JPS59105037A - Novel plasticizer - Google Patents

Abstract

PURPOSE:A general- and special-purpose plasticizer having a plasticizing effect comparable to those of conventional general-purpose plasticizers and excellent volatility, n-hexane extractability, migrating property, flexibility, antifouling property, and antistatic effect as well, comprising a specified phthalate ester compound. CONSTITUTION:A plasticizer for halogen-containing vinyl resins, comprising a phthalate ester compound of the formula (wherein R is a 3-15C linear or branched alkali, A is a 2-4C alkylene, m and n are each 1-7, with the proviso that the number of carbon atoms of A and R is 5-17), e.g., a phthalate diester obtained by using a compound prepared by an addition reaction between 1mol of propanol and 1-7mol of ethylene oxide. It is a general- and special-purpose plasticizer having a plasticizing efficiency comparable to those of general-purpose plasticizers such as DOP and DHP; being excellent in volatility, n-hexane extractability, migrating property, flexibility, and antifouling property, and a special effect like an antistatic effect.

Description

[Detailed Description of the Invention] Typical plasticizers for halogen-containing vinyl resins include:
Phthalic acid esters are well known, and many compounds with different types and performance have been reported and put into practical use.

Plasticizers are broadly classified into general-purpose and special-purpose plasticizers, but phthalate esters are the most popular general-purpose plasticizers and are the most used in terms of quantity. Also, the alkyl group is straight chain,
There are various types of branched and cyclic types, but usually they rarely contain elements other than carbon and hydrogen, and exceptionally there are hydroxyl groups, amino groups,
Only two or three types are known that contain an amide group or the like.

The present invention is a phthalate ester compound represented by the following general formula, and relates to a novel plasticizer having an ether bond in the alkyl chain.

(In the formula, R is a linear or branched alkyl having 3 to 15 carbon atoms, which may be the same or different, A is alkylene having 2 to 4 carbon atoms, and m and n may be the same or different. -7 positive number, provided that the number of carbon atoms in A+R is 5 to 17) The compound of the present invention is a representative general-purpose plasticizer.

Compared to P, DI-IP, etc., the plasticization efficiency is the same, and
It is a general-purpose and special plasticizer that has excellent volatility, n-hexane extractability, migration, flexibility, and stain resistance, as well as unique electrical properties and special antistatic effects. .

The compound of the present invention exhibits the above characteristics because it has an ether bond in the molecule, especially in the alkyl chain.
Those with a relatively small number of H1 carbon atoms in the alkyl chain can be directly applied to fields where conventional general-purpose plasticizers are used, and those with a relatively large total number of carbon atoms can be used in combination with general-purpose plasticizers. , exhibits its performance as a special plasticizer.

Of course, if a mixture of two or more types of diesters with a long total alkyl chain length and a diester with a short total alkyl chain length is used as a plasticizer contained in the compound of the present invention, it is possible to achieve both general-purpose and special performance without using conventional general-purpose plasticizers. Has characteristics that can be demonstrated.

The compound of the present invention has 1 to 7 alkylene oxides having 2 to 4 carbon atoms in a single chain or branched aliphatic alcohol having 3 to 15 carbon atoms.
It can be easily obtained by a general method for producing phthalic acid esters by molar addition and reaction of a terminal hydroxyl compound having a total carbon number of 5 to 17 in alcohol and alkylene oxide with phthalic acid.

Particularly in the case of secondary alcohols, converting them directly into phthalate esters is difficult in terms of reactivity, but if alkylene oxide is added to the secondary alcohols, it becomes primary alcohols, so the esterification reaction is smooth. Proceed to
There are great advantages during manufacturing. If the number of carbon atoms in the alcohol, the number of moles added to the alkylene oxide, and the total number of carbon atoms in the alcohol and alkylene oxide are out of the range specified in this application, the balance of properties of the compound of the present invention will be lost and the initial effect may not be exhibited. On the contrary, this is not desirable because it causes inconvenient problems. When alkylene oxide is added to alcohol, there are many cases in which the molar amount added is not uniform and is distributed in the front, but in the case of the present invention, as long as the general formula can be met, not only a single product but also a single molar amount is observed. , mixtures with different molar amounts of addition are sufficient and are included in the present invention without any change in performance. Further, as understood from the general formula, no difference is observed whether the two alkyls are the same or different.

Examples of the compounds of the present invention include propatool with 1 to 7 moles of ethylene oxide, 1 to 4 moles of propylene oxide, or 1 to 3 moles of butylene oxide, butanol with 1 to 6 moles of ethylene oxide, or 1 to 1 mole of propylene oxide.
4 moles, or 1 to 3 moles of butylene oxide, or 1 to 5 moles of ethylene oxide in hexanol, or 1 to 2 moles of propylene oxide, or 1 to 2 moles of butylene oxide, or 1 to 5 moles of ethylene oxide in heptatool, or 1 to 3 moles of propylene oxide. mole, or butylene oxide 1-2
mole, 1 to 4 moles of ethylene oxide in octatool, or 1 to 3 moles of propylene oxide, or 1 to 2 moles of butylene oxide, 1 to 4 moles of ethylene oxide in nonanol, or 11 to 2 moles of propylene oxide, or 1 to 2 moles of butylene oxide. 1 to 3 moles of ethylene oxide in decanol, or 1 to 2 moles of propylene oxide, or 1 mole of butylene oxide, 1 to 2 moles of ethylene oxide in dodecanol, or 1 mole of propylene oxide, or 1 mole of butylene oxide, 1 to 2 moles of ethylene oxide in tridecanol. mole, or 1 mole of propylene oxide, or 1 mole of butylene oxide, 1 mole of ethylene oxide or 1 mole of propylene oxide to tetradecanol, a compound in which 1 mole of ethylene oxide is added to pentadecanol, etc., and the corresponding secondary alkyl. Examples include 7-talic acid diesters (including mixed esters) of hydroxy compounds added with alkylene oxides corresponding to -l or as a mixture.

Furthermore, during alkylene oxide addition, adducts in which two or more alkylene oxides are added simultaneously or separately to have a total number of carbon atoms defined by the general formula are also included in the present invention.

Example 1 A phthalic acid diester was obtained by a conventional method using an alcohol prepared by adding 1 mole of ethylene oxide to heptatool.

, (Estere). Similarly, 7-tal diester (ester ■) of 2 mole ethylene oxide adduct to heptatool
Furthermore, an ethylene oxide diester of 2-ethylhexanol (Ester ■) and a phthalate diester of an adduct of 2 moles of ethylene oxide (Ester IV) were prepared, respectively.

Example 2 A phthalic acid diester obtained by adducting 2 moles of ethylene oxide with dodecanol was synthesized (Ester V) and blended at a ratio of 1 part (part by weight) of DOP to 1 part of this compound (Ester 2).

The plasticizer performance of each of the esters of Examples 1 and 2 above was measured and shown in Table 1.

The softness temperature in Table 1 was measured by the crush-velve method, and the stain resistance was measured by applying newspaper printing ink to a sheet prepared for surface resistance measurement, then wiping it with a cloth and visually checking the degree of stain. I judged it.

Claims (1)

[Scope of Claims] (In the formula, R is a linear or branched alkyl having 3 to 15 carbon atoms, which may be the same or different, A is alkylene having 2 to 4 carbon atoms, and m and n are the same or different. A plasticizer for halogen-containing vinyl resins comprising a compound represented by a positive number of 1 to 7, which may have carbon atoms of 1 to 7, provided that the number of carbon atoms in A+R is 5 to 17.