IP Library Granted Patent US 11,859,039
Granted Patent B2
US 11,859,039 · App. 17/309,495 · Granted Jan 2, 2024

Branched polymers made using multifunctional coupling agents

Inventors: Adrie van der Huizen (Amsterdam, NL); Wouter de Jong (Amsterdam, NL); Henk van de Weg (Amsterdam, NL); Maarten Tromp (Amsterdam, NL); Laurens Engelen (Amsterdam, NL)
Assignee: CARIFLEX PTE. LTD.
C08F297/044C08F8/42C08F297/046C08J5/18C08F2810/40C08J2353/02
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Quick Facts
Patent No.
US 11,859,039
App. No.
17/309,495
Granted
Jan 2, 2024
Kind
B2
Abstract

Branched block copolymers, derived from alkenyl aromatic hydrocarbon-1,3-diene monomer system, and branched polyisoprene homopolymers, derived from isoprene, are obtained by polymerization in the presence of an anionic initiator; at a temperature from 0° C. to 100° C.; followed by coupling with a multifunctional coupling agent of formula (R 1 O) 3 Si—Y—Si(OR 2 ) 3 , wherein R 1 and R 2 are independently C 1 -C 6 alkyl groups; and Y is a C 2 -C 8 alkylene group. The polymers thus obtained can be used in many applications, including rubber cements having high solids content and low zero shear viscosities, and for producing aqueous latices therefrom.

Claims (31)

1. A branched polymer having a formula of (C) m (R 1 O) 3-m Si—Y—Si(R 2 O) 3-n (C) n , wherein

each C block is independently a polyisoprene;

each C block has a weight average molecular weight from 400-1000 kg/mol;

R 1 and R 2 are independently H, or C 1 -C 6 alkyl groups;

Y is a C 2 -C 8 alkylene group;

m and n are integers independently having values from 1-3; and

wherein the branched polymer has a coupling efficiency (CE) of at least 40%.

2. The branched polymer of claim 1 , wherein (m+n) has a value from 3-6.

3. The branched polymer of claim 1 , wherein Y is —CH 2 CH 2 —, and R 1 and R 2 are hydrogen, methyl groups or ethyl groups.

4. The branched polymer of claim 1 , prepared using a multifunctional coupling agent is selected from the group consisting of 1,2-bis(trimethoxysilyl)ethane (BTMSE), 1,2-bis(triethoxysilyl)ethane (BTESE), and mixtures thereof.

5. The branched polymer of claim 1 , wherein the C block has a weight average molecular weight from 500-700 kg/mol.

6. A process for preparing a branched polymer, the process comprising:

(i) polymerizing isoprene at a temperature from 0° C. to 100° C., to form a polymer block C;

(ii) adding a multifunctional coupling agent of formula (R 1 O) 3 Si—Y—Si(OR 2 ) 3 ; and

forming a branched polyisoprene homopolymer having a formula (C) m (R 1 O) 3-m Si—Y—Si(R 2 O) 3-n (C) n from steps (i) and (ii); wherein

each C block is a polyisoprene block;

each C block independently has a weight average molecular weight from 400-1000 kg/mol;

R 1 and R 2 are independently H, or C 1 -C 6 alkyl groups;

Y is a C 2 -C 8 alkylene group;

m and n are integers independently having values from 1-3; and

the branched polymer has a coupling efficiency (CE) of at least 40%.

7. The process of claim 6 , wherein the branched polymer is formed as a rubber cement having a solids content from 5 wt. % to 35 wt. %.

8. The process of claim 7 , wherein the rubber cement has

a zero shear viscosity of less than 80,000 mPas in a solids content range from 15 wt. % to 25 wt. %;

a cis content from 70% to 95%; and

a weight average molecular weight from 1,000 to 3500 kg/mol.

9. The process of claim 7 , wherein the process further comprises an anionic initiator.

10. An article formed from the branched polymer of claim 9 .

11. A film formed from the branched polymer of claim 9 .

12. The film of claim 11 , wherein the film has a tensile strength of from MPa to 40 MPa.

13. The film of claim 11 , wherein the film has an elongation of from 500% to 1250% and a tear strength of from 15 kN/m to 35 kN/m.

Assignments (5)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 24, 2024
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: KRATON CHEMICAL, LLC; KRATON CORPORATION
Reel/Frame 068671/0836 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2023
From: KRATON POLYMERS LLC
To: CARIFLEX PTE. LTD.
Reel/Frame 063850/0995 →
SECURITY INTEREST Recorded Mar 18, 2022
From: KRATON CHEMICAL, LLC; KRATON POLYMERS LLC; KRATON POLYMERS U.S. LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 059525/0804 →
SECURITY INTEREST Recorded Mar 18, 2022
From: KRATON CHEMICAL, LLC; KRATON POLYMERS LLC; KRATON POLYMERS U.S. LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 059864/0455 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2021
From: VAN DER HUIZEN, ADRIE; DE JONG, WOUTER; VAN DE WEG, HENK; TROMP, MAARTEN; ENGELEN, LAURENS
To: KRATON POLYMERS LLC
Reel/Frame 058202/0789 →
Continuity (3)
Provisional Application 62889779 · Aug 21, 2019
Provisional Application 62775624 · Dec 5, 2018
Related Publication 20220064355A1 · Mar 3, 2022