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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, or the heat resistance and copper clad heat resistance required for lead-free solder demanded in recent years are insufficient
In addition, in the process of microfabrication and wiring formation, the adhesion, flexibility, and toughness of the copper foil are insufficient, and the circuit pattern is disconnected, peeled off, or cracked during processing such as drilling or punching. unpleasant sight
[0009] In addition, methylolated guanamine resins are also disclosed (for example, refer to Patent Document 8), but they also have the same problems as above in heat resistance, adhesiveness, processability, etc.
[0010] Furthermore, a thermosetting resin composition using an adduct of a bismaleimide compound and an aminobenzoic acid has been disclosed (Patent Document 9), but the cured product of this resin composition has a low thermal decomposition temperature, and in recent years, Insufficient heat resistance and copper clad heat resistance required for demanding lead-free solder
In addition, the resin composition has problems of low solubility in organic solvents, workability, etc.

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

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Effect test

Embodiment

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

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

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

[0099] By immersing the copper-clad laminate in a copper etchant, leaving a strip-shaped portion with a width of 1 cm, an evaluation substrate with the copper foil removed was prepared, and the thickness of the strip-shaped portion was measured by using an electronic universal testing machine [Shimadzu Corporation AG-100C]. Peel strength was evaluated.

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

[0101] By immersing the copper-clad laminate in a copper etching solution, a 5 mm square evaluation substrate with the copper foil removed was prepared, and measured from the thermal expansion characteristics of t...

manufacture example 1

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

[0113] Add 358.00 g of bis(4-maleimide benzene) 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.

manufacture example 2

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

[0115] Add bis(4-maleimidobenzene)methane 358.00g, 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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