JP2009132637A - Biphenyl compound comprising epoxy group, method of preparing the same, surface modifier, adhesion aid, and adhesive - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a highly heat resistant biphenyl compound comprising an epoxy group suitable for preparing a surface modifier, an adhesion aid and an adhesive, and a method of preparing the same. <P>SOLUTION: The biphenyl compound comprising an epoxy group prepared by way of a hydrosilylation process is represented by formula (2). In the formula, R represents an alkyl group, and m is a natural number of from 0 to 4. The biphenyl compound comprising an epoxy group represented by formula (2) wherein R is a methyl group and m is 3, is preferred. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a surface modification agent such as a silane coupling agent and a titanium coupling agent, an adhesion aid, or an epoxy group-containing biphenyl compound that can be used as a sealing material, a method for producing the same, and a surface modification agent, The present invention relates to an adhesion aid and an adhesive.

Conventionally, when an organic adhesive made of a thermosetting resin or the like is used as an adhesive for bonding an object to be bonded to a base material made of an inorganic substance, for example, the surface of the base material is made of, for example, a silane coupling agent or titanium Modification with a surface modifier such as a coupling agent has been performed.
As the surface modifier, in particular, a silane coupling agent containing an epoxy group is known as having a high surface modifier. This is because a strong siloxane network is formed on the surface of the substrate (modified surface), and high adhesion to the organic adhesive is imparted to the surface of the substrate. Non-Patent Document 1 and Patent Documents 1 and 2 disclose compounds having no surface modifying property but having an epoxy group and high heat resistance.

On the other hand, recently, circuit boards produced for increasing the density and functionality of electronic circuits have been laminated, and a demand for a laminated substrate of more than a dozen layers has begun. Conventionally, a circuit board made of a thermosetting resin has been used. However, the following drawbacks have been pointed out for the thermosetting resin.
That is, thermosetting resin is inferior to engineering plastics such as liquid crystal polymer film due to various physical properties such as dielectric constant and water absorption, or when thermosetting resin and liquid crystal polymer film made of thermoplastic resin are bonded In addition, it has been pointed out that the adhesiveness is insufficient and that the thermosetting resin cannot be recycled.
Therefore, it is considered that a laminated substrate made of a circuit board made of only thermoplastic engineering plastics will be indispensable in the future.

  However, at present, although an attempt is made to pretreat the surface of the copper foil with a silane coupling agent having an epoxy group and fuse the liquid crystal polymer film and the copper foil, the fusion point of the liquid crystal polymer film is 300. On the other hand, since a conventional silane coupling agent having an epoxy group (for example, “KBM-403” (manufactured by Shin-Etsu Chemical Co., Ltd.)) has low heat resistance, sufficient adhesion cannot be obtained in this fusion. There is a problem.

  Patent Document 3 proposes a heat-resistant silane coupling agent having a high surface modification property. This silane coupling agent has a fluoroalkyl chain, and thus has a water and oil repellent property. It is a heat-resistant release agent that exerts its action and thereby exhibits non-adhesiveness, non-adhesiveness, antifouling properties, lubricity, glossiness, etc., and has no adhesiveness.

J Nat Prod Vol. 64 no. 5 Page 608-611 (2001) JP-A-7-53671 Japanese Patent Laid-Open No. 5-301452 Japanese Patent No. 3939226

The present invention has been made in view of the above circumstances, and its purpose is to have an epoxy group-containing biphenyl compound, a surface modifier, and an adhesion assistant that have high heat resistance and can be used for adhesion. It is to provide an agent and an adhesive.
Another object of the present invention is to provide a method for producing an epoxy group-containing biphenyl compound capable of obtaining the epoxy group-containing biphenyl compound.

  The epoxy group-containing biphenyl compound of the present invention is represented by the following general formula (1).

[In the above general formula (1), Y is a group containing an epoxy group, Z is an alkylene group, M is a group IV element, X is a halogen atom, an alkoxy group, an acyloxy group or an isocyanate group. N is an integer of 1 to 3. ]

  In the epoxy group-containing biphenyl compound of the present invention, M is preferably Si or Ti.

  The epoxy group-containing biphenyl compound of the present invention is preferably represented by the following general formula (2).

[In the general formula (2), R represents an alkyl group. Moreover, m is an integer of 0-4. ]

  Moreover, as this epoxy group containing biphenyl compound, it is preferable that R is a methyl group and m is 3.

The method for producing an epoxy group-containing biphenyl compound of the present invention is a method for producing the above epoxy group-containing biphenyl compound,
The reaction shown in the following reaction formula (3) is performed to obtain an intermediate [A] represented by the following structural formula (4), and the reaction shown in the following reaction formula (5) using the intermediate [A]. The intermediate [B] represented by the following structural formula (6) is obtained, and the reaction shown in the following reaction formula (7) is performed using the intermediate [B].

The surface modifier of the present invention is characterized by comprising the above-mentioned epoxy group-containing biphenyl compound.
The adhesion assistant of the present invention is composed of the above-mentioned epoxy group-containing biphenyl compound, and is used for modifying the surface of a substrate made of an inorganic substance to which an organic adhesive is applied.
The organic adhesive is preferably made of an epoxy resin.

The adhesive of this invention consists of said epoxy-group containing biphenyl compound, and is used for adhesion | attachment with the base material consisting of an inorganic substance, and the adhesion target object consisting of an organic or inorganic substance.
This adhesive is suitably used when the object to be bonded is made of polypropylene resin, polystyrene resin, acrylic resin, nylon resin, urethane resin or polyether ether ketone (PEEK) resin.

According to the epoxy group-containing biphenyl compound of the present invention, high heat resistance can be obtained.
The reason for this is presumed to be derived from the thermal stability of the biphenyl ring.
According to the method for producing an epoxy group-containing biphenyl compound of the present invention, the epoxy group-containing biphenyl compound can be obtained.

According to the surface modifier of this invention, since the said surface modifier consists of an epoxy-group containing biphenyl compound which has high heat resistance, high heat resistance is obtained about the surface of the modified base material.
The reason for this is that it has two bonding systems of a siloxane network and a π-π interaction between regularly arranged biphenyl rings on the surface of the modified substrate, and further forms the π-π interaction. This is probably because each biphenyl ring has high thermal stability.

  According to the adhesion aid of the present invention, an object to be bonded to the surface of a base material made of an inorganic substance to which the organic adhesive is applied, for example, via the adhesion assistant and the organic adhesive. For example, even if this composite is heated at high temperature for each use for sterilization of a gastric camera or the like, the adhesive aid has high heat resistance. Since the epoxy group-containing biphenyl compound is included, the degree of thermal deterioration of the bonded portion can be suppressed to a low level, and thus high durability for use can be obtained for this composite.

  Further, according to the adhesive of the present invention, it is possible to obtain a composite in which the object to be bonded is bonded to the surface of a base material made of an inorganic substance via the adhesive, for example, As a result, the same effect as described above can be obtained.

  Hereinafter, the present invention will be specifically described.

The epoxy group-containing biphenyl compound of the present invention is represented by the above general formula (1).
In the general formula (1), Y is a group containing an epoxy group, Z is an alkylene group, M is a group IV (IVA group or IVB group) element, X is a halogen atom, an alkoxy group, an acyloxy group or an isocyanate group. .

  Specific examples of M in the general formula (1) include, for example, Si (silicon), Ti (titanium), Al (aluminum), Zr (zirconium), Sn (tin), etc. Among these, particularly Si And Ti are preferred.

Specific examples of the group Y containing an epoxy group constituting the epoxy group-containing biphenyl compound include those represented by the following formulas (8-a) to (8-d).
In the present invention, the “group containing an epoxy group” refers to an organic group including a site where —O— is in the form of a bridged structure.

Examples of the alkylene group Z constituting the epoxy group-containing biphenyl compound include those represented by the formula [— (CH ₂ ) _m —]. However, in the said formula, m is an integer of 0-4, Preferably m is 3.
Examples of the group Z include a methylene group [—CH ₂ —], an ethylene group [—CH ₂ CH ₂ —], a trimethylene group [—CH ₂ CH ₂ CH ₂ —], and a methylmethylene group [—CH (CH ₃ ) —. ], A methylethylene group [—CH (CH ₃ ) CH ₂ —] and the like, and among these, when used as a surface modifier or an adhesive, it should be closely arranged on the surface of the substrate. Therefore, a group having a shape close to a straight chain is preferable.

The group X constituting the epoxy group-containing biphenyl compound is a halogen atom, an alkoxy group, an acyloxy group or an isocyanate group.
Examples of the halogen atom include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).
The alkoxy group is represented by —OR (wherein R is an alkyl group), and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a butoxy group.
Examples of the acyloxy group include an acetyloxy group and a propionyloxy group.
Furthermore, an isocyanate group [—NCO] can be mentioned.

In the said General formula (1), n shows the integer of 1-3.
When n in the general formula (1) is 2, the epoxy group-containing biphenyl compound represented by the general formula (1) itself has high polymerizability.

  As an epoxy group containing biphenyl compound of this invention, what is represented by the said General formula (2) is preferable.

  The epoxy group-containing biphenyl compound of the present invention is, in particular, 4- (2,3-epoxypropyl) -4 ′-(3 wherein R is a methyl group and m is 3 in the general formula (2). -Trimethoxysilylpropyl) biphenyl can be preferably mentioned. Hereinafter, this compound is referred to as “specific epoxy group-containing biphenyl compound”.

[Method for producing specific epoxy group-containing biphenyl compound]
Specifically, as shown in the above reaction formula (3), such a specific epoxy group-containing biphenyl compound is obtained by the Grignard reaction of the starting material 4,4′-dibromobiphenyl and allyl bromide. 4-allyl-4′-bromobiphenyl (intermediate [A]) represented by (4) was obtained, and as shown in reaction formula (5), this intermediate [A] and epichlorohydrin A haloalcohol was introduced by a Grignard reaction (see the following reaction formula (5-a)), sodium hydroxide was added continuously without isolation, and represented by the above structural formula (6) by intramolecular Williamson synthesis. 4-allyl-4 ′-(2,3-epoxypropyl) biphenyl (intermediate [B]) was obtained (see the following reaction formula (5-b)), and then as shown in the reaction formula (7). This intermediate [B] is converted to platinum chloride. By reacting trimethoxysilane hydrosilylation in the presence of a catalyst, it can be obtained.

Specific examples of the chloroplatinic acid catalyst used in the step represented by the reaction formula (7) include platinum (IV) chloroplatinic acid hexahydrate (H ₂ PtCl ₆ .6H ₂ O).
It is preferable that the usage-amount of a chloroplatinic acid catalyst is 0.01-0.50 mass part with respect to 100 mass parts of intermediate [B], More preferably, it is 0.02-0.10 mass part.

[Use]
The epoxy group-containing biphenyl compound as described above is used to modify the surface of a substrate made of an inorganic substance such as glass or metal to which an organic adhesive such as a silane coupling agent or a titanium coupling agent is applied. It is preferably used as a surface modifier such as an adhesion aid, an adhesive provided for adhesion between a substrate made of an inorganic substance and an object to be bonded made of an organic or inorganic substance, or a sealing material. it can.
The epoxy group-containing biphenyl compound of the present invention can be used as an adhesive if it can be directly bonded by the epoxy group-containing biphenyl compound depending on the type of object to be bonded to the substrate, and cannot be directly bonded In this case, it may be used together with another organic adhesive applicable as an adhesion aid.

Organic adhesives applied to inorganic substances when used as adhesion aids are made of thermosetting resins such as epoxy resins, melamine resins, phenol resins, polyimide resins, diallyl phthalate resins, unsaturated polyester resins, and furan resins. Mention may be made of adhesives.
In addition, when used as an adhesive, the objects to be bonded are polyethylene resin, polypropylene resin, polystyrene resin, acrylic resin, polyvinyl chloride resin, polycarbonate resin, nylon resin, urethane resin, polybutylene terephthalate (PBT). Thermoplastic resins such as resins such as resins, polyethylene terephthalate (PET) resins, ABS resins, and polyether ether ketone (PEEK) resins having a high softening point; Thermosetting resins listed above; polybutadiene rubber, polyisoprene rubber Elastomers such as ethylene-propylene rubber (EPM, EPDM), styrene-butadiene rubber (SBR), nitrile rubber, epichlorohydrin rubber, neoprene rubber, butyl rubber, polysulfide, urethane rubber Rubber mention may be made of those so forth.

As described above, according to the epoxy group-containing biphenyl compound as described above, high heat resistance can be obtained.
The reason for this is presumed to be derived from the thermal stability of the biphenyl ring.

In addition, when the epoxy group-containing biphenyl compound as described above is used as a surface modifier, according to this surface modifier, the surface modifier is composed of an epoxy group-containing biphenyl compound having high heat resistance. High heat resistance is obtained for the surface of the modified substrate.
The reason for this is that it has two bonding systems of a siloxane network and a π-π interaction between regularly arranged biphenyl rings on the surface of the modified substrate, and further forms the π-π interaction. This is probably because each biphenyl ring has high thermal stability.
And when using such an epoxy group-containing biphenyl compound as an adhesion aid, according to this adhesion aid, for example, a group consisting of an inorganic substance to which an organic adhesive is applied, for example, is used. It is possible to obtain a composite in which the object to be bonded is bonded to the surface of the material via this bonding aid and organic adhesive. For example, this composite is heated at a high temperature every time it is used for sterilization such as a stomach camera. Even if the adhesive aid is composed of an epoxy group-containing biphenyl compound having high heat resistance, the degree of thermal degradation of the adhesion site can be suppressed to a small extent. High durability can be obtained.

  Moreover, when using the epoxy group-containing biphenyl compound as described above as an adhesive, according to the adhesive, the adhesive is used, for example, on the surface of a substrate made of an inorganic substance via the adhesive. A composite with the object to be bonded can be obtained, and thereby the same effect as described above can be obtained.

  As mentioned above, although this invention was demonstrated, this invention is not limited to this, A various change can be added.

  Hereinafter, specific examples of the present invention will be described, but the present invention is not limited thereto.

<Example 1>

[Synthesis Example of Intermediate [A]]
To a two-necked 500 mL eggplant flask equipped with a dropping funnel, 2.76 g (113.6 mmol) of magnesium and 5.0 mL of THF were added, and 27.28 g (87.4 mmol) of 4,4′-dibromobiphenyl dissolved in 185 mL of tetrahydrofuran (THF). ) And refluxed at 66 ° C. for 8 hours. Subsequently, after returning to room temperature, 22.2 mL (262.2 mmol) of allyl bromide was gradually added dropwise and stirred at room temperature for 24 hours. Furthermore, this was returned to room temperature, 50 mL of dilute hydrochloric acid (approximately 0.1 mol aqueous solution) was gradually added under ice-cooling, and extracted with THF. Thereafter, the product was distilled and recrystallized from methanol to obtain a white solid product in a yield of 22%. The product had a boiling point of 11 Pa and 110 ° C., and a melting point of 103 ° C.

This product was subjected to ¹ H-NMR spectrum measurement, FT-IR spectrum measurement, and Mass spectrum measurement. As a result of ¹ H-NMR spectrum measurement, a peak derived from methylene-CH _2- bonded to a biphenyl group. Of 3.42 ppm, a peak derived from —CH═CH ₂ was confirmed to be 5.05 ppm to 6.01 ppm, a peak derived from a biphenyl group was confirmed to be 7.23 to 7.55 ppm, the integration ratio was also consistent, and FT− absorption of νC-H derived from C-H biphenyl group near 2900～3100Cm ^-1 in the results of the IR spectrum measurement, νPh-Br absorption derived from the coupling of the benzene ring and bromine in the vicinity of 1100 cm ^-1, 1600 cm Absorption of νC = C derived from C = C near ⁻¹ , and absorption of σC = C derived from C = C near 900 cm ⁻¹ Further, molecular ion peaks were confirmed in the results of Mass spectrum measurement. From these results, the product was 4-allyl-4′-bromobiphenyl (intermediate) represented by the structural formula (4). [A]) was identified. The results of ¹ H-NMR spectrum measurement, Mass spectrum measurement, and FT-IR spectrum measurement are shown in FIGS. 1, 2, and 3, respectively.
In addition, ¹ H-NMR spectrum measurement is “Bruker DPX400 type (400 MHz)” (manufactured by Bruker), Mass spectrum measurement is “JMS-SX 102A” (manufactured by JEOL Ltd.), and FT-IR spectrum measurement is “Nicolet AVATAR 360”. (Manufactured by Nicolet).

[Synthesis Example of Intermediate [B]]
To a two-neck 200 mL eggplant flask equipped with a dropping funnel, 0.448 g (18.4 mmol) of Mg metal powder and 4 mL of THF were added, and 5.02 g (18.4 mmol) of Br2PA dissolved in 15 mL of THF was added. Next, after stirring for 18 hours, 2.17 mL (27.7 mmol) of epichlorohydrin was gradually added dropwise under ice cooling, followed by stirring for 20 hours. Further, 15 mL of dilute hydrochloric acid (approximately 0.1 molar aqueous solution) was gradually added dropwise under ice cooling and extracted with THF.
The extracted oil layer was distilled off under reduced pressure, the residue was dissolved in methanol, sodium hydroxide was added under ice cooling, and the mixture was stirred for 2 hours. After adding 20 mL of THF to the reaction solution and washing with water, the ether layer was distilled off under reduced pressure, and column separation (silica gel “Wakogel C-300” (Wako Pure Chemical Industries, Ltd.) was performed using a developing solution of chloroform: hexane = 3: 1. A glass column having a diameter of 6 cm and a length of 71 cm), and a white solid product was obtained with a yield of 43%. The melting point of this product was 67 ° C.

This product was subjected to ¹ H-NMR spectrum measurement, FT-IR spectrum measurement, and Mass spectrum measurement. As a result of ¹ H-NMR spectrum measurement, it was derived from methylene-CH ₂ — bonded to a biphenyl group. The peak is 2.88 ppm, the peak derived from —CH—O— is confirmed to be 3.18 ppm, the peaks derived from —O—CH ₂ — are confirmed to be 2.80 ppm and 2.59 ppm, and the integration ratios are also matched. In the result of FT-IR spectrum measurement, absorption of νC—O derived from —C—O—C— was confirmed near 1200 cm ⁻¹ , and in the result of Mass spectrum measurement, a molecular ion peak was confirmed, From these results, the product is 4-allyl-4 ′-(2,3-epoxypropyl) biphenyl represented by the structural formula (6). Was identified as nil (intermediate [B]). The results of ¹ H-NMR spectrum measurement, Mass spectrum measurement, and FT-IR spectrum measurement are shown in FIGS. 4, 5, and 6, respectively.
In addition, ¹ H-NMR spectrum measurement is “Bruker DPX400 type (400 MHz)” (manufactured by Bruker), Mass spectrum measurement is “JMS-SX 102A” (manufactured by JEOL Ltd.), and FT-IR spectrum measurement is “Nicolet AVATAR 360”. (Manufactured by Nicolet).

[Synthesis Example of Silane Coupling Agent [C]]
In a two-necked 100 mL eggplant flask, 3.03 g (12.12 mmol) of E2PA was collected under a nitrogen atmosphere, 8 mL of THF was added as a solvent, followed by 3.08 mL (24.24 mL) of trimethoxysilane, and finally 0.1 M of 0.1 M as a catalyst. 0.03 mL (0.003 mmol) of a H ₂ PtCl ₆ / THF solution was added with stirring. After stirring at 50 ° C. for 9 days, the solvent and excess trimethoxysilane were distilled off under reduced pressure to obtain a colorless and transparent liquid product as a residue.

The product was subjected to ¹ H-NMR spectrum measurement, FT-IR spectrum measurement, and Mass spectrum measurement. As a result of the ¹ H-NMR spectrum measurement, it was confirmed that almost only the product was obtained. . In the results of ¹ H-NMR spectrum measurement, peaks derived from —CH ₂ —CH ₂ —CH ₂ — are 2.67, 1.78, 0.72 ppm, and peaks derived from —OCH ₃ are 3. The integration ratio was confirmed to be 57 ppm, and in the results of FT-IR spectrum measurement, absorption of νSi—O derived from —Si—O— was confirmed in the vicinity of 1085 cm ⁻¹ , and mass spectrum measurement was further performed. In the results, molecular ion peaks were confirmed, and from these results, the product was represented by 4- (2,3-epoxypropyl) -4 ′-(3-trimethoxysilyl) represented by the following structural formula (9). Propyl) biphenyl was identified. Hereinafter, this is referred to as “silane coupling agent [C]”. The results of ¹ H-NMR spectrum measurement, Mass spectrum measurement, and FT-IR spectrum measurement are shown in FIGS. 7, 8, and 9, respectively.
In addition, ¹ H-NMR spectrum measurement is “Bruker DPX400 type (400 MHz)” (manufactured by Bruker), Mass spectrum measurement is “JMS-SX 102A” (manufactured by JEOL Ltd.), and FT-IR spectrum measurement is “Nicolet AVATAR 360”. (Manufactured by Nicolet).

  The silane coupling agent [C] obtained as described above was evaluated for heat resistance as follows.

<Experimental example G-1>
(1) Preparation of solution for evaluating modifier A silane coupling agent [C] was prepared as a toluene solution having a concentration of 15 mM. This is called a surface modification solution.
(2) Plate glass cleaning treatment The plate glass was immersed in a 1N aqueous sodium hydroxide solution for 2 hours, and then sufficiently washed with distilled water and dried under reduced pressure.
(3) Surface Modification Treatment of Plate Glass The plate glass washed in the above (2) was immediately immersed in a surface modification solution in a nitrogen atmosphere and subjected to surface modification treatment at 65 ° C. for 2 hours. Thereafter, the plate glass is thoroughly washed with toluene, and then immersed in distilled water for several minutes for the purpose of converting hydrolyzable groups (methoxy groups) into hydroxy groups, and subsequently in an oven for the purpose of building a siloxane network. Heated at 150 ° C. for 30 minutes at atmospheric pressure. Then, it cooled to room temperature in the desiccator, and surface-modified glass was obtained.
(4) Heat-exposure treatment of surface-modified glass This surface-modified glass was subjected to a heat-exposure treatment that was heated for a time β in an oven at a temperature α. However, in Experimental Example G-1, α is 20 ° C. and β is 120 minutes.
(5) Measurement of contact angle About the surface-modified glass which performed the heat exposure process, the contact angle of the water with respect to the surface was measured. The contact angle was measured by a droplet method in which 0.9 μL of water droplets were dropped on a horizontal plate glass. The results are shown in FIG.

<Experimental Examples G-2 to G-5>
In Experimental Example G-1, the heat exposure treatment was performed at temperatures of 200 ° C. (Experimental G-2), 250 ° C. (Experimental G-3), 300 ° C. (Experimental G-4), and 350 ° C. (Experimental G- The heat resistance was evaluated in the same manner except that the heating was performed in the oven of 5). The results are shown in FIG.

<Experimental Examples G-6 to G-13>
In Experimental Example G-1, the heat exposure treatment was performed in an oven at a temperature of 300 ° C. for 30 minutes (Experimental Example G-6), 60 minutes (Experimental Example G-7), 90 minutes (Experimental Example G-8), 120 Heat for 150 minutes (Experimental example G-10), 180 minutes (Experimental example G-11), 210 minutes (Experimental example G-12), 240 minutes (Experimental example G-13) In the same manner as described above, the heat resistance was evaluated. The results are shown in FIG.
Note that Experimental Example G-9 is a repeated experiment of Experimental Example G-4.

<Comparative Experimental Example N-1>
In the above experimental example G-1, 3-glycidoxypropyltrimethoxysilane “KBM-403” (manufactured by Shin-Etsu Chemical Co., Ltd.) represented by the following structural formula (10) is used instead of the silane coupling agent [C]. The heat resistance was evaluated in the same manner except that it was used. The results are shown in FIG.

<Comparative Experimental Examples N-2 to N-5>
In Comparative Experimental Example N-1, the heat exposure treatment was performed at temperatures of 200 ° C. (Comparative Experimental Example N-2), 250 ° C. (Comparative Experimental Example N-3), 300 ° C. (Comparative Experimental Example N-4), and 350 ° C. ( The heat resistance was evaluated in the same manner except that it was performed in the oven of Comparative Experimental Example N-5). The results are shown in FIG.

  As is clear from FIGS. 10 and 11, the silane coupling agent [C] according to the present invention has improved heat resistance compared to 3-glycidoxypropyltrimethoxysilane which does not contain a biphenyl ring used for comparison. It has been confirmed. Moreover, it was confirmed that the durability is about 3 hours at a heat resistant temperature of 300 ° C.

  The epoxy group-containing biphenyl compound of the present invention can be suitably used as a surface modifier such as a silane coupling agent or a titanium coupling agent, an adhesion assistant, or a sealing material.

2 is a graph showing the results of ¹ H-NMR spectrum measurement of the intermediate [A] obtained in Example 1. FIG. 3 is a graph showing the results of Mass spectrum measurement of the intermediate [A] obtained in Example 1. 2 is a graph showing the results of FT-IR spectrum measurement of the intermediate [A] obtained in Example 1. 2 is a graph showing the results of ¹ H-NMR spectrum measurement of the intermediate [B] obtained in Example 1. 2 is a graph showing the results of mass spectrum measurement of the intermediate [B] obtained in Example 1. 2 is a graph showing the results of FT-IR spectrum measurement of the intermediate [B] obtained in Example 1. 2 is a graph showing the results of ¹ H-NMR spectrum measurement of the silane coupling agent [C] obtained in Example 1. 3 is a graph showing the results of Mass spectrum measurement of the silane coupling agent [C] obtained in Example 1. 4 is a graph showing the results of FT-IR spectrum measurement of the silane coupling agent [C] obtained in Example 1. It is a graph which shows the result of Experimental example G-1 to Experimental example G-5 and Comparative experimental example N-1 to Comparative experimental example N-5. It is a graph which shows the result of Experimental example G-6-Experimental example G-13.

Claims (10)

An epoxy group-containing biphenyl compound represented by the following general formula (1):

[In the above general formula (1), Y is a group containing an epoxy group, Z is an alkylene group, M is a group IV element, X is a halogen atom, an alkoxy group, an acyloxy group or an isocyanate group. N is an integer of 1 to 3. ]   The epoxy group-containing biphenyl compound according to claim 1, wherein M is Si or Ti. The epoxy group-containing biphenyl compound according to claim 2, represented by the following general formula (2).

[In the general formula (2), R represents an alkyl group. Moreover, m is an integer of 0-4. ]   4. The epoxy group-containing biphenyl compound according to claim 3, wherein R is a methyl group and m is 3. A method for producing an epoxy group-containing biphenyl compound according to claim 4,
The reaction shown in the following reaction formula (3) is performed to obtain an intermediate [A] represented by the following structural formula (4), and the reaction shown in the following reaction formula (5) using the intermediate [A]. To obtain an intermediate [B] represented by the following structural formula (6), and carrying out the reaction represented by the following reaction formula (7) using the intermediate [B] A method for producing a biphenyl compound.




  A surface modifier comprising the epoxy group-containing biphenyl compound according to any one of claims 1 to 4.   An adhesion assistant comprising the epoxy group-containing biphenyl compound according to any one of claims 1 to 4 and being used for modifying a surface of a substrate made of an inorganic substance to which an organic adhesive is applied. Agent.   The adhesion assistant according to claim 7, wherein the organic adhesive is made of an epoxy resin.   It consists of the epoxy group containing biphenyl compound in any one of Claims 1-4, and is used for adhesion | attachment with the base material consisting of an inorganic substance, and the adhesion target object consisting of an organic or inorganic substance, adhesive.   The adhesive according to claim 9, wherein the object to be bonded is made of polypropylene resin, polystyrene resin, acrylic resin, nylon resin, urethane resin, or polyether ether ketone (PEEK) resin.