IP Library Granted Patent US 8,637,606
Granted Patent B2
US 8,637,606 · App. 12/814,433 · Granted Jan 28, 2014

Tires and tread formed from phenol-aromatic-terpene resin

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Quick Facts
Patent No.
US 8,637,606
App. No.
12/814,433
Granted
Jan 28, 2014
Kind
B2
Abstract

Tires and tread are made from resin formed from the polymerization of phenol, aromatic, and terpene and/or mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons.

Claims (16)

1. A tire tread composition comprising silica, carbon black, sulfur, a rubber component selected from the group consisting of synthetic diene rubber and natural rubber, and an oligomeric resin derived from component a) comprising at least one monomer selected from the group consisting of terpenes and mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons, component b) comprising at least one monomer selected from the group consisting of vinyl aromatic compounds and component c) comprising at least one monomer selected from the group consisting of phenolic compounds wherein the tire tread composition has improved handling performance as evidenced by an increased dynamic storage modulus (E′) at 50° C. or 60° C. compared with that of a similar composition prepared in the absence of the resin.

2. The tire tread composition of claim 1 , wherein component a) is an olefinically unsaturated non-acidic terpene compound, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

3. The tire tread composition of claim 1 , wherein component a) is a terpene selected from the group consisting of α-pinene, β-pinene, δ-3-carene, 3-carene, D-limonene, and dipentene, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

4. The tire tread composition of claim 1 , wherein component a) comprises at least one monomer selected from the group consisting of mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

5. A method of making a tire tread composition comprising contacting a composition comprising silica, carbon black, sulfur, and a rubber component selected from the group consisting of synthetic diene rubber and natural rubber, with an oligomeric resin derived from component a) comprising at least one monomer selected from the group consisting of terpenes and mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons, component b) comprising at least one monomer selected from the group consisting of vinyl aromatic compounds and component c) comprising at least one monomer selected from the group consisting of phenolic compounds wherein the tire tread composition has improved handling performance as evidenced by an increased dynamic storage modulus (E′) at 50° C. or 60° C. compared with that of a similar composition prepared in the absence of the resin.

6. The method of claim 5 , wherein component a) is an olefinically unsaturated non-acidic terpene compound, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

7. The method of claim 2 , wherein component a) is a terpene selected from the group consisting of α-pinene, β-pinene, δ-3-Carene, 3-Carene, D-limonene, and dipentene, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

8. The method of claim 5 , wherein component a) comprises at least one monomer selected from the group consisting of mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

9. The tire tread composition of claim 1 wherein the resin is used in an amount within the range of 4 to 12 parts by weight per 100 parts by weight of rubber component.

10. The tire tread composition of claim 1 having improved wet grip as evidenced by an increased tan delta at 0° C. or 10° C. compared with that of a similar composition prepared in the absence of the resin.

11. The tire tread composition of claim 1 having improved rolling resistance as evidenced by a decreased tan delta at 50° C. or 60° C. compared with that of a similar composition prepared in the absence of the resin.

12. A method which comprises formulating a silica-filled tire tread using, as an additive for the tire tread, a composition comprising an oligomeric resin derived from component a) comprising at least one monomer selected from the group consisting of terpenes and mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons, component b) comprising at least one monomer selected from the group consisting of vinyl aromatic compounds and component c) comprising at least one monomer selected from the group consisting of phenolic compounds wherein the tire tread composition comprises silica, carbon black, sulfur, and a rubber component selected from the group consisting of synthetic diene rubber and natural rubber; and

wherein the tire tread composition has improved handling performance as evidenced by an increased dynamic storage modulus (E′) at 50° C. or 60° C. compared with that of a similar composition prepared in the absence of the resin.

13. The method of claim 12 , wherein component a) is an olefinically unsaturated non-acidic terpene compound, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

14. The method of claim 12 , wherein component a) is a terpene selected from the group consisting of α-pinene, β-pinene, δ-3-carene, 3-carene, D-limonene, and dipentene, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

15. The method of claim 12 , wherein component a) comprises at least one monomer selected from the group consisting of mono- and bi-cyclic mono- and bi-unsaturated hydrocarbons, wherein component b) is selected from the group consisting of styrene and alkyl substituted styrene, and wherein component c) is selected from the group consisting of phenol and alkylated phenol.

Assignments (20)
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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NO. 8837224 TO PATENT NO. 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 11, 2022
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 060344/0919 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded Mar 16, 2022
From: BANK OF AMERICA, N.A.
To: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION; KRATON CHEMICAL B.V.
Reel/Frame 059910/0017 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 059366/0727 →
SECURITY INTEREST Recorded Apr 16, 2020
From: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 053020/0101 →
CHANGE OF NAME Recorded Apr 1, 2020
From: ARIZONA CHEMICAL COMPANY, LLC
To: KRATON CHEMICAL, LLC
Reel/Frame 052282/0011 →
PATENT SECURITY AGREEMENT Recorded Jan 7, 2016
From: ARIZONA CHEMICAL COMPANY, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 037457/0928 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 8837224 TO PATENT NUMBER 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jan 6, 2016
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 037448/0453 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL AT REEL/FRAME NO. 33146/0361 Recorded Jan 6, 2016
From: GOLDMAN SACHS BANK USA
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0169 →
RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Jan 6, 2016
From: ANTARES CAPITAL LP, AS SUCCESSOR TO GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0057 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 9, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS RETIRING AGENT
To: ANTARES CAPITAL LP, AS SUCCESSOR AGENT
Reel/Frame 036827/0443 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GOLDMAN SACHS BANK USA, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 033146/0361 →
RELEASE OF SECURITY INTEREST Recorded Jun 12, 2014
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 033146/0278 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 033146/0333 →
SECURITY AGREEMENT Recorded Jan 7, 2012
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 027497/0465 →
RELEASE OF SECURITY INTEREST Recorded Jan 6, 2012
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 027489/0030 →
SECURITY AGREEMENT Recorded Feb 2, 2011
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 025734/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 10, 2010
From: PILLE-WOLF, WOLFGANG; DESHPANDE, ABHAY
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 024811/0845 →