Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2000-07-06
2002-04-16
Lipman, Bernard (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S327900, C525S386000, C526S272000
Reexamination Certificate
active
06372851
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to functionalized hydrocarbon resin compositions having similar physical properties as natural rosin and to methods for their preparation. More particularly, this invention relates to acid-modified liquid C
5
hydrocarbon resin compositions prepared from piperylene and unsaturated carboxylic acids or anhydrides and their use as an alternative to natural rosin.
BACKGROUND OF THE INVENTION
Rosin is a natural resin extracted from pine trees and is a nonvolatile resin typically obtained from gum resin after distillation of turpentine. Rosin is a mixture of monocarboxylic diterpene acids. Rosin is often characterized by its color, softening point and its acidity. Rosin quality varies with many factors, such a species of pine tree, age and size of a tree, climate, tapping method, etc.
Natural rosin typically has a softening point from about 70° C. to about 85° C. and an acid number from about 150 to 190 mg KOH/g. These properties can be altered by processing techniques, such as hydrogenation, disproportionation, polymerization and chemical reaction, to yield a large number of derivatives.
Because rosin is an acidic material, its acid functionality is utilized in many commercial applications. Rosins are often used in the manufacture of adhesives, paper sizing agents, printing inks, solders and fluxes, various surface coatings, insulating materials for the electronics industry, synthetic rubber, chewing gums, soaps and detergents.
The characteristics of rosin as a natural product, however, are varied. Attempts have been made to provide a synthetic substitute for natural rosin. For example, polymerization of olefinic hydrocarbons may be used to produce resin synthetic substitutes for the naturally occurring resins in rosin. Post modification of olefinic hydrocarbons, such as by dicarboxylic acid or anhydride adduction, can be used to provide the desired acidity. Such modification, however, may also alter other properties of the modified-resin thereby making it unacceptable as a rosin alternative.
For example, U.S. Pat. No. 3,005,800 describes the maleic anhydride modification of a petroleum distillate having a distillation of 90% below 125° C. Friedel-Crafts is polymerization of the distillate yielded a steam-stripped resin having a softening point range from 70 to 100° C. and an unstripped resin having a softening point range from 50 to 60° C. From about 10 to 28 weight percent maleic anhydride was added to these resins. The maleic anhydride modification, however, increased the softening point to greater than 110° C., making these modified resins unsuitable as a natural rosin replacement.
U.S. Pat. No. 3,450,560 describes up to one percent maleic anhydride modification of a hydrocarbon resin to improve the resin's adhesion and dyeability characteristics. The resin, however, has a large molecular weight of at least 50,000 daltons for use as dyeable film on aluminum articles. Such a high molecular weight resin may be useful as an adhesive, but is not acceptable as a rosin alternative due to its high molecular weight.
U.S. Pat. No. 3,655,629 describes a hydrocarbon resin having improved adhesion than natural terpene resins. The hydrocarbon resin is obtained by a 5 to 10 per weight percent maleic anhydride addition to a hydrocarbon resin obtained cracked gasoline or light oil compositions. Although the patent describes a maleated resin with broad range of acid values, i.e., 30 to 250, and softening points, i.e., 0 to 150° C., no specifically described resin has characteristics similar to natural rosin. Disclosed resins that have similar softening points to natural rosin, however, exhibit lower acid numbers than that of natural rosin. Furthermore, disclosed resins that have similar acid numbers to natural rosin, however, exhibit lower softening points than that of natural rosin.
G.B. Patent No. 1,356,309 describes reacting from 25 to 35 weight percent maleic anhydride with a butadiene-cyclopentadiene copolymer. The maleated copolymer had acid numbers from about 200 to 370 and softening point from about 44 to 112. These maleated copolymers, however, have acid numbers that are higher than those typical of natural rosin.
U.S. Pat. No. 3,905,948 describes reacting from 5 to 20 weight percent maleic anhydride with a hydrocarbon resin formed from the Friedel-Crafts polymerization of a 30° to 300° C. boiling point hydrocarbon stream. The reaction product had softening points greater than 160° C. and low acid numbers of only 20 to 40. Such low acid numbers are not typical of natural rosin.
U.S. Pat. No. 3,933,720 describes acid modified hydrocarbon resins with good adhesive characteristics as compared to alkylphenolic resins. From 0.1 to 30 weight percent maleic acid or anhydride is reacted with a resin obtained by the Friedel-Crafts polymerization of a cracked hydrocarbon steam boiling at 140° C. to 280° C. or 20° C. to 140° C. The acid modified resins were combined with polychloroprene to provide adhesive compositions. The resins of this patent, however, had higher softening points than natural rosin prior to acid modification of 7 to 10 weight percent maleic anhydride.
U.S. Pat. No. 4,230,840 describes an acid modified hydrocarbon resin obtained from reacting a hydrocarbon resin obtained from reacting a hydrocarbon resin with from about 0.1 to about 5 weight percent unsaturated dicarboxylic anhydride. The hydrocarbon resin was formed from a hydrocarbon stream containing from 25 to 75 weight percent catatonically polymerizable aromatic hydrocarbons. Softening points of about 130° C. were obtained upon acid modification, which exceed the typical values of natural rosin.
E.P. Patent No. 074,273 describes acid modified hydrocarbon resins formed from the reaction product of 0.1 to 33 weight percent unsaturated dicarboxylic acid of anhydride with hydrocarbon resin. The maximum amount of acid, however, added to the resin in any given example was only about 2 weight percent. While acid values from 0.1 to 150 and softening points from 60° C. to 180° C. are described, only acid numbers of less than 15 and softening points in excess of 94° C. were demonstrated for acid-modified resins. Furthermore, the acid-modified resins of this patent contain significant quantities of 9,10-dihydrodicyclopentadiene to control the resin characteristics, such as softening point.
U.S. Pat. No. 4,401,791 described an acid modified hydrocarbon resin suitable for use as a binder in printing ink. The resin is a reaction product of 3 to 20 weight percent dicarboxylic acid units, an alkyl phenol-aldehyde resin and a hydrocarbon stream rich in olefinically unsaturated aromatics or cyclopentadiene. The acid modified resins have softening points of 120° C. to 180° C. and acid numbers of 30 to 50. Such softening points and acid numbers are not, however, typical of natural rosin.
E.P. Patent No. 300,624 describes a water dispersible tackifier resin that can be acid-modified with about 2.5 weight percent maleic anhydride to provide acid-modified resins having a softening point from about 70-140° C. and an acid number from about 10 to 30. The resin is produced from dicyclopentadiene, styrene and terpene monomers. The patent describes the potential for an acid-modified resin having a softening point below 150° C. and having an acid number from 10 to 150. Such properties, however, were not demonstrated in the patent. Maleated resins had softening points from 70 to 140° C., but had acid numbers of less than 30.
E.P. Patent No. 311,402 describes an ink composition formed from a cyclic or di-cyclic pentadiene, an unsaturated olefinic aromatic and unsaturated carboxylic acids or anhydrides. Softening points from about 150 to 170° C. and acid numbers from about 10 to 15 were obtained with 3 to 5 weight percent acid modification.
U.S. Pat. No. 3,953,407 describes a process for preparing an acid-modified hydrocarbon resin for controlling paper sizes. The resin is formed from hydrocarbons having 5 to 10 carbon atoms. The resin is acid-modified with up to 20 weight percent unsaturated dicarboxyl
Boshears B. J.
Eastman Chemical Resins Inc.
Graves, Jr. Bernard J.
Lipman Bernard
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