Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2000-05-31
2002-06-18
Szekely, Peter (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S270000, C530S210000, C530S214000, C530S221000
Reexamination Certificate
active
06407154
ABSTRACT:
BACKGROUND OF THE INVENTION
Both natural and synthetic elastomers usually require the use of processing aids to assist mechanical breakdown and compounding. Materials such as mixtures of oil soluble sulfonic acids of high molecular weight with a high boiling alcohol, paraffin oils, blends of sulfonated petroleum products and selected mineral oils are conventionally used as processing aids. Additional examples include petroleum, paraffinic and vegetable oils, coal tar, petroleum residues or pitches and naturally occurring or synthetic resins.
One advantage in using processing aids is they assist the incorporation of fillers and other ingredients with low power consumption since they reduce internal friction in calendering and extrusion. By reducing the amount of friction during compounding, the temperature of the rubber will remain lower and thus minimize the possibility of scorch.
Various types of rosin acids have been used as extenders for high molecular weight SBR. See
Properties of GR
-
S Extended With Rosin Type Acids,
L. H. Howland, J. A. Reynolds, and R. L. Provost, Industrial and Engineering Chemistry, Vol. 45, No. 5, May 1953. Whereas reasonably good cured physical properties can be obtained with the rosin type acids, there are problems associated with their use which include cure retardation, high tack and poor low temperature performance, which limit their use as an extender in rubber formulations.
U.S. Pat. No. 4,478,993 discloses the use of decarboxylated rosin acid also known as thermal oil as a total or partial replacement for oil in a rubber formulation. Compared with the use of aromatic extending oils in rubbers, decarboxylated rosin acids provide comparable processing and low temperature performance and superior abrasive resistance.
U.S. Pat. No. 5,134,184 relates to rosin monomaleimides which are useful as a total or partial replacement for extender or processing oil in rubber formulations. The rosin monomaleimides are prepared by reacting abietylamine and/or dehydroabietylamide with maleic anhydride.
SUMMARY OF THE INVENTION
The present invention relates to rosin modified succinamic acid of the formula:
or mixtures thereof.
DETAILED DESCRIPTION OF THE INVENTION
There is also disclosed a process for preparing rubber compositions which comprises a mixing a rubber selected from the group consisting of natural rubber, homopolymers of conjugated diolefins, copolymers of conjugated diolefins and ethylenically unsaturated monomers or mixtures thereof with a rosin modified succinamic acid.
There is also disclosed a rubber composition which comprises (1) a rubber selected from the group consisting of natural rubber, homopolymers of conjugated diolefins, copolymers of conjugated diolefins and ethylenically unsaturated monomers or mixtures thereof and a rosin modified succinamic acid of the formula:
or mixtures thereof.
The rosin modified succinamic acid is prepared by reacting abietylamine or dehydroabietylamine with succinic anhydride. The abietylamine and dehydroabietylamine are derived from rosin. Rosin is a solid resinous material that occurs naturally in pine trees. The three major sources of rosin are gum rosin, wood rosin and tall oil rosin. Gum rosin is from the oleoresin extrudate of the living pine tree. Wood rosin is from the oleoresin contained in the aged stumps. Tall oil rosin is from the waste liquor recovered as a by-product in the Kraft paper industry.
The aged virgin pine stump is the source of wood rosin. The stump is allowed to remain in the ground for about ten years so that its bark and sapwood may decay and slough off to leave the heartwood rich in resin. It is known that production of pine stump rosin can be artificially stimulated by injecting the herbicide, Paraquat, into the lower portion of the tree. This treatment of the stump produces Pinex™ rosin.
Rosins derived from both oleoresin and aged stump wood are composed of approximately 90% resin acids and 10% nonacidic components. Chemical treatment of rosins, such as hydrogenation, dehydrogenation, or polymerization are known which produce modified resins.
Succinic anhydride is reacted with abietylarnine or dehydroabietylamine under suitable conditions to form a compound having a rosin moiety connected to a succinamic acid. Dehydroabietylamine in a 90% purity is commercially available from Aldrich Chemical Company. Abietylarnine and dehydroabietylamine can be used individually or more commonly in mixtures with various amounts of other rosin amines including levopimarylamine, neoabietylamine, palustrylarmine, tetrahydroabietylarnine, pimarylamine, isopimarylamine, &Dgr;-isopimarylamine, elliotinoylamine and sandaracopimarylamine. Therefore, in connection with the above formula, the rosin modified succinamic acid may also be derived from use of the above amines which are commonly found in admixture with abietylamine and/or dehydroabietylamine.
The succinic acid anhydride may be reacted with the abietylamine and/or dehydroabietylamine in a variety of mole ratios. Generally the mole ratio of succinic anhydride to abietylamine and/or dehydroabietylamine ranges from about 1.5:1 to about 0.75:1 with a range of from about 1.1:1 to about 0.9:1 being preferred.
An organic solvent may be used to dissolve the abietylamine or dehydroabietylamine. The solvent is preferably inert to the reaction between the succinic anhydride and the abietylamine and/or dehydroabietylamine. Illustrative of solvents suitable for use in the practice of this invention include: saturated and aromatic hydrocarbons, e.g., hexane, octane, dodecane, naphtha, decalin, tetrahydronaphthalene, kerosene, mineral oil, cyclohexane, cycloheptane, alkyl cycloalkane, benzene, toluene, xylene, alkyl-naphthalene, and the like; ethers such as tetrahydrofuran, tetrahydropyran, diethylether, 1,2-dimethoxybenzene, 1,2-diethoxybenzene, the monoand dialkylethers of ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, oxyethyleneoxypropylene glycol, and the like; fluorinated hydrocarbons that are inert under the reaction conditions such as perfluoroethane, monofluorobenzene, and the like. Another class of solvents are sulfones such as dimethylsulfone, diethylsulfone, diphenolsulfone, sulfolane, and the like. Mixtures of the aforementioned solvents may be employed so long as they are compatible with each other under the conditions of the reaction and will adequately dissolve the abietylamine or dehydroabietylamine and not interfere with the reaction.
The reaction between the succinic anhydride and abietylamine and/or the dehydroabietylamine may be conducted in the absence or presence of a catalyst. Examples of catalysts that may be used include acid catalysts such as sulfuric acid, hydrochloric acid and toluenesulfonic acid. The amount of catalyst that may be used will vary depending on the particular catalyst that is selected. For example, when an acid catalyst is used, from about 5% to about 10% by weight of the abietylamine and/or dehydroabietylamine is recommended. However, it is preferred that no catalyst is used to avoid the formation of undesirable side products.
The reaction between the succinic anhydride and abietylamine and/or dehydroabietylamine may be conducted over wide temperatures. The temperatures may range from moderate to an elevated temperature. In general, the reaction may be conducted at a temperature of between about 0° C. to about 250° C. The preferred temperature range is from about 24° C. to about 150° C., while the most preferred temperature range is from about 56° C. to about 60° C.
The reaction may be conducted under a variety of pressures. Pressures ranging from about 0 psig to about 100 psig may be used to conduct the reaction.
The reaction is conducted for a period of time sufficient to produce the desired rosin modified succinamic acid. In general, the reaction time can vary from minutes to several hours. If the more sluggish reaction conditions are selected, then the reaction time will have to be extended until the desired product is produced. It is appreciated that the resid
Maly Neil Arthur
Sandstrom Paul Harry
Wideman Lawson Gibson
Bruce J. Hendricks
Szekely Peter
The Goodyear Tire & Rubber Company
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