selected from the group consisting of alkylene or alkoxy-(alkylene), each of which may be optionally branched; and
R 3 is independently selected from the group defined in R 2 .

12. The multifunctional monomer according to claim 11 , wherein each instance of R 1 and R 2 are independently C 1 -C 15 alkyl or C 3 -C 6 cycloalkyl,
each instance of R A or R B is independently H or a moiety corresponding to the formula:

-L- is a linking group selected from the group consisting of alkoxy-(alkylene); and
R 3 is independently selected from group defined in R 2 .

13. A multifunctional monomer according to the formula:

wherein:
each instance of R 1 and R 2 are independently C 1 -C 15 alkyl, C 2 -C 15 alkenyl, or C 3 -C 6 cycloalkyl,
-[A]- is —(CH 2 ) n —[CY]—(CH 2 ) n ;
each instance of n is independently an integer from 1 to 25;
each instance of Q is —O— or a direct bond; and
each instance of —[CY]— is an alkenyl, haloalkyl, cycloalkyl, halo cycloalkyl, or aryl-(alkyl) group.

14. The multifunctional monomer according to claim 13 , wherein each instance of R 1 and R 2 are independently C 1 -C 15 alkyl or C 3 -C 6 cycloalkyl,
each instance of —[CY]— is a cycloalkyl group; and
each instance of Q is —O—.

15. The multifunctional monomer according to claim 14 , wherein each instance of R 1 and R 2 are independently C 1 -C 15 alkyl or C 3 -C 6 cycloalkyl,
each instance of —[CY]— is a cycloalkyl group; and
each instance of Q is a direct bond.

Assignees

• Sirrus Inc

Inventors

• Malofsky Bernard M
• Malofsky Adam G
• Dey Tanmoy
• Ellison Matthew M
• Hines Larry

Classifications

• C08L21/00

  Compositions of unspecified rubbers · CPC title

• C07C49/794

  having unsaturation outside an aromatic ring · CPC title

• C07D307/54

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C08L35/02

  Homopolymers or copolymers of esters (C08L35/06, C08L35/08 take precedence) · CPC title

• C09J133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title