JP3254725B2 - New organic gelling agents - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an organic gelling agent. Here, the gelling agent is a general term for a compound having a function of eliminating the fluidity of a system when added to an organic liquid.

[0002]

2. Description of the Related Art In recent years, researches on not only high molecular gelling agents but also organic low molecular gelling agents have been actively conducted. However, compared to the high molecular gelling agent, the discovery of the invention of the low molecular gelling agent is delayed, so that the type thereof is small.

[0003] Organic low molecular gelling agents known so far include dibenzal sorbit and substituted aromatic nuclei thereof, 12-hydroxystearic acid, acylated amino acid amides, cholesterol derivatives and the like.

[0004] The conventional gelling agents have characteristics, respectively, such as flow regulators and solids for paints and inks, gelling and recovering agents for spilled oils, solidifying agents for agricultural chemicals, slump inhibitors for joints, It is used according to the properties of each gelling agent such as a polymer processing aid and a solidifying agent for an aromatic.

[0005] However, each field is not sufficiently satisfied, and the discovery of a gelling agent having new functions and features is expected. In particular, there is one expectation for the birth of a gelling agent which has a low melting point, is easily dissolved at a relatively low temperature, and has a characteristic of forming a stable gel.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a new organic gelling agent having a characteristic gelling function to the industry and thereby to contribute to the development of organic gel application fields. I do.

[0007]

Means for Solving the Problems The present inventors have conducted intensive studies in order to develop a novel and useful organic gelling agent. As a result, amides having a specific structure can achieve the intended purpose. The present invention has been found, and the present invention has been completed based on such findings.

That is, the organic gelling agent according to the present invention contains 12-hydroxyoctadecanoic acid amides represented by the following general formula (1) (hereinafter collectively referred to as “the present amides”) as an active ingredient. It is characterized by the following.

Embedded image [Wherein, R ¹ is a hydrogen atom,

Embedded image ,

Embedded image Or

Embedded image Represents p shows the integer of 1-3. R ² represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms. m shows the integer of 1-5. R ³ represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms. n shows the integer of 1-5. ]

The amides can be obtained almost quantitatively, for example, by condensing 12-hydroxyoctadecanoic acid or its methyl ester with the corresponding amine at 200 ° C. or lower in the absence or presence of a catalyst. be able to.

The amines used to obtain the amides include ammonia, alkanolamines having 1 to 3 carbon atoms, urea, cyclohexylamine, and cyclohexylamine having 1 to 5 alkyl groups (1 to 30 carbon atoms). , Aniline, 1 to 5 alkyl groups (1 to 3 carbon atoms)
An aniline having 0) is mentioned, and amides obtained by applying ammonia, aniline, or alkylaniline are particularly preferable.

In preparing the amides, examples of the catalyst used as needed include alkali alcoholates such as sodium methylate, caustic soda, caustic potash, aluminum hydroxide, alkyl titanate, paratoluenesulfonic acid, sulfuric acid and the like. Is done.

These amides all have a low melting point of 150 ° C. or less, and are characterized as gelling agents having good low-temperature solubility.

The amides are useful, for example, as gelling agents for mineral oil, waste cooking oil, asphalt, fragrance, pharmaceutical base, jointing agent, marking material, plasticizer, ethylene-vinyl acetate resin and the like.

An example of a formulation in which the amides are applied as a gelling agent is described below. That is, the object to be gelled (base material) and the amides (gelling agent) are mixed under heating to form a uniform solution, and then the mixing is stopped and the mixture is cooled. At this time, another conventionally known gelling agent may be used in combination as long as the predetermined effect is exhibited.

The amount of the amides applied when gelling the above substance is appropriately selected in consideration of the type of the target substance and the processing conditions. About 0.5 to 30% by weight, preferably 1 to 5%
% By weight.

The amides are used not only as gelling agents but also as crystallization accelerators such as crystalline polymers such as polyethylene, polypropylene, polyethylene terephthalate and polybutadiene resin, rigidity improvers and transparency improvers. It is also effective as a nucleating agent having a function.

In addition, it is also effective as a plasticizer that improves moldability without deteriorating various physical properties of these crystalline resin molded products.

[0018]

The present invention will be described in detail below with reference to examples. Production Example 1 3.14 g of methyl 12-hydroxyoctadecanoate was placed in a 100 ml four-necked flask equipped with a thermometer, a stirrer and a condenser.
(10 mmol) and 2.8 g (30 mmol) of aniline, and 1.6 g of sodium methylate catalyst were added thereto.
Reaction at 0 ° C for 2 hours, neutralization, washing with water, drying
g (90% yield) of 12-hydroxyoctadecanoic acid anilide (melting point 119 ° C.) was obtained. The compound was identified by matching the retention times of the gas chromatograms of the product and the standard and by FT.
This was facilitated by the disappearance of the characteristic absorption of the carbonyl group and the generation of the characteristic absorption of the amide group of the product by -IR.

Example 1 10 g of oleic acid was collected in a test tube, and 12 g of oleic acid obtained in Production Example 1 was obtained.
-Hydroxyoctadecanoic acid anilide (0.5 g) was dissolved by heating, cooled with water, and observed 2 minutes later. Even when the test tube was inverted, the oleic acid did not flow down, the fluidity of the system was apparently lost, and a gel was formed. When the temperature was raised, the solution became a homogeneous solution, and again formed a gel reversibly by water cooling.

Example 2 The presence or absence of gel formation was determined in the same manner as in Example 1 except that the object to be gelled was liquid paraffin. As a result, the fluidity of the system was apparently lost, and a gel was formed.

Example 3 Example 1 was repeated except that the object to be gelled was dioctyl phthalate, and that 12-hydroxyoctadecanoic acid amide (melting point 115 ° C.) prepared according to Production Example 1 was used as the gelling agent.
The presence or absence of gel formation was determined according to. As a result, the fluidity of the system was apparently lost, and a gel was formed.

Example 4 Ethanolamide 12-hydroxyoctadecanoate (melting point: 112 ° C.) prepared according to Production Example 1 as a gelling agent
The presence or absence of gel formation was determined according to Example 3 except that was used. As a result, the fluidity of the system was apparently lost, and a gel was formed.

Example 5 Isopropanolamide 12-hydroxyoctadecanoate (melting point: 10) prepared according to Production Example 1 as a gelling agent
1 ° C.), and the presence or absence of gel formation was determined according to Example 3. As a result, the fluidity of the system was apparently lost, and a gel was formed.

Example 6 Cyclohexyl amide 12-hydroxyoctadecanoate (melting point: 116) prepared according to Production Example 1 as a gelling agent
° C), the presence or absence of gel formation was determined according to Example 3. As a result, the fluidity of the system was apparently lost, and a gel was formed.

Example 7 p-Methylphenylamide 12-hydroxyoctadecanoate (melting point: 1) prepared according to Production Example 1 as a gelling agent
21 ° C.), and the presence or absence of gel formation was determined according to Example 3. As a result, the fluidity of the system was apparently lost, and a gel was formed.

Comparative Example 1 The presence or absence of gel formation was determined according to Example 3, except that butyl amide 12-hydroxyoctadecanoate was used as the gelling agent. As a result, the system was not gelled at all.

Comparative Example 2 The presence or absence of gel formation was determined according to Example 3, except that methyl 12-hydroxyoctadecanoate was used as the gelling agent. As a result, the system was not gelled at all.

Comparative Example 3 The presence or absence of gel formation was determined according to Example 3, except that diethanolamide 12-hydroxyoctadecanoate was used as the gelling agent. As a result, the system was not gelled at all.

[0029]

The organic gelling agent according to the present invention dissolves at a relatively low temperature to form a gel. For this reason, it is provided to industry as a new gel-forming material and can contribute to the development of new application fields of gel.

Continuation of the front page (58) Fields investigated (Int. Cl. ⁷ , DB name) C09K 3/00 103 C07C 235/06 C07C 235/08 C07C 235/14 C07C 235/16 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. An organic gelling agent comprising as an active ingredient a 12-hydroxyoctadecanoic acid amide represented by the following general formula (1). Embedded image [Wherein, R ¹ is a hydrogen atom, , Or Represents p shows the integer of 1-3. R ² represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms. m shows the integer of 1-5. R ³ represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms. n shows the integer of 1-5. ]