JPS61100587A - Organosilicon compound - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [R<1> is (CH3)3C; R<2> is CH2; R<3> is CH3; R<4> is H, 1-8C alkyl, CH3CH2OCH2CH2; m is 0-6; n is 1-3]. EXAMPLE:1-(Trimethoxysilyl)-3-[(4-hydroxy-3,5-di-tert.-butyl)phenyl]- propane. USE:A surface treatment agent for inorganic fillers such as silica or alumina, a scaling preventive for polymerizers in acrylic or methacrylic polymers, immobilized antioxidant or polymerization inhibitor. PREPARATION:A silylating agent and a compound of formula II or III is used to form a compound of formula IV or V and a compound of formula VII is synthesized from the product and a compound of formula VI. Then, a compound of the formula, R<4>OH is used to effect detrimethylsilylalkoxylation of the product.

Description

DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to an organosilicon compound having a functional group having anti-oxidation and anti-polymerization functions.

``Prior Art'' Various silane coupling agents having a hydrolyzable alkoxy group and various functional groups in one molecule are known, and are widely used for glass fibers, castings, sealants, surface treatment of inorganic materials, etc. There is.

Furthermore, silanes having both an alkyl group or an aryl group and an alkoxy group are also known.

However, as in the compounds of the present invention, a functional group having a function of preventing polymerization or oxidation can be used directly or via an alkylene group.
Alkoxysilanes bonded to silicon atoms are not known.

Conventionally, it has been used as an antioxidant or polymerization inhibitor (here M
e indicates CHs. same as below. ) etc. are known, but
These have high volatility and easily volatilize, which poses a problem in terms of long-term life when used as additives for plastics.

"Problems to be Solved by the Invention" The purpose of the present invention is to develop a compound that has the dual functions of BET and BHA, is not volatile, has a long-lasting effect, and has the property of binding to a certain substance. It is to provide.

"Means for Solving the Problems" That is, the present invention provides a general formula R2 is CH, R3 is CH, R4 is an alkyl group having 1 to 8 carbon atoms, OH, 0CHtCH, or 0M3CH, OC
H, CH, , m are integers of θ to 6, and n is an integer of 1 to 3. ) or a hydrolyzate thereof.

Compounds of the invention may be manufactured by the methods described below.

using a silylating agent <cHs), St -o(yRz
A method of alkoxylating the detrimethylsilylalkoxy I (an integer from 8-n to 4) using --ctl R4-OH and kI -8t-C1n in the same manner as in A by a hydrosilylation reaction using chloroplatinic acid or the like as a catalyst; Synthesize 321-n C2-R''3-81-(OR')n by a hydrosilylation reaction similar to method (2),
Due to the reaction between this and I
After synthesizing +-a -I 3s-n-8i-(OR')n, (
CH, ), methods for removing the St group, etc., but are not limited to these methods.

The compounds of the present invention produced by the above method include those exemplified below.
(Pr is CM, CMtCH.

Indicates e or CH(CHs)z. ), A-8t-(OP
r)t, phylum A-8i-0Pr % A-8i-(OBu)s (
Bu is CHt CHxCHt CHs, CHt CH(
CHs )2, or C(CH,)ae A-8i-(OCH,CH,0CHa)s, A-8i
-(OCR2CH2OCR,),,A-CHt-8t-
(OMe)s, A-CHtCH2-3t -(OMe
)s, A-CH, CH, CH, -SL --(OMe)
s, A-(CHt)+-8t-(OMe)s, A-
(CHt)s-8t-(OMe)s, A-(CHt
)s-8i-(OMe)s.

e A-(CHt)s-Si-(OMe)2, A-
(CHt)s-8x-(OEt)s,e A-(CHz)s-8i-(OEt)2,A-(CHI
)s-8l-(OPr)s se A-(CHt)s-8t-(OPr)z, A-(CHt
)s-8t-(OBu)s, e A-(CHt)s-8i-(OBu)z, A-(Cut
)a-8t-(OCHte CHtOCHs)s, A-(CHt)s-8i-COC
HtCH*0CHs)t, A-(CH,)s-8t-(
OCHtCH,0CHtCHs)s, e A -(CH2)3- S t -(0CHtCHt
0CHt CHa )t, A-(CHt )s -Sf
= (OCH, CHt CHtCH(CHtCHs
)! )s, e A-(CHt)s-8t-(OCH2CH,CH,CH
(CH,CHs)t), etc. However, it goes without saying that the compounds are not limited to the compounds listed above.

Furthermore, since the compounds of the present invention are used as coupling agents, they are usually used not only in their original form, but also in a hydrolyzed form if necessary. In this case, the degree of hydrolysis can range from 1 when a part of the alkoxy group (OR') is hydrolyzed to OH to 1 when it is completely hydrolyzed and further partially condensed. That is, the present invention also includes compounds in the form of such hydrolysates.

"Actions and Effects of the Invention" The compound according to the present invention has low volatility, and the alkoxy group portion is easily hydrolyzed to produce various inorganic substances such as silica, alumina, clay, Merck, glass, calcium carbonate, and metals. Therefore, when an inorganic material treated with the compound of the present invention is used as a filler in plastics, favorable results can be obtained in terms of long life, weather resistance, and heat resistance. Moreover, the compound of the present invention is vinyl chloride,
Polymerizable materials such as (meth)acrylic compounds and styrene
It is also useful as a scale inhibitor for polymerization vessels. Thus, the compounds of the present invention are useful as immobilized antioxidants or immobilized polymerization inhibitors, and are novel in that they have hitherto unknown structures and functions.

"Example" Next, the present invention will be specifically explained with reference to Examples.

Example 1 20 Da of 4-allyl-2,6-di-t-butylphenol was placed in a three-necked flask equipped with a stirrer, and H, P
tC4・6H,011/ isopropyl alcohol 20
Three drops of a catalyst solution prepared by dissolving yxlK were added. 18.6 f of trichlorosilane was added dropwise while maintaining the reaction temperature at 60°C. After aging at 60° C. for 1 hour, low-boiling components including unreacted substances were distilled off under reduced pressure. After this, add 10f of methanol and
The mixture was reacted at 0°C for 3 hours, and the mixture was cut at a low boiling point under reduced pressure to obtain a pale yellow liquid 21F'&.

Gas chromatography analysis of this material revealed that it was 90% pure and contained 3% unreacted raw material and 6% impurities derived from the raw material, but IHNMR (CC1,
: TMS') chart (Fig. 1), IR chart (
1-(trimethoxysilyl)-3-((4
-Hydroxy-3,5-ditertiarybutyl)phenyl]propane was identified as the main component.

(IHNMR) δ0.37-0.9(m): =st-ca2-,
2Hδ1.4(s): -C-(CHs)s
, 18 has δ1.6 to 1.93 (m): -C-CH,
-C-, 2Hδ2.3-2.63 (m): GCH,
-, 2Hδ8.47(a): -8i-(OCH
s)a, 9H*δ1.2(s) is @-C-C-CH,
This is the peak of impurity 1-((4-hydroxy-3,5-ditertiary-butyl)7) in the raw material.
1'enyl]propene-1.

(IR) 3650 equipment-12C region H 1100ff, Si-0-Example 2 In addition to Example 1, trimethoxysilane was used instead of trichlorosilane.12. : When similar reactions and operations were carried out using IMI, 18 g of product was obtained in one step of reaction. Since the IR chart and NMR chart of this product were exactly the same as in Example 1, 1-()rimethoxysilyl)-3
It was identified as -[(4-hydroxy-3,5-ditertiary-butyl)phenyl]propane.

Example 3 4-allyl-2,6-di-t-butylphenol 100
LI was placed in a three-necked flask equipped with a stirrer, and 5 drops of the catalyst solution from Example 1 were added thereto. 58 g of methyldichlorosilane was added dropwise while maintaining the reaction temperature at 60°C. 60'
After aging at C for 1 hour, low-boiling components including unreacted substances were removed under reduced pressure. After that, 19 g of methanol was added and the reaction was carried out at 30°C for 4 hours, and the low-boiling components were cut off under reduced pressure.
Sheet t-7'' thyl)phenyl]furopane 96F was obtained.

The resulting liquid was a pale yellow liquid.

Next, the following performance evaluation was performed on the compound obtained in Example 1.

Example 4 The compound obtained in Example 1 or its hydrolyzate was blended with polypropylene together with an inorganic filler, and pelletized at 200°C using a screw extruder with a diameter of 4Off. A portion of it was taken and put into an injection molding machine (2so°C) to make a test piece plate. As a comparative example, the same method as in the example was carried out except that the compound of the present invention was not blended. Next, this pellet and the test piece were placed in a gear open system, and the degree of discoloration and deterioration (sheet YI) of the test piece was examined. Melt 70-index was measured on the pellets. The results are shown in Table 1 below.

Table 1 17″.

Example 5 A solution prepared by thoroughly mixing compound 501 of Example 1 with 270 f of isopropyl alcohol, 16 f of water, and 14 g of N/2HC1 aqueous solution was applied to a part of the baffle (stainless steel F2) of a vinyl chloride suspension polymerization vessel, and After baking for 10 minutes at C, a normal polymerization reaction was carried out and dried again, and the degree of scale adhesion was examined.

As a result, the area where the compound of Example 1 was not applied was 2 to 3.
Although scale adhesion was clearly observed during the HIO process, no scale adhesion was observed even after the partial HIO process where the compound obtained in Example 1 was applied.

[Brief explanation of drawings]

Figure 1 shows the compound (1-
(trimethoxysilyl)-3-((4-hydroxy-3
, 5-ditertiarybutyl)phenyl]propane), and Figure 2 is an IR chart of the compound. Yasa woman 1

Claims (1)

[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (However, R^1 is (CH_3)_3C, R^2 is CH_
2, R^3 is CH_3, R^4 is hydrogen, carbon number is 1
-8 alkyl group, CH_3OCH_2CH_2 or C
H_3CH_2OCH_2CH_2 may be the same or different types within the same molecule, m is an integer of 0 to 6, and n is an integer of 1 to 3. ) Organosilicon compound represented by