JPH03291288A - Tris (2,4-di-t-butylphenyl) phosphite indicating modified physical characteristics - Google Patents

Abstract

PURPOSE: To obtain the subject compound which is excellent in the fluidity and free from dust and which can be effectively used as a stabilizer for a polymer or the like, by coating tris(2,4-di-t-butylphenyl) phosphate with polyolefin wax or the like by cocrystallization in a common solvent.

CONSTITUTION: 2-20 wt.%, based on the weight of tris(2,4-di-t-butylphenyl) phosphite, of polyolefin wax or paraffin hydrocarbon as wax an auxiliary agent and said phosphite derivative are dissolved in an aromatic solvent under the heating at 100-120°C, then the solvent is distilled off while keeping a temperature of a solution at 100-120°C under the reduced pressure, to remove a large amount of the solvent, and the temperature is slowly lowered when the crystallization of the phosphite coated with the auxiliary agent, is observed at 100-120°C, to cool the mixture to 0-10°C, whereby the desired modified phosphite can be formed.

COPYRIGHT: (C)1991,JPO

Description

DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to the use of tris (2°4-di-t-
The present invention relates to the presentation of a novel molding of (butylphenyl) phosphite.

BACKGROUND OF THE INVENTION Tris(2,4-di-t-butylphenyl) phosphite is a rare commercially useful organic phosphite because it is solid at room temperature. It is used as a stabilizer in various polymers, especially polyolefins or polyvinyl chloride.

While there are advantages, this formation has disadvantages, such as the tendency to:

The tendency of a compound to agglomerate (clump formation) in powder form. This creates problems in powder flow; - and a tendency for the formation of fine powders that become airborne. This creates environmental concerns and explosion hazards for those using the compounds.

The present invention includes a solution to this problem.

[Structure of the Invention J] Therefore, the present invention provides for the application of tris(2,4-di-1-butylphenyl)phosphite coated with 2 to 20% by weight of polyolefin wax or paraffinic hydrocarbon wax adjuvant, based on the weight of the tris(2,4-di-1-butylphenyl)phosphite. It consists of tris(2,4-di-t-butylphenyl) phosphite with improved flowability and virtually no dust.

Polyolefin waxes are, for example, waxes consisting essentially of polyethylene waxes, polypropylene waxes or copolymers of ethylene and vinyl acetate.

Polyolefins or hydrocarbon waxes suitable for the present invention have a melting point of 60°C to 120°C.

Preferably, the melting point of these waxes is between 70°C and 110°C.
It is ℃.

In fact, if the melting point of the wax is too high, the coating of particulates proves inadequate. If the melting point of the wax is too low, the resulting coated tris(2,4-di-t-butylphenyl) phosphite has a tendency to move poorly, which is contrary to the desired favorable flowability. becomes.

The amount of polyolefin wax or hydrocarbon wax coating the tris(2,4-di-t-butylphenyl) phosphite is preferably from 5% to 5% by weight of the weight of the phosphite.

The procedure for coating tris(2,4-di-t-butylphenyl) phosphite with a polyolefin wax or hydrocarbon wax adjuvant as previously described involves co-coating the phosphite and wax in a common suitable solvent. It consists of carrying out crystallization.

The solvent for the recrystallization of the phosphite must be able to completely dissolve the wax when hot, but not at room temperature or in cold solvents.

In particular, aromatic hydrocarbons fulfill this function.

Examples of these solvents that may be mentioned are benzene, toluene and xylene.

Generally, the use of xylene is preferred for safety reasons.

The coating comprises tris(2,4-di-t-butylphenyl) phosphite and a selected polyolefin in an amount of 2% to 20%, preferably 5% to 15% by weight, based on the weight of the phosphite. and hydrocarbon wax,
This can be done under hot conditions, for example by dissolving in an aromatic solvent of choice such as xylene at about 100°C to 120°C.

After dissolution, the solvent is distilled off under reduced pressure and the temperature of the solution is maintained at about 100<0>C to 120<0>C.

When considerable solvent is removed, crystallization of the coated phosphite is observed at temperatures between 100°C and 120°C.

The temperature is slowly lowered to about 80-90°C, a liquid that is a non-solvent for the phosphite and wax is added, if desired, and the mixture is cooled to a temperature of about 0°-10°C.

The coated phosphite, which has been crystallized and separated by filtration, can be washed using the previously used non-solvent liquid.

The applied phosphite is then dried at a temperature below the melting point of the wax used.

The major advantage of this coating method is that it can be applied to Tris (2,4
-t-butylphenyl) phosphite can be easily incorporated into the synthesis process.

Therefore, in most cases when the phosphite is prepared in an aromatic hydrocarbon, it is sufficient to add the wax at the end of the synthesis while the phosphite is in solution form.

The co-crystallization, filtration, washing and drying operations described above are
Equivalent to the operations necessary to isolate and purify the phosphite from the prepared reaction mixture.

The invention is illustrated by the following example.

[Explanation of Examples] Examples 1-4 Each test is performed in the following manner.

220 g of tris(2,4-di-tert-butylphenyl) phosphite are dissolved in 147 g of xylene at 100°C.

Then either 1 g or 5.5 g of wax was dissolved with stirring (these amounts are expressed as 5% and 2.5% by weight, respectively, based on the weight of the phosphite).
.

The waxes used were:

- Polyethylene wax: Hoechst
PE520 (trade name) commercially available from Allied Chemical Company, - Ethylene/vinyl acetate (EVA) copolymer nialide chemical (AC400 (trade name) commercially available from Allied Chemical J Co., Ltd., - Hydrocarbon wax: Henke 1) L commercially available from
oxiol G22 (product name).

It is.

88 g of xylene in the mixture is then distilled under reduced pressure at a temperature above 120°C.

The mixture is left to cool slowly.

Crystallization of the coated phosphite is observed between -100°C and 105°C.

147 g of methanol is added over a period of 1 hour at -60-65°C.

The mixture is then cooled to 10.degree. C., the phosphites are filtered off and washed twice with 100 g of methanol at 10.degree. The coated phosphite is dried at 80°C.

The indications regarding the wax used (nature, melting point, weight % based on phosphite) and the appearance of the coated phosphite obtained are given in the table below. The table also includes a control test of uncoated phosphite.

Description of the flowability test used: This test gives a relative value that correlates well with the behavior of the powder when it is introduced into an apparatus with a screw auxiliary device.

The device consists of a funnel with an inner diameter of 150+ am at the top, a conical part with a height of 110 mm, a total length of 105 mm (the bottom of the 6 axes of the funnel has a length of 11 mm), and an inner diameter of 1000 m; It consists of a tripod that is fixed, a vibrator (50 Hz) that is fixed on a horizontal bar that is fixed on a funnel on a vertical bar of the tripod.

Procedure: The powder to be tested is filled into a 100 g funnel. The chronometer and piebreak are activated at the same time.
The time required for all the powder to flow out of the funnel is measured with a chronometer.

Dust Test Instructions Fill a glass flask to mid-height with the phosphite to be tested.

Stir vigorously up and down, repeating 3 times.

Measure the time required for the fine powder to settle using a chronometer.

It is desirable that the compound has a settling time of fine powder of 10 seconds or less.

Tris(2,4-di-tert-butylphenyl) coated with a wax adjuvant as defined within the scope of the present invention
The phosphite exhibits no heat or very little fines, is not sticky, and the crystals have no tendency to agglomerate (set) in contrast to the control sample.

All of the coated phosphites according to Examples 1 to 4 required less than 5 minutes in the dust test whereas the control sample required more than 1 minute.

Example 5 After removing the unreacted catalyst and reactants, Tris (
The preparation of 2,4-di-t-butylphenyl) phosphite results in a solution of about 60% w/w phosphite in xylene.

367 g of this solution containing theoretically 220 g of tris(2,4-di-tert-butylphenyl) phosphite is taken; this theoretical amount is based on a 100% synthesis yield; it can therefore be isolated. More than the actual amount.

22.9 g of polystyrene wax PE520 (trade name) are added, corresponding to about 10.4% theoretically based on tris(2,4-di-tert-butylphenyl)phosphite.

The procedure is the same as in Examples 1-4.

The same test is repeated as a comparative test without the addition of wax.

The following result is obtained: Example 5 Less than 5 seconds in the dust test without a single dust)
, - No stickiness, no cohesiveness, - Flow time in the test described above: 5 seconds Comparison test with dust (time longer than 1 minute in dust test), - Tendency to agglomerate,

Claims (1)

[Claims] 1) Coated with 2 to 20% by weight of polyolefin wax or paraffinic hydrocarbon wax adjuvant based on the weight of tris(2,4-di-t-butylphenyl)phosphite. Tris(2,4-di-t-butylphenyl)phosphite characterized by improved flowability and virtually dust-free. 2) Tris(2,4-di-t-butylphenyl) phosphite according to claim 1, wherein the polyolefin wax is selected from polyethylene wax, polypropylene wax, or copolymer wax of ethylene and vinyl acetate. 3) Polyolefin or hydrocarbon wax at 60℃
Tris(2,4-di-t-butylphenyl)phosphite according to any one of claims 1 to 2 having a melting point of ~120<0>C. 4) Polyolefin or hydrocarbon wax at 70℃
Tris(2,4-di-t-butylphenyl)phosphite according to any one of claims 1 to 3 having a melting point of ~110<0>C. 5) The amount of polyolefin wax or hydrocarbon wax to coat the tris(2,4-di-t-butylphenyl) phosphite ranges from 5% to 1% by weight of the phosphite.
5% by weight of tris(2,4-di-t-butylphenyl)phosphite according to any one of claims 1 to 4. 6) Co-crystallization of phosphite and wax in a common suitable solvent for coating tris(2,4-di-t-butylphenyl) phosphite with polyolefin wax or hydrocarbon wax adjuvant. A method for coating tris(2,4-di-t-butylphenyl)phosphite, which is characterized in that it is carried out. 7) The method according to claim 6, wherein the solvent used is an aromatic hydrocarbon. 8) A method according to any of claims 6 to 7, wherein the solvent used is selected from benzene, toluene and xylene. 9) From 2% by weight based on the weight of tris(2,4-di-t-butylphenyl)phosphite and phosphite
The polyolefin and hydrocarbon wax in an amount of 20% by weight are dissolved in an aromatic solvent under heating conditions of about 100°C to 120°C, and after dissolution the temperature of the solution is reduced to about 100°C under reduced pressure.
The solvent was distilled while maintaining at ~120°C, and this temperature was slowly lowered when significant solvent was removed and crystallization of the coated phosphite was observed at temperatures between 100°C and 120°C. A method for coating tris(2,4-di-t-butylphenyl)phosphite, characterized in that the coating is carried out by cooling the mixture to a temperature of about 0°C to 10°C.