WO2003000784A1

WO2003000784A1 - Crosslinking agent for room-temperature curing and room-temperature-curable elastomer composition containing the crosslinking agent

Info

Publication number: WO2003000784A1
Application number: PCT/JP2002/006037
Authority: WO
Inventors: Tsuyoshi Itagaki; Mitsuru Kishine; Kazuyoshi Mimura
Original assignee: Daikin Industries, Ltd.
Priority date: 2001-06-22
Filing date: 2002-06-18
Publication date: 2003-01-03
Also published as: JPWO2003000784A1; JP4096878B2

Abstract

A novel crosslinking agent with which an elastomer can be sufficiently crosslinked throughout at room temperature; and a room-temperature-curable elastomer composition which contains the crosslinking agent and gives a cured article excellent in heat resistance, compression set, chemical resistance, etc. The crosslinking agent comprises a bischloroaldoxime compound represented by the formula (I): HON=CCl-A-CCl=NOH (wherein A is a divalent organic group). The composition comprises this crosslinking agent, a crosslinking accelerator, and an elastomer.

Description

Akira Itoda Sho Includes a crosslinking agent for curing at room temperature and the crosslinking agent

Room temperature curable elastomer composition

The present invention relates to a novel crosslinking agent suitable for curing an elastomer composition at room temperature, and a room temperature-curable elastomer composition using the same. Background art

As the curable composition, a thermosetting resin composition is best known, and is literally crosslinked and cured by applying high-temperature heat.

On the other hand, especially in the field of building materials, materials that harden at relatively low temperature (100 ° C or lower), especially at room temperature (ambient temperature) for applications such as building sealants, building paints, and adhesives are required. I have. Until now, materials that are cured by a cross-linking reaction utilizing the reactivity of isocyanate groups and mercapto groups, materials that are cured by condensation polymerization of hydrolyzable silyl groups with water (moisture), and heat treatment at a relatively low temperature by a hydrosilylation reaction Materials to be cured have been studied and some have been implemented.

However, materials that use an isocyanate group are toxic and difficult to construct on site, and the resulting cured products lack heat resistance. Materials utilizing mercapto groups have strong off-flavors and are difficult to use on site. Materials having a hydrolyzable silyl group have no problem with toxicity or odor, but require external moisture, so the inside of the molded product (deep curing) is insufficient. In the case of a cross-linking system utilizing a hydrosilylation reaction, if the cross-linking reaction is designed to proceed at room temperature, the pot life becomes too short, so It is designed so that the crosslinking reaction proceeds rapidly. Thus, even in the field of building materials where room temperature hardening is strongly desired, no room temperature curable material having no defects has been developed.

In recent years, room temperature curable materials have also been required in electronic component assembly factories to avoid damaging electronic components and to reduce production costs. Crosslinking by irradiation with energy rays such as ultraviolet rays is being studied. However, there remains a problem that the irradiated energy beam does not sufficiently reach the deep part of the molded body and the deep curing is insufficient. Thus, at present, there is no cross-linking system that can fully cure at room temperature to the depth.

Such a problem in the curable resin is directly applied to the room temperature crosslinking system of the elastomer composition, and there is no crosslinking system capable of providing a sufficient cured state at room temperature.

For example, U.S. Pat. No. 4,316,035 and U.S. Pat. No. 3,028,266 propose a crosslinked system of an elastomer having 1,2,4-oxadazole as a crosslinked structure. Have been. This cross-linking reaction is a reaction in which a bisadoxime compound acts as a cross-linking agent on a cyano group-containing elastomer to form a 1,2,4-oxadiazole structure and cross-links the resulting cured product. Excellent compression set. However, the crosslinking temperature is described as 40 to 100 in the above-mentioned U.S. Pat.No. 4,316,035, and the crosslinking temperature at 50 ° C. is as long as 89 hours. Is required. On the other hand, in Japanese Patent No. 3 082 266, a high crosslinking temperature of 150 to 220 ° C. is adopted. Disclosure of the invention

According to the present invention, the crosslinking reaction proceeds sufficiently at room temperature, and the elastomer molded body is deepened. An object of the present invention is to provide a novel cross-linking agent which can be cured by the above method and a room temperature curable elastomer composition using the same.

That is, the present invention provides a compound represented by the formula (I):

HO N = C C 1-A- C C 1 = N O H (I)

(Wherein, A is a divalent organic group). The present invention relates to a crosslinking agent for curing at room temperature, comprising a bischloroaldoxime compound represented by the formula:

A in the formula (I) is not particularly limited as long as it is a divalent organic group.

Further, A in the above formula (I) is an alkylene group or alkylidene group having 1 to 10 carbon atoms which may contain an oxygen atom, or a C 1 to 10 carbon atom which may contain an oxygen atom. A fluoroalkylene group or a perfluoroalkylidene group, an optionally substituted phenylene group, and a compound represented by the formula (Π):

(I I)

(Wherein, B is an alkylene group or alkylidene group having 1 to 6 carbon atoms, a perfluoroalkylene group or a perfluoroalkylidene group having 1 to 6 carbon atoms, a single bond, o o

II II

— S— — C—

Alternatively, at least one selected from the group consisting of an optionally substituted bisphenylene group represented by 1 o-) is preferable.

The present invention also provides a crosslinking agent comprising the bischloroaldoxime compound represented by the formula (I), an elastomer having a crosslinking group capable of reacting with the crosslinking agent, and a crosslinking capable of dehydrochlorinating the crosslinking agent. It relates to a room temperature curable elastomer composition containing an accelerator.

Further, the crosslinkable group is a cyano group, a formyl group, a carbonyl group, At least one selected from the group consisting of a quinyl group, an alkenyl group, a thiocarbonyl group and an imidoyl group is preferred.

Further, the crosslinkable group is preferably a cyano group.

Further, the crosslinking accelerator is preferably an organic base or an inorganic base.

Further, the present invention provides a bischloroaldoxime compound represented by the formula (I), wherein the compound represented by the formula (III):

BEST MODE FOR CARRYING OUT THE INVENTION The present invention relates to a bischloroaldoxime compound represented by the formula:

The present invention provides a compound of formula (I):

HON = CC 1 -A-CC 1 = NOH (I)

The cross-linking reaction of the cross-linking agent of the present invention is considered to proceed as follows, using the H〇N = CC 1- group (chloroaldoxime group) as a cross-linking point.

First, by making the crosslinking reaction system more basic with a basic crosslinking accelerator, the chloroaldoxime group is dehydrochlorinated and converted to a nitriloxide group.

(HON = CC 1-^-2— A + base (crosslinking accelerator)

~~ * · (0 ≡C -2 ~ A + HC I Next, the crosslinkable group of the elastomer (in the following formula, a cyano group) and the ditolyl oxide group undergo a 1,3-dipolar cycloaddition reaction. , 1, 2, 4 —Complete cross-linking by forming an oxadiazole structure.

This series of reactions proceeds sufficiently at a low temperature of 0 to 40 ° C and, unlike water crosslinking systems and energy beam crosslinking systems, is a reaction by a crosslinking agent incorporated inside. Is achieved to the depth of

The crosslinking agent of the present invention that achieves this crosslinking reaction is the bischloroaldoxime compound represented by the above formula (I). Since the cross-linking reaction proceeds as described above, the structure (1A-) connecting two chloroaldoxime groups is not particularly limited as long as there are two chloroaldoxime groups. However, if the chain is too long, the raw materials for the reaction become expensive, and the solubility is lowered to reduce the reaction. Therefore, the following is preferred.

Next, A in the formula (I) will be described.

(a) An alkylene group or alkylidene group having 1 to 10 carbon atoms which may contain an oxygen atom, and an alkylene group or alkylidene group having 2 to 8 carbon atoms is preferable from the viewpoint of cost and reactivity. . If the carbon number exceeds 10, purification of the cross-linking agent becomes difficult, and the properties of the cross-linking agent itself tend to have a large effect on the cured product.

Next, A is a specific example of the bischloroaldoxime compound in which the alkylene group or the alkylidene group is CC I = NOH,

HON = CC

HON = CC -CC I = NOH,

O

HON = CC CC NOH,

CH

HON = CC C—— CC I = NOH

CH

Is raised.

(b) a perfluoroalkylene group or a perfluoroalkylidene group having 1 to 10 carbon atoms which may contain an oxygen atom, and further having 4 to 8 carbon atoms because of its advantages in terms of cost and reactivity. Fluoroalkylene or perfluoroalkylidene groups are preferred. If the number of carbon atoms exceeds 10, purification of the cross-linking agent becomes difficult, and the properties of the cross-linking agent itself tend to have a greater effect on the cured product.

Next, as a specific example of the bischloroaldoxime compound wherein A is the perfluoroalkylene group or the perfluoroalkylidene group,

HON = CC I -CF ₂ CF ₂ CF CF ₂ -CC Ι = ΝΟΗ,

HON = CC I-CF ₂ CF OCF, 2C ^ F ¹ , 2-CC I = NOH,

HON = CC I-C FCF ₂ OCF_CC I = NOH

C C F

Is raised.

(c) an optionally substituted phenylene group, as well as cost and reactivity A phenylene group is preferred from the viewpoint of advantage.

Next, specific examples of the phenylene group which may be substituted include a phenylene group,

Is raised.

(d) Formula (II):

(In the formula, Β represents an alkylene group or an alkylidene group having 1 to 6 carbon atoms, a perfluoroalkylene group or a perfluoroalkylidene group having 1 to 6 carbon atoms, a single bond,

Or _〇—) optionally substituted bisphenylene group, and な is a single bond, since it is advantageous in terms of cost and reactivity.

C C H

C C

C C H

An optionally substituted bisphenylene group is preferred.

The number of carbon atoms of the alkylene group or the alkylidene group is more preferably 1 to 3, and the carbon number of the perfluoroalkylene group or the perfluoroalkylidene group is more preferable. The number is more preferably 1 to 3. When the number of carbon atoms in the alkylene group or the alkylidene group exceeds 6, synthesis tends to be difficult. When the number of carbon atoms in the perfluoroalkylene group or the perfluoroalkylidene group exceeds 6, the synthesis tends to be difficult.

Next, specific examples of the bisphenylene group which may be substituted include 2,2-bis (phenyl) hexafluoropropylidene,

Is raised.

Of these, 2,2-bis (phenyl) hexafluoropropylidene, 2,2-bis is advantageous in terms of cost and reactivity, and gives a crosslinked product with excellent heat resistance and chemical resistance. (Phenyl) propylidene (a group derived from so-called pisphenol A) is preferred.

Further, the compound represented by the above formula (III) is a novel compound.

The bisclonal aldoxime compound of the formula (I) can be obtained as follows. For example, formula (IV):

(I V)

(Wherein A is the same as described above) in a mixed solvent of alcohol and water, in the presence of a basic compound such as sodium hydroxide, in the presence of a basic compound such as sodium hydroxide. By reacting with amine, formula (V):

(V)

(Wherein A is the same as described above), to synthesize a bisaldoxime compound (V). This reaction proceeds easily in a few hours at ot to room temperature.

Then, the bisaldoxime compound (V) is dissolved in an organic solvent (for example, DMF), and chlorine gas or N-chlorosuccinimide (at least twice the molar amount (1 equivalent) of the bisaldoxime compound (V)) is dissolved. By reacting with NCS), the bischloroaldoxime compound of the formula (I) can be synthesized. This reaction is completed within a few hours at room temperature.

Next, a room temperature curable elastomer composition containing the crosslinking agent, an elastomer having a crosslinking group capable of reacting with the crosslinking agent, and a crosslinking accelerator capable of dehydrochlorinating the crosslinking agent will be described.

The crosslinkable group of the elastomer having the crosslinkable group suitable for the composition is selected from the group consisting of a cyano group, a formyl group, a carbonyl group, an alkynyl group, an alkenyl group, a thiocarbonyl group and an imidoyl group. There is at least one species. Particularly, a cyano group is preferred from the viewpoint of good reactivity and stability of the product. The elastomer body is not particularly limited. In addition to natural rubber (NR), isoprene rubber (IR), butadiene rubber (BR), chloroprene rubber (CR), butyl rubber (IIR), acrylonitrile butadiene rubber (NBR), styrene- Synthetic rubbers such as butadiene rubber (SBR), ethylene-propylene-butadiene rubber (EPDM), acrylic rubber, epichlorohydrin rubber, silicone rubber, fluorine rubber, and urethane rubber can be used.

The elastomer used in the present invention may be a high molecular weight elastomer, but a relatively low molecular weight elastomer, particularly a liquid elastomer at room temperature, is preferred from the viewpoint of effectively utilizing the advantage of room temperature curability. is there. “Liquid at room temperature” refers to a state having a viscosity of 1000 voids or less at room temperature. If it exceeds 100,000, there is a tendency that good flowability at the time of molding cannot be obtained. Specifically, although it differs depending on the type of the elastomer, it is usually one having a number average molecular weight of 1,000 to 500,000. If the number average molecular weight is less than 100, a good crosslinked product tends not to be obtained. If it exceeds 500, good flowability tends not to be obtained.

As a method for introducing the crosslinkable group into these elastomers, a conventionally known method can be employed. For example, a method of copolymerizing a monomer having a crosslinkable group (copolymerization method), a method of modifying a functional group of the elastomer into a crosslinkable group (functional group modification method), and the like can be exemplified.

Among these elastomers, one that makes the cross-linking group electron-withdrawing, such as fluorine, because it facilitates the 1,3-cycloaddition reaction with ditolyloxide generated by dehydrochlorination of the cross-linking agent. Rubber and perfluoroelastomer are preferred.

As described above, the crosslinking accelerator is not particularly limited as long as it is a compound that functions to promote the crosslinking reaction by dehydrochlorinating a bischloroaldoxime compound as a crosslinking agent to convert it to nitriloxide. In addition, the reaction system Any compound capable of promoting the dehydrochlorination by making it alkaline (alkaline) and capturing hydrogen chloride may be a compound that generates a base in situ of the reaction system.

Preferred crosslinking promoters are, for example Toryechiruamin, triethanolamine § Min, Anirin, pyridine, organic bases such as polyvinylpyridine; Anmo Nia, NaOH, K_〇_H, inorganic bases exemplified such as K ₂ C0 _3, N a HC_〇 ₃ it can. Of these, triethylamine and ammonia (gas) are preferred because of their low cost and excellent reactivity.

The room temperature-curable elastomer composition has a crosslinking agent of 0.2 to 50 PHR, preferably 0.3 to 20 PHR, based on 100 parts by weight of the elastomer (hereinafter referred to as “PHR”). The crosslinking promoter is 0.1 to 15 PHR, preferably 0.3 to 3 PHR.

If the cross-linking agent is less than 0.2 PHR, there is a tendency that the elastomer cannot be sufficiently cured. If it exceeds 50 PHR, the number of functional groups of the cross-linking agent becomes very large with respect to the functional groups of the elastomer, and there is a tendency that effective cross-linking is not achieved. The preferred lower limit of the crosslinking accelerator is 0.1 PHR, and the preferred upper limit is 15 PHR.

In addition, various known additives can be added to the composition according to the purpose of use, required physical properties, required cost, and the like. Examples of the additive include a filler, an antioxidant, and an ultraviolet absorber.

When a high molecular weight elastomer is used, a preferred method for preparing the composition is to dissolve the elastomer in a solvent. When an elastomer in the form of a liquid rubber is used, one of a crosslinking agent and a crosslinking accelerator is added to the liquid elastomer, and the other is blended when used (cured). It is preferable to use a liquid type. As a mixing method, use a static mixer, dynamic mixer, three-roll mill, etc. Then, a method of mixing in a solventless system is preferable.

The feature of the composition is that it can be cured (cross-linked) at room temperature and can be easily installed on site. Therefore, as a curing method, it is only necessary to mix a crosslinking agent, an elastomer and a crosslinking accelerator and leave the mixture at room temperature (or an ambient temperature, usually 0 to 40 ° C). Curing depends on the type and amount of the elastomer used and its crosslinkable group, crosslinking agent, crosslinking accelerator, etc., ambient temperature, ambient humidity, etc., but curing is usually completed in 0.5 to 24 hours. . To complete the curing in a short time, heating may be performed if necessary.

Since the room temperature stiffening elastomer composition is cured to form a 1,2,4-year-old oxadiazole crosslinked structure, it is possible to provide a crosslinked product excellent in chemical resistance, heat resistance, compression set and the like. . Therefore, it can be suitably used for the following applications, for example.

Seal material field:

O-rings for architectural sealants, semiconductor manufacturing equipment, etc., gaskets for automotive electronic components, etc.

Paint field:

High weather resistant paint, etc.

Molded body:

Rolls for OA equipment, diaphragms for transport equipment, linings for chemical plants, etc.

Next, the present invention will be described based on examples, but the present invention is not limited to only these examples.

Example 1 (1) Synthesis of bisaldoxime compound of formula (VI)

(VI)

Dissolve 4.4 g (12.2 mmol) of 2,2-bis (4-formylphenyl) hexafluoropropane in a mixture of 10 ml of ethanol and 10 ml of water, and stir at 0 ° C with hydroxyl. 1.87 g (26.9 mmol) of amine hydrochloride and 4.87 g (61.1 mmol) of a 50% aqueous sodium hydroxide solution were added dropwise. After reacting by stirring at room temperature for 2 hours, 30 ml of water was added, and the mixture was extracted twice with ether, washed with a saturated saline solution, and dried using anhydrous magnesium sulfate. After distilling out the ether under reduced pressure, the residue was recrystallized (chloroform / hexane) to obtain 3.87 g of 2,2-bis (4-aldoxyphenyl) hexafluoropropane represented by the formula (VI) ( Yield: 83%). (Physical properties)

_{H-NMR (CDC 1 3,} p pm):

7.37 (4H, d, J = 8.4 Hz), 7.62 (4H, d, J = 8.4 Hz), 8.08 (2H, s), 10.52 (2H, s)

_{F-NMR (CDC 1 3,} p pm) (CFC 1 3 reference):

-64.0 (s)

FT-IR (KB r, cm ^-1 ): 3334, 2988, 1244

MS:

390 (M / Z)

H-MAS S:

Calculated value: 390.08030

Found: 390. 07944

(2) Synthesis of bis-clonal aldoxime compound represented by formula (III)

(III)

1.5 g (3.85 mmol) of the bisaldoxime compound of the formula (VI) is dissolved in 15 ml of dimethylformamide, and N-chlorosuccinimide 1.O g (7.70 ml) is stirred at room temperature with stirring. Was added. After reacting with stirring at room temperature for 2 hours, 30 ml of water was added, and the mixture was extracted twice with ether, washed with brine and dried over anhydrous magnesium sulfate. After distilling off the ether under reduced pressure, the crystal was recrystallized (form-form Z hexane) to give 2,2-bis (4-form-aldoxyphenyl) hexafluoropropane represented by the formula (III) 1. 9 g was obtained (yield: 100%).

(Physical properties)

_{HN R (CDC 1 3, p} pm): 7.43 (4H, d, J = 8.4 Hz), 7.86 (4H, d, J = 8.4 Hz)> 8.87 (2H, s)

_{F-NMR (CDC 1 3,} p pm) (CFC 1 3 reference):

-64.0 (s)

FT-IR (KBr, cm- ¹ ):

3342, 2991, 1250

MS:

458 (M / Z)

HR-MAS S:

Calculated value: 458. 00235 (C 1 = 35)

Found: 458. 00206

Example 2 (Formation of 1,2,4-oxadiazole crosslinked structure)

Two

30 Omg (0.65 mmol) of the bischloroaldoxime compound of the formula (III) was dissolved in 5 ml of benzene, and triethylamine 1821 (1.31 mmol) was added with stirring at 0 ° C. Further, perfluorok-yunonitrile 652 1 (1.567 mmol) was added. After reacting with stirring at room temperature for 16 hours, 3 Om1 of water was added, extracted twice with ether, washed with saturated saline, and dried with anhydrous magnesium sulfate. After distilling off the ether under reduced pressure, the residue was purified by silica gel chromatography to obtain 588 mg of a bisoxaziazole compound represented by the formula (VII) (yield: 77%).

(Physical properties)

_{H-NMR (CDC 1 3,} p pm):

7.58 (4H, d, J = 8.4Hz), 8.18 (4H, d, J = 8.4Hz)

_{F-NMR (CDC 1 3,} pm) (CFC 1 3 reference):

-64.0 (6 F, s), -81.3 (6F, t, J = 1 OHz), 1 1 13.4 (4F, t, J = 12 Hz), -121. 0 to 1 124.0 (

16 F, m),-126.6 126.7 (4 F, m)

FT—IR (KB r, cm- ¹ ):

1254

MS:

1 176 (M / Z)

HR-MAS S:

Calculated value: 1176.007

Found: 1176. 009

Comparative Example 1 (Reaction between monoaldoxime compound and perfluoronitrile compound)

(IX)

15 Omg (1.103 mmol) of the benzaldoxime of the formula (VIII) was dissolved in 5 ml of chloroform, and perfluorooctanonitrile 3101 (1.1323 mmol) was added dropwise at room temperature with stirring. When the reaction was carried out at room temperature with stirring for 18 hours, a solid substance was deposited. Therefore, the precipitate was recrystallized (cloth form) and analyzed. As a result, no oxaziazole compound was formed, and only the adduct represented by the formula (IX) was found.

(Yield: 100%).

Example 3 (room temperature curing reaction)

Hydrogenated NBR (Zetpo 12000, manufactured by Zeon Corporation) was dissolved in a mixed solvent of tetrahydrofuran / toluene (2Z1) to prepare a hydrogenated NBR solution having a concentration of 5%. To 40 g of the hydrogenated NBR solution, 0.3 g of the bischloroaldoxime compound of the formula (III) synthesized in Example 1 was added, and the mixture was sufficiently stirred. Then add 0.13 g of triethylamine, pour the mixed solution into a tray, leave at room temperature for 24 hours, and cast about 200 m thick A film was prepared.

The cast film obtained was sufficiently cured. The 100% modulus, tensile strength at break (Tb) and elongation (Eb) measured at 23 ° C (tensile speed: 20 Omm / min) according to JIS K6301 were respectively 1.38 MPa, 4.08 MPa and 337%.

Comparative Example 2 (Mechanical properties of uncured hydrogenated NBR)

An uncured hydrogenated NBR (raw rubber) cast film was prepared in the same manner as in Example 3 except that the bischloroaldoxime compound of the formula (ΠI) was not used in Example 3, and the same procedure as in Example 3 was carried out. Mechanical properties were measured. As a result, the 100% modulus was 0.72 MPa, Tb was 0.84 MPa, and Eb was 1045%.

Example 4

Tetrafluoroethylene (TFE), perfluoromethyl vinyl ether (PMVE), and CF ₂ = CFOCF ₂ CF (CF ₃ ) OCF ₂ CF ₂ CN (Example 1 of WO00 / 29479 specification) CNVE) Copolymer (composition: TFE / PMVEZCNVE 56. 6/42. 3/1. 1) is dissolved in perfluoro (butyltetrahydrofuran) (FC 75, manufactured by Sumitomo 3LEM), and a 1% concentration polymer solution is dissolved. And After thoroughly stirring 0.1 g of the bischloroaldoxime compound of the formula (III) synthesized in Example 1 in 80 g of the polymer solution, pour the mixture into a tray, dry under reduced pressure at 80, and cast. A film was obtained. The film on this tray was placed in a stainless steel autoclave, purged with nitrogen, pressurized to 0.IMPa with ammonia gas, allowed to stand at room temperature for 24 hours, and then heated at 50 for 2 hours. . After cooling to room temperature, ammonia gas was released to obtain an ammonia-treated film. The film was sufficiently cured and did not dissolve when immersed again in FC75. Industrial applicability

ADVANTAGE OF THE INVENTION According to this invention, the novel crosslinking agent which can fully bridge | crosslink an elastomer at room temperature to an inside can be provided. The room temperature curable elastomer composition comprising the cross-linking agent, the cross-linking accelerator, and the elastomer provides a cured product having excellent heat resistance, compression set, chemical resistance, etc., and sealants, elastomer adhesives, paints, etc. Can be provided as a construction material of the above.

Claims

Scope of Word

1. Formula (I):

HO N = C C 1-A- C C 1 = N OH

(Wherein A is a divalent organic group) a crosslinking agent for room temperature curing comprising a bischloroaldoxime compound represented by the formula:

2. In the formula (I), A is an alkylene group or an alkylidene group having 1 to 10 carbon atoms which may contain an oxygen atom, or a perfluene having 1 to 10 carbon atoms which may contain an oxygen atom. A fluoroalkylene group or a perfluoroalkylidene group, an optionally substituted phenylene group, and a compound represented by the formula (II):

(Wherein B is an alkylene or alkylidene group having 1 to 6 carbon atoms, a perfluoroalkylene group or a perfluoroalkylidene group having 1 to 6 carbon atoms, a single bond,

0 0

II] 1

—— S— — c—

Or the crosslinking agent according to claim 1, wherein the crosslinking agent is at least one selected from the group consisting of a bisphenylene group which may be substituted and represented by 1 o-).

3. A room temperature curable elastomer composition comprising the crosslinking agent according to claim 1, an elastomer having a crosslinking group capable of reacting with the crosslinking agent, and a crosslinking accelerator capable of dehydrochlorinating the crosslinking agent. .

4. The method according to claim 3, wherein the crosslinkable group is at least one selected from the group consisting of a cyano group, a formyl group, a carbonyl group, an alkynyl group, an alkenyl group, a thiocarbonyl group and an imidoyl group. Room temperature curing Elastomer composition.

5. The room temperature curable elastomer composition according to claim 3, wherein the crosslinkable group is a cyano group.

6. The room temperature curable elastomer composition according to claim 3, wherein the crosslinking accelerator is an organic base or an inorganic base.

7. Formula (I I I):

A bischloroaldoxime compound represented by the formula: