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Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions

一种组合物、酚树脂的技术，应用在固化剂和促进剂领域，能够解决高使用水平、低固化温度等问题

Inactive Publication Date: 2015-01-21
EVONIK DEGUSSA GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The methods and curing agents listed above suffer from several disadvantages, including high usage levels, too low curing temperatures or precursor amines obtained by a multi-step process such as adduction with polyepoxides

Method used

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  • Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions
  • Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions
  • Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: Preparation of Amine Solution in Polyphenol Resin

[0072] in N 2 A two-piece 500 mL glass flask was charged with the amine under atmosphere and heated to 145-180 °C with a heating mantle. Slowly add the phenolic resin (PN-320) while stirring with a mechanical stirrer. After the addition was complete the mixture was maintained at 180°C for a further period of 1 hour. Pour this molten solution into on a block or aluminum sheet and allow to cool to room temperature. The cooled solid product is ground to a particle size of about 2 to about 50 μm by a coffee grinder or jet mill. Use this method to prepare the following amine solutions.

[0073] (a) 1,3-aminopropylimidazole solution in polyphenol resin (PN320)

[0074] Amine / polyphenol resins in 180 / 250, 180 / 500 and 180 / 750 weight ratios were prepared as follows:

[0075] Using (i) 37.18g 1,3-aminopropylimidazole and 103.69g polyphenol resin (PN320), (ii) 38.39g 1,3-aminopropylimidazole and 53.50g polyphen...

Embodiment 2

[0093] Example 2: Differential Scanning Calorimetry (DSC) of Amine Solutions in Polyphenol Resin

[0094] (A) The only curing agent

[0095] A sample of the amine solution prepared according to Example 1 was thoroughly mixed with bisphenol A diglycidyl ether (10:100 mass ratio) and analyzed by DSC (TA instruments QA20) to determine the initial curing temperature, heat of reaction (ΔH) and glass transition temperature (Tg). The DSC is run according to standard methods using the software contained in the DSC. The results are shown in the table below:

[0096]

[0097] (B) Amine / phenol solid solution as a DICY accelerator

[0098] A sample of the amine solution of Example 1 was mixed with dicyandiamide (DICY) and bisphenol A diglycidyl ether (2:6:100 mass ratio) in a 250 ml glass flask by using a mechanical stirrer. The mixture was analyzed by DSC in the manner described above to determine the onset temperature of cure, heat of reaction (ΔH) and glass transition temperatur...

Embodiment 3

[0100] Example 3: Latency of a solution of amine in polyphenol resin (PN320) in epoxy resin

[0101] The latency of the amine / polyphenol resin solution prepared according to Example 1 was monitored by a Brookfield cone and plate viscometer (Model HADV II+CP) with #52 spindle at 25°C using a 0.5 mL sample. Storage stability was also determined by visual observation to determine the gel time. The results are shown in the table below:

[0102] Sole curing agent (amine / bisphenol A diglycidyl ether (10 / 100))

[0103]

[0104]

[0105] Amine / DICY / Bisphenol A diglycidyl ether (2 / 6 / 100)

[0106]

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Abstract

The disclosure relates to solving problems associated with conventional latent epoxy curing agents by providing a new class of latent epoxy curing agents. In particular, the disclosure relates to epoxy curing agents with improved storage stability and low use level (e.g., less than about 10 wt % relative to the epoxy compound) by forming solid solutions of certain classes of amines in polyphenolic resins.

Description

Background technique [0001] The present invention relates to curing agents and accelerators for use in latent curing epoxy resin compositions. [0002] Compositions comprising epoxy resins and curing agents (also called hardeners) are known in the art. Many curing agents are reactive with epoxy resins at room temperature and therefore are used immediately after combining with epoxy. Other curing agents, known as latent hardeners, are stable in admixture with epoxy resins at ambient temperature and only achieve hardening when heated to elevated temperatures. [0003] US Patent Nos. 3,519,576 and 3,520,905 disclose the use of salts of monomeric polyphenols and polyamines as latent curing agents for epoxy resins. US Patent No. 4,866,133 discloses the use of solid solutions of polymerized polyphenols and polyamines to cure epoxy resins. The disclosed polyamines contain at least two amine groups, at least one of which is primary. US Patent No. 4,689,390 discloses a latent curin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/62C08G59/56
CPCC08G59/5033C08G59/5073C08L61/04C08G59/621C08G59/50C08L2205/05C08L63/00C08K5/17C08K5/3445C08L61/06
Inventor G·A·维达吉G·S·拉尔S·M·博伊斯A·H·阿布杜拉扎克D·N·沙
Owner EVONIK DEGUSSA GMBH
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