IP Library Granted Patent US 10,717,853
Granted Patent B2
US 10,717,853 · App. 15/784,440 · Granted Jul 21, 2020

Rubber compositions containing improved tread enhancement additives and use thereof

Inventors: Wolfgang Pille-Wolf (Tervuren, NL); Jérémie Guillaume Pichereau (Almere, NL); Hannes Hendrik Peter van Erp (Almere, NL); Jeffrey R Warmkessel (Savannah, GA); Blaisdell Benedict Willis (Savannah, GA)
Assignee: Kraton Chemical, LLC
C08L9/06C08G61/02C08G67/00C08L2205/02C08L2205/03
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Quick Facts
Patent No.
US 10,717,853
App. No.
15/784,440
Granted
Jul 21, 2020
Kind
B2
Abstract

The disclosure relates to a composition for use in a number of applications including tires. The composition comprises a blend of a rubber component, reinforcing particulate fillers, and based on 100 parts by weight (phr) of the rubber component; from about 5 phr to about 70 phr of a terpene phenol resin having a softening point temperature in the range of from about 100° C. to about 170° C. and having a hydroxyl value in the range from about 5 to about 30. In one embodiment, the terpene phenol resin has a number average molecular weight of from about 700 Da to about 790 Da, a weight average molecular weight of from about 930 Da to about 1090 Da, and a polydispersity index of from about 1.25 to about 1.45.

Claims (21)

1. A terpene phenol resin having a softening point temperature in the range of from about 100° C. to about 170° C., a hydroxyl value in the range from about 5 to about 18 mg KOH/g, a glass transition temperature of from 95° C. to 103° C.; and a number average molecular weight of from about 700 Da to about 790 Da, a weight average molecular weight of from about 930 Da to about 1090 Da, and a polydispersity index of from about 1.25 to about 1.45.

2. The terpene phenol resin of claim 1 , wherein the resin comprises monomers selected from the group consisting of piperylenes, cyclic pentadienes, aromatics, limonenes, pinenes, amylenes, and combinations thereof.

3. The terpene phenol resin of claim 1 , wherein the terpene phenol resin is obtained by polymerizing phenol and at least a terpene selected from the group consisting of α-pinene, β-pinene, dipentene, and limonene, at a molar ratio of terpene to phenol in the range from about 1:1 to about 4:1.

4. The terpene phenol resin of claim 1 , wherein the terpene phenol resin is obtained by adding a phenol to at least a terpene selected from the group consisting of α-pinene, β-pinene, dipentene, and limonene, in the presence of a Lewis acid catalyst, at a molar ratio of terpene to phenol in the range from about 1:1 to about 4:1, and wherein the Lewis acid catalysts is selected from ether complexes of boron trifluoride and organic acid complexes of boron trifluoride.

5. The terpene phenol resin of claim 1 , wherein the terpene phenol resin is obtained by polymerizing phenol and at least a terpene selected from the group consisting of α-pinene, β-pinene, dipentene, and limonene, at a molar ratio of terpene to phenol in the range from 95:5 to 60:40.

6. The terpene phenol resin of claim 1 , wherein the terpene phenol resin is obtained by adding a phenol to at least a terpene selected from the group consisting of α-pinene, β-pinene, dipentene, and limonene, in the presence of a Lewis acid catalyst, at a molar ratio of terpene to phenol in the range from 95:5 to 60:40,

wherein the Lewis acid catalyst is selected from ether complexes of boron trifluoride and organic acid complexes of boron trifluoride.

7. A composition comprising a blend of:

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

from about 50 to 200 phr of a filler;

from about 0 to 25 phr of a plasticizer; and

from about 5 phr to about 70 phr of the terpene phenol resin of claim 1 .

8. The composition of claim 7 , wherein the composition is for use as a tire tread formulation, and wherein the tire tread formulation has a tan δ at 0° C. of from 0.62 to 0.72, and a tan δ at 60° C. of from 0.14 to 0.20, measured using dynamic mechanical analysis in temperature-sweep/mode in double shear mode, with a heat rate of 1° C./min at 10 Hz, and a dynamic strain of 0.1% from −60° C. to −5° C., and a dynamic strain of 3% from −5° C. to 100° C.

9. The composition of claim 7 , wherein the tire tread formulation further comprises a coupling agent selected from the group of: a sulfur-based coupling agent, an organic peroxide-based coupling agent, an inorganic coupling agent, a polyamine coupling agent, a resin coupling agent, a sulfur compound-based coupling agent, oxime-nitrosamine-based coupling agent, and sulfur.

10. The composition of claim 7 , wherein the rubber component is selected from the group of natural rubber (NR), styrene-butadiene rubber (SBR), butadiene rubber (BR), synthetic polyisoprene rubber, epoxylated natural rubber, polybutadiene rubber, nitrile-hydrogenated butadiene rubber NHBR, hydrogenated styrene-butadiene rubber HSBR, ethylene propylene diene monomer rubber, ethylene propylene rubber, maleic acid-modified ethylene propylene rubber, butyl rubber, isobutylene-aromatic vinyl or diene monomer copolymers, brominated-NR, chlorinated-NR, brominated isobutylene p-methyl styrene copolymer, chloroprene rubber, epichlorohydrin homopolymers rubber, epichlorohydrin-ethylene oxide or allyl glycidyl ether copolymer rubbers, epichlorohydrin-ethylene oxide-allyl glycidyl ether terpolymer rubbers, chlorosulfonated polyethylene, chlorinated polyethylene, maleic acid-modified chlorinated polyethylene, methylvinyl silicone rubber, dimethyl silicone rubber, methylphenylvinyl silicone rubber, polysulfide rubber, vinylidene fluoride rubbers, tetrafluoroethylene-propylene rubbers, fluorinated silicone rubbers, fluorinated phosphagen rubbers, styrene elastomers, thermoplastic olefin elastomers, polyester elastomers, urethane elastomers, and polyamide elastomers.

11. The composition of claim 7 , wherein the rubber is coupled, star-branched, or functionalized with at least a sulfur compound, a silanol group, a silane group, an epoxy group.

12. The composition of claim 7 , wherein the plasticizer is selected from aliphatic acid esters, hydrocarbon processing oils, tall oil pitch and modified tall oil pitch, and combinations thereof.

13. The composition of claim 7 , wherein the filler is selected from calcium carbonate, clay, mica, silica, silicates, talc, titanium dioxide, alumina, zinc oxide, starch, wood flour, carbon black, ultra-high molecular weight polyethylene (UHMWPE), particulate polymer gels, plasticized starch composites, and mixtures thereof.

14. The composition of claim 7 , wherein the filler is surface treated prior to being added to the composition.

15. The composition of claim 7 , wherein the composition is extruded, compression molded, blow molded, injection molded, or laminated into a molded rubber part.

16. The composition of claim 7 , wherein the composition is extruded, compression molded, blow molded, injection molded, or laminated into any of fibers, films, laminates, layers, automotive parts, appliance housings, consumer products, and packaging products.

Assignments (7)
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2021
From: KRATON CHEMICAL, LLC
To: KRATON POLYMERS LLC
Reel/Frame 055366/0374 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2021
From: PILLE-WOLF, WOLFGANG; PICHEREAU, JEREMIE GUILLAUME; VAN ERP, HANNES HENDRIK PETER; WARMKESSEL, JEFFREY R; WILLIS, BLAISDELL BENEDICT
To: KRATON CHEMICAL, LLC
Reel/Frame 055366/0289 →
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 →
Continuity (2)
Provisional Application 62408210 · Oct 14, 2016
Related Publication 20180105681A1 · Apr 19, 2018
Cited By (1)
US 12,459,295