Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate

A maleimide-based, resin composition technology, applied in chemical instruments and methods, synthetic resin layered products, organic chemistry, etc., can solve the problem of insufficient heat resistance and copper cladding heat resistance, low solubility and processing. Solubility, low thermal decomposition temperature of the cured product, etc., to achieve the effects of good solubility, excellent performance, low dielectric loss tangent and excellent performance

Inactive Publication Date: 2009-06-17
HITACHI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, although thermosetting resins such as melamine resins and guanamine compounds are resins excellent in adhesiveness, flame retardancy, and heat resistance, they have insufficient solubility in organic solvents, so if N is not used in large amounts, which is highly toxic, Organic solvents containing N atoms, such as N-dimethylformamide, make it difficult to prepare thermosetting resin compositions, or have problems such as insufficient storage stability.
[0007] In addition, copper clad laminates and interlayer insulating materials using these thermosetting resin compositions also have the problem of contaminating various chemical solutions such as plating solutions when manufacturing electronic parts and the like.
[0008] A thermosetting resin composition using a thermosetting resin in which this melamine resin or guanamine compound is polymerized by aldehydes such as formaldehyde has improved solubility in organic solvents, but it is toxic due to its low thermal decomposition temperature. Decomposition gas from the environment deteriorates the operating environment,

Method used

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  • Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate
  • Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate
  • Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0095] Example

[0096] The present invention is illustrated in more detail by the following examples, but these examples do not limit the present invention.

[0097] The copper clad laminates obtained in the following examples were measured and evaluated for performance by the following methods.

[0098] (1) Evaluation of copper foil adhesion (copper foil peel strength)

[0099] The copper clad laminate was immersed in a copper etchant to leave a 1 cm wide strip to prepare an evaluation substrate from which the copper foil was removed, and an electronic universal testing machine (AG-100C, manufactured by Shimadzu Corporation) was used to measure the thickness of the strip. Peel strength was evaluated.

[0100] (2) Determination of glass transition temperature (Tg)

[0101] The copper clad laminate was immersed in a copper etchant to prepare a 5 mm square evaluation substrate from which copper foil was removed, and it was measured based on the thermal expansion characterist...

Example Embodiment

[0112] Production Example 1: Production of Curing Agent (A-1)

[0113] In a reaction vessel with a volume of 2 liters that can be heated and cooled with a thermometer, a stirring device, and a moisture quantifier with a reflux cooling tube, add 358.00 g of bis(4-maleimidobenzene)methane, m-amino 54.50 g of phenol and 412.50 g of an organic solvent (propylene glycol monomethyl ether) were reacted for 5 hours while refluxing to obtain a curing agent (A-1) containing an organic solvent.

Example Embodiment

[0114] Production Example 2: Production of Curing Agent (A-2)

[0115] In a reaction vessel with a volume of 2 liters that can be heated and cooled with a thermometer, a stirring device, and a moisture quantifier with a reflux cooling tube, add 358.00 g of bis(4-maleimidobenzene)methane, p-amino 54.50 g of phenol and 412.50 g of an organic solvent (propylene glycol monomethyl ether) were reacted for 5 hours while refluxing to obtain a curing agent (A-2) containing an organic solvent.

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Abstract

Disclosed is a method for producing a curing agent having an acidic substituent and an unsaturated maleimide group, wherein a maleimide compound (a) having at least two N-substituted maleimide groups in a molecule and an amine compound (b) having an acidic substituent represented by the general formula (I) below are reacted in an organic solvent. Also disclosed is a thermosetting resin composition containing a curing agent (A) obtained by the above-described method, and a compound (B) which is cured with the curing agent. A cured product of such a thermosetting resin composition has a glass transition temperature of not less than 200 DEG C. Further disclosed are a prepreg using such a thermosetting resin composition, and a laminate. The curing agent produced by this method enables to obtain a thermosetting resin composition having good solubility in an organic solvent, while being excellent in adhesion to metal foils, heat resistance, moisture resistance, flame retardance, copper cladding heat resistance, low dielectric characteristics and low dielectric loss tangent property. Consequently, the curing agent enables to obtain a prepreg or a laminate having excellent properties useful for printed wiring boards for electronic devices.

Description

technical field [0001] The present invention relates to a method for producing a curing agent having an acidic substituent and an unsaturated maleimide group (hereinafter simply referred to as a curing agent), a thermosetting resin composition, a prepreg, and a laminate. Production method of the curing agent with improved solubility in organic solvents and the curing agent obtained by the production method, copper foil adhesion, heat resistance, moisture resistance, flame retardancy, copper clad heat resistance (copper cladding heat resistance) and dielectric properties (dielectric constant, dielectric loss tangent) are all in balance, and thermosetting resin compositions, prepregs and laminates useful for printed wiring boards for electronic equipment . Background technique [0002] Because the unique bridge structure in thermosetting resins has high heat resistance and dimensional stability, thermosetting resins are widely used in fields requiring high reliability such as...

Claims

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Application Information

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IPC IPC(8): C08G59/40C08G73/12B32B27/38C08J5/24B32B27/42C08K3/00C07D207/452C08L63/00
Inventor 土川信次秋山雅则村井曜
Owner HITACHI CHEM CO LTD
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