Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
1999-02-16
2001-04-24
Pezzuto, Helen L. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S237000, C526S290000, C526S308000, C526S346000
Reexamination Certificate
active
06221990
ABSTRACT:
BACKGROUND OF THE INVENTION
Polymeric resins have been used in treads of tires to improve traction. Unfortunately, one consequence of their use is a decrease in durability and treadwear.
Polymeric resinous materials containing units derived from piperylene, units derived from 2-methyl-2-butene and units derived from dicyclopentadiene are commercially available from The Goodyear Tire & Rubber Company under the designation WINGTACK® 115. These polymeric resinous materials find use in adhesives.
SUMMARY OF THE INVENTION
The present invention relates to a polymeric resinous material derived from limonene, dicyclopentadiene and tert-butyl styrene.
DETAILED DESCRIPTION OF THE INVENTION
There is disclosed a polymeric resinous material comprising
(a) from 15 to 39 weight percent units derived from limonene;
(b) from 15 to 39 weight percent units derived from dicyclopentadiene; and
(c) from 46 to 70 weight percent units derived from tertiary-butyl styrene;
wherein the sum of the weight percent units derived from limonene and dicyclopentadiene range from 30 to 54 weight percent units of the resin.
In addition, there is disclosed a rubber composition comprising (a) a diene-based elastomer containing olefinic unsaturation and (b) 1 to 80 phr of a polymeric resinous material comprising
(1) from 15 to 39 weight percent units derived from limonene;
(2) from 15 to 39 weight percent units derived from dicyclopentadiene; and
(3) from 46 to 70 weight percent units derived from tertiary-butyl styrene;
wherein the sum of the weight percent units derived from limonene and dicyclopentadiene range from 30 to 54 weight percent units of the resin.
In addition, there is disclosed a pneumatic tire having a tread comprised of (a) a diene-based elastomer containing olefinic unsaturation and (b) 1 to 80 phr of a polymeric resinous material comprising
(1) from 15 to 39 weight percent units derived from limonene;
(2) from 15 to 39 weight percent units derived from dicyclopentadiene; and
(3) from 46 to 70 weight percent units derived from tertiary-butyl styrene;
wherein the sum of the weight percent units derived from limonene and dicyclopentadiene range from 30 to 54 weight percent units of the resin.
The polymeric resinous material for use in the present invention comprises from about 15 to about 39 weight percent units derived from limonene; from about 15 to about 39 weight percent units derived from dicyclopentadiene; and 46 to 70 weight percent units derived from tertiary-butyl styrene. Preferably, the resin comprises from about 22 to about 27 weight percent units derived from limonene; from about 22 to about 27 weight percent units derived from dicyclopentadiene; and from 46 to 56 weight percent units derived from tertiary-butyl styrene.
In a particularly preferred embodiment, the weight ratio of units derived from limonene:dicyclopentadiene:tertiary-butyl styrene is 1:1:2.
The polymeric resin is particularly suited for use in a diene-based elastomer in an amount ranging from about 1 to 80 phr (parts by weight per 100 parts by weight of rubber). Preferably, the polymeric resin is present in an amount ranging from 10 to 40 phr.
The resins may be prepared using various anhydrous metallic halide catalysts. Representative examples of such catalysts are fluorides, chlorides and bromides, of aluminum, tin and boron. Such catalysts include, for example, aluminum chloride, stannic chloride and boron trifluoride. Alkyl aluminum dihalides are also suitable, representative examples of which are methyl aluminum dichloride, ethyl aluminum dichloride and isopropyl aluminum dichloride.
In carrying out the polymerization reaction, the hydrocarbon mixture is brought into contact with the anhydrous halide catalyst. Generally, the catalyst is used in particulate form having a particle size in the range of from about 5 to about 200 mesh size, although larger or smaller particles can be used. The amount of catalyst used is not critical although sufficient catalyst must be used to cause a polymerization reaction to occur. The catalyst may be added to the olefinic hydrocarbon mixture or the hydrocarbon mixture may be added to the catalyst. If desired, the catalyst and mixture of hydrocarbons can be added simultaneously or intermittently to a reactor. The reaction can be conducted continuously or by batch process techniques generally known to those skilled in the art.
The reaction is conveniently carried out in the presence of a diluent because it is usually exothermic. Various diluents which are inert in that they do not enter into the polymerization reaction may be used. Representative examples of inert diluents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane, aromatic hydrocarbons such as toluene, xylene and benzene, and unreacted residual hydrocarbons from the reaction.
A wide range of temperatures can be used for the polymerization reaction. The polymerization can be carried out at temperatures in the range of from about −20° C. to about 100° C., although usually the reaction is carried out at a temperature in the range of from about 0° C. to about 50° C. The polymerization reaction pressure is not critical and may be atmospheric or above or below atmospheric pressure. Generally, a satisfactory polymerization can be conducted when the reaction is carried out at about autogenous pressure developed by the reactor under the operating conditions used. The time of the reaction is not generally critical and reaction times can vary from a few seconds to 12 hours or more.
Upon completion of the reaction the hydrocarbon mixture is neutralized followed by isolation of the resin solution. The resin solution is steam-distilled with the resulting resin being allowed to cool.
The resins can optionally be modified by the addition of up to about 25 weight percent of other unsaturated hydrocarbons and particularly hydrocarbons containing from 9 to 10 carbon atoms and mixtures thereof. Representative examples of such hydrocarbons are 3-methyl styrene, 4-methyl styrene, 1-methyl indene, 2-methyl indene, 3-methyl indene and mixtures thereof.
The resinous materials of this invention are characterized by having a Gardner color of from about 2 to about 10, a capillary tube melting point of from about 100° C. to about 200° C., good heat stability and a specific gravity of from about 0.85 to about 1.0. They typically have a capillary tube melting point of 100° C. to 200° C. after steam-stripping to remove lower molecular weight compounds; although, when prepared in the presence of a chlorinated hydrocarbon solvent, their softening point is increased within that range. These resins are generally soluble in aliphatic hydrocarbons such as pentane, hexane, heptane and aromatic hydrocarbons such as benzene and toluene.
The tread of the tire of the present invention contains an elastomer containing olefinic unsaturation. The phrase “rubber or elastomer containing olefinic unsaturation” is intended to include both natural rubber and its various raw and reclaim forms as well as various synthetic rubbers. In the description of this invention, the terms “rubber” and “elastomer” may be used interchangeably, unless otherwise prescribed. The terms “rubber composition,” “compounded rubber” and “rubber compound” are used interchangeably to refer to rubber which has been blended or mixed with various ingredients and materials and such terms are well known to those having skill in the rubber mixing or rubber compounding art. Representative synthetic polymers are the homopolymerization products of butadiene and its homologues and derivatives, for example, methylbutadiene, dimethylbutadiene and pentadiene as well as copolymers such as those formed from butadiene or its homologues or derivatives with other unsaturated monomers. Among the latter are acetylenes, for example, vinyl acetylene; olefins, for example, isobutylene, which copolymerizes with isoprene to form butyl rubber; vinyl compounds, for example, acrylic acid, acrylonitrile (which polymerize with butadiene to form NBR), methacrylic acid and styrene, the latter compound p
Blok Edward John
Kralevich, Jr. Mark Leslie
Ruscak Joseph Miles
Sandstrom Paul Harry
Wideman Lawson Gibson
Hendricks Bruce J.
Pezzuto Helen L.
The Goodyear Tire & Rubber Company
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