Process for the Preparation of a Polysulfide

Patent metadata

Field	Value
Publication number	US-2016145394-A1
Application number	US-201414897425-A
Country	US
Kind code	A1
Filing date	Jun 13, 2014
Priority date	Jun 17, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

Pre-polymer according to structure (I) X—(R 2 —O) n —CH 2 (R 1 —O) m —CH 2 —(O—R 2 ) p —X (I) wherein R 1 and R 2 can be the same or different and are selected from alkane chains containing 2-10 carbon atoms, X is a halogen atom, and n, m, and p are integers that can be the same of different and have a value in the range 1-6. The use of this pre-polymer in the preparation of a liquid polysulfide polymer allows better control over the sulfur and oxygen content and the polarity of the resulting polymer.

First claim

1 . Pre-polymer according to structure (I)
X—(R 2 —O) n —CH 2 —O—(R 1 —O) m —CH 2 —(O—R 2 ) p —X  (I)
wherein R 1 and R 2 can be the same or different and are selected from alkane chains containing 2-10 carbon atoms, X is a halogen atom, and n, m, and p are integers that can be the same or different and have a value in the range 1-6.

2 . Pre-polymer according to claim 1 wherein X is Cl.

3 . Pre-polymer according to claim 1 wherein R 1 is —CH 2 —CH 2 —.

4 . Pre-polymer according to claim 1 wherein R 2 is —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, or —CH 2 —CH 2 —CH 2 —CH 2 —.

5 . Process for the preparation of a pre-polymer according to claim 1 wherein a polyol is reacted with (para)formaldehyde and a halo-alcohol in the presence of an acid catalyst.

6 . Process according to claim 5 wherein the polyol is selected from the group consisting of monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, monopropyele glycol, dipropylene glycol, tripropylene glycol, 1,4-butanediol, and mixtures thereof.

7 . Process according to claim 5 wherein the halo-alcohol is a chloro-alcohol.

8 . Process according to claim 7 wherein the chloro-alcohol is ethylene chlorohydrin.

9 . Process for the preparation of a polysulfide comprising the step of reacting a bis(2-dihaloalkyl)formal and a dihaloalkane with sodium polysulfide in the presence of (i) the pre-polymer according to claim 1 or (ii) a pre-polymer obtainable by the process of claim 5 .

10 . Process according to claim 9 wherein the bis(2-dihaloalkyl)formal is bis(2-dichloroalkyl)formal.

11 . Process according to claim 9 wherein the dihaloalkane is an alpha-omega dihaloalkane.

12 . Process according to claim 9 wherein the dihaloalkane is a dichloroalkane.

13 . Process according to claim 12 wherein the dichloroalkane is selected from the group consisting of 1,2-dichloroethane, 1,2-dichloropropane, 1,3-dichloropropoane, 1,4-dichlorobutane, 1,5-dichloro pentane, 1,6-dichloro hexane, and isomers and combinations thereof.

14 . Process according to claim 9 wherein the product resulting from the reaction of the bis(2-dihaloalkyl)formal, the dihaloalkane, and sodium polysulfide in the presence of the pre-polymer is treated with a reducing agent in order to obtain a liquid polysulfide.

Assignees

• Akzo Nobel Chemicals Int Bv

Inventors

• Menzel Manfred
• Lungu Daniela
• Klobes Olaf
• Aldenhoven Heinz
• Van Pelt Antonius
• Burkhardt Volker

Classifications

• C08G75/14

  Polysulfides · CPC title

• C08G75/00 Primary

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title

• C07C41/56 Primary

  by condensation of aldehydes, paraformaldehyde, or ketones · CPC title

• C07C43/315

  containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms · CPC title

• C08G75/16 Primary

  by polycondensation of organic compounds with inorganic polysulfides · CPC title