JPH02138133A - Stabilizing agent - Google Patents

Abstract

PURPOSE:To provide a stabilizer containing a specific organic compound as an active component, having remarkably improved volatility, non-staining property and heat-resistance and effective in preventing an organic compound such as rubbery polymer, synthetic resin, fat and oil lubricant or grease from the deterioration and lowering of physical properties with heat, light, etc. CONSTITUTION:The compound of formula (n is 0-6) is compounded as a stabilizer to an organic compound. The compound of formula is e.g., 4,4- dithiodiphenol, bis(4-hydroxyphenylthio)methane and 1,1-bis(4-hydroxyphenylthio) ethane. The amount of the compound is 0.001-10wt.%, preferably 0.003-5wt.% based on the organic compound. It may be used in combination with conventional other stabilizers such as phenolic or amine-type stabilizer. The addition of the subject stabilizer is carried out, e.g., in the case of adding to a rubbery polymer, by dry-blending with a roll or Banbury mixer.

Description

DETAILED DESCRIPTION OF THE INVENTION OBJECTS OF THE INVENTION The present invention relates to novel stabilizers for organic compounds. More specifically, it relates to a stabilizer for organic compounds represented by the following general formula (where n is an integer of O to 6).

[Prior Art] Conventionally, it has been known that rubber polymer 2 synthetic resins, oils and fats, lubricating oils, greases, etc. are degraded by the action of heat, light, oxygen, ozone, etc., and their physical properties are significantly reduced. In order to prevent deterioration of these physical properties, various known stabilizers are used, and phenol-based, amine-based, sulfide-based, and phosphite-based stabilizers are generally used.

Among these, amine stabilizers are highly effective, but they stain, and cannot be used in products that require transparency and bright colors. Phenol, sulfide, and bosphite stabilizers are unavoidably less effective agent is used.

However, these stabilizers are not necessarily satisfactory in terms of solubility, compatibility, monodispersity, volatility, blooming property, etc. with respect to organic compounds. In particular, hindered phenol, which is a phenolic stabilizer, is widely used because it is non-staining and has a relatively good stabilizing effect. increasing,
As a result, due to problems with heat deterioration resistance and high volatility, the lifespan of the products themselves has come to vary. As a result, we have adopted a method of adding more stabilizers than necessary, but in liquid products, solubility, volatility,
Volatile in solid products.

There are limitations due to dispersibility, deterioration of physical properties, bloom, etc., and the price of the product has to rise.

In view of the recent trend toward high properties, especially long life, there is a strong desire to develop stabilizers with excellent performance.

[Means for solving the problem] As a result of intensive research in view of these points, the present inventors have found that the compound represented by the general formula below retains the non-contaminating property that is characteristic of phenolic compounds with respect to organic compounds. However, they have discovered that it is an industrially extremely useful compound that has virtually no volatility and a heat resistance comparable to that of amine stabilizers, leading to the completion of the present invention.

Specific examples of the phenolic compound referred to in the present invention include those shown below. 4゜4-dithiodiphenol, bis(4-hydroxyphenylthio)methane, 1.1-bis(4-hydroxyphenylthio)ethane, 1,2-bis(4hydroxyphenylthio)ethane, 1, 3-bis(4-hydroxyphenylthio)propane, 1°4-bis(4-hydroxyphenylthio)butane.

1,5-bis(4-hydroxyphenylthio)pentane, 1,6-bis(4-hydroxyphenylthio)hexane.

There are no particular restrictions on the amount of these compounds used, but 0.001 to 10% by weight based on the organic compound, preferably O, O
O is in an amount of 3 to 5% by weight, and if it is more than this, there is no problem in terms of effectiveness, but in the case of rubber-like polymers, it is not preferable because it causes effects other than the stabilizer effect, such as promoting scorch. mineral oil, vegetable oil,
Animal oils and water-insoluble liquid polymers can be used in a wide range of ways, depending on the type of fuel oil, lubricating oil, usage conditions, etc.
It is in the range of 0.001 to 10% by weight.

The stabilizer of the present invention may be used in combination with other conventionally known stabilizers such as other phenolic, amine, and sulfide stabilizers.

There are no particular restrictions on what the stabilizer of the present invention can be applied to, and various things can be mentioned. For example, natural comb (NR)
and imprene rubber (IR), butadiene rubber (BR)
, styrene-butadiene rubber (SBR), ethylene-propylene rubber (EPDM or EPM), acrylonitrile-butadiene rubber (NBR), chloroprene rubber (C
Synthetic rubbers such as R) or their blend rubbers, as well as diene compounds, modified polyolefins, polyvinyl chloride,
Synthetic resins such as acrylonitrile resin, maleic ester resin, acrylonitrile-butadiene-styrene resin (ABS), oils and fats, and lubricating oils.

It can be used for mineral oils such as grease, vegetable oils, animal oils, and organic compounds such as water-insoluble liquid polymers.

Furthermore, there are no particular restrictions on the method of adding the stabilizer of the present invention. For example, when used in a rubber-like polymer, a method of triblending with a roll or Banbury, a method of preparing a dispersion of the stabilizer and mixing it in liquid form into the rubber latex, etc. can be adopted.

[Examples] Hereinafter, the present invention will be described in detail with reference to Examples, but the scope of the present invention is not limited by the Examples.

Example 1 (Volatility test) 5 g of the stabilizer sample to be tested was accurately weighed into a glass weighing bottle with a diameter of 35 mm and a depth of 38 mm, and left in a constant temperature bath at 150°C for a predetermined period of time. The weight was accurately weighed to determine the percent weight loss after heat treatment of the sample. This percent weight loss was taken as a measure of volatility. The results are shown in Table 1.

Example 2 A compounded rubber was obtained using the compounding recipe shown in Table 2. The kneading was carried out using an 8-inch test roll at a roll surface temperature of 50° C. by a normal kneading method. Press vulcanization conditions for each compound are rheometer test tqo (minutes 2 seconds)
It was adopted.

The vulcanized sample obtained under the above conditions was JISK 630
1, after a heat resistance deterioration test for 120 hours in a gear oven at 100°C, the rate of change in physical properties was measured after being left at room temperature for one day. The results are shown in Table 3.

Example 3 A compounded rubber was obtained using the compounding recipe shown in Table 4. The kneading conditions and kneading method were the same as in Example 2.

The press vulcanization conditions for each compound are t of the rheometer test results.
,. (minute 2 seconds) was adopted.

The vulcanized sample obtained under the above conditions was
1, the rate of change in physical properties was measured after a 96-hour and 144-hour heat deterioration test in a gear oven and after being left at room temperature for one day. The results are shown in Table 5.

U Effects of the Invention] As is clear from the above examples, the phenolic compound of the present invention has remarkable improvement in volatility, non-staining property, and heat resistance, and is suitable for use in rubber-type composite 1 synthetic resins, oils and fats, lubricating oils, It is clear that it has high industrial utility value as a stabilizer for organic compounds such as grease.

Claims (2)

[Claims] (1) General formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, n is an integer from 0 to 6) Stabilizer for organic compounds represented by (2) The stabilizer according to claim 1, wherein the organic compound is one or more selected from rubber-like polymers, synthetic resins, mineral oils, vegetable oils, and water-insoluble liquid polymers.