Absorbent polymers, and methods and systems of producing thereof and uses thereof

Patent metadata

Field	Value
Publication number	US-2019255512-A1
Application number	US-201716346853-A
Country	US
Kind code	A1
Filing date	Oct 31, 2017
Priority date	Nov 2, 2016
Publication date	Aug 22, 2019
Grant date	—

Abstract

Provided herein are absorbent polymers produced from beta-propiolactone, and methods and systems of producing such polymers. The beta-propiolactone may be derived from ethylene oxide and carbon monoxide. The absorbent polymer may be bio-based and/or biodegradable. The absorbent polymers may be used for diapers, adult incontinence products, and feminine hygiene products, as well as for agricultural applications.

First claim

1 . A method of producing a polymer, comprising:
combining beta-propiolactone with a metal compound of formula M, M 2 O, MOH, or M + CH 2 ═CHCOO − ), or a combination thereof, to produce acrylic acid, a salt thereof, or a combination thereof; and polymerizing the acrylic acid, a salt thereof, or a combination thereof, with a polymerization initiator and optionally a cross-linker to produce the polymer.

2 . The method of claim 1 , wherein the polymerizing is performed neat or in a non-aqueous media.

3 . A method of producing a polymer, comprising:
a) polymerizing beta-propiolactone with an ionic initiator in a reactor to produce a polymer intermediate, wherein the polymer intermediate has a polyacrylic acid backbone and a plurality of polypropiolactone side chains; b) increasing the temperature of the reactor to produce acrylic acid from at least a portion of the side chains in the polymer intermediate, and to produce acrylate polymer from at least a portion of the polymeric backbone of the polymer intermediate by thermolysis of the polymer intermediate; c) adding a metal compound of formula M, M 2 O, MOH, or (CH 2 ═CHCOO − ), or a combination thereof, to the reactor to at least partially neutralize the acrylic acid in the reactor to produce a mixture, wherein the mixture in the reactor comprises acrylic acid and M + (CH 2 ═CHCOO − ), wherein M is a Group I metal; and d) polymerizing at least a portion of the mixture in the reactor to produce the polymer, wherein the polymer comprises repeating units of

or a combination thereof.

4 . The method of claim 3 , wherein steps (c) and (d) are performed neat or in a non-aqueous media.

5 . The method of claim 3 wherein the ionic initiator comprises a salt of an alkali metal, a salt of an alkali-earth metal, or a combination thereof.

6 . The method of claim 3 wherein the ionic initiator comprises a carboxylate salt of an alkali metal, a salt of an alkali-earth metal, or a combination thereof.

7 . The method of claim 3 wherein the ionic initiator is a salt of an alkali metal.

8 . The method of claim 3 wherein the ionic initiator has a structure of formula CH 2 ═CH 2 CO 2 − Z + , wherein Z + is an alkali metal, an alkali earth metal, ammonium, a quaternary ammonium cation, or phosphonium.

9 . The method of claim 8 , wherein the quaternary ammonium cation is a lower alkyl quaternary ammonium cation.

10 . The method of claim 3 wherein the ionic initiator is sodium acrylate, or potassium acrylate, or a combination thereof.

11 . The method of claim 3 wherein the ionic initiator is a methacrylate.

12 . The method of claim 1 wherein M is a Group I metal.

13 . The method of claim 1 wherein M is sodium.

14 . The method of claim 1 wherein the polymerizing is performed in the presence of a polymerization initiator.

15 . The method of claim 14 , wherein the polymerization initiator is a radical initiator.

16 . The method of claim 15 , wherein the radical initiator comprises a peroxide, a persulfate, or an azo compound, or a combination thereof.

17 . The method of claim 15 , wherein the radical initiator is a redox initiator.

18 . The method of claim 15 , wherein the radical initiator comprises a hydroperoxide.

19 . The method of claim 15 , wherein the radical initiator comprises hydrogen peroxide.

20 . The method of claim 14 , wherein the polymerization initiator is a thermal initiator, or a photo initiator, or a combination thereof.

21 . The method of claim 14 , wherein the polymerization initiator is a peroxide or an acid.

22 . The method of claim 3 further comprising adding a cross-linker to the reactor in step (d) to polymerize at least a portion of the mixture in the reactor to produce the polymer, wherein the polymer is cross-linked.

23 . The method of claim 3 further comprising:
isolating at least a portion of the polymer produced in step (d); and
combining the isolated polymer with additional beta-propiolactone to produce additional polymer intermediate.

24 . A method of producing a polymer, comprising:
combining beta-propiolactone with a metal compound in a main reactor, wherein the metal compound initiates the polymerization of at least a portion of the beta-propiolactone to produce polypropiolactone in the main reactor; thermolyzing at least a portion of the polypropiolactone in the main reactor to produce acrylic acid; volatizing at least a portion of the acrylic acid in the main reactor; passing the volatilized acrylic acid through a distillation column; combining acrylic acid obtained from the distillation column with a radical initiator, optional cross-linker, and additional metal compound in a kneader reactor to produce a partially neutralized polyacrylic acid; and feeding the partially neutralized polyacrylic acid from the kneader reactor to the main reactor, wherein the carboxylate end groups of the partially neutralized polyacrylic acid initiates polymerization of at least a portion of the beta-propiolactone in the main reactor to produce a polymer with polypropiolactone branches.

25 . The method of claim 24 , further comprising isolating a product stream from the main reactor, wherein the product stream comprises the polymer with polypropiolactone branches.

26 . The method of claim 25 , wherein the product stream further comprises unreacted beta-propiolactone.

27 . The method of claim 24 , further comprising separating a polymer stream comprising the polymer with polypropiolactone branches from a recycling stream comprising the unreacted beta-propiolactone.

28 . The method of claim 27 , further comprising feeding the recycling stream into the main reactor.

29 . The method of claim 24 , wherein the metal compound is a compound of formula M, M 2 O, MOH, or M + (CH 2 ═CHCOO − ), or a combination thereof.

30 . The method of claim 29 , wherein is a Group I metal.

31 . The method of claim 29 , wherein M is sodium.

32 . The method of claim 24 , wherein the radical initiator comprises a peroxide, a persulfate, or an azo compound, or a combination thereof.

33 . The method of claim 24 , wherein the radical initiator is a redox initiator.

34 . The method of claim 24 wherein the radical initiator comprises a hydroperoxide.

35 . The method of claim 24 , wherein the radical initiator comprises hydrogen peroxide.

36 . The method of claim 1 wherein the method is continuous.

37 . The method of claim 1 further comprising carbonylating ethylene oxide to produce the beta-propiolactone.

38 . The method of claim 1 further comprising combining ethylene oxide and carbon monoxide in the presence of a carbonylation catalyst and optionally a solvent to produce the beta-propiolactone.

39 . A polymer produced according to claim 1 .

40 . An absorbent article, comprising a polymer of claim 39 .

41 . The absorbent article of claim 40 , further comprising at least one inorganic or organic additive.

42 . The absorbent article of claim 40 wherein the a

Assignees

• Novomer Inc

Inventors

• Lee Han
• Ruhl John B
• Lapointe Robert E
• Sherry Kyle
• Tseitlin Alexander
• Sookraj Sadesh H

Classifications

• C08F220/06 Primary

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• B01J20/264 Primary

  derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers · CPC title

• B01J19/06

  Solidifying liquids (making microcapsules B01J13/02) · CPC title

• B01J19/0013

  Controlling the temperature of the process · CPC title

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title