Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1985-06-12
1987-09-22
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 85, 562480, C07C 6980
Patent
active
046956492
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF THE INVENTION
This invention relates to novel phthalates represented by the general formula: ##STR2## wherein R is alkyl having 1-8 carbon atoms, e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, tert-octyl, etc. or benzyl.
The compounds of formula (I) can be readily prepared by making to react a compound of the formula: ##STR3## wherein X is halogen, e.g., chlorine or bromine, with a compound of the formula: ##STR4## wherein R is the same as defined above, in a suitable solvent such as toluene, benzene, xylene, etc. in the presence of an amine such as triethylamine, pyridine, dimethylaniline, etc.
The resulting product is purified by a conventional method such as column chromatography, recrystallization.
The compounds of this invention have a repellency action against unhygienic pests, e.g., cockroaches, termites, etc. and accordingly, are useful as a pest-repellent.
In using the compound of this invention as a pest-repellent, it is mixed with a conventional carrier for a pest-repellent, kneaded in a synthetic resin, e.g., polyvinyl chloride or any other material intended for repellency of unhygienic pests, coated or impregnated with a brush or by spraying.
The amount in which the compound is used varies depending on the mode of use and is such that is enough to exhibit a repellency action to unhygienic pests. For example, 0.5 to 10 parts by weight of it may be compounded to 1 part by weight of a carrier.
Further, the compounds of this invention impart a superior plasticization efficiency to a thermoplastic polymer and increase its suppleness, elasticity, plasticity with a low volatility. Hence, they are also useful as a plasticizer for polymers.
Particularly, they are suitable as a plasticizer for nylon resins (nylon 6, nylon 66, etc.). For instance, it is preferred that the compound of this invention is added in an amount of 0.5 to 5% by weight, preferably 1 to 4% by weight to nylon chips, and the mixture is preheated to 70.degree.-80.degree. C. for a few hours and subjected to molding treatment according to conventional method.
It is a further feature that the compounds of this invention, when incorporated in a nylon resin, lower the softening temperature of it. As a consequence, it is possible to lower the processing temperature of it and to perform stable processing because of a low thermal volatility.
The invention will be hereinbelow described in detail with reference to examples and experimental examples.
EXAMPLE 1
Into a 500 ml four-neck flask equipped with a condenser tube and a thermometer are charged 56 g of benzyl p-hydroxybenzoate, 25 g of triethylamine and 60 ml of toluene. A suspension of 25 g of terephthalic dichloride in 100 ml of toluene is added dropwise with stirring while retaining the mixture at 0.degree.-5.degree. C. over 3 hours. After addition, the mixture is further allowed to react at 0.degree.-5.degree. C. for 1 hour. Thereafter the resulting reaction product is collected by filtration to obtain white crystals. The crystals are washed with 1500 ml of water twice and then with 1000 ml of methanol twice and subsequently, recrystallized from chloroform to give di(p-benzyloxycarbonylphenyl)terephthalate melting at 186.degree.-187.degree. C. as white crystals.
EXAMPLE 2
Into a 500 ml four-neck flask equipped with a condenser tube and a thermometer are charged 56 g of benzyl p-hydroxybenzoate, 25 g of triethylamine and 160 ml of toluene. A suspension of 25 g of isophthalic dichloride in 100 ml of toluene is added dropwise with stirring while maintaining the mixture at 0.degree.-3.degree. C. over 3 hours. After addition, the mixture is further allowed to react at 0.degree.-3.degree. C. for 1 hour. Thereafter, the resulting reaction product is collected by filtration to obtain white crystals. The crystalline product is washed with 1500 ml of water twice and then with 1000 ml of methanol twice and subsequently, recrystallized from a mixture solvent of hexane-chloroform (1:1)
REFERENCES:
patent: 1912734 (1933-06-01), Stand et al.
patent: 3966685 (1976-06-01), Allard
patent: 4440945 (1984-04-01), Conciatori et al.
Chemical Abstracts, Tenth Collective Index, Formulas, p. 14802F, entry C.sub.24 H.sub.18 O.sub.8, (1983).
Inoue Takeshi
Magami Masato
Miura Takanori
Saeki Kazumi
Clarke Vera C.
Lone Werren B.
Yoshitomi Pharmaceutical Industries Ltd.
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