IP Library Granted Patent US 9,631,055
Granted Patent B2
US 9,631,055 · App. 14/897,425 · Granted Apr 25, 2017

Process for the preparation of a polysulfide

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Quick Facts
Patent No.
US 9,631,055
App. No.
14/897,425
Granted
Apr 25, 2017
Kind
B2
Abstract

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 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.

Claims (13)

1. 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

the 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. Process according to claim 1 wherein the bis(2-dihaloalkyl)formal is bis(2-dichloroalkyl)formal.

3. Process according to claim 1 wherein the dihaloalkane is an alpha-omega dihaloalkane.

4. Process according to claim 1 wherein the dihaloalkane is a dichloroalkane.

5. Process according to claim 1 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.

6. Process according to claim 1 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.

7. 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 a pre-polymer obtained by a process wherein a polyol is reacted with (para)formaldehyde and a halo-alcohol in the presence of an acid catalyst.

8. Process according to claim 7 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.

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

10. Process according to claim 9 wherein the chloro-alcohol is ethylene chlorohydrin.

Assignments (3)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2016
From: MENZEL, MANFRED; LUNGU, DANIELA; KLOBES, OLAF; VAN PELT, ANTONIUS; BURKHARDT, VOLKER; ALDENHOVEN, HEINZ
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 040516/0030 →