JPS6284090A - Norbornyltrialkoxysilane - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R is 1-8C monofunctional hydrocarbon). EXAMPLE:Norbornyltriethoxysilane expressed by formula II. USE:An adhesive property improver for polysulfide based sealing materials, having improved compatibility with organic rubbers, e.g EPDM, and utilizable for various applications. PREPARATION:Norbornene in an equimolar amount or more with the number of mol of Si-H bonds in a trialkoxysilane having H linked to Si is subjected to addition reaction with the trialkoxysilane in the presence of a platinum compound, e.g. chloroplatinic acid, as a catalyst, preferably at 20-200 deg.C for 1-60hr.

Description

DETAILED DESCRIPTION OF THE INVENTION [Technical Field of the Invention] The present invention relates to a novel alkoxysilane compound containing a norbornyl group.

[Technical background of the invention and its problems] A norbornyl group is bonded to a silicon atom, and 3
As a silane compound with silicon functional groups bonded to it,
Although the existence of norbornyltrichlorosilane is known, norbornyltrialkoxysilane is not known.

On the other hand, alkoxysilanes such as 2-norbornen-5-yltrimethoxysilane that have similar groups containing double bonds or bonded to silicon atoms are known, and sulfur powder and sulfur powder are bonded to the double bonds of such alkoxysilanes. It is known to react gas phase ammonia to obtain mercaptonorbornyltrimethoxysilane. (U.S. Patent 4.10
0.172). Also known is chloromethylnorbornyltriethoxysilane.

These alkoxysilanes in which a double bond or an anionic group is present have uses that utilize their reactivity, such as the use of the aforementioned mercaptonorbornyl group-containing silane as an adhesion improver for polysulfide sealants. (Canadian Patent No. 1.071.038), but silicon-functional silanes with simply unsubstituted norbornyl groups are desired for applications that do not require or would be advantageous to have such carbon functional groups. . Norbornyltrichlorosilane meets these conditions, but when the existing silicon-chlorine bond undergoes gradual hydrolysis with moisture in the atmosphere, it generates hydrogen chloride, which may affect the surrounding area. , may be subject to usage restrictions.

Further, regarding norbornylmethyljethoxysilane and its oxidative cleavage reaction with hydrogen peroxide, see Organometa II 1cs, 1983.
, No. 2, pp. 1694-1696, but there is no disclosure regarding its physical properties. Furthermore, since this compound has only two silicon functionalities, it cannot be used as a trifunctional compound like the compounds of the present invention.

[Object of the Invention] The present inventors have succeeded in synthesizing norbornyltrialkoxysilane, which is a new compound, and have completed the present invention.

[Structure of the Invention] That is, the norbornyltrialkoxysilane of the present invention is characterized by being represented by the general formula (wherein R represents a monovalent hydrocarbon group having 1 to 8 carbon atoms).

In the above general formula, R is a monovalent hydrocarbon group having 1 to 8 carbon atoms, exemplified by alkyl groups such as methyl group, ethyl group, propyl group, butyl group, and having appropriate reactivity; A methyl group or an ethyl group is preferred because it is easy to synthesize and handle.

Representative examples of such norbornyltrialkoxysilane compounds are norbornyltriethoxysilane and norbornyltriethoxysilane.

Such norbornyltrialkoxysilane can be synthesized using an alkoxysilane having a hydrogen atom bonded to a silicon atom and norbornene as starting materials.

In other words, the desired product can be obtained by using preferably equal moles or more of norbornene with respect to the number of moles of 5i-H bonds in the alkoxysilane, and using a platinum compound such as chloroplatinic acid as a catalyst to avoid an addition reaction. . The conditions for the addition reaction vary depending on the target product, and cannot be generalized, but generally 20 to 2
00'C for 1 to 60 hours.

The obtained compound can be isolated as is or by known methods.

[Examples of the Invention] The present invention will be explained below with reference to Examples. In the examples, all parts indicate parts by weight.

Example 1 A flask equipped with a dropping funnel was charged with 100 parts of norbornene and 10.02 parts of platinum chloride as a catalyst, and heated to 60°C. Next, from the dropping funnel, triethoxysilane 17
4 parts were slowly added dropwise, and the addition reaction was carried out for 20 hours while keeping the liquid temperature at 60'C. Reduce pressure at 90'C (20mmHC!>
After stripping to remove unreacted substances, the mixture was distilled to obtain 167 parts (yield: 61%) of a compound represented by the following formula.

Boiling point 130'C/28mmHCl
Refractive index (r+2” > 1.4385 molecules @ 258 (gas-mass spectrum analysis) (blank below) Elemental analysis actual value Calculated value (as CI 3 H26S iCh) C60,860
,4 1-110,610,1 018,118,6 Si 10.4 10.9 IR spectrum Figure 1 NMR spectrum Figure 2 Example 2 100 parts of norbornene and chloroplatinic acid as a catalyst were placed in a flask equipped with a dropping funnel. 0.02 part was charged and heated to 50'C. Next, from the dropping funnel, trimethoxysilane 1
29 parts were slowly added dropwise, and the addition reaction was carried out for 40 hours while keeping the liquid temperature at 50'C.

After stripping at 60° C. under reduced pressure (10 mmHQ) to remove unreacted substances, the mixture was distilled to obtain 103 parts of a compound represented by the following formula.

(Purity 96%, yield 45%) Boiling point 125°C/25mmHQ Molecular weight 216 (Gas-mass vector analysis) Actual elemental analysis value Calculated value (CIoH2oSiO3): C55,6255,51 H9,269,32 021,9822, 19 Si 13.14 12.98 IR spectrum Figure 3 NMR spectrum Figure 4 [Effects of the invention] Since the silane compound of the present invention has a norbornyl group and a trifunctional group, it is compatible with organic rubbers such as EPDM. It is in good condition and is expected to be used for various purposes.

[Brief explanation of drawings]

Figures 1 and 2 show the compound obtained in Example 1, and Figure 3 shows the compound obtained in Example 1.
Figure 4 shows the IR spectrum and NMR spectrum of the compound obtained in Example 2, respectively.

Claims (3)

[Claims] (1) Norbornyltrialkoxysilane characterized by being represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents a monovalent hydrocarbon group having 1 to 8 carbon atoms) . (2) The norbornyltrialkoxysilane according to claim 1, wherein R is a methyl group. (3) The norbornyltrialkoxysilane according to claim 1, wherein R is an ethyl group.