IP Library Granted Patent US 10,179,838
Granted Patent B2
US 10,179,838 · App. 15/534,399 · Granted Jan 15, 2019

Low-salt process for the preparation of a polysulfide

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Quick Facts
Patent No.
US 10,179,838
App. No.
15/534,399
Granted
Jan 15, 2019
Kind
B2
Abstract

Process for the preparation of a polysulfide comprising the step of reacting in the absence of a dihaloalkane a bis(2-dihaloalkyl)formal in the presence of (i) a pre-polymer (I) according to structure (I) X—(R2—O) n —CH2—O—(R1—O) m —CH2—(O—R2) p —X  (I), wherein R1 and R2 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, with either (i) sodium polysulfide or (ii) a combination of sodium hydrosulfide and sulfur.

Claims (15)

1. Process for the preparation of a polysulfide comprising the step of reacting a bis(2-haloalkyl)formal with either (i) sodium polysulfide or (ii) a combination of sodium hydrosulfide and sulfur, the reaction being performed in the absence of a dihaloalkane and in the presence of a pre-polymer (I) 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-haloalkyl)formal is bis(2-chloroalkyl)formal.

3. Process according to claim 1 wherein the X is a halogen selected from Cl, Br, and I.

4. Process according to claim 3 wherein the X is Cl.

5. Process according to claim 1 , wherein the R 1 of the pre-polymer (I) is —CH 2 CH 2 —.

6. Process according to claim 1 , wherein the R 2 of the pre-polymer (I) is —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, or —CH 2 —CH 2 —CH 2 —CH 2 —.

7. Process according to claim 1 , wherein the product resulting from the reaction of the bis(2-haloalkyl)formal with sodium polysulfide in the presence of the pre-polymer (I) is treated with a reduction agent to obtain a liquid polysulfide.

8. Process according to claim 1 , wherein the molar ratio of sodium polysulfide (calculated as Na 2 S x ) relative to the bis(2-haloalkyl)formal is in the range 0.8-1.4.

9. Process according to claim 1 , wherein a mixture comprising bis(2-haloalkyl)formal and the pre-polymer (I) is added to an aqueous solution of sodium hydrosulfide and sulfur.

10. Process according to claim 9 , wherein the aqueous solution has a temperature in the range of 60 to 100° C.

11. Process according to claim 1 , wherein the weight ratio of the bis(2-haloalkyl)formal to the pre-polymer (I) is in the range of 90:10 to 10:90.

12. Product obtained by the process according to claim 1 .

13. A composition comprising a product obtained by the process according to claim 1 , said composition selected from sealants, adhesives and coating compositions.

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 Jun 28, 2017
From: MENZEL, MANFRED; BURKHARDT, VOLKER; KLOBES, OLAF
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 042851/0343 →