IP Library Granted Patent US 11,365,270
Granted Patent B2
US 11,365,270 · App. 17/066,921 · Granted Jun 21, 2022

Polybutadiene, production and use thereof

Inventors: Kai-Steffen Krannig (Dortmund, DE); Jürgen Herwig (Hünxe, DE); Andreas Berlineanu (Marl, DE); Miriam Ammer (Recklinghausen, DE); Philip Kemper (Ahaus, DE); Alexander Pschantka (Coesfeld, DE); Yvonne Groß-Onnebrink (Raesfeld, DE); Gudula Beuers (Dülmen, DE); Margit Bukohl (Marl, DE); Kirsten Luce (Herne, DE); Siegfried Jittenmeier (Marl, DE)
Assignee: Evonik Operations GmbH
C08F36/06C08F2/06C08F4/6097C08F4/61912C08F4/7096C08L9/00
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Quick Facts
Patent No.
US 11,365,270
App. No.
17/066,921
Granted
Jun 21, 2022
Kind
B2
Abstract

The invention relates to polybutadiene, which contains the monomer units derived from 1,3-butadiene having a vinyl double bond in a proportion of 25 to 75 mole percent, having a trans-double bond in a proportion of 0 to 10 mole percent and a cis-double bond in a proportion of 25 to 75 mole percent, wherein the totality of the monomer units (A), (B) and (C) is supplemented to 100 mole percent, and which is characterized in that it has a number-average mole mass of 1,000 to 3,000 g/mole. The invention further relates to a method for producing polybutadienes, the use of the polybutadiene according to the invention and compositions containing polybutadiene according to the invention.

Claims (24)

1. A method for preparing a polybutadiene comprising monomer units derived from 1,3-butadiene

wherein the proportion of monomer units of the formula (A) in the entirety of the monomer units derived from 1,3-butadiene present in the polybutadiene is 25 to 75 mole percent, the proportion of units of the formula (B) in the entirety of the monomer units derived from 1,3-butadiene present in the polybutadiene is from 2 to 6 mole percent and the proportion of monomer units of the formula (C) in the entirety of the monomer units derived from 1,3-butadiene present in the polybutadiene is 25 to 75 mole percent, wherein the entirety of the monomer units (A), (B) and (C) add up to 100 mole percent, and the polybutadiene has a number-average molar mass of 1000 to 3000 g/mol,

the method comprising the step of

polymerizing 1,3-butadiene in the presence of a solvent and a catalyst system comprising a) a cobalt compound, b) an organoaluminium compound, c) an organophosphorus compound and d) water, wherein a mixture of catalyst system and solvent is initially charged and the 1,3-butadiene is metered into this mixture,

wherein the polymerization is carried out at a pressure of from 2 to 7 bar.

2. The method according to claim 1 , wherein the polymerization is carried out at a pressure of from 3 to 7 bar.

3. The method according to claim 1 , wherein the polymerization is carried out at a temperature of the reaction mixture of from 20 to 60° C.

4. The method according to claim 1 , wherein the cobalt compound is cobalt 2-ethylhexanoate.

5. The method according to claim 1 , wherein the organophosphorus compound is tris(2,4-di-tert-butylphenyl) phosphite or tris(ortho-phenylphenyl) phosphite.

6. The method according to claim 1 , wherein the organoaluminium compound is ethylaluminium sesquichloride or diethylaluminium chloride.

7. The method according to claim 1 , wherein the molar ratio of cobalt compound to total amount of 1,3-butadiene used is from 1:2500 to 1:15,000.

8. The method according to claim 1 , wherein the cobalt compound is cobalt 2-ethylhexanoate.

9. The method according to claim 1 , wherein the organophosphorus compound is tris(2,4-di-tert-butylphenyl) phosphite or tris(ortho-phenylphenyl) phosphite.

10. The method according to claim 3 , wherein the organoaluminium compound is ethylaluminium sesquichloride or diethylaluminium chloride.

11. The method according to claim 3 , wherein the molar ratio of cobalt compound to total amount of 1,3-butadiene is from 1:2500 to 1:15,000.

12. The method according to claim 1 , wherein the polybutadiene has a viscosity of 2000 to 8000 mPa s at 20° C.

13. The method according to claim 1 , wherein the polybutadiene has a dispersity of 2.1 to 3.0.

14. The method according to claim 1 , wherein the proportion of monomer units of the formula (A) in the entirety of the monomer units derived from 1,3-butadiene present in the polybutadiene is 50 to 65 mole percent, the proportion of units of the formula (B) in the entirety of the monomer units derived from 1,3-butadiene present in the polybutadiene is 2 to 6 mole percent and the proportion of monomer units of the formula (C) in the entirety of the monomer units derived from 1,3-butadiene present in the polybutadiene is 25 to 40 mole percent, wherein the entirety of the monomer units (A), (B) and (C) add up to 100 mole percent, and the polybutadiene has a number-average molar mass of 1200 to 1700 g/mol.

15. A product comprising the polybutadiene according to the method of claim 1 wherein the product is selected from the group consisting of rubber, synthetic rubber, tyres, adhesive formulations, coating compositions, flexographic printing plates, coating agents, coating agent components, and plasticizers.

16. A composition comprising the polybutadiene according to the method of claim 1 or conversion products of polybutadiene with other compounds.

17. The composition according to claim 16 , wherein the proportion of the polybutadiene, which are present in the composition or were used for preparing the conversion products, based on the composition, is from 0.1 to 90% by weight.

18. The method according to claim 1 , wherein said polybutadiene has a dispersity of 2.1 to 3.0.

19. The composition according to claim 16 , wherein the polybutadiene has a viscosity of 2000 to 8000 mPa s at 20° C.

20. The composition according to claim 16 , wherein the polybutadiene has a dispersity of 2.1 to 3.0.

Assignments (1)
CHANGE OF ADDRESS Recorded Jul 17, 2026
From: EVONIK OPERATIONS GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 075999/0525 →
Priority Claims (1)
EP 17151585 · Jan 16, 2017 · regional
Continuity (2)
Division 16469855
Related Publication 20210024666A1 · Jan 28, 2021
Cited By (1)
US 12,466,906