JPH07119429B2 - Method for producing high softening point wax - Google Patents

Description

TECHNICAL FIELD The present invention relates to a method for producing a carboxylic acid amide wax, particularly to a method for producing a carboxylic acid amide wax having a high softening point by reacting a carboxylic acid and a diamine. .

[Conventional technology]

Higher fatty acid bisamides conventionally produced from higher aliphatic monocarboxylic acids and diamines, such as ethylene bisstearamide, have a relatively high softening point (for example, 142 to 1).
It is known as wax, and is used as a lubricant and release agent for thermoplastic resins, and also as a dispersant for pigments.

In recent years, a thermoplastic resin having a high molding processing temperature has been developed as an engineering plastic, and its use in many fields has been remarkably increased as a material that can replace metal. Examples of such engineering plastics include polyphenylene oxide, polyester, polyacetal, polycarbonate, polyamide, and the like, and plastics reinforced with various reinforcing fillers. The processing temperature of such engineering plastics is relatively high,
Some even reach 350 ° C above 180 ° C.

[Problems to be Solved by the Invention]

If a conventional higher aliphatic bisamide is used as a lubricant or a mold release agent in an engineering plastic with a high processing temperature as described above, it causes smoke during processing, or causes discoloration to color the plastic molded product, or the resin itself. It causes problems such as impairing thermal stability.

Therefore, a wax having a high softening point that can withstand the high processing temperature without the above-mentioned drawbacks is required.

Accordingly, the object of the present invention is to provide engineering plastics having a high possible temperature, such as the aforementioned engineering plastics, ABS resin (including heat-resistant ABS resin such as α-methyl modified ABS resin and N-phenylmaleido modified ABS resin),
Polyphenylene sulfide resin, polysulfone resin,
It is an object of the present invention to provide a wax having a high softening point that does not emit smoke or hardly emits smoke during processing of a polyetherketone resin, a polyimide resin or the like, and has little coloring or discoloration.

[Means for Solving the Problems]

The present invention is a method for producing a carboxylic acid amide type wax by reacting a carboxylic acid and a diamine, wherein a softening point of a mixture of a higher aliphatic monocarboxylic acid and a polybasic acid as a carboxylic acid is higher than 170 ° C. There is a manufacturing method.

The higher aliphatic monocarboxylic acid used in the present invention is preferably a saturated aliphatic monocarboxylic acid having 16 or more carbon atoms and a hydroxycarboxylic acid, and those conventionally used for wax production can be used. For example, palmitic acid, stearic acid, behenic acid, montanic acid, hydroxystearic acid, etc. can be used.

The polybasic acid used in the present invention is a carboxylic acid of a dibasic acid or more, and examples thereof include aliphatic dicarboxylic acids such as malonic acid, succinic acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, phthalic acid and terephthalic acid Aromatic dicarboxylic acids such as, cyclohexanedicarboxylic acid, and cycloaliphatic dicarboxylic acids such as cyclohexylsuccinic acid can be used.

As the diamine used in the present invention, a diamine conventionally used in the production of wax, for example, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, hexamethylenediamine, metaxylylenediamine, tolylenediamine, Paraxylylenediamine, phenylenediamine, isophoronediamine, etc. can be used.

In carrying out the method of the present invention, higher aliphatic monocarboxylic acid and polybasic acid are reacted with diamine by heating. Generally, the reaction temperature is preferably 180 to 300 ° C and 200 to 270 ° C.
Is more preferable. The reaction time is 3 to 7 hours, preferably 3
~ 5 hours. In carrying out this amidation reaction, phosphorous acid, hypophosphorous acid or the like may be added as a coloring inhibitor. The amine value of the reaction product is 10 or less, preferably 5 or less.

The high softening point wax according to the present invention can be obtained by a heat dehydration reaction of a higher aliphatic monocarboxylic acid and a polybasic acid with a diamine. The softening point of the wax depends on the kind of the higher aliphatic monocarboxylic acid used. Although varying, for a certain aliphatic monocarboxylic acid, various high softening points can be obtained by changing the amount of polybasic acid used.

The amount of the polybasic acid used is preferably in the range of 0.18 mol to 1.0 mol with respect to 2 mol of the higher aliphatic monocarboxylic acid.

The amount of the diamine used is preferably in the range of 1.2 mol to 2.0 mol with respect to 2 mol of the higher aliphatic monocarboxylic acid, and this amount varies depending on the amount of polybasic acid used in combination.

When the amount of the above-mentioned polybasic acid used is less than 0.18 mol, the softening point of the wax produced is not much different from the softening point of the conventional higher aliphatic bisamide, for example, 170 ° C. or less, the engineering plastics The desired high softening point wax of the present invention, which is suitable for use in processing, cannot be obtained. Also, if the amount of polybasic acid used exceeds 1 mol, the amount of diamine used corresponding to it will not remain, and carboxyl groups will remain at the ends of the wax produced, depending on the type of plastic. This is not preferable because it may cause decomposition.

The amount of diamine used may be such that it reacts with the higher aliphatic monocarboxylic acid and polybasic acid used to form an acid amide.

Further, the high melting point wax obtained by the method of the present invention can be mixed with a conventional amide of a higher aliphatic carboxylic acid and used to adjust the melting point thereof.

[Action]

The carboxylic acid amide wax produced by the method of the present invention is a conventional wax (usually having a melting point of 150 because it is reacted with a diamine by using a polybasic acid in addition to a higher aliphatic monocarboxylic acid as a reaction component. It is a wax having a melting point higher than (° C. or lower), and does not emit smoke or hardly emits smoke even at the processing temperature of an engineering plastic which is processed at a high temperature, and has little coloring.

〔Example〕

Examples will be shown below, but the present invention is not limited thereto.

The high softening point wax was evaluated by the following method.

(1) Softening point: Measured according to JIS K-2531-1960 petroleum asphalt softening point test method (ring and ball method). However, silicone oil was used as the heat medium.

(2) Smoke emission and colorability: The surface temperature of a 20 mm thick hot plate is heated to 220 ° C, 250 ° C, 280 ° C, each sample is placed on the hot plate, and the smoked state and the colored state are visually observed. Compared.

Examples 1 to 10 In a four-necked flask equipped with a thermometer, a test tube with a condenser, a nitrogen introduction tube and a stirrer, each acid component except diamine was blended at a ratio shown in Table 1 below, and the mixture was heated and dissolved. After that, gradually add each diamine and in a nitrogen stream.
Start the dehydration reaction at 160 ℃ and make the amine value 5 at 250 ℃.
After reacting for 4 to 7 hours until the temperature became the following, each wax was collected by pouring into butts.

Comparative Examples 1 to 3 The same operations as in Examples 1 to 10 were performed at the ratios shown in Table 2 below, and dehydration reaction was performed at 160 to 210 ° C for 4 to 6 hours to give an amine value of 5
The reaction was carried out until the followings were obtained to obtain each comparative wax.

Example 11 90 g of the wax obtained in Example 5 and 10 g of ethylenebisstearoamide obtained in Comparative Example 1 were melt mixed to obtain a mixed wax.

Example 12 70 g of the wax obtained in Example 5 and 30 g of ethylene bis stearoamide obtained in Comparative Example 1 were melt-mixed to obtain a mixed wax.

Table 3 shows the results of the softening point, smoke generation state, and coloring state of the waxes obtained in each of the examples and comparative examples.

[Effects of the Invention] As is clear from the data in Table 3, the wax according to the present invention has a high softening point and is excellent in terms of smoke generation and coloring at a high temperature as compared with the conventional wax.

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Claims (1)

[Claims] 1. A method for producing a carboxylic acid amide wax by reacting a carboxylic acid and a diamine, wherein a mixture of a higher aliphatic monocarboxylic acid and a polybasic acid is used as the carboxylic acid. A method for producing solid wax above 170 ° C.