Water-mediated polyester (meth)acrylation systems

Patent metadata

Field	Value
Publication number	US-11866523-B2
Application number	US-202117223722-A
Country	US
Kind code	B2
Filing date	Apr 6, 2021
Priority date	Apr 6, 2020
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

A water-mediated process prepares a polymeric (meth)acrylation composition. In some embodiments, the process includes providing a stabilized aqueous solution including a (meth)acrylation component and a polyol monomer in a vessel under an inert atmosphere and adding a diacid monomer to the vessel under the inert atmosphere. In some embodiments, the process includes providing a stabilized aqueous solution including a (meth)acrylation component and a copolymer of a polyol monomer and a diacid monomer in a vessel under an inert atmosphere. The process further includes heating and removing water from the vessel under the inert atmosphere to produce the polymeric (meth)acrylation composition. The polymeric (meth)acrylation composition includes a (meth)acrylation polyester copolymer of the diacid monomer and the polyol monomer with the (meth)acrylation component conjugated to the (meth)acrylation polyester copolymer. In some embodiments, the polymeric (meth)acrylation composition is free of mineral acid and free of cytotoxic solvents, catalysts, and scavengers.

First claim

What is claimed is:

1. A water-mediated process of preparing a polymeric (meth)acrylation composition, comprising the steps of:
providing a stabilized aqueous solution comprising at least one (meth)acrylation component and a polyol monomer in a vessel under an inert atmosphere;
adding a diacid monomer to the vessel under the inert atmosphere; and
heating and removing water from the vessel under the inert atmosphere to produce the polymeric (meth)acrylation composition;
wherein the polymeric (meth)acrylation composition comprises a (meth)acrylation polyester copolymer of the diacid monomer and the polyol monomer with the at least one (meth)acrylation component conjugated to the (meth)acrylation polyester copolymer.

2. The process of claim 1 , wherein the stabilized aqueous solution aids in preventing propagation and initiation of a free radical polymerization of the (meth)acrylate during the combining, the adding; and the heating and removing.

3. The process of claim 1 further comprising degassing an aqueous solution to form the stabilized aqueous solution.

4. The process of claim 1 further comprising adding a free radical stabilizer, a polymerization inhibitor, or a combination thereof to an aqueous solution to form the stabilized aqueous solution.

5. The process of claim 1 , wherein the at least one (meth)acrylation component comprises a (meth)acrylate.

6. The process of claim 1 , wherein the at least one (meth)acrylation component comprises a photoinitiator.

7. The process of claim 6 , wherein the photoinitiator is selected from the group consisting of ethyl eosin, eosin Y, fluorescein, 2,2-dimethoxy, 2-phenylacetophenone, 2-methoxy, 2-phenylacetophenone, camphorquinone, rose bengal, methylene blue, erythrosin, phloxime, thionine, riboflavin, and methylene green.

8. The process of claim 6 , wherein the photoinitiator comprises riboflavin.

9. The process of claim 1 , wherein the at least one (meth)acrylation component comprises a co-initiator.

10. The process of claim 9 , wherein the co-initiator is selected from the group consisting of triethanolamine, triethylamine, ethanolamine, N-methyl diethanolamine, N,N-dimethyl benzylamine, N-benzyl ethanolamine, N-isopropyl benzylamine, tetramethyl ethylenediamine, potassium persulfate, tetramethyl ethylenediamine, lysine, ornithine, histidine, and arginine.

11. The process of claim 9 , wherein the co-initiator comprises arginine.

12. The process of claim 1 , wherein the heating and removing water from the vessel comprises refluxing the at least one (meth)acrylation component, the polyol monomer, the aqueous solution, and the diacid monomer.

13. The process of claim 1 , wherein the polyol monomer comprises glycerol.

14. The process of claim 1 , wherein the diacid monomer comprises sebacic acid.

15. The process of claim 1 , wherein the polymeric (meth)acrylation composition is free of mineral acid and free of cytotoxic solvents, catalysts, and scavengers.

Assignees

• Secant Group Llc

Inventors

• Gabriele Peter D
• Radzinski Scott
• Harris Jeremy J
• Ginn Brian

Classifications

• C08F2/10 Primary

  Aqueous solvent · CPC title

• C08F2/50

  with sensitising agents · CPC title

• C08F120/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F2438/02

  Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO] · CPC title

• C08G63/20

  Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups · CPC title