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

• US 10,428,177 B2
• Filed: 06/01/2017
• Issued: 10/01/2019
• Est. Priority Date: 06/03/2016
• Status: Active Grant

• Current Assignee: Nippon Shokubai Company Limited
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Sullivan, Jeffrey M., Doshi, Ami
• Primary Examiner(s): Nguyen, Vu A
• Application Number:
  US15/610,854
• Publication Number:
  US 20170349701A1
• Time in Patent Office: 852 Days
• CPC Class Codes: B32B 27/36 comprising polyesters
• CPC Class Codes: C08G 63/52 Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C09D 151/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C12P 7/625 Polyesters of hydroxy carboxylic acids

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.

Claims

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.

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:

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

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.

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.

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:

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

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.