IP Library Granted Patent US 10,858,457
Granted Patent B2
US 10,858,457 · App. 16/033,718 · Granted Dec 8, 2020

Particulate polyvinyl alcohol copolymers, process for making and uses of the same

Inventors: Ghebrehiwet Ghebremeskel (Houston, TX); Masaki Kato (Houston, TX); Yuta Taoka (Houston, TX)
Assignee: KURARAY CO., LTD.
C08F8/12C09D129/04C08F216/06C08F218/08
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Quick Facts
Patent No.
US 10,858,457
App. No.
16/033,718
Granted
Dec 8, 2020
Kind
B2
Abstract

The present invention relates generally to a highly-hydrolyzed polyvinyl alcohol composition having increased cold-water solubility, a process for making such a polyvinyl alcohol composition, and various end uses thereof.

Claims (29)

1. A polyvinyl alcohol composition of particulate agglomerated polyvinyl alcohol particles, wherein:

(1) the polyvinyl alcohol is a copolymer of a monomer component consisting essentially of vinyl acetate with one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers in an amount up to about 20 mol %, based on the total monomer component, with a degree polymerization of from about 400 to about 10000, and a degree of hydrolysis of about 93% or greater; and

(2) the composition has a D(90) particle size of from about 1 μm to about 1000 μm, a bulk density of about 0.55 g/cm 3 or less, and a cold-water (20° C.) solubles of about 50% or greater.

2. The polyvinyl alcohol composition of claim 1 , having a cold-water (20° C.) solubles of about 60% or greater.

3. The polyvinyl alcohol composition of claim 1 , having a cold-water (20° C.) solubles of about 75% or greater.

4. The polyvinyl alcohol composition of claim 1 , having a cold-water (20° C.) solubles of about 80% or greater.

5. The polyvinyl alcohol composition of claim 1 , having a cold-water (20° C.) solubles of about 90% or greater.

6. The polyvinyl alcohol composition of claim 1 , having a bulk density of about 0.50 g/cm3 or less.

7. The polyvinyl alcohol composition of claim 1 , wherein an amount of the one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers is up to about 10 mol %, based on the total monomer component.

8. The polyvinyl alcohol composition of claim 1 , wherein the one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers are selected from the group consisting of methyl acrylate, methyl methacrylate and mixtures thereof.

9. The polyvinyl alcohol composition of claim 8 , wherein the polyvinyl acetate is a copolymer of a monomer component consisting essentially of vinyl acetate and methyl acrylate.

10. A polyvinyl alcohol composition produced in a slurry alcoholysis process using an alcoholysis catalyst, in which the alcoholysis catalyst has not been predominantly neutralized, wherein a polyvinyl acetate subjected to the slurry alcoholysis process is a copolymer of a monomer component consisting essentially of vinyl acetate with one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers in an amount up to about 20 mol %, based on the total monomer component; and wherein the polyvinyl alcohol of the composition has a reduced lactone ring content as compared to a polyvinyl alcohol produced under the same conditions except that a predominant amount of a residual catalyst has been neutralized;

wherein the composition is in the form of agglomerated particles having a D(90) particle size from about 1 μm to about 1000 μm, and a bulk density of less than 0.50 g/cm 3 or less.

11. A process for preparing the polyvinyl alcohol composition of particulate agglomerated polyvinyl alcohol particles of claim 1 , comprising the steps of:

(A) providing to an alcoholysis unit (i) a solution of a polyvinyl acetate in a solvent and (ii) an alkali catalyst, wherein the polyvinyl acetate is a copolymer of a monomer component consisting essentially of vinyl acetate with one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers in an amount up to about 20 mol %, based on the total monomer component;

(B) combining the solution and the alkali catalyst in the alcoholysis unit under agitation to hydrolyze the polyvinyl acetate to produce a first slurry comprising (i) a polyvinyl alcohol having a degree of hydrolysis of about 93% or greater and (ii) residual alkali catalyst;

(C) removing the first slurry from the alcoholysis unit;

(D) separating polyvinyl alcohol from the first slurry to produce a polyvinyl alcohol wet cake; and

(E) drying the polyvinyl alcohol wet cake to produce the particulate agglomerated polyvinyl alcohol particles,

wherein the residual alkali catalyst in the first slurry is predominantly not neutralized prior to the drying step.

12. The process of claim 11 , wherein the polyvinyl acetate has (i) a degree of polymerization of from about 400 to about 10000, or (ii) a degree of hydrolysis of about 99% or greater, or (iii) both (i) and (ii).

13. The process of claim 11 , wherein the polyvinyl acetate is a copolymer of a monomer component consisting essentially of vinyl acetate with one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers in an amount up to about 10 mol %, based on the total monomer component.

14. The process of claim 11 , wherein the one or more C 1 to C 8 alkyl acrylate ester monomers and/or one or more C 1 to C 8 alkyl methacrylate ester monomers are selected from the group consisting of methyl acrylate, methyl methacrylate and mixtures thereof.

15. The process of claim 14 , wherein the polyvinyl acetate is a copolymer of a monomer component consisting essentially of vinyl acetate and methyl acrylate.

16. The process of claim 11 , wherein the residual alkali catalyst in the first slurry is substantially not neutralized prior to the drying step.

17. The process of claim 11 , wherein the first slurry is removed from the alcoholysis unit at a first temperature, and the temperature of the first slurry is reduced to less than the first temperature prior to or concurrently with the separating step.

18. The process of claim 17 , wherein the temperature of the first slurry is reduced to less than 50° C.

19. The process of claim 11 , wherein the process further comprises the step of washing the polyvinyl alcohol wet cake to produce a purified polyvinyl alcohol wet cake, which is then subject to the drying step.

20. The process of claim 11 , wherein the particulate agglomerated polyvinyl alcohol particles from the drying step are substantially free-flowing particles.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 13, 2018
From: KURARAY AMERICA, INC.
To: KURARAY CO., LTD.
Reel/Frame 047762/0358 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2018
From: GHEBREMESKEL, GHEBREHIWET; KATO, MASAKI; TAOKA, YUTA
To: KURARAY AMERICA, INC.
Reel/Frame 047758/0286 →