DE953657C - Plasticizers for thermoplastics - Google Patents

Description

Plasticizers for thermoplastics It is known γ-chlorobutyric acid ester To be used as a solvent and plasticizer for paints and plastic compounds. There is also the use of halogen-containing aromatic-aliphatic carboxylic acids known as a plasticizer for plastic masses. This is also the case with these plasticizers the halogen is attached to aliphatic carbon. The plasticizers mentioned are sufficient not in any case the requirements for stability, which is likely due to the not always due to sufficient inertia of the aliphatically bonded halogen is.

It has now been found that low-volatility esters of p-chloro-y-phenylbutyric acid excellent plasticizers for thermoplastics, especially those containing halogens thermoplastics represent.

The p-chloro-y-phenylbutyric acid can be converted into chlorobenzene and produce butyrolactone in the presence of Friedel-Crafts catalysts and can be esterified in the usual way. It is beneficial in esterification to remove the water formed, which is expediently carried out by azeotropic distillation with the help of aromatic hydrocarbons or halogenated aliphatic Can reach hydrocarbons. The non-volatile can be used as the alcoholic component Esters of p-chloro-y-phenylbutyric acid contain mono- or polyhydric alcohols. Particularly suitable are o, co'-glycols with at least 4 carbon atoms between the hydroxyl groups, like I, 4-butanediol, I, 6-hexanediol and I, Io-decanediol. Also polyethylene glycols, such as di-, tri- or tetraethylene glycol are useful.

Suitable monohydric alcohols are, for. B. 2-ethylhexanol, dodecyl alcohol, Benzyl alcohol and other monohydric alcohols, expediently at least 6 carbon atoms included, called. From higher quality Alcohols come glycerin, Butanetriol, trimethylolpropane, hexanetriol and pentaerythritol into consideration.

The non-volatile esters of p-chloro-y-phenylbutyric acid, for their Manufacture here no protection is claimed, are particularly suitable for softening of polymers and copolymers of vinyl or vinylidene chloride. With these monomers can contain other vinyl compounds such as vinyl acetate, acrylonitrile, Acrylic acid or methacrylic acid esters and the like in the plastics to be plasticized be copolymerized.

The plasticizers can be added to the thermoplastics by mixing, z. B. on rolling mills, kneaders and the like, at room temperature or moderately increased Temperatures are incorporated.

As a rule, about 20 to 50%, based on plasticizer, are used the weight of the thermoplastic.

The plasticized plastic masses are characterized by excellent mechanical properties and good cold and heat resistance. You can can be used in many ways and serve z. B. for the production of films, moldings of any kind, electrical insulation, coatings, coverings and the like.

The parts given in the examples below are parts by weight.

Example I In a stirred tank equipped with a reflux condenser and a Separator is provided, a mixture of 397 parts of p-chloro-y-phenylbutyric acid, 260 parts of 2-ethylhexanol, 1500 parts of toluene and 7 parts of p-toluenesulfonic acid about Held in brisk simmering for eight hours; it collects in the separator 36 parts of water. After adding 30 parts of decolorizing charcoal, the contents of the kettle become heated to boiling for another 2 hours, then the charcoal removed by filtering and the cold solution in the usual way first with 5% soda solution and then several times washed neutral with water. After the toluene has been distilled off in vacuo, one obtains 585 parts of the pale yellowish p-chloro-yphenylbutyric acid-2-ethylhexyl ester.

Mixtures of this plasticizing ester and polyvinyl chloride can be processed into films with the following properties: Polyvinyl chloride 60 parts 75 parts p-chloro-y-phenylbutyric acid 2-ethylhexyl ester 40 parts 1 25 parts Tensile strength in kg / cm2 .... I67 258 Elongation at break in% ........ 380 240 Cold resistance 35 -35 to 40a -20 to 250 specific resistance in Q cm cm I-IOll 7 1013 EXAMPLE 2 In the same way as in Example 1, an ester is prepared from a mixture of 596 parts of p-chloro-γ-phenylbutyric acid and 140 parts of butanediol (1.4). The esterification takes place in the presence of 2000 parts of toluene and 7.5 parts of p-toluenesulfonic acid.

652 parts of the pale yellowish 1,4-butanediol ester are obtained of p-chloro-y-phenylbutyric acid.

The following values were measured on films made of polyvinyl chloride and this plasticizing ester: Polyvinyl chloride 60 parts to 75 parts Plasticizers Parts 1 25 parts Tensile strength in kg / cm2 a) before aging 210 305 b) after aging ....... 232 323 Elongation at break in% a) before aging 380 235 b) after aging ....... 370 230 Cold resistance a) before aging -2O to-250 ° 5 to 10 ° b) after aging -15bi5-200 obis- 50 specific resistance in Q cm cm ................. 5 1010 6 1013 The aging is carried out at go "via IITage.

Claims (1)

PATENT CLAIM: The use of low-volatility esters of p-chlorophenylbutyric acid as a plasticizer for thermoplastics. Considered publications, German patent specifications No. 802 894, 868 969; U.S. Patent No. 2,559,146.