JP2010235775A - Organic solvent for printing ink - Google Patents

Abstract

Provided is an organic solvent composition for printing inks that can be produced using a raw material derived from vegetable oil, and is excellent in drying properties. An organic solvent composition for printing ink containing an alkylene oxide adduct to which is added, an alcohol having 4 to 18 carbon atoms, and / or an ester having a total carbon number of 2 to 12 composed of an alcohol component and a carboxylic acid component. And at least any one of the alcohol having 8 to 18 carbon atoms, the alcohol having 4 to 18 carbon atoms, and the raw material of the ester having 2 to 12 carbon atoms and / or the carboxylic acid is at least a plant. The organic solvent composition for printing inks which is a raw material.
[Selection figure] None

Description

  The present invention relates to an organic solvent composition for printing ink.

  Conventionally, petroleum-based solvents have been used as printing ink solvents. On the other hand, from the viewpoint of environmental protection and improvement of the working environment, attempts have been made to use vegetable oil components such as linseed oil, tung oil, soybean oil, and the like as a solvent for printing ink (Patent Document 1). Moreover, using fatty acid ester as a solvent for printing ink as an aroma-free solvent is also disclosed (Patent Document 2). However, the ink solvent based on vegetable oil generally has a problem that the drying property is not sufficient as compared with the petroleum solvent.

  Printing inks intended to improve drying properties include printing inks containing amines (Patent Document 3), colored compositions containing a lactate organic solvent (A) and a diethylene glycol acetate organic solvent (B) (patent) Document 4) and printing inks containing a fatty acid ester such as caproic acid (Patent Document 5) are disclosed.

JP 2005-1113070 A [Summary, Claim 1] JP 2005-105273 A [Summary] JP-A-3-269070 [Claim 1, Effect of the Invention] Japanese Patent Laying-Open No. 2005-330422 [Abstract, Claim 1] JP 2006-176754 A [Summary]

  In the organic solvent for printing ink which can be manufactured using the raw material derived from vegetable oil, the further improvement of drying property is calculated | required. Then, this invention is the organic solvent composition for printing inks which can be manufactured using a vegetable oil origin raw material, Comprising: The organic solvent composition for printing inks which is excellent in drying property is provided.

  The present invention provides an alkylene oxide adduct obtained by adding an alkylene oxide to an alcohol having 8 to 18 carbon atoms, an alcohol having 4 to 18 carbon atoms, and / or an alcohol component and a carboxylic acid component. It is the organic solvent composition for printing ink containing 12 ester, Comprising: It is a raw material of the said C8-C18 alcohol, the said C4-C18 alcohol, and the said total C2-C12 ester. The present invention relates to an organic solvent composition for printing ink in which any one of alcohol and / or carboxylic acid is at least a plant-derived raw material.

  ADVANTAGE OF THE INVENTION According to this invention, the organic solvent composition for printing inks excellent in drying property, its manufacturing method, and printing ink excellent in drying property can be provided.

  The present invention is based on the finding that an alkylene oxide adduct of a predetermined alcohol and a mixture of the predetermined alcohol and / or a predetermined ester can be used as an organic solvent composition for printing ink and have excellent drying properties.

  Although the details of the mechanism of the effect that the organic solvent composition for printing ink of the present invention is excellent in drying properties are not clear, the functions for printing inks such as drying properties, adhesive properties, and pigment dispersibility are added to the alkylene oxide of alcohol. It is thought that alcohol and / or ester are responsible for the improvement of drying properties. That is, the alkylene oxide adduct of alcohol has a complete decomposition temperature (described later) that is relatively higher than that of alcohol and ester, and its own drying property is insufficient. By mixing with low alcohol and / or ester, it is estimated that the complete decomposition temperature as a mixture falls, As a result, the drying property as the whole solvent improves. However, the present invention is not limited to this mechanism.

  That is, the present invention relates to an alkylene oxide adduct obtained by adding an alkylene oxide to an alcohol having 8 to 18 carbon atoms, an alcohol having 4 to 18 carbon atoms, and / or an alcohol component and a carboxylic acid component. An organic solvent composition for printing ink containing 2 to 12 esters, the raw material for the alcohol having 8 to 18 carbon atoms, the alcohol having 4 to 18 carbon atoms, and the ester having 2 to 12 carbon atoms in total. Is an organic solvent composition for printing ink (hereinafter, also referred to as “organic solvent composition of the present invention”) in which at least one of alcohol and / or carboxylic acid is a plant-derived raw material.

  ADVANTAGE OF THE INVENTION According to this invention, the organic solvent composition and / or printing ink for printing inks which are excellent in drying property can be provided. Preferably, according to the present invention, an organic solvent composition for printing ink and / or printing ink that does not contain a petroleum solvent can be provided. More preferably, according to this invention, the organic solvent composition for printing inks and / or printing ink which can be manufactured using a vegetable oil origin raw material can be provided. As used herein, the term “petroleum solvent” refers to a solvent mainly composed of hydrocarbons refined from crude oil, and specifically, at least paraffin hydrocarbons, naphthene hydrocarbons, and aromatic hydrocarbons. Contains one. Moreover, the organic solvent composition for printing ink which can be manufactured using a vegetable oil origin raw material is C8-C18 alcohol in the alkylene oxide adduct which added alkylene oxide to C8-C18 alcohol, C4. It means that any of -18 alcohol and alcohol component and carboxylic acid component constituting an ester having 2 to 12 carbon atoms is obtained by using plant-derived raw materials. From the viewpoint of improving the environment, it is preferable that all are plant-derived materials.

[Alkylene oxide adduct]
The organic solvent composition of the present invention includes an alkylene oxide adduct obtained by adding an alkylene oxide to an alcohol having 8 to 18 carbon atoms. The number of carbon atoms of the alcohol in the alkylene oxide adduct is preferably from 10 to 18, more preferably from 10 to 16, and even more preferably from 10 to 14 from the viewpoint of improving printability and drying properties. Specifically, octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, and mixtures thereof are preferred, and octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, and these More preferred are decyl alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, and mixtures thereof.

  In the alkylene oxide adduct, the alkylene oxide added to the alcohol is preferably ethylene oxide, propylene oxide, butylene oxide or the like, more preferably propylene oxide, from the viewpoint of improving printability and drying property.

  The average addition mole number of the oxyalkylene group in the alkylene oxide adduct is preferably 0.1 to 2.0 moles with respect to 1 mole of alcohol, from the viewpoint of improving printability and drying property and reducing odor. 0.4-1.8 mol is more preferable, and 1.0-1.6 mol is more preferable.

The alkylene oxide adduct may be represented by the following formula (I) as an embodiment.
R ¹ -O- (AO) _n -H (I)
[In the formula (I), R ¹ represents an alkyl or alkenyl group having 8 to 18 carbon atoms, AO represents an oxyalkylene group having 2 to 4 carbon atoms, and n represents an average added mole number of AO. It is a number between 0.1 and 2.0. ]

The alkyl or alkenyl group of R ^{1 in} the formula (I) may be linear or branched and may contain a cyclic structure. The number of carbon atoms of R ¹ is preferably 10-18, more preferably 10-16, and even more preferably 10-14, from the viewpoint of improving printability and drying properties. The number of carbon atoms of AO is more preferably 2 to 3, and even more preferably 3 from the viewpoint of improving printability and drying properties. Specifically, as AO, an oxyethylene group, an oxypropylene group, and an oxybutylene group are preferable, and an oxypropylene group is more preferable from the viewpoint of improving printability and drying properties. n (average number of added moles) is preferably 0.4 to 1.8 mol, and more preferably 1.0 to 1.6 mol from the viewpoints of improving printability and drying properties and reducing odor. In addition, the preferable form of alcohol (R < ¹ > OH) before the alkylene oxide derived from an oxyalkylene group is added is as above-mentioned.

  Moreover, the alkylene oxide adduct in the organic solvent composition of the present invention may be one type or a combination of two or more types.

  An alkylene oxide adduct can be produced by adding an alkylene oxide to the alcohol. The addition of alkylene oxide can be performed according to a conventional method. As one embodiment of addition of alkylene oxide, for example, as described in JP-A-4-3221637, there is a method in which potassium hydroxide is added as an alcohol and a catalyst in an autoclave, and alkylene oxide is charged and reacted.

  In the present invention, the alcohol used for the production of the alkylene oxide adduct is preferably produced from a vegetable oil from the viewpoint of environmental protection and improvement of the working environment. Examples of the vegetable oil include coconut oil, palm oil, cacao oil, olive oil, corn oil, a mixture thereof, and waste cooking oil thereof. The said waste cooking oil contains the oil used for manufacture of food-drinks, for example. Production of alcohol from these vegetable oils can be appropriately carried out by those skilled in the art according to conventional methods.

[alcohol]
The organic solvent composition of the present invention contains an alcohol having 4 to 18 carbon atoms and / or an ester having a total carbon number of 2 to 12 composed of an alcohol component and a carboxylic acid component. The number of carbon atoms of the alcohol is preferably 6 to 14, more preferably 8 to 14, and still more preferably 10 to 12, from the viewpoint of improving printability and drying properties. As the alcohol, butyl alcohol, hexyl alcohol, octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, and mixtures thereof are preferable from the viewpoint of improving printability and drying properties. Decyl alcohol and lauryl alcohol are preferred from the viewpoints of drying properties of organic solvents and odor reduction.

  It is preferable that the said alcohol is manufactured from vegetable oil from a viewpoint of environmental conservation or a work environment improvement. As said vegetable oil, the above-mentioned similar vegetable oil is mentioned.

[ester]
The organic solvent composition of the present invention contains an alcohol having 4 to 18 carbon atoms and / or an ester having a total carbon number of 2 to 12 composed of an alcohol component and a carboxylic acid component. The total number of carbon atoms of the ester is preferably 4 to 11 and more preferably 5 to 10 from the viewpoint of improving printability and drying properties. As one embodiment, the ester may be represented by the following formula (II).
R ² -COO-R ³ (II)
[In the formula (II), R ² represents a hydrogen atom, an alkyl having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms which may be substituted with hydroxy or an alkoxy group having 1 to 4 carbon atoms. R ³ represents an alkyl group having 1 to 6 carbon atoms. ]

In the formula (II), R ² is more preferably an alkyl or alkenyl group having 2 to 10 carbon atoms which may be substituted with a hydroxy group from the viewpoint of improving printability and drying property, and R ² is substituted with a hydroxy group. The alkyl or alkenyl group having 2 to 8 carbon atoms may be more preferable, and the alkyl or alkenyl group having 2 to 6 carbon atoms which may be substituted with a hydroxy group is still more preferable. The number of substitution of the hydroxy group or the alkoxy group having 1 to 4 carbon atoms in R ² is not particularly limited, and examples thereof include 1, 2, or 3. Further, the alkyl or alkenyl group in R ² may be linear or branched.

In the above formula (II), the carbon number of R ³ is preferably 1 to 4 and more preferably 2 to 4 from the viewpoint of improving printability and drying property.

  Specifically, the ester is preferably ethyl acetate, ethyl propionate, ethyl lactate, or butyl lactate, and more preferably ethyl lactate or butyl lactate from the viewpoint of the drying property of the organic solvent composition.

  In the case where the ester is produced from a compound having a carboxyl group (hereinafter referred to as a carboxylic acid compound) and an alcohol, the carboxylic acid compound and / or the alcohol is produced from a vegetable oil from the viewpoint of environmental conservation or improvement of the working environment. It is preferable that As said vegetable oil, the above-mentioned similar vegetable oil is mentioned. As for the lactic acid, lactic acid may be produced from starch derived from corn, sweet potato, rice, wheat, potato, and the like. A method is mentioned.

  In the organic solvent composition of the present invention, each of the alcohol and the ester may be one kind or a combination of two or more kinds, or one of the alcohol and the ester, or a combination thereof. .

  In the organic solvent composition of the present invention, a ratio of the content (% by weight) of the alkylene oxide adduct to the total content (% by weight) of the alcohol and the ester (the alkylene oxide adduct) / (the above The total of the alcohol and the ester is preferably 95/5 to 40/60, more preferably 92/8 to 45/55, and 85/15 from the viewpoints of improving printability and drying properties and reducing odor. -48/52 is more preferable, and 75 / 25-48 / 52 is still more preferable.

  In the organic solvent composition of the present invention, the total content of the alkylene oxide adduct and the alcohol and / or the ester is preferably 50% by weight or more from the viewpoint of improving printability and drying property. % By weight or more is more preferred, 90% by weight or more is more preferred, 99% by weight or more is even more preferred, and 99.9% by weight or more is even more preferred.

[Method for producing organic solvent composition for printing ink]
The organic solvent composition of the present invention can be produced by mixing the alkylene oxide adduct and the alcohol and / or the ester. The mixing is preferably performed with a stirrer such as a stirrer or a disper from the viewpoint of improving printability and drying property. The rotational speed is preferably 50 to 300 rpm, more preferably 100 to 250 rpm, from the viewpoint of improving printability and drying property. The mixing time is preferably 0.5 to 15 minutes and more preferably 2 to 10 minutes from the viewpoint of improving printability and drying property. The temperature in the system at the time of mixing (concentration of the mixture) is preferably adjusted to 15 to 50 ° C, more preferably 20 to 40 ° C, from the viewpoint of improving printability and drying property.

[Organic solvent composition for printing ink]
The organic solvent composition of the present invention can be produced by the method for producing the organic solvent composition of the present invention. The organic solvent composition of the present invention preferably uses a vegetable oil-derived raw material, and more preferably does not contain a petroleum-based solvent, from the viewpoint of environmental protection and improvement of the working environment. According to the organic solvent composition of the present invention, it is preferable to produce a printing ink having improved drying properties.

  The complete decomposition temperature (described later) of the organic solvent composition of the present invention is preferably 230 ° C. or lower, more preferably 225 ° C., further preferably 220 ° C. or lower, from the viewpoint of drying properties of the organic solvent composition. The following is more preferable. Moreover, from the point of printability, 140 degreeC or more is preferable and 150 degreeC or more is more preferable. Therefore, from printability and dryness, 140-230 degreeC is preferable, 140-225 degreeC is more preferable, 150-220 degreeC is further more preferable, 150-215 degreeC is still more preferable. In addition, when preparing a mixture containing the alkylene oxide adduct of the organic solvent composition of the present invention and the alcohol and / or the ester in a content ratio in the organic solvent composition of the present invention, the complete decomposition temperature of the mixture Is preferably in the same range as described above.

[Complete decomposition temperature]
In the present invention, the complete decomposition temperature is a temperature measured by a thermogravimetry method (heat loss method) (hereinafter, also referred to as “TG method”). The TG method is excellent in quantitativeness in thermal analysis, and is a method of recording a change in weight of a sample due to an increase in air temperature with respect to temperature (or time). A curve representing this recording is referred to as a TG curve. In the present invention, the complete decomposition temperature refers to the temperature at which the sample has completely disappeared (TG curve has become 0). Specifically, the complete decomposition temperature can be measured by the method described in Examples.

  The complete decomposition temperature of the alkylene oxide adduct is preferably 210 to 300 ° C, more preferably 215 to 285 ° C, and further preferably 215 to 260 ° C from the viewpoint of printability. Moreover, as a complete decomposition temperature of the said alcohol and / or the said ester, 100-220 degreeC is preferable from a dry point, 110-208 degreeC is more preferable, and 110-200 degreeC is further more preferable. The complete decomposition temperature can be adjusted to a higher temperature, for example, by increasing the number of added alkylene oxides in the alkylene oxide adduct or by lengthening the alkyl chain. Conversely, if the alkyl chain is shortened, the complete decomposition temperature can be adjusted to be low. By performing such adjustment, the complete decomposition temperature of the organic solvent composition of the present invention can be adjusted.

  In addition, the complete decomposition temperature of the alkylene oxide adduct contained in the organic solvent composition of the present invention is preferably higher than the complete decomposition temperature of the alcohol and / or the ester. From the viewpoint of solvent compatibility and printability, 35 to 95 ° C is preferable, and 45 to 75 ° C is more preferable.

[Printing ink]
The printing ink of the present invention includes the organic solvent composition of the present invention, and therefore includes the alkylene oxide adduct and the alcohol and / or the ester. The printing ink of this invention can be manufactured by the manufacturing method including the process of mixing the organic solvent composition of this invention, resin, and a pigment | dye, for example.

  In the printing ink of the present invention, the ratio of the alkylene oxide adduct content (% by weight) to the total content (% by weight) of the alcohol and the ester (the alkylene oxide adduct) / (the alcohol and The total of the ester) is preferably 95/5 to 40/60, more preferably 92/8 to 45/55, and 85/15 to 48/52 from the viewpoint of improving the printability and the drying property of the organic solvent. More preferably, 75/25 to 48/52 is even more preferable. Furthermore, the total content of the alkylene oxide adduct and the alcohol and / or the ester in the printing ink of the present invention is preferably 25 to 45% by weight from the viewpoint of improving printability and drying property, and 28 to 42 weight% is more preferable and 31-39 weight% is still more preferable.

  As said pigment | dye, an organic or inorganic pigment can be used individually or in mixture of 2 or more types. Examples of the resin include a transparent resin including a thermosetting resin, a radiation curable resin, and a thermoplastic resin, a precursor thereof, or a mixture thereof.

[Preparation of organic solvent composition]
The organic solvent compositions of Examples 1-8, Reference Examples 1-2, and Comparative Examples 1-5 were prepared as follows.

[Examples 1 to 5]
Propylene oxide (PO) is added to an alcohol mixture derived from vegetable oil having 12 and 14 carbon atoms (trade name: Calcoal 2470, C ₁₂ H ₂₅ OH / C ₁₄ H ₂₉ OH = 70/30 mol%, manufactured by Kao Corporation) 1 mol adduct of C12 / C14 alcohol (PO) (average addition mole number of PO to the alcohol is 1.0, manufactured by Kao Corporation) and butyl lactate obtained using vegetable oil-derived lactic acid (Musashino Chemicals) Manufactured by Research Institute Co., Ltd.) were mixed at the ratio shown in Table 1 below and stirred and mixed at 30 ° C. and 200 rpm for 5 minutes to prepare organic solvent compositions of Examples 1 to 5.

[Examples 6 to 8]
C12 alcohol (PO) 1 mol adduct (PO to the alcohol) obtained by adding PO to vegetable oil-derived alcohol having 12 carbon atoms (trade name: Calcoal 2098, C ₁₂ H ₂₅ OH = 100 mol%, manufactured by Kao Corporation) The average number of moles added is 1.0, manufactured by Kao Corporation, and alcohol derived from vegetable oil having 12 carbon atoms (trade name: Calcoal 2098, manufactured by Kao Corporation) in a 1 liter mixer (trade name: Pyrex (registered trademark) beaker, manufactured by Iwaki Glass Co., Ltd.) was added so that the total amount of both was 500 g and the mixing ratio shown in Table 1 below, and the mixture was stirred and mixed at 30 ° C. and 200 rpm for 5 minutes. Six to eight organic solvent compositions were prepared.

[Reference Examples 1 and 2]
The C12 / C14 alcohol (PO) 1 mol adduct of Examples 1 to 5 and the C12 alcohol (PO) 1 mol adduct of Examples 6 to 8 were used as the organic solvent compositions of Reference Examples 1 and 2, respectively. (Table 1 below).

[Comparative Example 1]
An organic solvent composition was prepared in the same manner as in Example 3 except that octylamine (trade name: Farmin 08, manufactured by Kao Corporation) was used instead of butyl lactate (Table 1 below).

[Comparative Example 2]
Diethylene glycol monoethyl ether acetate (reagent: manufactured by Wako Pure Chemical Industries, Ltd.) and ethyl lactate (reagent: manufactured by Wako Pure Chemical Industries, Ltd.) obtained using vegetable oil-derived lactic acid were mixed at the ratio shown in Table 1 below. The mixture was stirred and mixed at 30 ° C. and 200 rpm for 5 minutes to prepare the organic solvent composition of Comparative Example 4.

[Comparative Examples 3 to 5]
Isooleic acid 2-ethylhexyl ester (manufactured by Aldrich Reagent), linoleic acid butyl ester (reagent: Sigma-Aldrich Japan), and caproic acid 3,5,5-trimethylhexyl ester (reagent: Sigma-Aldrich Japan) The organic solvent compositions of Comparative Examples 3, 4 and 5 were used (Table 1 below).

[Evaluation of organic solvent composition]
About the organic solvent composition of Examples 1-8, Reference Examples 1-2, and Comparative Examples 1-5, complete decomposition temperature was measured by the thermogravimetry method (TG method) of the following conditions. Moreover, the drying test was done on condition of the following. These results are shown in Table 1 below.

[Measurement of complete decomposition temperature]
The complete decomposition temperature was measured by a TG method (Thermogravimetry). Specifically, the measurement was started with the following apparatus and conditions, and the temperature at which the organic solvent composition was completely decomposed and disappeared (temperature at which the amount of the sample was 0 mg) was defined as the complete decomposition temperature.
Equipment: TG / DTA200 manufactured by Seiko Instruments Inc.
Measurement sample amount: 15mg
Starting temperature: 30 ° C
Temperature increase rate: 5 ° C./min Air flow rate: 200 mL / min

[Drying test]
The organic solvent compositions of Examples 1 to 8, Reference Examples 1 to 2 and Comparative Examples 1 to 5 were applied on a PET film with an applicator (manufactured by Yasuda Seiki Seisakusho Co., Ltd.) to a thickness of 100 μm, 25 ° C., 50% RH. Was kept in a constant temperature and humidity chamber, and the time until complete drying was measured.

  As shown in Table 1 above, the organic solvents of Examples 1-8 were shorter in drying time than the organic solvents of Reference Examples 1-2 and Comparative Examples 1-5, and were excellent in drying properties. Therefore, it can be expected that the printing ink using the organic solvent for printing ink of the present invention is excellent in drying property.

  The present invention is useful, for example, in the field of printing inks and printing using the same.

Claims (5)

C2-C12 ester composed of an alkylene oxide adduct obtained by adding alkylene oxide to C8-C18 alcohol, C4-C18 alcohol, and / or alcohol component and carboxylic acid component An organic solvent composition for printing ink containing
Any one of the alcohol having 8 to 18 carbon atoms, the alcohol having 4 to 18 carbon atoms, and the alcohol and / or the carboxylic acid that is the raw material of the ester having 2 to 12 carbon atoms in total is a plant-derived raw material, Organic solvent composition for printing ink. The organic solvent composition for printing ink according to claim 1, wherein the alkylene oxide adduct is represented by the following formula (I), and the ester having 2 to 12 total carbon atoms is represented by the following formula (II).
R ¹ -O- (AO) _n -H (I)
R ² -COO-R ³ (II)
[In the above formula (I), R ¹ represents an alkyl or alkenyl group having 8 to 18 carbon atoms, AO represents an oxyalkylene group having 2 to 4 carbon atoms, and n represents the average number of moles of AO added. .1 to 2.0,
In the above formula (II), R ² represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms which may be substituted with hydroxy or an alkoxy group having 1 to 4 carbon atoms, R ³ represents an alkyl group having 1 to 6 carbon atoms. ] All of the alcohol component and the carboxylic acid component constituting the alcohol having 8 to 18 carbon atoms, the alcohol having 4 to 18 carbon atoms, and the ester having 2 to 12 carbon atoms are obtained using plant-derived materials. The organic solvent composition for printing inks according to claim 1 or 2. The organic solvent composition for printing ink according to any one of claims 1 to 3, wherein the complete decomposition temperature measured by a thermogravimetry (Thermogravimetry) is 140 to 230 ° C. The ratio of the content (% by weight) of the alkylene oxide adduct to the total content (% by weight) of the alcohol and the ester (the alkylene oxide adduct) / (the total of the alcohol and the ester) is 95. It is / 5-40 / 60, The organic solvent composition for printing inks in any one of Claims 1-4.