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Phenolphthalein type cyanate monomer, polymeric compounds and methods of formulating same

A technology of phenolphthalein-type cyanate and cyanate, applied in the direction of organic chemistry, can solve the problems of reducing key physical properties, no cyanate compounds containing phenolphthalein structure, etc., and achieve good thermal stability and high glass transition temperature , the effect of low water absorption

Inactive Publication Date: 2008-09-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with other resin matrices such as polymaleimide, epoxy resin, etc., cyanate resin has better toughness, but many of its other properties, such as fracture resistance, need to be improved. Many additives, including thermoplastic resins, epoxy resins, etc. , bismaleimide, etc. are used for their toughening, but it will always reduce one or more of the key physical properties
However, there are no reports on cyanate compounds containing phenolphthalein structure

Method used

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  • Phenolphthalein type cyanate monomer, polymeric compounds and methods of formulating same
  • Phenolphthalein type cyanate monomer, polymeric compounds and methods of formulating same
  • Phenolphthalein type cyanate monomer, polymeric compounds and methods of formulating same

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis and curing of phenolphthalein cyanate: Dissolve phenolphthalein (2.387g, 0.0106mol) in 40ml of acetone, cool to -10°C, add cyanogen bromide (2.595g, 0.0245mol) and triethylamine (3ml, 0.02152mol ), and continue to insulate and stir for 0.5 hours to terminate the reaction.

[0030] The above mixture was filtered, the filtrate was concentrated under reduced pressure, poured into a large amount of n-hexane to settle, filtered to obtain the crude product, recrystallized in ether to obtain white crystals, and dried to obtain cyanate ester 3.86g, yield 91%, mp: 135.4°C.

[0031] Infrared spectrum display (see figure 1 ), at 2239, 2268cm -1 A strong infrared absorption peak appears at , which is the characteristic absorption peak of the cyano group, and at the same time 3373cm -1 The vibration peak of the phenolphthalein hydroxyl group becomes very gentle, indicating that the reaction is relatively complete.

[0032] After the cyanate compound prepared above was ...

Embodiment 2

[0035] Synthesis and solidification of o-cresol phthalocyanate: dissolve o-cresol phthalein (3.689g, 0.0106mol) in 40ml of chloroform, cool to -20°C, add cyanogen bromide (2.595g, 0.0245mol) and triethylamine ( 3ml, 0.02152mol), the reaction was terminated after stirring for 120 minutes.

[0036] The above mixture was filtered, poured into a large amount of petroleum ether for sedimentation, recrystallized with ethyl acetate, and filtered to obtain 4.04 g of cyanate, with a yield of 89%, and mp: 146.8°C.

[0037] Infrared spectrum display (see image 3 ), at 2253, 2275cm -1 A strong infrared absorption peak appears at , which is the characteristic absorption peak of cyano group, and at the same time 3412cm -1 The vibration peak of the o-cresolphthalein hydroxyl group becomes very gentle, indicating that the reaction is relatively complete.

[0038] After the cyanate ester monomer prepared above was degassed at 170°C for 1h, it was cured according to the temperature rise pro...

Embodiment 3

[0041] Synthesis and solidification of thymolphthalein cyanate: dissolve thymolphthalein (3.057g, 0.0071mol) in 40ml toluene, cool to -5°C, add cyanogen bromide (1.729g, 0.0163mol) and triethylamine ( 2ml, 0.0071mol), stirred for 4 hours to terminate the reaction.

[0042] The above mixture was filtered through a large amount of cyclohexane to obtain a crude product, which was recrystallized with petroleum ether at 60-90°C, filtered and dried to obtain 3.34 g of cyanate, with a yield of 92%, and mp: 196°C.

[0043] Infrared spectrum display (see Figure 5 ), at 2231, 2263cm -1 A strong infrared absorption peak appears at , which is the characteristic absorption peak of the cyano group, and at the same time 3403cm -1 The vibration peak of the phenolphthalein hydroxyl group becomes very gentle, indicating that the reaction is relatively complete.

[0044] After the cyanate compound prepared above was degassed at 200°C for 1h, it was cured according to the heating program of 2...

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Abstract

The present invention provides a category of phenolphthalein-cyanate resin and a preparation method thereof. The structure of the cyanate resin is shown in the right; wherein, the substituents from R1 to R6 can be hydrogen atom, halogen atom, nitro, or the same or different fat alkanes from C1 to C20 and derivatives thereof, or the same or different arenes from C6 to C12 and derivatives thereof. In the preparation method, cyanate monomer and derivatives thereof react with cyan halide to prepare the phenolphthalein-cyanate resin. The cyanate monomer is cured at the temperature between 120 DEG C and 300 DEG C to prepare poly cyanic ester. The cyanate monomer with the structure of phenolphthalein has high reaction activity and wide processing window. The temperature of the initial thermal loss of the poly cyanic ester is above 400 DEG C. The cyanate monomer can be used a suitable matrix for preparing a category of novel high-performance polymer materials and can be used in printed circuit boards, materials of aerospace, and other field.

Description

technical field [0001] The invention relates to a class of cyanate monomers and polymers and a preparation method thereof, in particular to a class of phenolphthalein type cyanate monomers and polymers and a preparation method thereof. technical background [0002] Cyanate resin is a new type of resin matrix containing two or more cyanate functional groups (-O-C≡N), which has the characteristics of excellent heat resistance, low toxicity and low moisture absorption of polyimide , and can be cured by a molding process similar to epoxy resin, and the monomer or prepolymer does not emit volatile components during curing. This kind of high-performance thermosetting resin has high glass transition temperature, low dielectric constant and dielectric loss, small thermal expansion coefficient, high bonding strength to metal and other excellent properties, and is widely used in the fields of electronics, aviation and adhesive industries. Compared with other resin matrices such as po...

Claims

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Application Information

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IPC IPC(8): C07D307/88
Inventor 王忠刚张步峰
Owner DALIAN UNIV OF TECH
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