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(19) 11 Patent Number: 6022947

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(19) 11 Patent Number: 6022947 US006022947A United States Patent (19) 11 Patent Number: 6,022,947 Frihart et al. (45) Date of Patent: Feb. 8, 2000 54) LIGHT-COLORED, LOW MOLECULAR 4,391,640 7/1983 Okoshi et al.. WEIGHT PHENOLC-MODIFIED ROSIN 4,398,016 8/1983 Homma et al. ...................... 528/158.5 ESTERS 4,744,925 5/1988 Lampo et al.. 4,857,624 8/1989 DeBlasi et al. ......................... 528/129 5,162,496 11/1992 Johnson, Jr. ............................ 530/212 (75) Inventors: Charles R. Frihart, Lawrenceville, 5,177.133 1/1993 Peck et al. .............................. 524/139 N.J.; Kenneth E. Krajca; Brett A. 5,405,932 4/1995 Bender et al. .......................... 528/104 Neumann, both of Savannah, Ga. 5.830,992 11/1998 Whalen ................................... 530/215 73 Assignee: Union Camp Corporation, Wayne, OTHER PUBLICATIONS N.J. Union Camp. Uni-Rez(R) Product Data, “Uni-Rez(R 9200 Phenolic Modified Resin,” Union Camp Corporation 21 Appl. No.: 09/156,337 Chemical Products Division, Sep.1994, 2 pages. 22 Filed: Sep. 18, 1998 Primary Examiner Nathan M. Nutter (51) Int. Cl." .................................. C09F1/02; CO9F1/04 Attorney, Agent, or Firm Seed and Berry LLP 52 U.S. Cl. .......................... 530/212; 530/213; 530/215; 530/216; 530/218; 530/219; 528/86; 528/167; 57 ABSTRACT 528/171; 528/176; 528/211; 156/327; 156/335; Light-colored phenolic-modified roSin esters, Suitable for 52.5/54.4 use as, for example, tackifiers in adhesive compositions, are 58 Field of Search ..................................... 530/212, 213, prepared by reacting together rosin, a phenolic compound, 530/215, 216, 218, 219; 528/86, 167, 171, formaldehyde or a reactive equivalent thereof, and a non 176, 211; 156/327, 335; 525/54.4 phenolic hydroxyl-containing organic compound in the presence of at least one lightening agent Selected from 56) References Cited phenol Sulfide compounds, phosphorous acid, esters of U.S. PATENT DOCUMENTS phosphorous acid, and hypophosphite Salts. The formalde hyde or reactive equivalent is present in an amount ranging 1,623,901 4/1927 Amann et al.. from about 1.1 to about 3.5 equivalents of -CHO moieties 1923,507 8/1933 Rosenblum. per 1 equivalent of Ar-OH moiety of the phenolic 1988,353 1/1935 Hönel. compound, in order to obtain roSin esters having desirably 2,007,983 7/1935 Rosenblum. low color, and adequately low molecular weight to effec 2,081,153 5/1937 Rosenblum. 2,084.203 6/1937 Kneale et al.. tively function as tackifiers. 2,311,200 2/1943 Auer. 4,002.585 1/1977 Oishi et al.. 28 Claims, No Drawings 6,022,947 1 2 LIGHT-COLORED, LOW MOLECULAR these Solvents. This particular property is largely irrelevant WEIGHT PHENOLC-MODIFIED ROSIN for a tackifier resin. ESTERS There is a continuing need for new and improved tackifier resins, which meet the basic requirements of low color, good TECHNICAL FIELD OF THE INVENTION compatibility with elastomers, and reasonable manufactur The present invention is related to resinous compositions, ing costs. The present invention fulfills this need and pro and more specifically relates to rosin-containing resins and vides related advantages as described herein. adhesives containing Same. SUMMARY OF THE INVENTION BACKGROUND OF THE INVENTION In one aspect, the present invention provides a process for The reaction products of rosin, polyhydric alcohols, form preparing a light-colored phenolic-modified rosin ester. The aldehyde and phenols (hereinafter “phenolic-modified rosin process includes the Step of reacting together reactants esters”) have been known for over 60 years. See, e.g., U.S. including rosin, a phenolic compound, formaldehyde or a Pat. No. 2,007,983 to Rosenblum. They are typically pre reactive equivalent thereof, and a non-phenolic hydroxyl pared by the reaction of rosin (a mixture of isomeric Co 15 containing organic compound. The Step of reacting is con tricyclic mono-carboxylic acids) with a formaldehyde ducted in the presence of at least one lightening agent containing compound, and a phenolic compound. This phe Selected from phenol Sulfide compounds, phosphorous acid, nolic resin is then esterified with a polyhydric alcohol esters of phosphorous acid, and hypophosphite Salts. The (hereinafter “polyol”) providing the phenolic-modified rosin reactants are combined Such that the formaldehyde or reac esters. These materials are typically dark colored and of tive equivalent thereof is present, i.e., charged to the reaction moderately high molecular weight. Phenolic-modified rosin flask, in an amount ranging from about 1.1 to about 3.5 esters currently find widespread commercial use as binders equivalents of -CHO moieties per 1 equivalent of Ar-OH for offset printing inkS. See, e.g., Roger E. Burke, "Rosin moiety of the phenolic compound. In one embodiment, the based Printing Inks”, Naval Stores, Chapter 10. Pulp Chemi process further includes the Step of mixing at least one of an cals Association (1989). 25 antioxidant or a UV stabilizer with the light-colored The prior art contains numerous description of phenolic phenolic-modified roSin ester. The invention also provides modified rosin esters which are reportedly useful in offset for light-colored phenolic-modified rosin esters prepared by printing inks. Exemplary are U.S. Pat. No. 4,398,016 to this process. Homma et al. and U.S. Pat. No. 4,391,640 to Okoshi et al., In another embodiment, the present invention provides an which are both directed to processes for producing phenolic adhesive which contains an adhesive polymer and a light modified rosin esters, which are further modified with an colored phenolic-modified rosin ester as described above. animal or vegetable oil. U.S. Pat. No. 4,002.585 to Oishi et DETAILED DESCRIPTION OF THE al. discloses a reaction product of roSin, an O.f3-ethylenically INVENTION unsaturated carboxylic acid-modified petroleum resin, a 35 resole-type phenol-formaldehyde pre-condensate and a The present invention provides a process for preparing a polyhydric alcohol having a high Softening point and high light-colored phenolic-modified roSin ester, and further pro solubility in a hydrocarbon solvent. U.S. Pat. No. 4,857,624 vides the rosin ester prepared by the described process. The to DeBlasi at al relates to a reportedly inexpensive proceSS inventive process includes the Step of reacting together for producing a phenolic-modified rosinester which exhibits 40 various reactants. The reactants include, at a minimum, high hold-out, excellent printability and excellent reducibil rosin, phenolic compound, formaldehyde or a reactive ity. U.S. Pat. No. 4,744,925 relates to a method of preparing equivalent thereof, and non-phenolic hydroxyl-containing esters of rosin, wherein rosin and polyhydric alcohol are organic compound. The reaction is conducted in the pres reacted in the presence of phosphinic acid and a phenol ence of a lightening agent. The relative amounts of the Sulfide compound, as combined catalyst, to reduce the 45 reactants are Selected with a view toward providing a rosin reaction time for ester formation and to provide a roSin ester ester having little or no coloration, and a desirably low of improved color and oxidative stability; however, no molecular weight. A Suitable range of molecular weights is particular utility is reported for the roSin esters disclosed in obtained when the formaldehyde or reactive equivalent is the 925 patent. present among the reactants in an amount ranging from Phenolic-modified roSin esters are Seldom employed as 50 about 1.1 to about 3.5 equivalents of -CHO moieties per tackifiers. In part, this is probably due to the very dark color each I equivalent of Ar-OH moiety of the phenolic com and high molecular weight of phenolic-modified rosin pound. This range is also Suitable for obtaining phenolic esters. Currently, rosin esters (made without phenol or modified rosin esters of light color. Before describing the formaldehyde modification) and terpene phenolics (made process in further detail, the various reactants will be dis from terpenes and phenols) are commercially used as 55 cussed. tackifiers, and these materials have colors, as measured on The roSin useful in the present invention is the Standard the Gardner Scale, of less than about 6, where lower numbers material of commerce known as “roSin', or a feedstock correspond to lighter-colored resins. In contrast, phenolic containing rosin. Rosin is mainly a mixture of Co, tricyclic modified rosinesters typically have Gardner colors in exceSS fused-ring, monocarboxylic acids, typified by pimaric and of 10. Thus, color alone effectively precludes phenolic 60 abietic acids, which are commonly referred to as “resin modified rosinesters from being employed as commercially acids.” Any one or more of the Co cyclic carboxylic viable tackifiers. acid-containing isomers present in rosin may be used as the In addition, Since phenolic-modified roSin esters have “rosin' of the invention. been primarily developed for use in offset printing inks, a Rosin which is suitable for use in the present invention critical property for these esters is oil solubility. Offset 65 can be obtained from many Sources, and can have a wide printing inkS contain a large amount of hydrocarbon Solvent, range of purities. For example, Woodrosin may be employed and therefore the binder resins must have good solubility in in the present invention, where wood rosin is obtained from 6,022,947 3 4 Pinus Stumps after harvesting the Stumps, chipping the 100-300 C. Typical dehydrogenation catalysts include, Stumps into Small chips, extracting the chips with hexane or without limitation, palladium, rhodium and platinum metals. higher-boiling paraffin, and distilling the hexane or paraffin These metals may be Supported on a Solid Support, where to yield wood rosin. Gum rosin, which is the name given to Silica, alumina and carbon are Suitable Solid Supports. An rosin that is obtained after Scoring a pine tree, collecting the amount of dehydrogenation catalyst ranging from 0.01 to exudate Sap, and then distilling away the volatile 5% by weight, based on the amount of roSin employed, is components, may also be employed in the invention.
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