Diamine, acid dianhydride, polyimide composition having reactive group obtained therefrom, and processes for producing these

A technology of reactive groups and acid dianhydrides, applied in the field of new polyimide compositions, can solve problems such as unknown diamines

Inactive Publication Date: 2004-06-02
KANEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, diamines having reactive groups at the ends of the alkyl and fluoroalkyl groups are not known.

Method used

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  • Diamine, acid dianhydride, polyimide composition having reactive group obtained therefrom, and processes for producing these
  • Diamine, acid dianhydride, polyimide composition having reactive group obtained therefrom, and processes for producing these
  • Diamine, acid dianhydride, polyimide composition having reactive group obtained therefrom, and processes for producing these

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0306] (1-1) Synthesis of 12-bromododecane-1-(4-fluorocinnamate)

[0307] Put 4.6g (25 mmol) of 4-fluorocinnamic acid chloride and 50 ml of methyl ethyl ketone into the reactor, then slowly add 5.0 g (18.9 mmol) of 12-bromododecanol, three A solution of 3.0 g (30 mmol) of ethylamine dissolved in 50 ml of methyl ethyl ketone was stirred under reflux under a nitrogen stream. The generated onium salt was filtered off, concentrated to dryness, and then recrystallized from methanol to obtain 7.4 g (17.9 mmol) of 12-bromododecane-1-(4-fluorocinnamate). Yield 95%.

[0308] 1 H-NMR (solvent CDCl 3 ): δ7.85~6.93(m, Ph-H, 4H), 6.50(s, CH=CH, 1H), 6.25(s, CH=CH, 1H), 4.20(t, CH, 2H), 3.40( t, CH, 2H), 1.90~0.9 (m, CH, 20H)

[0309] (1-2) Synthesis of 12-(4-fluorocinnamic acid)-dodecane-1-(2,5-dihydroxybenzoate)

[0310] 7.33 g (17.5 mmol) of 12-bromododecane-1-(4-fluorocinnamate), 5.72 g (20 mmol) of cesium salt of 2,5-dihydroxybenzoic acid, dimethylformamide 50 ml was used as a r...

Embodiment 2～6

[0317] The following examples 2 to 6 are synthesis examples of diamines with reactive groups of the present invention

Embodiment 2

[0319] (2-1) Synthesis of 1-dodecanol-12-(4-fluorocinnamate)

[0320] Put 7.23g (25 mmol) of cesium salt of cinnamic acid, 5.0 g (18.9 mmol) of 12-bromododecanol, and 50 ml of dimethylformamide (hereinafter referred to as DMF) into the reactor, and carry out the process at 100 ° C. Heating was continued with stirring for 2 hours. (The reaction was carried out under nitrogen flow). After filtering the reaction solution, the filtrate was poured into water, and the precipitated white solid was filtered to obtain 6.26 g (18.3 mmol) of 1-dodecanol-12-(4-fluorocinnamate). (yield 97%)

[0321] 1 H-NMR (solvent CDCl 3 ): δ7.85~6.93(m, Ph-H, 4H), 6.50(s, CH=CH, 1H), 6.26(s, CH=CH, 1H), 4.20(t, CH, 4H), 3.76( t, CH, 4H), 1.90~0.8(m, CH, 20H), 1.8(s, OH, 1H)

[0322] (2-2) Synthesis of 12-(4-fluorocinnamic acid)-dodecane-1-(3,5-dinitrobenzoate)

[0323] Put 1-dodecanol-12-(4-fluorocinnamate) 6.15g (18 mmol), triethylamine 2.5g (25 mmol), methyl ethyl ketone 60ml into the reactor, ...

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Abstract

The present invention relates to a novel diamine, a novel acid dianhydride, and a novel composition containing a polyimide produced from such diamine and acid dianhydride. Specifically, the present invention relates to an acid dianhydride that has a photosensitive group bonded through the mediation of an alkylene group or a fluoroalkylene group, a diamine that has a reactive group bonded through the mediation of an alkylene group or a fluoroalkylene group, and a polyimide composition that contains a novel polyimide having at least one of such acid dianhydride residue and diamine residue in a molecule thereof. Particularly, an object of the present invention is to provide a novel polyimide that has both photoreactivity and thermoreactivity specific to the reactive group and whose reactive group is selected from the group consisting of: organic groups derived from cinnamic acid, chalcone, furylacryloyl, benzalacetophenone, stilbene, coumarin, and pyrone; allyl; propargyl; ethinyl; CH2=CH-; CH2=C(CH3)-; and skeletons derived therefrom, and it to provide a novel diamine and a novel acid dianhydride that may be contained in the polyimide composition.

Description

technical field [0001] The present invention relates to compositions using novel diamines, novel acid dianhydrides and novel polyimides produced therefrom. Specifically, it is a composition containing the following components: an acid dianhydride having a photosensitive group through an alkylene group, a diamine having a reactive group through an alkylene group, and one of these components in the molecule Or two new polyimides. In particular, the reactive group is a backbone derived from cinnamic acid, aryl acryloyl arene, furyl acryloyl, benzylidene acetophenone, stilbene, coumarin, pyroxone, allyl radical, propargyl, ethynyl, CH 2 = CH- and CH 2 =C(CH 3 )-organic groups or their derivative skeletons, a new type of polyimide composition that has both photoreactivity and thermal reactivity specific to these reactive groups, and a new type of diamine and a new type of acid diamine composed of this material anhydride. Background technique [0002] Polyimide, because of i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/56C07D307/89C07D309/32C08G73/10
CPCC07D307/89C08G73/10C08G73/1053C07C229/56C07D407/12
Inventor 冈田好史
Owner KANEKA CORP
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