IP Library Granted Patent US 11,891,516
Granted Patent B2
US 11,891,516 · App. 17/644,405 · Granted Feb 6, 2024

Tire composition and method for making thereof

Inventors: Jochem H. W. Vervelde (Almere, NL); Jeremie G. Pichereau (Almere, NL); Jeroen van Herrikhuyzen (Almere, NL); Mark Schaapman (Almere, NL); Pieter Eduard (Almere, NL)
Assignee: KRATON CORPORATION
C08L9/06B60C1/0016C08J3/18C08K3/04C08K3/22C08K3/36C08K5/09C08K5/5419C08J2309/06C08J2493/04C08K2003/2296
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Quick Facts
Patent No.
US 11,891,516
App. No.
17/644,405
Granted
Feb 6, 2024
Kind
B2
Abstract

The disclosure relates to a composition for use in tires. The rubber composition comprises a blend of a rubber component and based on 100 parts by weight (phr) of the rubber component, from 50 to 200 phr of a filler, from 0 to 25 phr of a plasticizer, and from 5 to 90 phr dimeric decarboxylated rosin (DDCR). The DDCR resin comprises 50 to 100 wt. % of polycyclic hydrocarbon compounds having one or more aliphatic, unsaturated, or aromatic groups, and 34-80 carbon atoms, with a molecular weight M n of 250-900 Da, a polydispersity index of 1.0-1.35, and an oxygen to carbon ratio of <5%.

Claims (55)

1. A rubber composition comprising a blend of:

a rubber component and based on 100 parts by weight (phr) of the rubber component;

from 50 to 200 phr of a filler;

from 0 to 25 phr of a plasticizer;

from 5 to 90 phr dimeric decarboxylated rosin (DDCR) resin comprising 50 to 100 wt. % of polycyclic hydrocarbon compounds having one or more aliphatic, unsaturated or aromatic groups, and 34-80 carbon atoms;

wherein the DDCR has:

a molecular weight M n of 250-900 Da, measured using gel permeation chromatography and polystyrene calibration standards;

a polydispersity index of 1.0-1.35; and

an oxygen to carbon ratio of <5%;

wherein the DDCR is formed by decarboxylating a dimeric rosin acid or by dimerizing a decarboxylated rosin.

2. The rubber composition of claim 1 , wherein the DDCR resin is characterized as having one or more of:

an acid value of <80 mg KOH/g, measured using ASTM D 465;

a flash point of >150° C. per ASTM D 92;

a ring and ball softening point (Tsp) from >30° C., per ASTM E28-18;

a Brookfield viscosity of 15-1000 mPa·s, at 177° C. ASTM D2196;

a glass transition temperature (Tg) of −20-110° C., per ASTM E1356;

a density of 1.00-1.05 g/cm 3 per ASTM D792-13;

a T g /M n (K/Da) ratio of >0.6; and

a cloud point in polyolefins of <70° C.

3. The rubber composition of claim 1 , wherein the DDCR resin comprises dimeric and trimer species, with a sum of the dimer and trimer species of >=75 wt. %.

4. The rubber composition of claim 1 , wherein the DDCR resin comprises >=50 wt. % dimeric species, and remainder monomeric, trimeric, and larger polymeric species.

5. The rubber composition of claim 1 , wherein the DDCR resin comprises >=50 wt. % trimeric species, and remainder monomeric, dimeric, and larger polymeric species.

6. The rubber composition of claim 1 , wherein the DDCR resin has a polydispersity index (PDI) (GPC) of 1.05-1.2.

7. The rubber composition of claim 1 , wherein the DDCR resin has a T g /M n ratio (K/Da) of 0.6-1.0.

8. The rubber composition of claim 1 , wherein the DDCR resin has an oxygen content ratio of <3%.

9. The rubber composition of claim 1 , wherein the DDCR resin has an acid value of <50 mg KOH/g.

10. The rubber composition of claim 1 , wherein the DDCR resin is unhydrogenated, partially hydrogenated or fully hydrogenated.

11. The rubber composition of claim 1 , wherein the rubber composition is extruded, compression molded, injection molded, or laminated into a molded rubber part.

12. A method for preparing a tire rubber composition comprising:

providing 0-100 parts by weight (phr) of a rubber component,

providing from 5-75 phr of a dimeric decarboxylated rosin (DDCR) comprising 50-100 wt. % of polycyclic hydrocarbon compounds having one or more aliphatic, unsaturated, or aromatic groups, and 34-80 carbon atoms, having:

a molecular weight M n of 250-900 Da, measured using gel permeation chromatography and polystyrene calibration standards;

a polydispersity index of 1.0-1.35; and

an oxygen to carbon ratio of <5%;

wherein the DDCR is formed by decarboxylating a dimeric rosin acid or by dimerizing a decarboxylated rosin;

providing from 50-200 phr of a filler, and optionally up to 75 phr of a plasticizer;

mixing the rubber component, the DDCR resin, the filler, and the optional plasticizer to form a mixture;

kneading the mixture; and

incorporating a cross-linking system into the kneaded mixture to form the tire rubber composition.

13. The method of claim 12 , wherein the DDCR resin is characterized as having one or more of:

an acid value of <80 mg KOH/g, measured using ASTM D 465;

a flash point of >150° C. per ASTM D 92;

a ring and ball softening point (T sp ) from >30° C., per ASTM E28-18;

a Brookfield viscosity of 15-1000 mPa·s, at 177° C. ASTM D2196;

a glass transition temperature (Tg) of −20-110° C., per ASTM E1356;

a density of 1.00-1.05 g/cm 3 per ASTM D792-13;

a T g /M n (K/Da) ratio of >0.6; and

a cloud point in polyolefins of <70° C.

14. The method of claim 12 , wherein the DDCR resin comprises dimeric and trimer species, with a sum of the dimer and trimer species of >=75 wt. %.

15. The method of claim 12 , wherein the DDCR resin comprises a sum of dimeric and trimeric species of >=75 wt. %.

16. The method of claim 12 , wherein the DDCR resin has a polydispersity index (PDI) (GPC) of 1.05-1.15.

17. The method of claim 12 , wherein the DDCR resin has a T g /M n ratio (K/Da) of 0.6-1.0.

18. The method of claim 12 , wherein the DDCR resin has an oxygen content ratio of <3%.

19. The method of claim 12 , wherein the DDCR resin has an acid value of <50 mg KOH/g.

20. The method of claim 12 , wherein the DDCR resin is unhydrogenated, partially hydrogenated or fully hydrogenated.

Assignments (4)
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 →
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 Mar 1, 2022
From: VERVELDE, JOCHEM H. W.; PICHEREAU, JEREMIE G.; VAN HERRIKHUYZEN, JEROEN; SCHAAPMAN, MARK; EDUARD, PIETER
To: KRATON POLYMERS LLC
Reel/Frame 059125/0270 →
Continuity (2)
Provisional Application 63199335 · Dec 21, 2020
Related Publication 20220195155A1 · Jun 23, 2022