IP Library Granted Patent US 10,982,087
Granted Patent B2
US 10,982,087 · App. 16/906,472 · Granted Apr 20, 2021

Rubber compositions containing tackifiers

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Quick Facts
Patent No.
US 10,982,087
App. No.
16/906,472
Granted
Apr 20, 2021
Kind
B2
Abstract

A composition comprising, a rubber component selected from the group consisting of a rubber polymer, a synthetic rubber polymer, and combinations thereof; and an alkylphenol resin which is a reaction product of: at least one phenolic monomer selected from the group consisting of phenol, cresol, resorcinol, xylenol, ethyl phenol, alkylresorcinols, and combinations thereof; and at least one alkyl aldehyde having from 5 to 12 carbon atom alkyl groups, is disclosed. The composition can be used to prepare articles of manufacture such as tires, tire treads, tire shoulders, tire sidewalls, rubber belts, and rubber hoses.

Claims (18)

1. A method of forming a composition, comprising:

making a resole alkylphenol resin comprising:

reacting at least one phenolic monomer selected from the group consisting of phenol, cresol, resorcinol, xylenol, ethyl phenol, alkylresorcinols, and combinations thereof and at least one alkyl aldehyde having from 5 to 12 carbon atom alkyl groups in the presence of an acid catalyst, and optionally, an organic solvent that forms an azeotrope with water;

adding a base catalyst and formaldehyde;

reacting the at least one phenolic monomer, the at least one alkyl aldehyde, and the formaldehyde in the presence of the base catalyst; and

performing a reflux or azeotropic distillation process; and

adding the alkylphenol resin to a composition comprising a rubber component.

2. The method of claim 1 , wherein the rubber component is selected from the group consisting of a rubber polymer, a synthetic rubber polymer, and combinations thereof.

3. The method of claim 1 , wherein the alkylphenol resin acts as a tackifier.

4. The method of claim 1 , wherein the alkyl aldehyde is selected from the group consisting of 3,5,5-trimethyl hexanal, nonanal, 2-ethyl hexanal, and combinations thereof.

5. The method of claim 2 , wherein the synthetic rubber polymer is selected from the group consisting of styrene butadiene rubber, polybutadiene rubber, halogenated butyl rubber, butyl rubber, polyisoprene rubber, styrene/isoprene/butadiene rubber, and combinations thereof.

6. The method of claim 1 , wherein the composition has a tan δ at 0° C. as measured by Dynamic Mechanical Analysis in the range of from 0.12 to 0.17.

7. The method of claim 6 , wherein the composition has a tan δ at 60° C. as measured by Dynamic Mechanical Analysis in the range of from 0.10 to 0.16.

8. The method of claim 1 , wherein the composition has an ultimate elongation as measured by ASTM D412 in the range of from 550% to 800%.

9. The method of claim 1 , wherein the composition has an elastic modulus at 60° C. as measured by Dynamic Mechanical Analysis in the range of from 3.60×10 6 Pa to 5.00×10 6 Pa.

10. The method of claim 1 , wherein the alkylresorcinols comprise dihydroxy benzenes having one or two alkyl chains present on a ring.

11. The method of claim 10 , wherein the alkyl chains comprise from 1 to 3 carbons.

12. The method of claim 1 , wherein the alkylphenol resin can be present in the composition in the range of from 1 to 10 parts per hundred rubber.

Assignments (13)
SECURITY INTEREST Recorded May 12, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071090/0740 →
ASSIGNMENT OF PATENT AND TRADEMARK SECURITY INTEREST Recorded May 12, 2025
From: MACQUARIE CAPITAL FUNDING LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071276/0379 →
SECURITY INTEREST Recorded Jan 23, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK LIMITED
To: GOLDMAN SACHS BANK USA
Reel/Frame 069981/0468 →
RELEASE OF SECURITY INTEREST Recorded Jun 15, 2022
From: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P.
To: HEXION VAD LLC
Reel/Frame 060209/0558 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.
To: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0327 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
CHANGE OF NAME Recorded May 3, 2022
From: HEXION VAD LLC
To: BAKELITE LLC
Reel/Frame 059926/0973 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2022
From: BAKELITE LLC
To: BAKELITE UK HOLDING LTD.
Reel/Frame 060377/0699 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2021
From: HEXION INC.
To: HEXION VAD LLC
Reel/Frame 057323/0086 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0582 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0677 →
SECURITY INTEREST Recorded May 5, 2021
From: HEXION VAD LLC
To: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT
Reel/Frame 056145/0957 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 19, 2020
From: REDDY, ASHOK; ZIRKLE, CRAIG; WILLMAN, JUSTYNE
To: HEXION
Reel/Frame 052991/0150 →