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
2001-05-18
2004-03-23
Shosho, Callie (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...
C528S338000, C528S339300, C523S160000
Reexamination Certificate
active
06710121
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to inks and resins useful in inks, especially to resins for laminating inks, and resins that are compatible with nitrocellulose.
BACKGROUND OF THE INVENTION
Inks for printing on flexible substrates (e.g., synthetic polymer films) and laminating inks (i.e., inks that are placed between two substrates and must both provide the traditional properties of an ink resin as well as not interfere with, and hopefully augment the adhesion between the two substrates) that contain polyamide resins are known in the art. See, e.g., U.S. Pat. Nos. 5,658,968; and 5,338,785. Historically, those polyamide resins that have a high solution viscosity and that are used in laminating inks exhibit poor ink rheology and poor compatibility with nitrocellulose. The present invention provides a solution to this problem and provides other related advantages as disclosed below.
SUMMARY OF THE INVENTION
Briefly, in one aspect, the present invention provides a polyamide resin. The polyamide resin may be described by the process by which it may be prepared. According to this description, the polyamide resin is prepared by reacting together reactants that include polymerized fatty acid, co-diacid, monoacid, secondary diamine and C
6
diamine, or reactive equivalents thereof, where any one of these components may be a blend of materials that meets the definitions set forth below.
In various aspect, the polymerized fatty acid includes at least 75 weight percent dimer acid; and/or the polymerized fatty acid comprises dimer acid and trimer acid; and/or the co-diacid has the formula HOOC—R
1
—COOH and R
1
is a C
1
-C
24
aliphatic hydrocarbyl; and/or the co-diacid is selected from adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and 1,4-cyclohexanedicarboxylic acid; and/or the co-diacid is 1,4-cyclohexanedicarboxylic acid; and/or the monoacid has the formula R
3
—COOH and R
3
is a hydrocarbyl group; and/or the monoacid includes a C
2
-C
4
monoacid selected from acetic acid, propionic acid and butanoic acid; and/or the secondary diamine includes piperazine; and/or the C
6
diamine is selected from hexamethylene diamine and methylpentamethylenediamine; and/or the reactants further includes one or more auxiliary diamines; and/or the auxiliary diamine is ethylene diamine; and/or the auxiliary diamine includes one or more of ethylenediamine (EDA), 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, 1,2-diamino-2-methylpropane, 1,3-diaminopentane, 1,5-diaminopentane, 2,2-dimethyl-1,3-propanediamine, 1,7-diaminoheptane, 1,8-diaminooctane, 2,5-dimethyl-2,5-hexanediamine, 1,9-diaminononane, 1,10-diaminodecane, 1,12-diaminododecane, diaminophenanthrene (all isomers, including 9,10), 4,4′-methylenebis(cyclohexylamine), 2,7-diaminofluorene, phenylene diamine (1,2; 1,3 and/or 1,4 isomers), adamantane diamine, 2,4,6-trimethyl-1,3-phenylenediamine, 1,3-cyclohexane-bis(methylamine), 1,8-diamino-p-menthane, 2,3,5,6-tetramethyl-1,4-phenylenediamine, diaminonaphthalene (all isomers, including 1,5; 1,8; and 2,3) 4-amino-2,2,6,6-tetramethylpiperidine, xylene diamine and naphthalene diamine (all isomers); and/or polymerized fatty acid contributes 60-95 equivalent percent of the total equivalents provided by polymerized fatty acid, monoacid and co-diacid; and/or monoacid contributes 5-20 equivalent percent of the total equivalents provided by polymerized fatty acid, monoacid and co-diacid; and/or co-diacid contributes 5-15 equivalent percent of the total equivalents provided by polymerized fatty acid, C
2
-C
4
monoacid and co-diacid; and/or C
6
diamine contributes 40-80 equivalent percent of the total equivalents provided by C
6
diamine and secondary diamine; and/or secondary diamine contributes 20-60 equivalent percent of the total equivalents provided by C
6
diamine and secondary diamine; and/or polymerized fatty acid contributes 75-80 equivalent percent of the total acid equivalents of all of the reactants, monoacid contributes 8-15 equivalent percent of the total acid equivalents of all of the reactants, co-diacid contributes 8-15 equivalent percent of the total acid equivalents of all of the reactants, C
6
diamine contributes 55-65 equivalent percent of the total amine equivalents of all of the reactants, and secondary diamine contributes 35-45 equivalent percent of the total amine equivalents of all of the reactants, and the total acid equivalents is within 10% of the total amine equivalents.
In another aspect, the present invention provides a process for preparing a polyamide resin comprising condensing reactants that include polymerized fatty acid, co-diacid, monoacid, secondary diamine and C
6
diamine, or reactive equivalents thereof, as mentioned above and as described in more detail below.
In another aspect, the present invention provides an ink composition that includes a polyamide resin as described above, and in a further aspect, the ink composition additionally includes nitrocellulose. The ink composition, particularly when the resin is compatible with nitrocellulose, may be useful as a laminating ink resin. When the polyamide resin is not compatible with nitrocellulose, the resin may be formed into an ink for other printing needs, particularly printing onto porous substrate such as paper products. Even if the resin is compatible with nitrocellulose, it may be used to form an ink to be printed onto porous, e.g., paper, substrates.
In another aspect, the present invention provides a method of printing with an ink composition as described above, where in a further aspect, the printing method is a method of printing on film, and may be a method of laminating printing.
In another aspect, the present invention provides an article of manufacture comprising a polyamide resin prepared by the process of reacting together reactants comprising polymerized fatty acid, co-diacid, monoacid, secondary diamine and C
6
diamine, or reactive equivalents thereof. The article of manufacture may be, for example, a printed article of manufacture, such as a piece of paper, a cardboard box, a container having printing thereon prepared with the polyamide of the present invention. The polyamides of the present invention have some adhesive properties, and accordingly the article of manufacture may be an article having two components that are adhered together by an intermediate adhesive layer comprising the polyamide of the present invention.
These and related aspects of the invention are described further below.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a resin, and in particular a polyamide resin. In a preferred aspect, the polyamide resin of the invention has good compatibility with nitrocellulose. In a preferred aspect, inks containing the polyamide resin of the present invention exhibit good bond strength when printed on films, particularly when used as laminating inks. The polyamide resin of the present invention may, in one respect, be characterized in terms of the reactants that will lead to its formation. These reactants include polymerized fatty acid, co-diacid, monoacid, secondary diamine and C
6
diamine, and reactive equivalents thereof. Each of these reactants is discussed in detail below.
The polymerized fatty acid, also known as dimer acid and dimerized fatty acid, is a well-known material of commerce. Polymerized fatty acid is typically formed by heating long-chain unsaturated fatty acids, e.g., C
18
monocarboxylic acids, to about 200-250° C. in the presence of a clay catalyst in order that the fatty acids polymerize. The polymerization product typically comprises dimer acid, i.e., C
36
dicarboxylic acid formed by dimerization of the fatty acid, and trimer acid, i.e., C
54
tricarboxylic acid formed by trimerization of the fatty acid. Polymerized fatty acid is typically a mixture of structures, where individual dimer acids may be saturated, unsaturated, cyclic, acyclic, etc. A more detailed discussion of fatty acid polymerization may be found in, e.g., U.S. Pat. No. 3,157,681 and
Naval Stores—Production, Chemi
Arizona Chemical Company
Seed Intellectual Property Law Group PLLC
Shosho Callie
LandOfFree
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