IP Library Granted Patent US 11,059,779
Granted Patent B2
US 11,059,779 · App. 16/083,904 · Granted Jul 13, 2021

Storage stable aqueous organic peroxide emulsions

Inventors: René Gerritsen (Loosdrecht, NL); Richard Hermannes Johannes Hekkert (Deventer, NL); Ester Elisabeth Antonia Keijzer (Deventer, NL)
Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
C07C407/006C08F2/22C08F2/40C08F4/34C08F14/06C07C409/36C07C409/38
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Quick Facts
Patent No.
US 11,059,779
App. No.
16/083,904
Granted
Jul 13, 2021
Kind
B2
Abstract

Aqueous emulsion comprising: —25-70 wt % organic peroxide, based on the weight of the emulsion, —a cyclohexane dicarboxylate ester, and —water. This emulsion is storage stable and can be used for the production of polymers, in particular PVC, that come into contact with food products.

Claims (49)

1. An aqueous organic peroxide emulsion comprising:

25-70 wt % organic peroxide, based on the weight of the emulsion,

a droplet growth inhibitor comprising a cyclohexane dicarboxylate ester, wherein the cyclohexane dicarboxylate ester is present in an amount of 0.1-10 wt. %, based on the weight of the emulsion, and

water.

2. Emulsion according to claim 1 , wherein the cyclohexane dicarboxylate ester is di-isononyl cyclohexane dicarboxylate (DINCH).

3. Emulsion according to claim 1 , additionally comprising an anti-freeze agent.

4. Emulsion according to claim 3 , wherein the anti-freeze agent is selected from the group consisting of methanol, ethanol, isopropanol, glycols, propanediol, glycerol, and mixtures thereof.

5. The emulsion according to claim 4 , wherein the water/anti-freeze agent weight ratio is from 3/1 to 2/1.

6. Emulsion according to claim 1 , additionally comprising a protective colloid.

7. Emulsion according to claim 1 , additionally comprising an emulsifier.

8. Emulsion according to claim 7 , wherein the emulsifier is a non-ionic surfactant.

9. A method of polymerizing a vinyl chloride monomer wherein the emulsion according to claim 1 is added to a vinyl chloride monomer in an effective amount.

10. The aqueous emulsion according to claim 1 , wherein the 99 th percentile of the droplet volume distribution of the organic peroxide does not exceed 15 microns during 12 weeks of storage at −20° C.

11. The emulsion according to claim 1 , wherein the cyclohexane dicarboxylate ester is present in an amount of 0.5-5 wt %, based on the weight of the emulsion.

12. The emulsion according to claim 1 , wherein the organic peroxide is chosen from cumyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, tert-butyl peroxyneoheptanoate, 1-(2-ethylhexyl-peroxy)-1,3-dimethylbutyl peroxypivalate, or di(3,5,5-trimethylhexanoyl) peroxide.

13. The emulsion according to claim 12 , wherein the organic peroxide is present in an amount of from 40-60 wt %, based on the weight of the emulsion.

14. The emulsion according to claim 13 , wherein the amount of water in the emulsion is from 20 to 70 wt %, based on the weight of the emulsion.

15. The emulsion according to claim 13 , wherein the amount of water in the emulsion is from 25 to 40 wt %, based on the weight of the emulsion.

16. An aqueous organic peroxide emulsion comprising:

25-70 wt % of an organic peroxide chosen from tert-butyl peroxyheptanoate, tert-butyl peroxyneodecanoate, tert-amyl peroxyneodecanoate and combinations thereof, based on the weight of the emulsion,

0.5 to 2 wt % di-isononyl cyclohexane dicarboxylate, based on the weight of the emulsion,

0.5 to 5 wt % of a protective colloid chosen from partially hydrolysed/saponified polyvinyl acetates, cellulose, cellulose derivatives, starch, starch derivatives, and combinations thereof;

a non-ionic surfactant having a hydrophile-lipophile balance of 16 or higher,

an anti-freeze agent chosen from methanol, ethanol, isopropanol, ethylene glycol, propanediol, glycerol, and mixtures thereof; and

water,

wherein a water/anti-freeze agent weight ratio is from 3/1 to 2/1.

17. The emulsion of claim 16 consisting of the organic peroxide, the di-isononyl cyclohexane dicarboxylate, the protective colloid, the non-ionic surfactant, the anti-freeze agent, and the water.

18. The emulsion of claim 16 consisting of:

the organic peroxide present in an amount of 50 wt % based on the weight of the emulsion,

the di-isononyl cyclohexane dicarboxylate present in an amount of 0.9 wt % based on the weight of the emulsion,

the protective colloid present in an amount of 2.8 to 3 wt % based on the weight of the emulsion,

the non-ionic surfactant present in an amount of 0.5 wt % based on the weight of the emulsion,

the anti-freeze agent present in an amount of 12.5 to 12.7 wt % based on the weight of the emulsion; and

the water.

19. The emulsion of claim 16 consisting of:

the organic peroxide present in an amount of 50 wt % based on the weight of the emulsion,

the di-isononyl cyclohexane dicarboxylate present in an amount of 0.9 wt % based on the weight of the emulsion,

the protective colloid which is polyvinylacetate having an average degree of hydrolysis of 62.5-67.5% and is present in an amount of 2.8 to 3 wt % based on the weight of the emulsion,

the non-ionic surfactant which is a C16/C18 ethoxylated alcohol and is present in an amount of 0.5 wt % based on the weight of the emulsion,

the anti-freeze agent which is methanol and is present in an amount of 12.5 to 12.7 wt % based on the weight of the emulsion; and

the water.

20. The emulsion of claim 16 consisting of:

the organic peroxide present in an amount of 50 wt % based on the weight of the emulsion,

the di-isononyl cyclohexane dicarboxylate present in an amount of 0.9 wt % based on the weight of the emulsion,

the protective colloid which is polyvinylacetate having an average degree of hydrolysis of 62.5-67.5% and is present in an amount of 2.8 to 3 wt % based on the weight of the emulsion,

the non-ionic surfactant which is a C16/C18 ethoxylated alcohol and is present in an amount of 0.5 wt % based on the weight of the emulsion,

the anti-freeze agent which is methanol and is present in an amount of 12.5 to 12.7 wt % based on the weight of the emulsion; and

the water present in an amount of 32.8 to 33.3 wt % based on the weight of the emulsion, and

wherein the 99 th percentile of the droplet volume distribution of the organic peroxide does not exceed 15 microns during 12 weeks of storage at −20° C.

Assignments (2)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2018
From: GERRITSEN, RENÉ; HEKKERT, RICHARD HERMANNES JOHANNES; KEIJZER, ESTER ELISABETH ANTONIA
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 047091/0663 →
Priority Claims (1)
EP 16161148 · Mar 18, 2016 · regional
Continuity (1)
Related Publication 20190071397A1 · Mar 7, 2019