JPS63168443A - Adjuvant composition for resin - Google Patents

Abstract

PURPOSE:To impart excellent antistatic property, stain resistance, oil resistance, etc., as well as plasticity, low-temperature resistance, etc., to a resin, by adding a specified ester compound having a carbon-nitrogen bond in an alkyl chain as a modifying adjuvant to the resin. CONSTITUTION:A compound of the formula (wherein X is a 2-22C aliphatic, alicyclic or aromatic mono- or poly-carboxylic acid residue which may be substituted, A<1> and A<2> are each a 2-4C alkylene, R<1>, R<2> and R<3> are each H or a 1-18C alkyl or aryl which may be substituted, m is 0-3 and n is 1-6) is prepared. Examples of the ester compounds of the formula include those formed by esterifying an aminoalcohol such as 2-aminoethanol or 2-(N,N- diethylamino)ethanol with an acid component such as phthalic anhydride or benzoic acid.

Description

[Detailed description of the invention] [Industrial application field] The present invention relates to an auxiliary material composition for resin.

[Prior art and problems to be solved by the invention] Conventionally, ester compounds used as auxiliary materials for resins include:
Compounds such as phthalic acid esters, aliphatic basic acids or dibasic acid esters, polyvalent aromatic carboxylic acids, and polyesters are well known.

Each of these ester compounds has its own characteristics.
For example, when applied as a plasticizer, it is extremely difficult to satisfy all the performance requirements with only one type. Specifically, di(2-ethylhexyl) phthalate (hereinafter referred to as rDOPJ) has poor cold resistance;
-Ethylhexyl) adipate has good cold resistance, but lacks compatibility and volatility resistance and tends to bleed. For this reason, at present, several types of plasticizers are usually used in combination depending on the purpose.

The present inventors evaluated the characteristics of various ester compounds, and while conducting intensive research to develop subsidiary material compositions with new functions, discovered that ester compounds with specific structures have unique performance. The present invention was completed based on this knowledge.

That is, an object of the present invention is to provide a new auxiliary material composition for resin.

[Means for Solving the Problems] The auxiliary material composition for resin according to the present invention is an ester compound having a bond with a different atom, that is, a carbon-nitrogen bond in the alkyl chain as shown by the following general formula. It is characterized by containing.

(In the formula, X has 2 to 22 carbon atoms, which may have a substituent.
aliphatic, alicyclic or aromatic mono- or polycarboxylic acid residues, A1 and A2 are alkylene groups having 2 to 4 carbon atoms which may be the same, R1, R2 and R3 are hydrogen or Represents an alkyl group or aryl group having 1 to 18 carbon atoms which may have a substituent. m is an integer from O to 3,
n is an integer from 1 to 6. ) The compound according to the present invention is a combination of an amino alcohol and an aliphatic, alicyclic or aromatic compound represented by the following general formula.
It can be easily obtained by a general ester production method by reaction with a mono- or polyhydric carboxylic acid.

(However, R1, R2, and R3 are hydrogen or an argyl group or aryl group having 1 to 18 carbon atoms that may have a substituent, and A1 and A2 are argyl groups or aryl groups having 2 to 4 carbon atoms that may be the same.) (Represents an alkylene group. m is an integer of O to 3.) Specifically, 2-amine ethanol, 2-aminopropatol, 2-aminobutanol, 2-amino-2-methylpropatol, 2-amino -2-methylpropane-1
, 3-diol, 2-amino-2-ethylpropane-1
, 3-diol, 2-(N-methylamine)ethanol, 2-(N-laurylamino)ethanol, N-n-
Stearyl-2-aminoni[tanol, 2-hydroxyethylamine methanol, jetanolamine, 2-(
N,N-dimethylamino)ethanol, 2-(N,N-
dibutylamino) ethanol, triethanolamine,
N-methyljetanolamine, (2-aminoethyl)
Ethanolamine, 1,2-bis(hydroxyethylamino)ethane, N.

Hydroxy compounds such as N--bis(hydroxyethyl)diethylenetriamine are exemplified.

If the number of carbon atoms in the alcohol deviates from the range specified above, the balance of properties will be lost and the desired effect will not be exhibited.

For example, if the number of carbon atoms exceeds this range, the gelatinability and compatibility tend to be poor.

In addition, acid components include aliphatic carboxylic acids such as acetic acid, acetic acid, capric acid, caproic acid, citric acid, sebacic acid, citraconic acid, adipic acid, butanetetracarboxylic acid, benzoic acid, phthalic acid, terephthalic acid, and tricarboxylic acid. Aromatic carboxylic acids such as mellitic acid and pyromellitic acid, alicyclic carboxylic acids such as tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, and methylhexahydrophthalic acid, and anhydrides of these carboxylic acids. Illustrated.

These alcohol components and acid components may be used alone or as a mixture of two or more.

The ester compounds obtained in this way have a structure in which a nitrogen atom is added, unlike conventional ester compounds, which are composed of carbon atoms, hydrogen atoms, and oxygen atoms, so the polarity of the ester group changes, and the characteristics that conventional ester compounds have For example, in addition to plasticity, cold resistance, volatility, migration properties, etc., it exhibits excellent antistatic properties, antifouling properties, drip proof properties, oil resistance, etc.

The ester compound according to the present invention can achieve a desired effect by blending up to 200 parts by weight with respect to 100 parts by weight of the resin, and can be used alone or in combination with other ester compounds.

Other ester compounds used in combination include those having 1 to 1 carbon atoms.
Aliphatic base acid ester, aliphatic polybasic acid ester, aromatic base acid ester, having 8 alkyl groups and/or alkenyl groups
Examples include basic acid esters, aromatic polybasic acid esters, and phosphoric acid esters. Specifically, dioquidyl phthalate,
Examples include diheptyl phthalate, dioctyl adipate, and tricresyl phosphate.

Examples of resins to which the compound of the present invention is applied include polyvinyl chloride, vinylidene chloride, vinyl chloride or copolymers of vinylidene chloride and vinyl acetate and other vinyl compounds, ethylene-vinyl acetate copolymers, polyamides, polyethylene , polypropylene, polymethacrylate polyvinyl butyral, urea, polyester, etc., and furthermore, natural rubber, acrylonitrile-butadiene copolymer, styrene-butadiene copolymer, polybutadiene, epichlorohydrin rubber, butyl rubber, silicone rubber, fluororubber, and It can also be applied to elastomers such as rene-propylene copolymers, polyacrylic esters, polychloroprene, polyisoprene, urethanes, and sulfur-crosslinked and peroxide-crosslinked products thereof.

The above resin composition includes stabilizers, lubricants, ultraviolet absorbers, antifogging agents, antistatic agents, fillers, colorants, flame retardants, blowing agents,
Various additives such as antibacterial/antifungal agents, crosslinking agents, and reinforcing agents can be appropriately blended.

Such resin compositions are useful in various fields such as leather, films, flooring materials, wallpapers, footwear, hoses, electric wires, paste sol, packaging materials, roofing materials, and tents.

[Example] Next, the present invention will be explained in detail with reference to examples.

Example 1 1i equipped with a stirrer, thermometer, water separator, and cooling pipe! 148 g (1.0 mol) of phthalic anhydride and 26 g of 2-(N,N-diethylamine)ethanol were placed in a four-piece flask.
7 g (3.0 mol) and 4.29 g of para-toluenesulfonic acid as an esterification catalyst were charged, the system was replaced with nitrogen, and the esterification reaction was carried out for 4 hours while distilling off the condensed water at a reaction temperature of 150'C. I did it.

After distilling off a predetermined amount of condensed water, neutralizing with alkali, washing with water, and distilling, bis phthalate [2-(N,N-
diethylamino)ethylco (hereinafter referred to as "ester ■") is 2909N8 (yield 94%).

Next, a resin composition was prepared by blending ester (1) according to the following composition, and its properties were evaluated. The results obtained are shown in the table.

Blend composition Polyvinyl chloride Heavy product (Geo
n 101 EP: Nippon Zeon (41> 100 Ester I 50 Stabilizer Calcium Stearate 0.3 Zinc Stearate
0.2 Kneading with melon and soybean rolls under supervision Press molding at 163-165°C for 4 minutes 165°C and 100°C for minutes (1) Mechanical properties: JIS K-7113 (2) Electrical properties: JIS K- 6723 (3) Softness temperature test: JIS K-6745 (4) Migration resistance: Measurement of weight loss under specific conditions Example 2 Using 2-(N,N-dipropylamino)ethanol and phthalic anhydride Ester (1) was synthesized according to Example 1, and this compound was further blended to prepare a resin composition, and its properties were evaluated. The results obtained are shown in the table.

Example 3 2- J Stell ■ was synthesized according to Example 1 using 2-(N,N-dibutylamino)ethanol and phthalic anhydride, and this was further blended to prepare a resin composition, Its characteristics were evaluated. The results obtained are shown in the table.

Example 4 Ester IV was synthesized according to Q in Example 1 using 2-(N,N-dibutylamino)ethanol and benzoic acid, and this was further blended to prepare a resin composition. Characteristics were evaluated. The results obtained are not shown in the table.

Example 5 Ester V according to Example 1 using 2-(N,N-dibutylamino)ethanol and pyromellitic anhydride
This product was further blended to prepare a resin composition, and its properties were evaluated. The results obtained are shown in the table.

Comparative Example 1 Table 1 shows the physical properties of a resin composition obtained by blending DOP according to Example 1.

[Effects of the Invention] In addition to the characteristics of conventional products such as plasticity, cold resistance, and migration resistance, the auxiliary material composition for resins comprising the ester compound according to the present invention has excellent antistatic properties and antifouling properties. It shows properties such as water resistance, drip resistance, and oil resistance.

Claims (1)

[Scope of Claims] An auxiliary material composition for a resin, characterized by containing a compound represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X has 2 to 22 carbon atoms, which may have a substituent.
aliphatic, alicyclic or aromatic mono- or polyhydric carboxylic acid residue, A^1 and A^2 are alkylene groups having 2 to 4 carbon atoms, which may be the same, R^1, R^2, R
^3 is hydrogen or 1 to 1 carbon atoms which may have a substituent
8 represents an alkyl group or an aryl group. m is 0~
An integer of 3, n is an integer of 1 to 6. )