Polymers based on glycerol carbonate

Patent metadata

Field	Value
Publication number	US-9994674-B2
Application number	US-201213397879-A
Country	US
Kind code	B2
Filing date	Feb 16, 2012
Priority date	Feb 22, 2011
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The present invention relates to a polymer and the associated polymerization process, and to the use of the polymers according to the invention for example as foam suppressant, for the dispersion of solids or as surfactant for washing or cleaning purposes. The polymer is prepared by polymerization of
a) at least one alkylene oxide or a cyclic carbonate of the formula (I)

where
n is 1 to 10,
m is 0 to 3 and
R 1 is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, aryl or aralkyl,

b) glycerol carbonate,
where the polymerization is carried out in the presence of at least one base.

First claim

I claim:

1. A polymer prepared by a process of polymerization of monomers, the monomers consisting of
a) at least one alkylene oxide, and
b) glycerol carbonate,
wherein the polymerization is carried out in the presence of at least one base with the release of CO 2 , and the polymer has no ester bonds, wherein the component a) comprises as alkylene oxide a monomer selected from the group consisting of styrene oxide, epichlorohydrin, glycidol, 1-nonene oxide, 1-decene oxide, 1-undecene oxide, and 1-dodecene oxide.

2. The polymer according to claim 1 , wherein the polymerization is carried out as base-initiated polyaddition or a base selected from the group consisting of KOH, KOCH 3 , KO(t-Bu), KH, NaOH, NaO(t-Bu), NaOCH 3 , NaH, Na, K, trimethylamine, N,N-dimethylethanolamine, N,N-dimethylcyclohexylamine and higher N,Ndimethylalkylamines, N,N-dimethylaniline, N,N-dimethylbenzylamine, N,N,NN-tetramethylethylenediamine, N,N,N′,N″,N″-pentamethyldiethylenetriamine, imidazole, N-methylimidazole, 2-methylimidazole, 2,2-dimethylimidazole, 4-methylimidazole, 2,4,5-trimethylimidazole and 2-ethyl-4-methylimidazole.

3. The polymer according to claim 2 , wherein the base is used in amounts of from 0.05 to 20% by weight (based on the amount of polymer).

4. The polymer according to claim 1 , wherein the polymer is a random copolymer, a block copolymer, a comb polymer, a multiblock copolymer or a gradient copolymer.

5. The polymer according to claim 1 , wherein the polymer comprises one or more fragments according to the formulae (II) to (IV)

where A, B and C, independently of one another, are formed from the component a), Gly is formed from the component b),
where, in the formula (II), n and m, independently of one another, have values between 1 and 1000 and p has values between 0 and 1000,
where, in the formula (III), n, m, p and q, independently of one another, have values between 1 and 1000,
where, in the formula (IV), n, m, p, v and y, independently of one another, have values between 1 and 1000 and q, s, t, u, w and x, independently of one another, have values between 0 and 1000.

6. A material which comprises the polymer according to claim 1 , wherein the material is a foam suppressant; a foam regulator; a foam booster; a dispersant; an emulsifier; a wetting agent; a lubricant; a process for dispersing solids; a thickener for thickening aqueous solutions; a carrier or filling material for pharmaceutical preparations; a surfactant for washing or cleaning purposes; a surfactant for the cleaning of hard surfaces; a humectant; a cosmetic formulation; a pharmaceutical formulation; a crop protection formulation; an adjuvant or solubilizer for active ingredients; a paint; an ink; a pigment preparation; a coating composition; an adhesive; a leather degreasing composition; a formulation for the textile industry, a fiber processing, a water treatment or the production of drinking water; a food industry composition; a paper industry composition; a construction auxiliary; a di- or polyol for the preparation of polyadducts or polymers; a coolant and lubricant; a fermentation composition; a mineral processing or metal processing composition.

7. The polymer according to claim 1 , wherein the polymerization is carried out at 120° C. to 205° C.

8. A polymer prepared by polymerization of monomers consisting of components a) and b):
a) at least a cyclic carbonate of the formula (I)

where

n is 1 to 10,
m is 0 to 3 and
R 1 is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, aryl or aralkyl,
b) glycerol carbonate,

wherein the polymerization is carried out in the presence of at least one base and with the release of CO 2 , and wherein the polymer has no ester bonds.

9. The polymer according to claim 8 , wherein the polymerization is carried out as base-initiated polyaddition or a base selected from the group consisting of KOH, KOCH 3 , KO(t-Bu), KH, NaOH, NaO(t-Bu), NaOCH 3 , NaH, Na, K, trimethylamine, N,N-dimethylethanolamine, N,N-dimethylcyclohexylamine and higher N,Ndimethylalkylamines, N,N-dimethylaniline, N,N-dimethylbenzylamine, N,N,N′N′-tetramethylethylenediamine, N,N,N′,N″,N″-pentamethyldiethylenetriamine, imidazole, N-methylimidazole, 2-methylimidazole, 2,2-dimethylimidazole, 4-methylimidazole, 2,4,5-trimethylimidazole and 2-ethyl-4-methylimidazole.

10. The polymer according to claim 9 , wherein the base is used in amounts of from 0.05 to 20% by weight (based on the amount of polymer).

11. The polymer according to claim 8 , wherein the polymer is a random copolymer, a block copolymer, a comb polymer, a multiblock copolymer or a gradient copolymer.

12. The polymer according to claim 8 , wherein the polymer comprises one or more fragments according to the formulae (II) to (IV)

where A, B and C, independently of one another, are formed from the component a), Gly is formed from the component b),
where, in the formula (II), n and m, independently of one another, have values between 1 and 1000 and p has values between 0 and 1000,
where, in the formula (III), n, m, p and q, independently of one another, have values between 1 and 1000,
where, in the formula (IV), n, m, p, v and y, independently of one another, have values between 1 and 1000 and q, s, t, u, w and x, independently of one another, have values between 0 and 1000.

13. The polymer according to claim 1 , wherein the base is selected from the group consisting of KH, NaH, Na, K, trimethylamine, N,N-dimethylethanolamine, N,N-dimethylcyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, N,N,N′N′-tetramethylethylenediamine, N,N,N′,N″,N″-pentamethyldiethylenetriamine, imidazole, N-methylimidazole, 2-methylimidazole, 2,2-dimethylimidazole, 4-methylimidazole, 2,4,5-trimethylimidazole and 2-ethyl-4-methylimidazole.

14. The polymer according to claim 8 , wherein the base is present from 0.05 to 20% by weight (based on the amount of polymer), the base is selected from the group consisting of KH, NaH, Na, K, trimethylamine, N,N-dimethylethanolamine, N,N-dimethylcyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, N,N,NN-tetramethylethylenediamine, N,N,N′,N″,N″-pentamethyldiethylenetriamine, imidazole, N-methylimidazole, 2-methylimidazole, 2,2-dimethylimidazole, 4-methylimidazole, 2,4,5-trimethylimidazole and 2-ethyl-4-methylimidazole.

Assignees

• Raether Roman Benedikt
• Basf Se

Inventors

• Raether Roman Benedikt

Classifications

• C08G64/302 Primary

  and cyclic ethers · CPC title

• C08G65/2603

  the other compounds containing oxygen · CPC title

• C08G64/30

  using carbonates · CPC title