IP Library Granted Patent US 10,800,867
Granted Patent B2
US 10,800,867 · App. 14/648,885 · Granted Oct 13, 2020

Process to produce polyvinyl-ester compositions with low residual monomer and the use thereof

Inventors: François Simal (Ottignies-Louvain-la-Neuve, BE); Nathalie Haveaux (Ottignies-Louvain-la-Neuve, BE); Aurélien Laurant (Ottignies-Louvain-la-Neuve, BE)
Assignee: HEXION INC.
C08F220/68C08F2/001C08F6/003C08F6/006C08F218/10
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Quick Facts
Patent No.
US 10,800,867
App. No.
14/648,885
Granted
Oct 13, 2020
Kind
B2
Abstract

A process for reducing the amount of residual monomer in aqueous polymerization emulsion by using a sequential polymerization steps, The first step consists in adding an emulsion, of vinyl ester of alkyl of C1 to C18 carboxylic acids, to water containing a radical initiator, the second step consists in adding further an emulsion of alkyl acrylate and/or methacrylate, and the third step consists in c) adding to polymeric emulsion, resulting of the steps a) and b), pure liquid acrylate or methacrylate with alkyl chain of C 1 to C 12 .

Claims (10)

1. A process for reducing the amount of residual vinyl ester monomer in a vinyl ester-acrylate co-polymeric emulsion by using sequential polymerization steps consisting essentially of:

a) adding a pre-emulsion consisting essentially of monomers of vinyl ester of alkyl of C1 to C18 carboxylic acids to water containing a radical initiator;

b) adding to a) a pre-emulsion consisting essentially of monomers of alkyl acrylate, an emulsion consisting essentially of monomers of alkyl methacrylate, or a combination thereof to form a polymeric emulsion; and

c) adding to the polymeric emulsion one or more monomers of liquid acrylates, methacrylates, or combinations thereof, wherein each of the one or more liquid acrylates or methacrylates monomers comprise an alkyl chain of C1 to C16, and forming the vinyl ester-acrylate co-polymeric emulsion, wherein the vinyl ester-acrylate co-polymer is a co-polymer of vinyl ester monomers and acrylate monomers, methacrylate monomers, or combinations thereof.

2. The process of claim 1 , wherein the vinyl ester of alkyl of C1 to C18 carboxylic acids consists of a linear alkyl chain, from 3 carbon atoms as a branched alkyl chain, from 5 carbon atoms as a branched tertiary alkyl chain, or a mixture thereof.

3. The process of claim 2 , wherein the vinyl ester of alkyl of C1 to C18 carboxylic acids is vinyl propionate, vinyl n-butyrate, vinyl laurate, vinyl ester of 2-ethyl hexanoic acid, vinyl caprate, and vinyl stearate, vinyl neodecanoates, vinyl pivalate or a mixture thereof.

4. The process of claim 1 , wherein the monomers of alkyl acrylate or alkyl methacrylate are reaction products of ethylenically unsaturated carboxylic acids and C1 to C20 alcohols.

5. The process of claim 4 , wherein the monomers of alkyl acrylate or alkyl methacrylate are selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, n-octyl (meth)acrylate, iso-octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, 2-propyl heptyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, stearyl (meth)acrylate, isobornyl (meth)acrylate, norbornyl (meth)acrylate, 4-tertbutylcyclohexyl (meth)acrylate, 3,3,5-trimethylcyclohexyl (meth)acrylate or a mixture thereof.

6. The process of claim 1 , wherein the monomers of alkyl acrylate or the alkyl methacrylate of c) is selected from methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, n-octyl (meth)acrylate, iso-octyl (meth)acrylate or a mixture thereof.

7. The process of claim 3 , wherein the vinyl ester of alkyl of C1 to C18 carboxylic acids is a vinyl ester of neodecanoic acids.

Assignments (14)
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0748 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: HEXION INC.
Reel/Frame 041793/0965 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2016
From: SIMAL, FRANCOIS; HAVAUX, NATHALIE; LAURENT, AURELIEN
To: HEXION INC.
Reel/Frame 038343/0152 →
SECURITY INTEREST Recorded Feb 2, 2016
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 037639/0795 →
SECURITY INTEREST Recorded Jul 24, 2015
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 036169/0670 →
SECURITY INTEREST Recorded Jul 24, 2015
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 036177/0574 →