Галерея 2749602
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Mouser Electronics� | 1000 North Main Street | Mansfield, TX 76063-1514
Provided are a polyurethane polyurea resin composition that has high storage stability without a decrease in viscosity or turbidity over time and a printing ink that has high storage stability without a decrease in viscosity or coloration over time. The resin composition contains, as essential components, a polyurethane polyurea resin (A), a polyhydroxymonocarboxylic acid (B) having an acid value of 340 to 500 mg KOH/g and a hydroxyl value of 680 to 1,300 mg KOH/g, and at least one solvent selected from the group consisting of an ester solvent (C1) and an alcohol solvent (C2).
The present invention relates to polyurethane polyurea resin compositions that have high storage stability without changes over time such as turbidity, coloration, and a decrease in viscosity.
Polyurethane polyurea resins are frequently used as binder resins for printing inks and coatings. For example, gravure printing inks containing polyurethane polyurea resins are frequently used for printing on plastic films for packaging various products such as confectionery and food. Polyurethane polyurea resins often contain solvents such as toluene and ketones, in which these resins are highly soluble. Recently, these solvents have increasingly been replaced by alcohol solvents and ester solvents with the revision of the Industrial Safety and Health Law and the increasing awareness of work environments. Polyurethane polyurea resins containing alcohol and ester solvents, however, have a problem in that they have low storage stability because their viscosity tends to decrease over time. The decrease in viscosity is attributed to the fact that water contained in the ester and alcohol solvents reacts with amino groups in the polyurethane polyurea resins to produce hydroxide ions, which cleave ester bonds in the polyurethane polyurea resins.
As a method for preventing the decrease in viscosity over time, a technique is known in which malic acid is added to a resin composition containing a polyurethane polyurea resin and a mixture of ethyl acetate of isopropyl alcohol to inhibit the activity of amino groups, thereby reducing the decrease in viscosity (see PTL 1). However, although this reduces the decrease in viscosity over time, the resin composition becomes turbid over time and also has an odor. In addition, an ink prepared from the resin composition colors over time.
PTL 1: Japanese Unexamined Patent Application Publication No. 2003-221539 (Japanese Patent No. 3972666 )
Accordingly, an object of the present invention is to provide a polyurethane polyurea resin composition that has high storage stability without a decrease in viscosity or turbidity over time and a printing ink that has high storage stability without a decrease in viscosity or coloration over time.
After conducting intensive research to achieve the above object, the inventors have found that the addition of a polyhydroxymonocarboxylic acid having an acid value of 340 to 500 mg KOH/g and a hydroxyl value of 680 to 1,300 mg KOH/g to a resin composition containing a polyurethane polyurea resin and ester and alcohol solvents provides a resin composition that has high storage stability without changes over time such as a decrease in viscosity and turbidity. The inventors have also found that a printing ink prepared using the polyurethane polyurea resin composition as a binder has high storage stability without a decrease in viscosity or coloration over time. These and other findings have led to the present invention.
Specifically, the present invention relates to a resin composition containing, as essential components, a polyurethane polyurea resin (A), a polyhydroxymonocarboxylic acid (B) having an acid value of 340 to 500 mg KOH/g and a hydroxyl value of 680 to 1,300 mg KOH/g, and at least one solvent selected from the group consisting of an ester solvent (C1) and an alcohol solvent (C2).
The present invention also relates to a printing ink binder containing the resin composition.
The present invention also relates to a printing ink containing the printing ink binder.
The present invention can provide a resin composition that has high storage stability without changes over time such as a decrease in viscosity and turbidity as compared to known polyurethane polyurea resin compositions. The present invention can also provide a printing ink that has high storage stability without changes over time such as a decrease in viscosity and coloration.
According to the present invention, a polyhydroxymonocarboxylic acid (B) is added to a resin composition containing a polyurethane polyurea resin (A) and at least one solvent selected from the group consisting of an ester solvent (C1) and an alcohol solvent (C2) to prevent a decrease in the viscosity of the resin composition over time. Generally, a polyurethane polyurea resin composition containing these solvents exhibits a decrease in viscosity as water contained in the ester and alcohol solvents reacts with amino groups in the polyurethane polyurea resin to produce hydroxide ions, which cleave ester bonds in the polyurethane polyurea resin. The addition of the dihydroxymonocarboxylic acid, however, causes the amino groups to form a salt with the polyhydroxymonocarboxylic acid. This inhibits the reaction of the amino groups with water and thus prevents a decrease in viscosity.
The polyurethane polyurea resin (A) used in the present invention will be described first.
The polyurethane polyurea resin (A) can be prepared, for example, by reacting a polyl compound (a1) with a polyisocyanate compound (a2) such that the number of moles of isocyanate groups in the polyisocyanate compound exceeds the number of moles of hydroxyl groups in the polyol compound to prepare an isocyanate-containing prepolymer and then reacting the isocyanate groups in the prepolymer with a polyamine compound (a3).
The polyol compound (a1) used as a reactant material for the polyurethane polyurea resin (A) may be a diol compound (a1-1), which has two hydroxyl groups in the molecular structure thereof, or a polyol compound (a1-2), which has three or more hydroxyl groups in the molecular structure thereof.
Examples of diol compounds (a1-1) include aliphatic diols such as ethylene glycol, diethylene glycol, propylene glycol, 1,3-propanediol, 1,2,2-trimethyl-1,3-propanediol, 2,2-dimethyl-3-isopropyl-1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 3-methyl-1,3-butanediol, 1,5-pentanediol, 3-methyll,5-pentanediol, neopentyl glycol, 1,6-hexanediol, and 2,2,4-trimethyl-1,3-pentanediol;
polyether diols such as polyoxyethylene glycol and polyoxypropylene glycol;
alicyclic diols such as 1,4-cyclohexanedimethanol and hydrogenated bisphenol A;
modified polyether diols prepared by ring-opening polymerization of the aliphatic diols with various cyclic-ether-bond containing compounds such as ethylene oxide, propylene oxide, tetrahydrofuran, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, and allyl glycidyl ether;
lactone polyester polyols prepared by polycondensation reactions of the aliphatic diols with various lactones such as ε-caprolactone; and
polyester diols prepared by co-condensation of the aliphatic diols with aliphatic dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, and sebacic acid; aromatic dicarboxylic acids such as phthalic acid (anhydride), terephthalic acid, isophthalic acid, and orthophthalic acid; alicyclic dicarboxylic acids such as hexahydrophthalic acid and 1,4-cyclohexanedicarboxylic acid; or aliphatic unsaturated dicarboxylic acids such as tetrahydrophthalic acid, maleic acid (anhydride), fumaric acid, citraconic acid, itaconic acid, and glutaconic acid.
Examples of polyol compounds (a1-2) include aliphatic polyols such as trimethylolethane, trimethylolpropane, glycerol, hexanetriol, and pentaerythritol;
modified polyether polyols prepared by ring-opening polymerization of the aliphatic polyols with various cyclic-ether-bond containing compounds such as ethylene oxide, propylene oxide, tetrahydrofuran, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, and allyl glycidyl ether;
lactone polyester polyols prepared by polycondensation reactions of the aliphatic polyols with various lactones such as ε-caprolactone;
polyester polyols prepared by co-condensation of the aliphatic polyols with aliphatic dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, and sebacic acid; aromatic dicarboxylic acids such as phthalic acid (anhydride), terephthalic acid, isophthalic acid, and orthophthalic acid; alicyclic dicarboxylic acids such as hexahydrophthalic acid and 1,4-cyclohexanedicarboxylic acid; or aliphatic unsaturated dicarboxylic acids such as tetrahydrophthalic acid, maleic acid (anhydride), fumaric acid, citraconic acid, itaconic acid, and glutaconic acid; and
polyester polyols prepared by co-condensation of the aliphatic diols or the aliphatic polyols with various tricarboxylic acids such as 1,2,5-hexanetricarboxylic acid, trimellitic acid, 1,2,5-benzenetricarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, and 2,5,7-naphthalenetricarboxylic acid.
The above polyol compounds (a1) may be used alone or in a combination of two or more. In particular, the diol compounds (a1-1) are preferred because the resulting polyurethane polyurea resin (A) is highly soluble in the ester solvent (C1) and the alcohol solvent (C2), and the polyester diols, the polyether diols, and the modified polyether diols are more preferred.
The polyisocyanate compound (a2) used as a reactant material for the polyurethane polyurea resin (A) may be a diisocyanate compound (a2-1), which has two isocyanate groups in the molecular structure thereof, or a polyisocyanate compound (a2-2), which has three or more isocyanate groups in the molecular structure thereof.
Examples of diisocyanate compounds (a2-1) include aliphatic diisocyanates such as butane-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, xylylene diisocyanate, and m-tetramethylxylylene diisocyanate;
alicyclic diisocyanates such as cyclohexane-1,4-diisocyanate, isophorone diisocyanate, lysine diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, methylcyclohexane diisocyanate, isopropylidenedicyclohexyl-4,4'-diisocyanate, and norbornane diisocyanate; and
aromatic diisocyanates such as 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and tetramethylxylylene diisocyanate.
Examples of polyisocyanate compounds (a2-2) include adduct-type polyisocyanate compounds, which have a urethane bond site in the molecule thereof, and nurate-type polyisocyanate compounds, which have an isocyanurate ring structure in the molecule thereof.
Adduct-type polyisocyanate compounds, which have a urethane bond site in the molecule thereof, are prepared, for example, by reacting a diisocyanate compound with a polyol compound. Examples of diisocyanate compounds used for the reaction include the various diisocyanate compounds illustrated as the diisocyanate compound (a2-1), which may be used alone or in a combination of two or more. Examples of polyol compounds used for the reaction include the various polyol compounds illustrated as the polyol compound (a1), which may be used alone or in a combination of two or more.
Nurate-type polyisocyanate compounds, which have an isocyanurate ring structure in the molecule thereof in the molecule thereof, are prepared, for example, by reacting a diisocyanate compound with a monoalcohol and/or a diol. Examples of diisocyanate compounds used for the reaction include the various diisocyanate compounds illustrated as the diisocyanate compound, which may be used alone or in a combination of two or more. Examples of monoalcohols used for the reaction include hexanol, 2-ethylhexanol, octanol, n-decanol, n-undecanol, n-dodecanol, n-tridecanol, n-tetradecanol, n-pentadecanol, n-heptadecanol, n-octadecanol, n-nonadecanol, eicosanol, 5-ethyl-2-nonanol, trimethylnonyl alcohol, 2-hexyldecanol, 3,9-diethyl-6-tridecanol, 2-isoheptylisoundecanol, 2-octyldodecanol, and 2-decyltetradecanol. Examples of diols include the various diols illustrated as the diol compound (a1-1). These monoalcohols and diols may be used alone or in a combination of two or more.
The above polyisocyanate compounds (a2) may be used alone or in a combination of two or more. In particular, the diisocyanate compounds (a2-1) are preferred because the resulting polyurethane polyurea resin (A) is highly soluble in the ester solvent (C1) and the alcohol solvent (C2), and hexamethylene diisocyanate and isophorone diisocyanate are more preferred.
To prepare the isocyanate-containing prepolymer by reacting a diol compound (a1) with a diisocyanate compound (a2), they may be reacted, for example, such that the ratio [(OH)/(NCO)] of the number of moles (OH) of hydroxyl groups in the diol compound (a1) to the number of moles (NCO) of isocyanate groups in the diisocyanate compound (a2) is 1.0/1.1 to 1.0/5.0. The reaction may be effected in the temperature range of 60°C to 130°C, optionally in the presence of an urethanization catalyst such as tin(II) octanoate.
Examples of polyamine compounds (a3) used as a reactant material for the polyurethane polyurea resin (A) include diamine compounds such as ethylenediamine, propylenediamine, hexamethylenediamine, isophoronediamine, dicyclohexylmethane-4,4'-diamine, 2-hydroxyethylethylenediamine, 2-hydroxyethylpropylenediamine, di-2-hydroxyethylethylenediamine, di-2-hydroxyethylpropylenediamine, 2-hydroxypropylethylenediamine, and di-2-hydroxypropylethylenediamine; triamine compounds such as diethylenetriamine and pentane-1,2,5-triamine; and tetramine compounds such as triethylenetetramine. These may be used alone or in a combination of two or more. In particular, diamine compounds are preferred because the resulting polyurethane polyurea resin (A) is highly soluble in the ester solvent (C1) and the alcohol solvent (C2), and ethylenediamine and isophoronediamine are more preferred.
To prepare the polyurethane polyurea resin (A) by reacting the isocyanate-containing prepolymer with a diamine compound (a3), they may be reacted, for example, by preparing a solutio
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