Water absorbing or water soluble polymers, intermediate compounds, and methods thereof

Patent metadata

Field	Value
Publication number	US-10428177-B2
Application number	US-201715610854-A
Country	US
Kind code	B2
Filing date	Jun 1, 2017
Priority date	Jun 3, 2016
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

Disclosed are graft copolymers, compositions including graft copolymers, intermediate materials, and related methods, where the graft copolymer includes a first polymer component including a 1,1-disubstituted-1-alkene compound (preferably a methylene malonate compound) and is grafted to a second component. The resulting graft copolymer may be hydrophilic or water soluble. The second component preferably is a hydrophilic component.

First claim

What is claimed is:

1. A grafted polymer comprising:
i. a first component including a polymer formed by polymerizing the alkene groups of one or more monomers including a 1,1-diester-1-alkene compound, attached to;
ii. a second component that is a hydrophilic component, wherein the hydrophilic component includes a cation or a water-soluble polymer;
wherein the grafted polymer has a network structure.

2. The grafted polymer of claim 1 , wherein the polymer of the first component has a first end and a second end and a backbone connecting the first and a second ends, the backbone including about 92 atomic percent or more carbon atoms.

3. The grafted polymer of claim 1 , wherein the hydrophilic component is a water-soluble polymer selected from the group consisting of a polyacrylamide, a polyvinyl alcohol, a polyacrylic acid, a polyalkoxide, a water soluble amine containing polymer, a polyethyleneimine, a polymer including quaternary ammonium compounds, a copolymer of vinyl methyl ether and maleic anhydride, polyvinylpyrrolidone, or any combination thereof.

4. The grafted polymer of claim 1 , wherein the second, component includes: i) a quaternary ammonium compound; or ii) a polyalkoxide wherein the polyalkoxide includes 65 weight percent or more ethylene oxide groups, based on the total weight of the polyalkoxide.

5. A grafted polymer comprising:
i. a first component including a polymer formed by polymerizing the alkene groups of one or more monomers including a 1,1-diester-1-alkene compound, attached to;
ii. a second component that is a hydrophilic component, wherein the hydrophilic component includes a cation or a water-soluble polymer;
wherein the one or more monomers includes a multifunctional 1,1-disubstituted-1-alkene monomer having two or more polymerizable alkene groups.

6. The grafted polymer of claim 1 , wherein the grafted polymer is characterized by one or any combination of the following:
i) about 20 atomic percent or more of the monomers of the first component are directly attached to the second component; or
ii) the first component is present in an amount of about 10 weight percent or more based on the total weight of the graft polymer; or
iii) the second component is present in an amount of about 20 weight percent or more based on the total weight of the graft polymer; or
iv) the total amount of the first component and the second component is about 50 weight percent or more based on the total weight of the graft polymer.

7. The grafted polymer of claim 1 , wherein about 10 atomic percent or more of the monomers of the first component are 1,1-diester-1-alkenes that are free of direct attachment to the hydrophilic component.

8. The grafted polymer of claim 1 , wherein:
i) the grafted polymer consists essentially of the first component consisting only of one or more 1,1-diester-1-alkene compounds, and the second component consisting only of the water-soluble polymer or the cation; and/or
ii) the grafted polymer is associated with an anion that includes a sulfonate ion or a sulfate ion.

9. The grafted polymer of claim 1 , wherein the 1,1-diester-1-alkene compound includes one or more 1,1-diester-1-alkenes having a structure:

wherein R is a hydrocarbyl group which may contain one or more heteroatoms and X is oxygen.

10. The grafted polymer of claim 1 , wherein the 1,1-diester-1-alkene compound is a methylene malonate having a structure:

wherein R is separately in each occurrence alkyl, alkenyl, C 3-9 cycloalkyl, heterocyclyl, alkyl heterocyclyl, aryl, aralkyl, alkaryl, heteroaryl, or polyoxyalkylene, or both of the R's form a 5-7 membered cyclic or heterocyclic ring.

11. The grafted polymer of claim 1 , wherein the grafted polymer includes about 30 to about 95 weight percent of the water-soluble polymer, based on the total weight of the grafted polymer.

12. The grafted polymer of claim 5 , wherein the polymer of the first component has a first end and a second end and a backbone connecting the first and a second ends, the backbone including about 92 atomic percent or more carbon atoms, based on the total atomic percent.

13. The grafted polymer of claim 5 , wherein the hydrophilic component is a water-soluble polymer selected from the group consisting of a polyacrylamide, a polyvinyl alcohol, a polyacrylic acid, a polyalkoxide, a water soluble amine containing polymer, a polyethyleneimine, a polymer including quaternary ammonium compounds, a copolymer of vinyl methyl ether and maleic anhydride, polyvinylpyrrolidone, or any combination thereof.

14. The grafted polymer of claim 5 , wherein the second component includes: i) a quaternary ammonium compound; or ii) a polyalkoxide wherein the polyalkoxide includes 65 weight percent or more ethylene oxide groups, based on the total weight of the polyalkoxide.

15. The grafted polymer of claim 5 , wherein the grafted polymer is characterized by one or any combination of the following:
i) about 20 atomic percent or more of the monomers of the first component e directly attached to the second component; or
ii) the first component is present in an amount of about 10 weight percent or more based on the total weight of the graft polymer; or
iii) the second component is present in an amount of about 20 weight percent or more based on the total weight of the graft polymer; or
iv) the total amount of the first component and the second component is about 50 weight percent or more based on the total weight of the graft polymer.

16. The grafted polymer of claim 5 , wherein about 10 atomic percent or more of the monomers of the first component are 1,1-diester-1-alkenes that are free of direct attachment to the hydrophilic component.

17. The grafted polymer of claim 5 , wherein:
i) the grafted polymer consists essentially of the first component consisting only of one or more 1,1-diester-1-alkene compounds, and the second component consisting only of the water-soluble polymer or the cation; and/or
ii) the grafted polymer is associated with an anion that includes a sulfonate ion or a sulfate ion.

18. The grafted polymer of claim 5 , wherein the 1,1-diester-1-alkene compound includes one or more 1,1-diester-1-alkenes having a structure:

wherein R is a hydrocarbyl group which may contain one or more heteroatoms and X is oxygen.

19. The grafted polymer of claim 5 , wherein the 1,1-diester-1-alkene compound is a methylene malonate having a structure:

wherein R is separately in each occurrence alkyl, alkenyl, C 3-9 cycloalkyl, heterocyclyl, alkyl heterocyclyl, aryl, aralkyl, alkaryl, heteroaryl, or polyoxyalkylene, or both of the R's form a 5-7 membered cyclic or heterocyclic ring.

20. The grafted polymer of claim 5 , wherein the grafted polymer includes about 30 to about 95 weight percent of the water-soluble polymer, based on the total weight of the grafted polymer.

Assignees

• Sirrus Inc

Inventors

• Sullivan Jeffrey M
• Doshi Ami

Classifications

• B32B27/36

  comprising polyesters · CPC title

• C08G63/52 Primary

  Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title

• C09D151/08

  grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C12P7/625 Primary

  Polyesters of hydroxy carboxylic acids · CPC title