JPH06256663A - Isocyanate-modified wax and toluene solution of this wax - Google Patents

Abstract

PURPOSE:To obtain a substitute natural wax or a modifier for a natural wax having a low melting point, a low viscosity and a high hardness equivalent to those of a vegetable natural wax and excelling in solubility in an organic solvent. CONSTITUTION:This wax is one obtained by reacting an isocyanate with a mixture of a 10-30C linear aliphatic prim. monoalcohol with 1-50mol% aliphatic polyalcohol.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention is used as an alternative to plant-based natural waxes or as a modifier for natural waxes.
The present invention relates to an isocyanate-modified wax having a low melting point, low viscosity, high hardness, and excellent solubility in an organic solvent, which is suitable for use as a base material or compounding agent for lubricants, paints, binders for casting, inks for printing media such as thermal transfer, etc. .

[0002]

2. Description of the Related Art Conventionally, natural waxes such as carnauba wax, candelia wax, and rice wax have been used for the above-mentioned applications because of their excellent luster, hardness, uniform film formation, and moisture resistance, and also with other compounding agents. It has been used because of its good compatibility.

[0003]

However, these natural waxes have limited production areas, it is difficult to obtain constant quality wax due to changes in harvest time, growing climate conditions, etc., supply is unstable, and it is expensive. It has the drawback of being.

Further, the natural waxes currently used generally have poor solubility in organic solvents, and a large amount of organic solvents are used for the dissolution, which is not preferable from the environmental point of view.

Therefore, as a wax which substitutes or modifies a part of these natural waxes, oxidized microcrystalline wax, synthetic oxidized wax, montan wax and modified products thereof are studied and partially used. However, there is a problem that the suitable one is not obtained in the balance of melting point, hardness, viscosity and solvent solubility, or the manufacturing method thereof is complicated, and the price is high.

[0006]

SUMMARY OF THE INVENTION In view of the above-mentioned circumstances, the inventors of the present invention have found that the solubility of organic solvents in organic solvents is maintained while maintaining the low melting point, low viscosity and high hardness characteristics of plant natural wax. We have earnestly researched for the purpose of developing excellent new wax.

As a result, 1 to 5 aliphatic polyhydric alcohols are added to linear aliphatic primary monoalcohols having 10 to 30 carbon atoms.
The inventors have found that an isocyanate-modified wax obtained by reacting an alcohol mixture containing 0 mol% with diisocyanate meets the above-mentioned object, and thus completed the present invention.

The isocyanate-modified wax of the present invention will be described in detail below.

The reaction itself between alcohol and isocyanate is known (for example, "New Experimental Chemistry Account 14, Synthesis and Reaction III of Organic Compounds", page 1652, Maruzen (1).
However, in order to maintain the low melting point, low viscosity and high hardness characteristics of the natural plant wax, and to exhibit excellent solubility in organic solvents, both components should be used. It needs to be strictly limited.

In the present invention, a mixture of a linear aliphatic monoalcohol and an aliphatic polyhydric alcohol is used as an alcohol component, and tolylene diisocyanate is an essential component as an isocyanate component.

Aliphatic monoalcohols include straight chain primary, branched primary and secondary alcohols with 10 carbon atoms.
Only ~ 30 linear aliphatic primary monoalcohols can provide performance consistent with the purposes of the present invention. Other branched primary or secondary alcohols are not preferable because the melting point of the final product becomes too low.

The above linear aliphatic primary monoalcohol is
They can be used alone or in combination as appropriate, and specific examples include 1-decanol, 1-tetradecanol, 1
Examples thereof include octadecanol and 1-docosanol.

The aliphatic polyhydric alcohol used as the alcohol component for further improving the hardness of the final product and the solubility in an organic solvent is a commonly used one, such as glycerin, diglycerin and pentaerythrium. Tall, neopentyl glycol, sorbitol,
Sucrose, ethylene glycol, propylene glycol, dipentaerythritol, 1,6-hexanediol,
Examples thereof include 1,8-octanediol and 1,10-decanediol. Of these, ethylene glycol, glycerin, 1,10-decanediol and the like are particularly preferably used.

The above-mentioned straight-chain aliphatic first aliphatic high alcohol
If the addition rate to the grade monoalcohol is less than 1 mol%, the hardness of the final product and the solubility in an organic solvent will be insufficient, and if it is more than 50 mol%, the viscosity of the final product will be too high, so 1 to 50 mol% is preferable. , Particularly preferably 3 to 30 mol%.

Although many kinds of compounds having an isocyanate group are known, tolylene diisocyanate is most suitable for the reaction with the above-mentioned aliphatic alcohol mixture, and has a low melting point, a low viscosity and a high value which a vegetable wax has. It is possible to obtain an isocyanate-modified wax having excellent solubility in an organic solvent while maintaining hardness characteristics.

The addition ratio of tolylene diisocyanate to the aliphatic alcohol is preferably 75 to 100% of the alcohol hydroxyl value equivalent, particularly preferably 85 to 98%, and the desired addition reaction proceeds in this range.

The isocyanate-modified wax of the present invention thus obtained is used as a substitute for a plant-based natural wax,
Alternatively, as a modifier for natural wax, it has a low melting point, low viscosity, high hardness and solubility in organic solvents suitable for use as a base material or compounding material for lubricants, paints, binders for casting, inks for printing media such as thermal transfer. It has excellent properties. Especially when used as a thermal transfer ink,
Solubility in organic solvents, solvent drying, ink stability,
Both coatability and printability (print density) are excellent.

The present invention will be described in more detail below with reference to production examples of the isocyanate-modified wax of the present invention as examples. However, these examples are illustrative only and do not limit the invention thereto.

[0019]

【Example】

Example 1 1-Octadecanol (manufactured by Kishida Chemical Co., Ltd.) 1
47.0 g (0.543 mol) and ethylene glycol (manufactured by Kanto Chemical Co., Inc.) 3.0 g (0.048 mo)
The mixture of 1) was heated to 120 ° C., and while stirring, tolylene diisocyanate (manufactured by Nippon Polyurethane Industry Co., Ltd., Coronate T-80, trademark) 55.7 g (0.32).
0 mol) was added dropwise, and the mixture was reacted at 120 ° C. for 3 hours to obtain 200 g of the isocyanate-modified wax of the present invention.

Example 2 1-Octadecanol (Kishida Chemical Co., Ltd.) 1
A mixture of 37.2 g (0.507 mol) and glycerin (Kanto Chemical Co., Inc.) 2.8 g (0.03 mol) was heated to 120 ° C. and stirred while tolylene diisocyanate (Nippon Polyurethane Industry Co., Ltd., Coronate T). -80, trademark 52.1 g (0.299 mol) was added dropwise and reacted at 120 ° C. for 3 hours to obtain 190 g of the isocyanate-modified wax of the present invention.

Example 3 1-Octadecanol (manufactured by Kishida Chemical Co., Ltd.) 1
26.0 g (0.466 mol) and 1,10-decanediol (Tokyo Chemical Industry Co., Ltd.) 14.0 g
A mixture of (0.080 mol) is heated to 120 ° C.,
Tolylene diisocyanate (Nippon Polyurethane Industry Co., Ltd., Coronate T-80, trademark) 5 with stirring
4.5 g (0.313 mol) was added dropwise, and at 120 ° C, 3
The isocyanate-modified wax 1 of the present invention is reacted for a time.
90 g were obtained.

Comparative Example 1 1-Octadecanol (Kishida Chemical Co., Ltd.) 2
Heating 00.0 g (0.739 mol) to 120 ° C.,
With stirring, tolylene diisocyanate (Nippon Polyurethane Industry Co., Ltd., Coronate T-80, trademark) 3
3.1 g (0.190 mol) was added dropwise, and at 120 ° C., 3
After reacting for a time, 230 g of an isocyanate-modified wax was obtained.

The following physical properties of the waxes obtained in the above Examples and Comparative Examples were measured and evaluated.

Appearance: Measured visually.

Softening point: According to JIS K2207 5.4 Viscosity: According to JIS K6862 Penetration: According to JIS K2235 5.4 Toluene solubility: Toluene (special reagent grade) 50 g and 100 g in a glass sample bottle (manufactured by uchi) having a capacity of 100 ml. Add 2.5 to 25 g of the material and dissolve in a water bath. Thermometer at the bottom of the sample bottle (JISB7410 No. 10)
After fixing the thermometer with a cork so that the tip of the
The sample was left to stand at room temperature or in a cooling bath, and the temperature at which cloudiness occurred at the bottom of the sample solution was read to evaluate the solubility.

The results obtained are shown in Tables 1 and 2. Also, in the table, for comparison, carnauba wax No. 1 and candelia wax No. 2 are shown as examples of plant-based natural wax.
The characteristics of the issue are also listed.

[Table 1]

[Table 2] From the above results, it was confirmed that the isocyanate-modified wax according to the present invention has a low melting point, low viscosity, high hardness, and excellent solubility in an organic solvent.

EFFECT OF THE INVENTION The isocyanate-modified wax according to the present invention maintains the low melting point, low viscosity, and high hardness characteristics of a plant-based natural wax and has excellent solubility in organic solvents. It is preferably used as a substitute for natural waxes or as a modifier for natural waxes, as a base material or compounding material for lubricants, paints, binders for casting, inks for printing media such as heat transfer.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masashi Yamamoto 850 Oshima Oshima, Tokuyama City, Yamaguchi Pref. Japan Seiwa Co., Ltd. (72) Inventor Toshihiko Negoro 5-4-14 Mishimajima, Nishiyodogawa-ku, Osaka Fujiko, Osaka Pian Co., Ltd. Technical Center (72) Inventor Takao Arimura 5-4-14 Mishimajima, Nishiyodogawa-ku, Osaka Fujiko Pian Co., Ltd. Technical Center

Claims (3)

[Claims] 1. A linear aliphatic primary monoalcohol having 10 to 30 carbon atoms and 1 to 50 mo of an aliphatic polyhydric alcohol.
An isocyanate-modified wax, which is obtained by reacting an alcohol mixture prepared by blending 1% with an isocyanate. 2. The isocyanate-modified wax according to claim 1, wherein the isocyanate is tolylene diisocyanate. 3. 20 wt% at 20 ° C. with respect to toluene
% Or more of the toluene solution of the isocyanate-modified wax according to claim 1 or 2 obtained by dissolving.