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Polyhydroxy compound, method for manufacturing the same and epoxy resin composition, cured product thereof

A technology of polyhydric hydroxyl and epoxy resin, which is applied in the preparation of amino hydroxyl compounds, organic compounds, and lubricating compositions. It can solve the problems of large steric barriers and fragility, and achieve excellent flame retardancy and high heat resistance. , High adhesion and excellent effect

Inactive Publication Date: 2011-04-13
NIPPON STEEL CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The resulting resin has the problem of forming a brittle cured product due to its large steric hindrance

Method used

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  • Polyhydroxy compound, method for manufacturing the same and epoxy resin composition, cured product thereof
  • Polyhydroxy compound, method for manufacturing the same and epoxy resin composition, cured product thereof
  • Polyhydroxy compound, method for manufacturing the same and epoxy resin composition, cured product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Add 46.5g (0.5 mol) of aniline and 200g (1.0 mol) of 4,4'-dihydroxydiphenylmethane, heat to 80°C while introducing nitrogen, and drop 40.5g (0.5 mol) of 37% formalin aqueous solution . Next, the temperature was raised to 95° C. and refluxed for 2 hours while stirring, and after further dehydration, the temperature was raised to 180° C. and reacted for 2 hours. Thereafter, unreacted aniline was removed under reduced pressure at 180° C. to obtain 238.5 g of an amino group-containing resin. The hydroxyl equivalent of the obtained resin was 117.4 g / eq., the amine equivalent was 626.4 g / eq., the softening point was 62° C., and the melt viscosity at 150° C. was 31 mPa·s.

[0109] 1 The H-NMR spectrum is shown in figure 1 , the infrared absorption spectrum is shown in figure 2 , the FDMS spectrum is shown in image 3 , the GPC spectrum is shown in Figure 4 . In the FDMS spectrogram, it can be observed that m / z=200 corresponding to n=1 and m=0 in formula (1), m / z=305 c...

Embodiment 2

[0111] 60 g of the amino group-containing resin obtained in Example 1 and 14.2 g of phthalic anhydride were charged, and heated to 150° C. to dissolve and react for 1 hour while introducing nitrogen. Meanwhile, the water generated by the reaction was excluded from the reaction system. Thereafter, unreacted phthalic anhydride was removed under reduced pressure at 230° C. to obtain 57.1 g of imino group-containing resin (resin A). The obtained resin had a hydroxyl equivalent of 157 g / eq., an amine equivalent of 74950 g / eq., a softening point of 76°C, and a melt viscosity of 0.11 Pa·s at 150°C.

[0112] 1 The H-NMR spectrum is shown in Figure 5 , the infrared absorption spectrum is shown in Figure 6 , the FDMS spectrum is shown in Figure 7 , the GPC spectrum is shown in Figure 8 . In the FDMS spectrogram, it can be observed that m / z=200 corresponding to n=1 and m=0 in formula (5), m / z=435 corresponding to n=1 and m=1, corresponding to n=2 And m / z=647 of m=1, m / z=670 co...

Embodiment 3

[0114] Add 60 g of the amino group-containing resin obtained in Example 1, 9.4 g of maleic anhydride, and 120 g of toluene, heat to 110° C. while introducing nitrogen, and react for 2 hours while removing water from the reaction system by azeotroping with toluene. Thereafter, it was heated to 180° C. under reduced pressure to remove toluene and unreacted maleic anhydride to obtain 64.3 g of an imino group-containing resin (resin B). The hydroxyl equivalent of the obtained resin was 144 g / eq., the amine equivalent was 138400 g / eq., the softening point was 88.5°C, and the melt viscosity at 150°C was 0.44 Pa·s. The GPC spectrum is shown in Figure 9 .

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Abstract

The present invention provides a polyhydroxy compound which comprises amino groups or imino groups. The polyhydroxy compound has excellent flame retardance and can become a solidifying agent, a modifying agent and an intermediate of an epoxy resin used for obtaining a cured product with high heat resistance, high moisture resistance and excellent jointing performance with different kinds of materials. The polyhydroxy compound containing amino groups can be represented by a general formula (1), and can be obtained through the reaction between 0.05-1.5 mols of aromatic amines and aldehydes relatively to one mol of phenol rings in phenols. The polyhydroxy compound containing the imino groups can be obtained through the reaction between the polyhydroxy compound containing the amino groups and dicarboxylic anhydrides for imine formation of aminoacyl. Additionally, in the general formula, X is direct bonding, -O-, -S-, -SO2-, -CO- or divalent alkyl, and the average value of m is 0.05-1.5.

Description

technical field [0001] The present invention relates to a polyhydric hydroxyl compound that can be effectively used as a curing agent, a modifier, etc. Base resin for insulating materials, coating materials and composite materials in electrical and electronic fields. Background technique [0002] Epoxy resins are industrially used for a wide range of purposes, and their required performance has been increasing in recent years. For example, in the field represented by the resin composition with epoxy resin as the main agent, there are semiconductor sealing materials, but with the improvement of the integration of semiconductor elements, the package size (package size) tends to be larger and thinner, and at the same time The mounting method is also advancing in the direction of surface mounting, and it is desired to develop materials with excellent soldering heat resistance. In addition, with the recent development of semiconductors for automobiles, there is a need to improv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/74C07C213/08C07D209/48C07D207/452C08G59/62C08L63/00C08L63/04
CPCC07C213/08C07C215/74C07D333/18C10M159/12C10M2207/026
Inventor 大村昌己梶正史中原和彦山田尚史
Owner NIPPON STEEL CHEMICAL CO LTD
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