JP2002121247A - Active energy ray curable aqueous composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an active energy ray curable aqueous composition having active energy ray curability and especially having excellent scratch and scuff resistances and further adhesion and chemical resistances and capable of solving safety, environmental problems, or the like, usable as active energy ray curable type coating materials, coating agents, inks, or the like, dilutable with water and washable with water and effective in the fields without especially requiring slipperiness. SOLUTION: This energy ray curable aqueous composition is characterized by comprising an aqueous composition containing a compound having an active energy ray curable unsaturated double bond and a group of a salt in combination in the molecule and (I) a wax component having >=125 deg.C melting point and <=0.1 μm particle diameter.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention is particularly excellent in scratch resistance, scratch resistance, adhesion and chemical resistance.
The present invention relates to an active energy ray-curable aqueous composition which is useful for a composition used for an active energy ray-curable coating material, a coating agent, an ink and the like which cures for a short time.

[0002]

2. Description of the Related Art Paints, coating agents, inks, etc., which are cured by irradiation with active energy rays such as ultraviolet rays (UV) or electron beams (EB), are energy-saving as compared with conventional systems using thermosetting resins. In many cases, the protective coating agent is required to have scratch resistance and scratch resistance particularly because of its space saving, short curing time, and excellent film strength. Under these circumstances, the usual active energy ray-curable composition may use a solvent as a diluent for the purpose of lowering the viscosity due to the convenience of the printing or coating process. For this reason, the paint work environment is deteriorated and air pollution is caused. On the other hand, as a countermeasure against air pollution, there is a solventless type. In this case, the solvent drying step is not necessary, but there are still problems such as heating for obtaining the coating viscosity, skin toxicity and odor of the diluted monomer to be added, as in the solvent type. In addition, polymer materials cannot be used due to the limitation of coating viscosity, and it is not easy to improve the chemical and physical performance of the coating. Also,
The use of the means of painting and printing requires the operation of washing the coating machine and the printing machine, and solvent washing is usually employed. Therefore, the cleaning solvent also causes deterioration of the working environment and air pollution.

[0003] Specific applications of the paint having scratch resistance and scratch resistance are as follows: interior materials, especially surfaces of members for floors and stairs, or a protective agent such as a plastic pallet, or falling when stacking cardboard. Among them, there are inhibitors and the like. Among them, it is important that the painted surface applied to the surface of the wood or decorative sheet for floors or stairs is not slippery in order to prevent domestic accidents. However, in the coating of paint and the subsequent processes, packaging work is started immediately after coating and curing, and several floor materials with painted surfaces or painted surfaces are bundled and packed. Blocking properties are also required. Usually, when imparting scratch resistance and scratch resistance, waxes having both properties of slipperiness and anti-blocking are often used on the surface, but these have a problem that they also impart slipperiness. .

Conventionally, waxes to be used by adding to paints and inks are roughly classified into aliphatic hydrocarbons, higher aliphatic alcohols / higher fatty acids, fatty acid amides, metal soaps, and silicones. Among them, carnauba wax, wood wax, lanolin, montan wax, paraffin wax, polyethylene wax, polypropylene wax, polytetrafluoroethylene, and their modified products, oxides, etc. It is often done.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to cure in particular a short time, to be excellent in scratch resistance, scratch resistance, adhesion and chemical resistance, and to solve safety and environmental problems. To obtain an active energy ray-curable aqueous composition which is used in active energy ray-curable paints, coating agents, inks, etc., which can be diluted with water and washed with water, and which is particularly effective in fields where lubricity is not required. is there.

[0006]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have found that a compound containing an active energy ray-curable unsaturated double bond and a salt group in a molecule is contained. The active energy ray-curable aqueous composition containing the active energy ray-curable aqueous composition and the wax component (I) having a melting point of 125 ° C. or more and a particle size of 0.1 μm or less is particularly short. It cures in time, has excellent scratch and scratch resistance, and has both adhesion and chemical resistance.
Since water dilution and washing are possible, safety and environmental issues can be solved.
It was found to be an active energy ray-curable aqueous composition that is useful for coating agents, inks, etc., and is particularly effective in fields that do not require slipperiness.

That is, the constitution of the present invention is as follows. An aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule, and a wax component (I) having a melting point of 125 ° C. or more and a particle size of 0.1 μm or less, 1. An active energy ray-curable aqueous composition characterized by containing 2. The active energy ray-curable aqueous composition according to the above item 1, wherein the aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule is a polyurethane aqueous composition. . The active energy ray-curable composition according to the above 1 or 2, wherein the salt group in the aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule is a carboxyl group. 3. an aqueous composition; 4. The tertiary amine according to the above 3, wherein the basic compound that neutralizes a carboxyl group in an aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule is a tertiary amine. 4. an active energy ray-curable aqueous composition; The active energy ray-curable aqueous composition according to any one of the above items 1 to 4, wherein the wax component (I) is at least one selected from polyethylene, polyethylene oxide, and polypropylene.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. In the present invention, the unsaturated double bond in the aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in the molecule includes a methacryloyl group or an acryloyl group, In order to obtain sufficient active energy ray curability and excellent cured film performance, the unsaturated double bond concentration is preferably 1.0 to 5.0 equivalents / kg, more preferably 1.5 to 3.5 equivalents. / Kg is desirable. Examples of the aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule thereof include polyester, polyether, and polyurethane compositions whose main skeleton is a skeleton. It is desirable to use a polyurethane composition because of its wide variety of designs and excellent coating performance can be easily obtained. Alternatively, the salt group in the aqueous composition is a carboxyl group, and further has an acid value of 3 to 80 KOH mg / g, preferably 5 to 80 in order to achieve both water solubility and water resistance of the cured film. Desirably, it is 60 KOHmg / g.

[0009] In the case of an aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in the molecule, when the main skeleton is a polyurethane composition, a typical production method is as follows. First, a compound having a salt group, a polyisocyanate compound having two or more functional groups, and a polyol compound are blended so as to have an excess of isocyanate groups to obtain an isocyanate group-terminated polyurethane prepolymer. Then, the isocyanate group-terminated polyurethane prepolymer is reacted with an active energy ray-curable compound having one or two hydroxyl groups and at least one unsaturated double bond, so that the terminal is unsaturated double bond, or A polyurethane composition having both an active energy ray-curable unsaturated double bond and a salt group in the molecule, which is an isocyanate group, is obtained. These reactions are carried out in a solvent that does not react with isocyanate groups at a temperature in the range of 20 to 80 ° C. At this time, known polymerization inhibitors and reaction catalysts can be arbitrarily added in appropriate amounts. After completion of the reaction, if necessary, the polyurethane composition may contain a known active energy ray-curable resin, a polymerization initiator for active energy ray curing, a known resin compound, an aminoplast, a diluent, a surfactant, and a plasticizer. In addition, various resins such as a hydrolysis inhibitor, an emulsifier, a leveling agent, an antifoaming agent, an antioxidant, and an antibacterial agent, additives, and auxiliaries can be mixed. Alternatively, the wax can be mixed and dispersed here. Next, this polyurethane composition is neutralized at 50 ° C. or lower, and a solution is prepared which is ionized and dispersed in water.
Thereafter, if necessary, a crosslinking agent dissolved in water or an organic solvent can be added. Finally, the reaction solvent is distilled off under reduced pressure, whereby an aqueous polyurethane composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in the molecule can be obtained.

In obtaining the aqueous polyurethane composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in the molecule, the salt group may be, for example, a phosphate ester Suitable are diols and diamines having any of a group, a sulfonic acid group, a tertiary amino group, a carboxyl group, or a neutralizing base thereof.
Specific examples include polyoxyethylene glycol, polyoxyethylene diaminopropyl ether, trimethylolpropane monophosphate, trimethylolpropane monosulfate, and at least a portion of the dibasic acid component is sodium sulfosuccinic acid or sodium sulfoisophthalate. Polyester diols which are acids, N-methyldiethanolamine, diaminocarboxylic acids such as lysine, cystine and 3,5-diaminocarboxylic acid,
6-dihydroxybenzoic acid and 3,5 dihydroxybenzoic acid, 2,2-bis (hydroxymethyl) propionic acid, 2,2-bis (hydroxymethyl) butanoic acid,
2,2-bis (hydroxyethyl) propionic acid, 2,
2-bis (hydroxypropyl) propionic acid, bis (hydroxymethyl) acetic acid, bis (4-hydroxyfinyl) acetic acid, 2,2-bis (4-hydroxyphenyl)
Examples include pentanoic acid, tartaric acid, N, N-dihydroxyethylglycine, N, N-bis (2-hydroxyethyl) -3-carboxy-propionamide, and polycaprolactone diol containing a carboxyl group.

The required amount of the salt group is determined by the kind and combination of the hydrophilic groups. Among the examples described above, particularly preferred as the hydrophilic group are those having one or two selected from a carboxyl group and a sulfonate group in the molecule, or a mixture of these. In particular, introduction of a carboxyl group is easy to balance in various points and easy to operate.

The above-mentioned bifunctional or higher polyisocyanate compounds include, for example, aliphatic diisocyanates such as 1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, and the above-mentioned aliphatic diisocyanates. Aliphatic polyisocyanates such as a trimer of a low molecular weight triol and an adduct of the aliphatic isocyanate, isophorone diisocyanate, hydrogenated 4,4-diphenylmethane diisocyanate, hydrogenated tolylene diisocyanate, methylcyclohexylene diisocyanate, isopropylidenecyclohexyl Alicyclic diisocyanates such as -4,4-diisocyanate and norbornene diisocyanate, trimers of the alicyclic diisocyanate, low molecular weight triols and the alicyclic Alicyclic polyisocyanates such as adducts of socyanates, araliphatic diisocyanates such as xylylene diisocyanate, trimers of the xylylene diisocyanate, araliphatic polyisocyanates such as adducts of low molecular weight triols and xylylene diisocyanate, 4,4-diphenylmethane diisocyanate, aromatic diisocyanates such as tolylene diisocyanate, trimers of the aromatic diisocyanates, adducts of low molecular weight triols and the aromatic isocyanates,
Aromatic polyisocyanates such as triphenylmethane triisocyanate; trifunctional or higher polyisocyanates such as polymethylene polyphenylisocyanate; and mixtures of two or more thereof.

The above-mentioned polyol compounds include:
For example, ethylene glycol, propylene glycol,
Diethylene glycol, cyclohexane-1,4-dimethanol, 1,3-butylene glycol, 1,4-butylene glycol, neopentyl glycol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 2-ethyl -1,3-hexanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-methyl-1,8-octanediol, 1,9-nonanediol, cyclohexyldimethanol, bisphenol A,
Examples thereof include bisphenol F, hydrogenated bisphenol A, hydrogenated bisphenol F, castor oil-modified diol, castor oil-modified polyol, and other alkyd-modified polyols.

Further, the above-mentioned polyols as high molecular polyols such as polyester polyol and the like, and ethyl glycidyl ether, methyl glycidyl ether, butyl glycidyl ether,
Alkyl monoglycidyl ethers such as 2-ethylhexyl glycidyl ether, lauryl glycidyl ether, decyl glycidyl ether, stearyl glycidyl ether, or alkyl glycidyl esters (product name: Kadura E10: manufactured by Shell Japan) and the like, and adipic acid, azelaic acid, sebacic acid Dibasic acid such as dimer acid, or aromatic polybasic acid such as phthalic anhydride, isophthalic acid, terephthalic acid, trimellitic anhydride, or hydrophthalic anhydride, dimethyl-1,4-cyclohexanedicarboxylic acid And polyester polyols obtained by a condensation reaction with an alicyclic polybasic acid or the like. Furthermore, polyester polyols obtained by ring-opening polymerization of ε-caprolactone and β-methyl-δ-valerolactone are exemplified.

Further, as polymer polyols such as polyether polyols, alkylene oxide adducts such as ethylene glycol, propylene glycol and 1,4-butanediol, and polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and poly (diethylene glycol) Mixtures of more than one species.

In producing the polyurethane composition, if necessary, a conventionally known urethanizing catalyst such as dibutyltin dilaurate, tin octylate, triethylamine,
N, N-dimethylbenzylamine, sodium hydroxide,
And diethyl zinc tetra (n-butoxy) titanium. As the reaction solvent, it is preferable to react in an organic solvent inert to the isocyanate group, for example, acetone, methyl ethyl ketone, ethyl acetate, dioxane, acetonitrile, tetrahydrofuran, benzene, toluene, xylene, diglyme, dimethyl sulfoxide, N-methylpyrrolidone and the like. These can be used alone or as a mixture.

The active energy ray-curable compounds having one or two hydroxyl groups and one or more unsaturated double bonds include, for example, 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth). A) Monohydroxy mono (meth) acrylate such as acrylate, hydroxybutyl (meth) acrylate or glycerin di (meth) acrylate, light ester G-201P
(Manufactured by Kyoeisha Chemical Co., Ltd.) such as monohydroxyacrylic methacrylate and monohydroxytriacrylate such as pentaerythritol triacrylate, monohydroxypentaacrylate such as dipentaerythritol pentaacrylate, and dihydroxy such as glycerin mono (meth) acrylate. Mono (meth) acrylates, and compounds obtained by addition-polymerizing ethylene oxide, propylene oxide, tetrahydrofuran, or ε-caprolactone thereto, and the like are exemplified.

Further, trimethylolpropane triacrylate, pentaerythritol tetraacrylate,
Polyfunctional acrylates such as dipentaerythritol hexaacrylate and dialkanolamines such as diethanolamine, diisopropanolamine, dipropanolamine and dibutanolamine, or monoalkyl monoalkanolamines such as methylethanolamine, ethylethanolamine and methylpropanolamine Or a diisocyanate having two isocyanate groups having different reactivities such as isophorone diisocyanate and tolylene diisocyanate with a monohydroxy monoacrylate, monohydroxy di (meth) acrylate, etc. The resulting half urethane or methacrylic isocyanate is combined with the dialkanolamines or the monoalkylmonoalkanolamine. The product obtained and emissions such reacted also may be cited.

In the reaction for introducing an unsaturated double bond of the present invention or in other reactions after the introduction of an unsaturated double bond, a polymerization inhibitor such as hydroquinone, tertiary butyl hydroquine or methoquinone is used. It is desirable to use.

Among the above-mentioned representatives of the salt groups, the basic compounds that neutralize the carboxyl group include:
Tertiary amines are preferred, for example, trimethylamine,
Examples thereof include triethylamine, dimethylbutylamine, tributylamine, dimethylmonoethanolamine, diethylethanolamine, diethanolmonomethylamine, N-ethylmorpholine, and 2-aminopropyl-2-methylpropanol. These tertiary amines may be used alone or in combination of two or more, depending on the properties of the desired cured product.

As described above, the melting point is 125 ° C. or more and the particle size is 0.1. Examples of the wax component (I) having a size of not more than μm include:
An Aqueser series manufactured by BYK and the like can be mentioned. Alternatively, high-density polyethylene or oxidized high-density polyethylene having the highest melting point among polyethylenes, and an aqueous dispersion of polypropylene having a higher melting point, etc., impart particularly excellent scratch resistance, scratch resistance, and blocking resistance. When these are added in an amount of 0.5 to 10.0 wt% based on the solid content of the aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in the molecule,
Sufficient scratch resistance, blocking resistance, stability as a paint, transparency of a coating film, and a smooth surface state are achieved. More preferably, the addition is 1.0 to 5.0 wt%.

The active energy ray-curable aqueous composition of the present invention can be cured by a known method. First, the base material is applied, and if water and a small amount of an organic solvent are contained, this is evaporated and dried. Next, in the case of curing with an electron beam, a polymerization initiator is not particularly required, and an acceleration voltage of 20 to 2000 KeV, preferably 150
Using an electron beam irradiation apparatus of ~ 300 KeV, the total irradiation amount is 5 ~ 2 in an atmosphere containing a small amount of oxygen or in an inert gas atmosphere.
By irradiating so as to be 00 kGy, preferably 10 to 100 kGy, a cured coating film can be obtained.

As other curing means, for example, there is an illegal method of curing in air or an inert gas atmosphere by ultraviolet rays obtained from a mercury lamp, a xenon lamp, or the like, or a method of heat curing, and in these cases, photopolymerization is used. An initiator or a thermal polymerization initiator is added. The addition amount is, for example, 0.2% based on the solid content of the active energy ray-curable composition.
About 20%, preferably 0.5 to 10%.

Next, as a specific example of the present invention, an active energy ray-curable aqueous polyurethane composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule is synthesized. Example 1 additionally has a melting point of 125
Wax component (I) having a particle size of 0.1 μm or less at a temperature of at least
Alternatively, an example in which another wax component is used will be specifically described. In the following, all parts and percentages represent weight ratios.

[Synthesis Example 1] As a method for obtaining an aqueous polyurethane composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group as described above, for example, a reflux condenser, a nitrogen condenser, In a reactor equipped with a stirrer equipped with an inlet tube and a thermometer, Praxel L205AL (molecular weight 5
00 Daicel Chemical Industries, Ltd., 400.0 parts of lactone polyester diol), polyethylene glycol (Mw
= 600) 176.7 parts, 2,4-bis (hydroxymethyl) propionic acid 174.2 parts, trimethylolpropane 53.6 parts, butylethylpropanediol 11
2.2 parts, norbornane diisocyanate methyl 100
9.4 parts and 1926.1 parts of methyl ethyl ketone were added, and the temperature was raised to 70 ° C. in 0.5 hour while stirring, and 70 to 75
After reacting at 5 ° C for 5 hours, replace the nitrogen inlet tube with an air inlet tube,
Methoquinone 1.21 parts, light ester G-201P
499.8 parts (manufactured by Kyoeisha Chemical Co., Ltd.), 0.39 parts of tin octylate and 499.8 parts of methyl ethyl ketone were added.
The reaction was performed again at 70 to 75 ° C. for 15 hours to obtain a polyurethane resin skeleton. The solution was cooled to 50 ° C. or lower, 131.3 parts of triethylamine and 7277.7 parts of pure water were added, and the mixture was kept at 30 ° C. for 2 hours. Then, Surfynol AK-02 was added.
After adding 2.4 parts (manufactured by Air Products Japan Co., Ltd.), methyl ethyl ketone was distilled off under reduced pressure at 50 ° C., and the active energy ray curing was a transparent liquid having a nonvolatile content of 29.3% and a Gardner viscosity of UV. An aqueous polyurethane composition having a group having an unsaturated double bond and a salt group was obtained. Acrylic concentration: 1.731 m. mol / g. Solid acid value:
30.1.

4% by weight of a photoinitiator (Darocur D-1173) based on the solid content of the aqueous polyurethane composition having a group having an active energy ray-curable unsaturated double bond and a salt group obtained above. And 3 wt% of various waxes shown in Tables 1 and 2 were mixed, and pure water was added thereto to obtain a nonvolatile matter 2
Adjusted to 5%. These preparations were drawn down on a 100 μm PET film by drawdown # 10 (about 3μ) and # 30.
(Approximately 10 μm) and dried with a blast dryer at 80 ° C. Then, with 120 W high pressure mercury, irradiation amount 450 mJ
/ Cm ² was irradiated. The solution state of these blended paints and the obtained test specimens were subjected to a nail scratch property and a lubricity test.

(Solution State) With respect to the solutions (Examples 1, 2 and Comparative Examples 1 to 10) prepared by blending various waxes shown in Tables 1 and 2, the state of the solution left at room temperature for one day is shown below. Observed. ○: No change △: Slight separation ×: Separation

(Nail Scratch Property) The surface of the test piece was rubbed with a nail, and the scratch property was visually observed. ：: No scratches △: Slight scratches ×: Large scratches

(Measurement of Dynamic Friction Coefficient) With respect to the above-mentioned test pieces, load: 1 kg, pulling speed: 1000 mm /
Second, measurement start time: 0.5 seconds, measurement time: 5.0 seconds, surface material: stainless steel three-point steel ball type, measurement temperature: 25 ° C, number of measurements: dynamic friction coefficient measured under the conditions of 3 times Three simple averages are shown. ：: 0.40 to 0.60 Slippery. Δ: 0.25 to 0.40 Slightly slipped. ×: Slippage of 0.00 to 0.25 or no slippage of 0.60 or more.

[0030]

[Table 1]

In the table, # 10 and # 30 indicate the numbers of the coated drawdowns, respectively.

[0032]

[Table 2]

In the wax components in Table 2, the mixture is a mixed wax of polyethylene and a low melting point wax, and the PTFE means polytetrafluoroethylene.

[0034]

As is apparent from the above results, the active energy ray-curable aqueous composition of the present invention contains a compound having both an active energy ray-curable unsaturated double bond and a salt group in the molecule. The active energy ray-curable aqueous composition, which comprises a product and a wax component (I) having a melting point of 125 ° C. or more and a particle size of 0.1 μm or less, is particularly excellent in scratch resistance and scratch resistance. Cures in a short time,
It can also be used for active energy ray-curable paints, coatings, inks, etc. that have both adhesiveness and chemical resistance and can be used for water dilution and washing, which solves safety and environmental issues.
In particular, the present invention is useful for an active energy ray-curable aqueous composition which is useful even in a field not requiring lubrication.

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Claims (5)

[Claims] 1. An aqueous composition containing a compound having both an active energy ray-curable unsaturated double bond and a salt group in a molecule, and a wax component having a melting point of 125 ° C. or more and a particle size of 0.1 μm or less. (I). An active energy ray-curable aqueous composition comprising: 2. The active energy ray-curable aqueous composition according to claim 1, wherein the aqueous composition is a polyurethane aqueous composition. 3. The active energy ray-curable aqueous composition according to claim 1, wherein the salt group in the aqueous composition is a carboxyl group. 4. The active energy ray-curable aqueous composition according to claim 3, wherein the basic compound for neutralizing a carboxyl group in the aqueous composition is a tertiary amine. 5. The method according to claim 1, wherein the wax component (I) is polyethylene,
The active energy ray-curable aqueous composition according to any one of claims 1 to 4, which is at least one selected from oxidized polyethylene and polypropylene.