Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
1999-11-24
2003-04-08
Berman, Susan W. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S008000, C522S013000, C522S015000, C522S017000, C522S018000, C522S021000, C522S031000, C522S042000, C522S046000, C522S064000, C522S181000, C522S173000, C526S328000
Reexamination Certificate
active
06545064
ABSTRACT:
TECHNICAL FIELD
This invention relates to coating compositions. More particularly, this invention relates to coating compositions which may be applied to substrates such as polymeric films to improve their printability and other surface characteristics.
BACKGROUND OF THE INVENTION
Polymeric films generally are smooth and have low surface tensions due to their inherent characteristics. Printing on untreated films often results in unsatisfactory print quality due to insufficient surface wetting and insufficient ink adhesion. There is also the possibility of surface contaminants on film surfaces which can further reduce print quality.
Various coatings have been applied to the surfaces of polymeric films to improve their printability. The improved ink performance of such coated films may be due to improved surface tension, altered polarity; different degrees of micro-roughness, or other physical or chemical factors.
A problem in the art relates to the fact that the coating compositions currently available for improving ink adhesion have been found to be less than satisfactory for many inks, including water-based flexo inks. Another problem relates to the fact that many of these coating compositions are inadequate for beverage container applications due to the fact that the ink adhesion provided by such coatings is inadequate when subjected to standard water-soak beverage test procedures. Still another problem relates to the fact that many of these coatings are inadequate due to the fact that they exhibit inadequate chemical resistance properties. The present invention overcomes these problems by providing, in one embodiment a coating that provides enhanced adhesion for a wide variety of inks, including water-based flexo inks, and in one embodiment a coating that exhibits enhanced water-soak beverage characteristics, and in one embodiment a coating that exhibits enhanced chemical resistance characteristics.
U.S. Pat. No. 5,804,301 discloses a radiation-curable coating composition which comprises (A) from about 70% to about 99% by weight of at least one polyfunctional acrylate monomer containing at least one internal flexible unit; (B) from about 1% to about 30% by weight of at least one other reactive vinyl or unsaturated monomer provided the reactive vinyl or unsaturated monomer (B) is not the same as the monomer of (A); and (C) from about 0% to about 10% by weight of at least one photoinitiator, provided that the composition is free of methacrylic functionalized colloidal silica. A method of coating a substrate utilizing the foregoing radiation-curable compositions, as well as a substrate coated in accordance such method are also disclosed.
SUMMARY OF THE INVENTION
This invention relates to a curable coating composition which comprises: (A) a compound represented by the formula
wherein in formula (A-I) each R independently is hydrogen or a hydrocarbyl group of 1 to about 8 carbon atoms, and n is a number that is about 4 or higher; and (B) a reactive vinyl or unsaturated monomer, provided said reactive vinyl or unsaturated monomer is not the same as (A). In one embodiment, the inventive composition further comprises (C) a photoinitiator. In one embodiment, the inventive composition further comprises (D) a thermal initiator. In one embodiment, the inventive composition further comprises (E) a latent acid catalyst. The invention also relates to a method of coating a substrate utilizing the foregoing coating composition, as well as to a substrate coated in accordance with foregoing method. The invention also relates to composite articles comprised of a substrate with a cured printable coating derived from the foregoing composition adhered to a surface of said substrate.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Component (A) of the inventive coating composition is a compound represented by the formula
wherein in formula (A-I) each R independently is hydrogen or a hydrocarbyl group of 1 to about 8 carbon atoms, and n is a number that is about 4 or higher, and in one embodiment about 6 or higher. The hydrocarbyl groups include aliphatic groups, especially alkyl and alkenyl groups. In one embodiment, the hydrocarbyl groups are alkyl groups. In one embodiment, each R independently is hydrogen or a hydrocarbyl group of 1 to about 4 carbon atoms, and in one embodiment 1 or 2 carbon atoms. In one embodiment, each R independently is hydrogen or methyl. In one embodiment, each R is hydrogen. In one embodiment, each R is methyl. In one embodiment, n is a number in the range of about 4 to about 30, and in one embodiment about 6 to about 30, and in one embodiment about 8 to about 30, and in one embodiment about 8 to about 20, and in one embodiment about 8 to about 6. In one embodiment, n is in the range of about 8 to about 10, and in one embodiment it is in the range of about 12 to about 15. Examples include polyethylene glycol (number average molecular weight (Mn)=600) diacrylate, polyethylene glycol (Mn=400) diacrylate, polyethylene glycol (MN=200) diacrylate.
These compounds may be prepared by procedures well known to those skilled in the art. One method of preparing such compounds involves condensing ethylene glycol to form ether linkages and thereafter reacting the intermediate ether with sufficient acrylic or methacrylic acid, or esters or derivatives thereof to form the desired compound.
The inventive coating compositions also contain (B) a reactive vinyl or unsaturated monomer or oligomer, provided that the reactive vinyl or unsaturated monomer or oligomer is not the same as component (A). The reactive vinyl or unsaturated monomers (B) that are useful include vinyl ethers, mono- and polyfunctional acrylate monomers or oligomers, vinyl esters, vinyl carboxylic acids, vinyl carboxylic acid salts, vinyl amides, and unsaturated dicarboxylic acids and derivatives thereof such as maleic and fumaric acids and derivatives thereof. In one embodiment, component (B) is selected from the group consisting of vinyl ethers, mono- or polyfunctional acrylate monomers or oligomers, and mixtures of two or more thereof. In one embodiment, component (B) is at least one vinyl ether and is free of any mono- or polyfunctional acrylate monomers or oligomers.
Various vinyl ethers may be included in the coating compositions of the present invention as component (B), and these include ethers containing one or more vinyl groups. Specific examples of useful vinyl ethers include ethyl vinyl ether, butyl vinyl ether, hydroxy butyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, octyl vinyl ether, decyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, cyclohexane dimethanol monovinyl ether, phenyl vinyl ether, 1,6-hexanediol divinyl ether, 1,4-cyclohexane dimethanol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, dipropylene glycol divinyl ether, tripropylene glycol divinyl ether, tetrapropylene glycol divinyl ether, and the propenyl ether of propylene carbonate. Ethers with more than one vinyl group such as 1-hexanediol divinyl ether, 1,4-cyclohexane dimethanol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, dipropylene glycol divinyl ether, tripropylene glycol divinyl ether and tetrapropylene glycol divinyl ether may be used. Diethylene glycol divinyl ether, triethylene glycol divinyl ether, dipropylene glycol divinyl ether and tripropylene glycol divinyl ether are useful. Vinyl ethers available from International Specialty Products, Wayne, N.J., under the trade designation Rapi-Cure may be used.
Examples of suitable polyfunctional acrylate monomers and oligomers useful as component (B) include the following types of acrylates:
aliphatic polyether urethane acrylates, diacrylates and polyacrylates;
aliphatic polyester urethane acrylates, diacrylates and polyacrylates;
aromatic polyether urethane acrylates, diacrylates and polyacrylates;
aromatic polyester urethane acrylates, diacrylates and polyacrylates;
polyester acrylates, d
Avery Dennison Corporation
Berman Susan W.
Renner , Otto, Boisselle & Sklar, LLP
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