CN1569822A - Process for preparing phenol addition compound cyanate of dicyclopentadiene - Google Patents
Process for preparing phenol addition compound cyanate of dicyclopentadiene Download PDFInfo
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- CN1569822A CN1569822A CN 03141621 CN03141621A CN1569822A CN 1569822 A CN1569822 A CN 1569822A CN 03141621 CN03141621 CN 03141621 CN 03141621 A CN03141621 A CN 03141621A CN 1569822 A CN1569822 A CN 1569822A
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- dicyclopentadiene
- phenol
- cyanate
- addition compound
- affixture
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Abstract
The invention discloses a process for preparing phenol addition compound cyanate of dicyclopentadiene which comprises first preparing cyanogen chloride, then further obtaining cyanate. The cyanate of dicyclopentadiene obtained has high quality, after being poured in to trimer resin, the dielectric constant is < 3, the dielectric loss is less than 0.0022.
Description
Technical field
The invention belongs to chemical field, relate to a kind of preparation method of cyanate, further, the present invention relates to a kind of preparation method of phenol addition compound cyanate of dicyclopentadiene.
Background technology
Cyanate ester resin is owing to its favorable mechanical performance, higher second-order transition temperature and good electrical property are applied to high-tech areas such as Aeronautics and Astronautics high-speed printed circuit board.
A kind of preparation method of phenol addition compound cyanate of dicyclopentadiene is disclosed in the U.S. Pat 4748270, its method is at low temperatures at first with the dichloromethane solution of chlorine and the reactant aqueous solution of sodium cyanide, separate the dichloromethane solution that water layer obtains mauguinite, then above-mentioned solution is joined in the dichloromethane solution of phenol affixture of dicyclopentadiene, add triethylamine again and finish reaction, with removing solvent behind the buck acid rinsing, obtain product.But the problem of using this method to exist is to be difficult to obtain purified mauguinite, and the impure meeting of mauguinite directly influences the quality of cyanate.
In the China national Department of Intellectual Property patent network, application number 03114874.3 disclosed method then is under-20-10 ℃ temperature, the phenol affixture of dicyclopentadiene is dissolved in the solution such as acetone or toluene, add mauguinite and triethylamine, reaction finishes the back and collects target product with conventional method from reactant.But the required mauguinite of the described method of this patent is difficult to directly buy from the market.
This shows, in the preparation field of the phenol addition compound cyanate of dicyclopentadiene, also need to provide a kind of efficient preparation method,, use conventional raw material just can obtain cyanate, and the cyanate that obtains has high quality by this method.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of preparation method of phenol addition compound cyanate of dicyclopentadiene, and this method may further comprise the steps:
(1) aqueous solution and the chlorine with sodium cyanide enters gas-liquid separator through behind the mixing tank, and gas is collected through condenser and obtained liquid colourless pure mauguinite.
(2) join in the organic solvent solution of phenol affixture of dicyclopentadiene at the mauguinite that below 0 ℃ (1) is made, add triethylamine then, remove salt and other impurity, obtain the phenol addition compound cyanate of high-quality dicyclopentadiene.
As one of embodiments of the present invention, the organic solvent solution of the phenol affixture of described dicyclopentadiene can be the phenol affixture of dicyclopentadiene and the mixing solutions of methylene dichloride.
As another embodiment of the present invention, the organic solvent solution of the phenol affixture of described dicyclopentadiene also can be the phenol affixture of dicyclopentadiene and the mixing solutions of butanone.
In the present invention, the removal of salt and other impurity can realize by the mode of filtering or wash.
Use method of the present invention, the phenol addition compound cyanate of the dicyclopentadiene of acquisition has high quality, pour into the tripolymer resin after, specific inductivity is less than 3, dielectric loss is less than 0.0022.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention:
The preparation of embodiment 1 mauguinite
Sodium cyanide solution with 14% and gaseous state N-Serve amount ground enter gas-liquid separator through batch reactor, and the mauguinite condensation of gas is obtained colourless pure mauguinite.
The preparation of the phenol addition compound cyanate of embodiment 2 cyclopentadiene
The preparation method 1:
1285 milliliters of methylene dichloride of the interior adding of 2000 ml flasks of stirring, cooling and dropper are housed, stir the phenol affixture that adds 120 gram dicyclopentadiene down, dissolve complete postcooling to-10 ℃, mauguinite 50.4 grams that adding makes by 1 method, add the back and drip triethylamine 84.1 grams, maintain the temperature at below-10 ℃, stirred 15 minutes.With sodium bicarbonate aqueous solution and aqueous hydrochloric acid washing, separate, moisture and solvent are removed in 40-50 ℃ of following vacuum-evaporation, obtain the finished product of the phenol addition compound cyanate of dicyclopentadiene.
The preparation method 2:
Prepare 10 liters enamel reactor, add 3600 milliliters of butanone within it, stir phenol affixture 2000 grams that add dicyclopentadiene down, dissolve complete postcooling to-10 ℃, mauguinite 1153 grams that adding makes by 1 method, add the back and drip 2600 milliliters of triethylamines, maintain the temperature at below-10 ℃, stirred 15 minutes, filter with 1000 milliliters of butanone washing leaching cakes, filtrate and washings are merged, remove and desolvate, obtain the phenol addition compound cyanate of dicyclopentadiene.
Claims (5)
1. the preparation method of the phenol addition compound cyanate of a dicyclopentadiene is characterized in that, this method may further comprise the steps:
(1) aqueous solution and the chlorine with sodium cyanide enters gas-liquid separator through behind the mixing tank, and gas is collected through condenser and obtained liquid colourless pure mauguinite;
(2) join in the organic solvent solution of phenol affixture of dicyclopentadiene at the mauguinite that below 0 ℃ (1) is made, add triethylamine then, remove salt and other impurity, obtain the phenol addition compound cyanate of dicyclopentadiene.
2. method according to claim 1 is characterized in that, the organic solvent solution of the phenol affixture of described dicyclopentadiene can be the phenol affixture of dicyclopentadiene and the solution of methylene dichloride.
3. method according to claim 1 is characterized in that, the organic solvent solution of the phenol affixture of described dicyclopentadiene can be the phenol affixture of dicyclopentadiene and the solution of butanone.
4. method according to claim 1 is characterized in that, can remove the salt described in (2) and other impurity by filtering mode.
5. method according to claim 1 is characterized in that, can remove the salt described in (2) and other impurity by the mode of washing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031416217A CN100364965C (en) | 2003-07-15 | 2003-07-15 | Process for preparing phenol addition compound cyanate of dicyclopentadiene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031416217A CN100364965C (en) | 2003-07-15 | 2003-07-15 | Process for preparing phenol addition compound cyanate of dicyclopentadiene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1569822A true CN1569822A (en) | 2005-01-26 |
| CN100364965C CN100364965C (en) | 2008-01-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031416217A Expired - Fee Related CN100364965C (en) | 2003-07-15 | 2003-07-15 | Process for preparing phenol addition compound cyanate of dicyclopentadiene |
Country Status (1)
| Country | Link |
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| CN (1) | CN100364965C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102206173A (en) * | 2011-04-08 | 2011-10-05 | 扬州天启化学股份有限公司 | Preparation method for tetramethyl bisphenol F cyanate resin |
| CN104755422A (en) * | 2012-10-26 | 2015-07-01 | 三菱瓦斯化学株式会社 | Cyanogen-halide production method, cyanate ester compound and production method therefor, and resin composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4748270A (en) * | 1983-11-16 | 1988-05-31 | The Dow Chemical Company | Preparation of aromatic cyanates |
| EP0979815A1 (en) * | 1998-08-11 | 2000-02-16 | Lonza A.G. | Unsaturated oligophenolcyanates |
-
2003
- 2003-07-15 CN CNB031416217A patent/CN100364965C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102206173A (en) * | 2011-04-08 | 2011-10-05 | 扬州天启化学股份有限公司 | Preparation method for tetramethyl bisphenol F cyanate resin |
| CN104755422A (en) * | 2012-10-26 | 2015-07-01 | 三菱瓦斯化学株式会社 | Cyanogen-halide production method, cyanate ester compound and production method therefor, and resin composition |
| US9475761B2 (en) | 2012-10-26 | 2016-10-25 | Mitsubishi Gas Chemical Company, Inc. | Method for producing cyanogen-halide, cyanate ester compound and method for producing the same, and resin composition |
| CN104755422B (en) * | 2012-10-26 | 2016-11-09 | 三菱瓦斯化学株式会社 | The manufacture method of cyanogen halides, cyanate esters and manufacture method thereof and resin combination |
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| Publication number | Publication date |
|---|---|
| CN100364965C (en) | 2008-01-30 |
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Granted publication date: 20080130 Termination date: 20120715 |