Process for preparing a powdery organic peroxide formulation

Patent metadata

Field	Value
Publication number	US-11098011-B2
Application number	US-201816954551-A
Country	US
Kind code	B2
Filing date	Dec 14, 2018
Priority date	Dec 19, 2017
Publication date	Aug 24, 2021
Grant date	Aug 24, 2021

Abstract

Process for preparing a powdery organic peroxide formulation, said process comprises the following steps:a) preparing a reaction mixture comprising:40-80 wt % water10-25 wt % of an acid chloride or chloroformate,1-4 wt % hydrogen peroxide,2-8 wt % alkali metal hydroxide,1-25 wt % of a phlegmatizer selected from the group consisting of ethylene glycol dibenzoate, phenyl benzoate, trimethylol propane tribenzoate, glyceryl tribenzoate, ethylene glycol ditoluate, 1,3-propanediol ditoluate, ethylene glycol 4-tert-butylbenzoate, ethylene glycol monobenzoate monotoluate, 2,3-butanediol dibenzoate, 4-methylphenyl benzoate acid ester, trimethylolpropane dibenzoate, and combinations thereof0.002-0.20 wt % of a surfactant, and0.25-5.0 wt % of an inert organic solvent,all percentages based on the weight of the reaction mixture,b) heating the reaction mixture at a temperature in the range 5-50° C.

First claim

What is claimed is:

1. A process for preparing a powdery organic peroxide formulation, comprising:
a) preparing a reaction mixture comprising:
40-80 wt % water
10-25 wt % of an acid chloride or chloroformate,
1-4 wt % hydrogen peroxide,
2-8 wt % alkali metal hydroxide,
1-25 wt % of a phlegmatizer selected from the group consisting of ethylene glycol dibenzoate, phenyl benzoate, trimethylol propane tribenzoate, glyceryl tribenzoate, ethylene glycol ditoluate, 1,3-propanediol ditoluate, ethylene glycol 4-tert-butylbenzoate, ethylene glycol monobenzoate monotoluate, 2,3-butanediol dibenzoate, 4-methylphenyl benzoate acid ester, trimethylolpropane dibenzoate,
0.002-0.20 wt % of a surfactant, and
0.25-5.0 wt % of an inert organic solvent,
wherein all percentages based on the weight of the reaction mixture, and

b) heating the reaction mixture at a temperature in the range 5-50° C.,
wherein less than 10 wt % of the powdery organic peroxide formulation has a particle size that is smaller than 100 microns.

2. The process according to claim 1 , wherein the reaction mixture comprises an acid chloride selected from the group consisting of benzoyl chloride, p-methylbenzoyl chloride, m-methylbenzoyl chloride, methoxy-substituted benzoyl chloride, and 2,4-dichlorobenzoyl chloride.

3. The process according to claim 1 , wherein the reaction mixture comprises a chloroformate selected from the group consisting of 4-tertbutylcyclohexyl chloroformate, cetyl chloroformate, and myristyl chloroformate.

4. The process according to claim 1 , wherein the inert organic solvent is selected from the group consisting of chlorinated solvents, alkanes, ethyl acetate, and ethers.

5. The process according to claim 1 , wherein the inert organic solvent comprises a solvent selected from the group consisting of methylene chloride, chloroform, tetrachloromethane, trichloromethane, heptane, petroleum ether, ethyl acetate, cyclopentyl methyl ether (CPME), and methyl tert-butyl ether (MTBE).

6. The process according to claim 1 , wherein the surfactant comprises a linear alkyl(benzene)sulfonate.

7. The process according to claim 1 , wherein the surfactant comprises sodium dodecylbenzenesulfonate (SDBS), sodium lauryl ether sulfate (SLES), sodium dodecylsulfate (SDS), or sodium N-methyl-N-oleoyl taurate.

8. The process according to claim 1 , wherein the reaction mixture comprises a phlegmatizer selected from the group consisting of ethylene glycol dibenzoate (EGDB), phenyl benzoate, and trimethylolpropane tribenzoate.

9. The process according to claim 8 , wherein the reaction mixture comprises ethylene glycol dibenzoate (EGDB).

10. The process according to claim 1 , wherein the reaction mixture is prepared by combining a mixture comprising water, hydrogen peroxide, alkali metal hydroxide, surfactants, inert organic solvent, and H 2 O 2 stabilizer, with a solution of the phlegmatizer in the acid chloride.

11. The process according to claim 1 , wherein the reaction mixture is prepared by combining a mixture comprising water, hydrogen peroxide, alkali metal hydroxide, surfactant, inert organic solvent, and H 2 O 2 stabilizer, with a solution of the phlegmatizer in the chloroformate.

12. The process according to claim 10 , wherein the H 2 O 2 stabilizer comprises MgSO 4 and wherein the acid chloride comprises benzoyl chloride, p-methylbenzoyl chloride, m-methylbenzoyl chloride, methoxy-substituted benzoyl chloride, or 2,4-dichlorobenzoyl chloride.

13. The process according to claim 12 , wherein the acid chloride comprises benzoyl chloride and the phlegmatizer comprises ethylene glycol dibutyrate.

14. The process according to claim 13 , wherein the solution of ethylene glycol dibenzoate in benzoyl chloride is obtained by reacting benzoyl chloride and ethane-1,2-diol in a molar ratio range from 2.5:1 to 4.5:1 or in a molar ratio range from 4:1 to 4.5:1 at a temperature in the range 80-130° C.

15. A powdery organic peroxide formulation made by the process according to claim 1 .

16. A polymer modification process comprising curing an unsaturated resin using the powdery organic peroxide formulation according to claim 15 .

17. The polymer modification process according to claim 16 , wherein the resin comprises an unsaturated polyester resin, a vinyl ester resin, an acrylate resin, or a dicylopentadiene resin.

18. The polymer modification process of claim 1 ,
wherein the acid chloride or chloroformate comprises benzoyl chloride;
wherein the alkali metal hydroxide comprises sodium hydroxide;
wherein the phlegmatizer comprises ethylene glycol dibenzoate, glyceryl tribenzoate, or combinations thereof;
wherein the inert organic solvent comprises dichloromethane, isohexane, or combinations thereof;
wherein the surfactant comprises sodium methyl oleoyl taurate, hydroxypropylmethylcellulose, sodium dodecyl benzene sulfonate, or combinations thereof;
wherein the reaction mixture further comprises magnesium sulfate, diethylenetriamine penta(methylene-phosphonic) acid, or combinations thereof;
wherein the benzoyl chloride, ethylene glycol dibenzoate, and dichloromethane are optionally premixed and then combined with ethane-1,2-diol to form HCl which is then removed; and
wherein less than 2.5 wt % of the powdery organic peroxide formulation has a particle size that is smaller than 100 microns.

19. The polymer modification process of claim 1 ,
wherein the acid chloride or chloroformate comprises 4-t-butylcyclohexyl chloroformate;
wherein the alkali metal hydroxide comprises sodium hydroxide;
wherein the phlegmatizer comprises ethylene glycol dibenzoate;
wherein the inert organic solvent comprises petroleum ether;
wherein the surfactant comprises hydroxypropylmethylcellulose; and
wherein the reaction mixture further comprises magnesium sulfate.

20. The polymer modification process of claim 1 ,
wherein the acid chloride or chloroformate comprises 4-t-butylcyclohexyl chloroformate;
wherein the alkali metal hydroxide comprises sodium hydroxide;
wherein the phlegmatizer comprises glyceryl tribenzoate;
wherein the inert organic solvent comprises petroleum ether;
wherein the surfactant comprises sodium 2-methyl-7-ethyl-undecyl-4-sulfonate; and
wherein the reaction mixture further comprises magnesium sulfate.

Assignees

• Nouryon Chemicals Int Bv

Inventors

• Van Den Berg Michel
• Overkamp Johannes Willibrordus Antonius
• Talma Auke Gerardus
• Krosendijk Edgard Everick

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C407/006 Primary

  Stabilisation; Use of additives · CPC title

• C08K5/14

  Peroxides · CPC title

• C07C409/34

  both belonging to carboxylic acids · CPC title