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
1999-10-15
2004-02-10
Reddick, Judy M. (Department: 1713)
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...
C524S140000, C524S270000, C524S272000, C524S284000, C524S314000, C524S292000, C524S297000, C524S376000, C524S487000
Reexamination Certificate
active
06689830
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to organic polymer compositions. More particularly, this invention relates to film-forming polymer compositions containing from 0 &mgr;p to about 50 weight percent of pigments and a specified class of esters of benzoic acid to improve certain properties of film-forming compositions and/or films prepared using these compositions. The film-forming polymer in the present compositions is prepared from at least one ethylenically unsaturated ester.
2. Description of the Prior Art
Esters derived from benzoic acid and alcohols containing from 2 to 20 or more carbon atoms are known as plasticizers for homopolymers and copolymers of vinyl chloride. For example, German published application (Offenlegungsschrift) No. 1,962,500 teaches using benzoic acid esters of the formula PhC(O)OR or succinic acid esters as plasticizers for polymers derived at least in part from vinyl chloride. In this formula Ph represents a phenyl radical and R represents an alkyl radical containing from 8 to 13 carbon atoms. The alcohol portion of the succinic acid esters contains from 8 to 13 carbon atoms.
Depending upon the desired end use application, the vinyl chloride polymer can be in the form of an aqueous emulsion that is used either alone or in combination with a powdered solid form of the polymer.
Another group of organic polymers that are useful in film-forming compositions are homopolymers and copolymers prepared from ethylenically unsaturated esters. The ethylenic unsaturation can be in the carboxylic acid or alcohol portion of the ester molecule. Suitable ethylenically unsaturated acids include but are not limited to acrylic and methacrylic acids. The alcohol portion of these esters typically contains from 1 to 4 or more carbon atoms. This family of polymers is referred to as “acrylic polymers”. These polymers can optionally include repeating units derived from ethylenically unsaturated hydrocarbons such as ethylene and styrene.
Vinyl acetate is an example of a polymerizable ester derived from an ethylenically unsaturated alcohol and a saturated carboxylic acid. Copolymers of vinyl acetate and olefins such as ethylene are useful for aqueous adhesive compositions.
U.S. Pat. No. 5,236,987 to William Arendt, which issued on Aug. 17, 1993, teaches using certain esters of benzoic acid as coalescents and plasticizing agents for water-based paint compositions containing an emulsified acrylic polymer as the film-forming material. The alcohol portion of the benzoic acid ester contains from 8 to 12 carbon atoms and the polymer is typically present in the composition as an aqueous emulsion.
The major ingredients of the paints described in the Arendt patent typically comprise an emulsified film-forming polymer derived from at least one ester of acrylic and/or methacrylic acid, water, a pigment, a thickening agent and at least one surfactant. The combination of pigment and thickening agent typically constitutes from 20 to 50 percent by weight of the total paint composition.
Film-forming compositions such as inks, adhesives and floor polishes contain different ingredients and types of film forming polymers than paints. Even though the polymers in these compositions are prepared from the same class of monomers as those present in paints, the type(s) of monomer(s), the molecular weight of the polymer, and the presence and interaction of the additional ingredients present in the various types of compositions make it difficult to predict how a coalescent, leveling agent and/or plasticizer suitable for use paint compositions will affect the properties of other film-forming compositions, such as adhesives and polish formulations, and the properties of the resultant films.
European Patent No. 668,338 issued to Rohm and Haas describes adhesive compositions wherein the film-forming material is an acrylic polymer. In addition to the polymer the compositions also include from 0.1 to 40 parts by weight per 100 parts of polymer of a plasticizer. Suitable plasticizers include benzoic acid esters derived from diethylene glycol and/or dipropylene glycol. No benzoate esters derived from aliphatic alcohols are disclosed.
U.S. Pat. No. 5,368,795, which issued on Nov. 29, 1994 to Quadir describes aqueous ceramic slurries containing an ethylene/vinyl acetate copolymer and a plasticizer. While esters of benzoic acid are disclosed as a class, the only specific ester mentioned is dipropylene glycol dibenzoate.
Published PCT Application No. 9,856,867 published on Dec. 17, 1998 describes an adhesive for polyvinyl chloride-based flooring materials. The adhesive contains an aqueous dispersion of an acrylic polymer and a plasticizer. To reduce the volatility of the composition the plasticizer is preferably diethylene glycol dibenzoate and/or dipropylene glycol dibenzoate.
Other classes of compounds disclosed as being effective coalescing, leveling, and/or plasticizing agents for compositions containing polymerized ethylenically unsaturated esters as the film-forming polymer include but are not limited to organic esters such as dioctyl adipate and 2,2,4-trimethyl-1,4-pentanediol mono- and diisobutyrates, esters of phthalic acid wherein the alcohol portion of the ester typically contains from 3 to 10 carbon atoms, partially etherified diols and triols such as 2-(2-ethoxyethoxy)ethanol, and trialkoxyalkyl phosphates such as tributoxyethyl phosphate. Some of these materials, particularly esters derived from aliphatic carboxylic acids such as adipic acid, do not substantially improve either the film-forming properties of aqueous polymer compositions typically used as adhesives, inks, floor polishes and unpigmented coatings, or the appearance of films formed from these compositions.
The present invention is based on the discovery that of the many known classes of coalescing, leveling and plasticizing agents, benzoic acid esters of monohydric alcohols containing 8 carbon atoms are unique with respect to their ability to improve the properties of many types of film-forming compositions, including adhesives, floor polishes and non-pigmented coatings. In many instances the properties of films formed from these compositions are also improved.
Because the various types of film-forming compositions differ considerably from one another with respect to composition and molecular weight of the film-forming polymer and the types of additional required and optional ingredients, one skilled in the art would consider it unlikely that one type of plasticizer would improve the properties of these substantially different compositions.
The present compositions comprise at least one acrylic, vinyl acetate or epoxide polymer or copolymer as the film-forming ingredient and, as a plasticizer, an ester of benzoic acid wherein the alcohol portion of the ester is alkyl and contains eight carbon atoms. In preferred compositions this alcohol portion is derived from 2-ethylhexyl.
Additionally, in some of the present compositions the benzoic acid ester has been found to interact synergistically with benzoic acid esters derived from oligomeric ethylene glycols.
SUMMARY OF THE INVENTION
The present invention provides a film-forming composition comprising:
A) a polymer selected from the group consisting of
(1) homopolymers and copolymers of esters of acrylic and methacrylic acids;
(2) said copolymers wherein a portion of the repeating units are derived from at least one acid selected from the group consisting of acrylic and methacrylic acids;
(3) copolymers of styrene and at least one member selected from the group consisting of esters of acrylic and methacrylic acids;
(4) said copolymers of styrene wherein a portion of the repeating units are derived from at least one acid selected from the group consisting of acrylic and methacrylic acids;
(5) homopolymers of vinyl acetate;
(6) copolymers of ethylene and vinyl acetate; and
(7) homopolymers and copolymers of organic compounds containing at least two epoxide groups per molecule
B) an amount sufficient to improve the properties of said films of at least one
Arendt William D.
Holt Mark S.
Stanhope Bruce E.
Streeter Bruce E.
Zimmerman Eric R.
Fitch Even Tabin & Flannery
Reddick Judy M.
Velsicol Chemical Corporation
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