JP2859432B2 - Sulfur-containing compound and method for producing the same - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a novel sulfur-containing compound and a method for producing the same.

These sulfur-containing compounds are useful as modifiers and stabilizers for various resins, and are also used as release agents for thermosetting resins such as unsaturated polyester, epoxy, urethane, urethane / urea, urea, and phenol resins. Can be used as

[Conventional technology]

Conventionally, for example, regarding release agent separation, generally,
When resin is injection molded, it is important that the molded product is easily released from the mold. To achieve these objectives, various types of external release agents as well as internal release agents have been developed. Have been. Among the release agents, fatty acids or metal salts of fatty acids are usually used as the internal release agent.
For these release agents, depending on the resin to be molded,
It is necessary that the internal release agent is dissolved in the raw material,
It is desired that the release agent attached to the resin surface for coating after molding can be removed by washing with an organic solvent. However, these fatty acids or metal salts of fatty acids have various problems to be improved in terms of solubility in resin raw materials, solubility in various organic solvents used for washing after molding, and the like.

[Problems to be solved by the invention]

The purpose of the present invention, for example, when used as a release agent,
The problems as described above, ie, poor solubility in resin raw materials,
An object of the present invention is to provide a novel compound having excellent release performance in which defects such as poor solubility in various organic solvents used for washing a molded article are improved, and a method for producing the same.

[Means for solving the problem]

The present inventors have conducted intensive studies to achieve the above object, and as a result, completed the present invention.

That is, the present invention provides a compound represented by the general formula (I): (Wherein R represents a C _B -C ₃₀ aliphatic saturated or unsaturated hydrocarbon) and a sulfur-containing compound represented by the formula (II): And a halide represented by the general formula (III) RX (III) (wherein R has the same meaning as in the formula (I) and X represents a halogen atom) The present invention relates to a method for producing a sulfur-containing compound represented by the formula (I) which is reacted in the presence of a base.

The features of the sulfur-containing compound of the present invention, for example, when used as a mold release agent during resin molding, shows excellent mold release properties, and also adheres to the resin surface after resin molding and solubility in resin materials. In this case, the organic solvent is also excellent in cleaning properties.

Hereinafter, the method for producing the sulfur-containing compound of the present invention will be specifically described.

A method for producing the mercapto compound represented by the formula (II) used in the present invention is known.
As disclosed in JP-A-270859, epihalohydrin and 2-mercaptoethanol are reacted with triol obtained in the presence of a base, and thiourea is reacted in the presence of a mineral acid, followed by hydrolysis. can get.

The halide represented by the general formula (III) is a monohalide of an aliphatic saturated or unsaturated hydrocarbon of C _{8 to} C ₃₀ , and is caprylic chloride, lauryl chloride, myristyl chloride, palmityl chloride, stearyl chloride. , Aralkyl chloride, behenyl chloride, lignoseryl chloride, zomaryl chloride,
Oleyl chloride, linoleyl chloride, gadreyl chloride, erkir chloride, seracoleyl chloride, capryl bromide, lauryl bromide, myristyl bromide, palmityl bromide, stearyl bromide, araquil bromide, behenyl bromide, lignoceryl bromide, zomalyl bromide,
Oleyl bromide, linoleyl bromide, gadreyl bromide, erquil bromide, seracoleyl bromide, capryl iodide, lauryl iodide, myristyl iodide, palmityl iodide, stearyl iodide, araquil iodide,
Examples include behenyl iodide, lignoceryl iodide, zomaryl iodide, oleyl iodide, linoleyl ioid, gadrail iodide, erkir iodide, and serracoyl iodide.

The amount of the halide to be used is 2 to 5 mol, preferably 2 to 3 mol, per 1 mol of the mercapto compound.

In addition, as the base used in the present invention, NaOH, KO
_{H, NaHCO 3, Na 2 CO} 3, K 2 CO 3 and the like inorganic bases, triethylamine, pyridine, N- methylmorpholine, 1,4-diazabicyclo [2,2,2] tertiary amines such as octane or the like However, it is a matter of course that the present invention is not limited to these.

The base may be used in an amount of 3 mol or more per 1 mol of the mercapto compound. Considering the complexity of treatment after the reaction, 3 to 4 mol is preferable.

In the reaction, a solvent can be used. As the solvent,
There is no particular limitation as long as it does not cause a chemical reaction with the raw material system, and hydrocarbons such as benzene, toluene, xylene, hexane, octane and decane, ether solvents such as tetrahydrofuran and dioxane, N, N-dimethylformamide, N , N-dimethylacetamide, N-methylpyrrolidone, N, N'-dimethylimidazolidinone, and other nitrogen-containing polar solvents can be used. These solvents can be used alone, but two or more of these solvents can be used as a mixture.

The reaction temperature is -10 ° C to 200 ° C, preferably 30 ° C to 150 ° C.
Can be performed in the range of

 The reaction time is 1 to 10 hours.

When an alkyl chloride or the like which is generally considered to have low reactivity is used, the reaction can be promoted by adding a catalytic amount of sodium iodide, potassium iodide or the like.

The end point of the reaction can be determined by infrared absorption spectrum and high performance liquid chromatography.

After completion of the reaction, the reaction mixture is washed with water, and the reaction solvent is distilled off to obtain a sulfur-containing compound represented by the general formula (I).

When a high-purity sulfur-containing compound is required, it can be purified by recrystallization or sludge using an appropriate organic solvent.

[Action] The sulfur-containing compound of the present invention obtained in this manner exhibits easy solubility in an organic solvent, and is, for example, a compound exhibiting excellent releasability when used as a release agent in molding a resin. is there.

〔Example〕

Hereinafter, the method for synthesizing the sulfur-containing compound of the present invention will be described in detail with reference to examples, but the present invention is not limited thereto.

Example 1 Stirrer, reflux condenser, Dean-Stark water separator,
In a reactor equipped with a nitrogen inlet tube, 150 g of a mercapto compound represented by the formula (II), N, N'-dimethylimidazolidinone 700
ml, toluene 700 ml and 95% -NaOH 88.51 g were inserted, and the mixture was stirred at 20 ° C under a nitrogen atmosphere. Thereto, 656.3 g of stearyl bromide was added dropwise at 20 ° C. After completion of the dropwise addition, the temperature was raised to 120 ° C., and the mixture was stirred for 5 hours.

After completion of the reaction, the reaction mixture was washed with warm water at 70 ° C., and the yellow solid obtained by distilling off the solvent was recrystallized with ethanol / toluene to obtain a pale yellow solid of a sulfur-containing compound.

Yield: 519.7 g (88.6% yield) Melting point: 51.0-52.8 ° C. The results of elemental analysis and mass spectrum (Ms) of the obtained compound were as follows.

Elemental analysis (C ₆₁ as H ₁₂₄ S ₅₎ C H S Calcd (%) 71.97 12.28 15.75 analysis (%) 72.05 12.02 15.69 Ms ( FD Method): 1018 (M +) [Effect of the invention The present invention relates, A new sulfur-containing compound that has improved solubility in resin materials and organic solvents, and exhibits excellent release properties, for example, when used as a release agent during resin molding. And a method for producing the same.

──────────────────────────────────────────────────の Continued on the front page (58) Field surveyed (Int. Cl. ⁶ , DB name) C07C 321/14 C07C 321/18 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. The compound of the general formula (I) (Wherein, R represents a saturated or unsaturated hydrocarbon aliphatic C ₈ -C ₃₀₎ sulfur-containing compound represented by the. 2. Formula (II) And mercapto compounds represented in, the general formula (III) R-X (III ) ( wherein R represents a saturated or unsaturated hydrocarbon aliphatic C ₈ -C _30, X is a halogen atom) The method for producing a sulfur-containing compound according to claim 1, wherein the represented halide is reacted in the presence of a base.