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Aluminum chelate compound and room temperature-curable resin composition containing same

a technology of aluminum chelate and resin composition, which is applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, other chemical processes, etc., can solve the problems of insufficient fast curability, low activity insufficient heat resistance of aluminum chelate compound, etc., to achieve superior heat resistance, water resistance and moisture resistance, superior catalyst activity, and preservation stability. the effect of stability

Inactive Publication Date: 2016-03-24
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention describes a novel aluminum chelate compound that is highly effective as a curing catalyst for room temperature-curable resins. This compound is superior in terms of heat resistance, water resistance, and moisture resistance, and is particularly useful in applications requiring adhesive agents for architecture and electrical and electronic purposes. The composition also exhibits fast curability and does not require the use of tin compounds that are environmentally burdensome. Additionally, the composition is stable and can be stored for extended periods without losing its effectiveness. Overall, this patent presents a novel and effective solution for creating heat-resistant, water-resistant, and moisture-resistant adhesive agents with good curability and stability.

Problems solved by technology

However, such known aluminum chelate compound often exhibits a low activity when used as a curing catalyst for a sealant or the like.
That is, such known aluminum chelate compound may not necessarily be the most appropriate option depending on the intended use.
Although these compositions are superior in preservation stability, water resistance and moisture resistance, they have exhibited insufficient fast curabilities.
However, since an alcohol-type curable composition has a low reactivity with the water in the air as compared to heretofore known curable compositions of other curing types such as an oxime-type, an acetic acid-type and an acetone-type, restrictions are imposed on locations where an alcohol-type curable composition can be used.
However, there exist downsides including a still insufficient curability; a negative impact inflicted on durability by the adjacent functional group (linking group); and a low restorability of a cured product.
In addition, by attempting to solve the problem of the curability, there arises another problem where yellowing occurs after performing an anti-UV discoloration test.

Method used

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  • Aluminum chelate compound and room temperature-curable resin composition containing same
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  • Aluminum chelate compound and room temperature-curable resin composition containing same

Examples

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working example

[0105]Next, working and comparative examples are shown to describe the present invention in detail. However, the present invention is not limited to the following working examples.

working example 1

[0106]Aluminum triethoxide of 0.81 g (5.0 mmol) and toluene of 2.0 ml were placed in a 50 ml eggplant-shaped flask, followed by delivering thereinto 1.58 g (10.0 mmol) of 4,4-dimethyl-3-oxopentanoic acid methyl and then 0.50 g (5.0 mmol) of 2,4-pentanedione by drops while performing stirring. After performing stirring under a room temperature for 24 hours, the ethanol generated was then distilled to obtain 2.20 g (yield 100%) of a yellow viscous fluid having an average structure of that of a monoacetylacetonate aluminum bis (methylpivaloylacetoacetate) chelate.

[0107]A measurement through 1H-NMR spectrum was performed (FIG. 1) to confirm the average structure of the product generated.

[0108]1H-NMR spectrum:

[0109]δ 0.91 to 0.98 ppm (ratio of H: 6, —C(O)—C(CH3)3)

[0110]1.84 to 1.92 ppm (ratio of H: 6, —C(O)—CH3)

[0111]4.11 to 4.18 ppm (ratio of H: 6, —OCH3)

[0112]4.90 to 5.40 ppm (ratio of H: 3, —C(O)CHC(O)—)

[0113]According to the results of the measurement through 1H-NMR spectrum, it is r...

working example 2

[0114]Aluminum triethoxide of 0.81 g (5.0 mmol) and toluene of 2.0 ml were placed in a 50 ml eggplant-shaped flask, followed by delivering thereinto 1.84 g (10.0 mmol) of 4,4,4-ethyl trifluoroacetoacetate and then 0.50 g (5.0 mmol) of 2,4-pentanedione by drops while performing stirring. After performing stirring under a room temperature for 24 hours, the ethanol generated was then distilled to obtain 2.46 g (yield 100%) of a yellow viscous fluid having an average structure of that of a monoacetylacetonate aluminum bis (ethyl-4,4,4-trifluoroacetoacetate) chelate.

[0115]A measurement through 1H-NMR spectrum was performed (FIG. 2) to confirm the average structure of the product generated.

[0116]1H-NMR spectrum:

[0117]δ 1.17 to 1.21 ppm (ratio of H: 6, —OCH2CH3)

[0118]1.89 to 1.93 ppm (ratio of H: 6, —C(O)—CH3)

[0119]4.11 to 4.18 ppm (ratio of H: 4, —OCH2CH3)

[0120]5.29 to 5.43 ppm (ratio of H: 3, —C(O)CHC(O)—)

[0121]According to the results of the measurement through 1H-NMR spectrum, it is re...

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Abstract

Provided are an aluminum chelate compound useful as, for example, a curing catalyst for a room temperature-curable resin; and a room temperature-curable resin composition containing such aluminum chelate compound.This aluminum chelate compound is an aluminum chelate compound having a β-dicarbonyl compound represented by the following general formula (1):(wherein each of R1 to R3 represents a monovalent hydrocarbon group or a halogen atom; R4 represents a hydrogen atom or a monovalent hydrocarbon group; and A is a group selected from a group represented by the following formula (2) and a group represented by —OR8:wherein each of R5 to R7 represents a monovalent hydrocarbon group or a halogen atom; and R8 represents a monovalent hydrocarbon group).

Description

TECHNICAL FIELD[0001]The present invention relates to an aluminum chelate compound useful as, for example, a catalyst of a room temperature-curable resin; and a room temperature-curable resin composition containing the same. Particularly, the present invention relates to a room temperature-curable organopolysiloxane composition as well as a molded product obtained by curing such composition.BACKGROUND ART[0002]A β-diketo compound enabling keto-enol transformation is capable of forming a complex compound with aluminum in an enol structure. That is, there is produced an aluminum chelate compound as a compound containing a β-diketo group(s). Because an alkyl group(s) bonded to a β-diketo group(s) is usually included in a β-diketo compound, such aluminum chelate compound also has an affinity for many kinds of organic polymeric materials. For this reason, such aluminum chelate compound has been used in compositions containing organic polymeric materials, such as paints, adhesive agents a...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G77/08C07F5/06C08G77/20C09D183/04C09J183/04C09K3/10
CPCC08G77/08C07F5/069C09K3/1018C09D183/04C09J183/04C08G77/20C08G77/18C08L83/04C08K5/0091B01J31/22
Inventor KATAYAMA, TAIKIYAMAGUCHI, TAKAHIROSAKAMOTO, TAKAFUMI
Owner SHIN ETSU CHEM IND CO LTD
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