CN103626786B - A kind of synthetic method of chloride screw ring orthocarbonicester monomer - Google Patents
A kind of synthetic method of chloride screw ring orthocarbonicester monomer Download PDFInfo
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- CN103626786B CN103626786B CN201310582214.XA CN201310582214A CN103626786B CN 103626786 B CN103626786 B CN 103626786B CN 201310582214 A CN201310582214 A CN 201310582214A CN 103626786 B CN103626786 B CN 103626786B
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- APFVLAQUOGATEI-UHFFFAOYSA-N NCC(CO1)OC2C1OCC(CN)CC2 Chemical compound NCC(CO1)OC2C1OCC(CN)CC2 APFVLAQUOGATEI-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Abstract
A synthetic method for chloride screw ring orthocarbonicester monomer, relates to a kind of synthetic method of functional high molecule material orthocarbonic ester monomer, with epoxy chloropropane hydrolysate for raw material ester-interchange method synthesizing spiro orthocarbonic ester; Its process is: adding epoxy chloropropane hydrolysate is 3-chloro-1,2-propylene glycol, when utilizing the hydrolysate of epoxy chloropropane and tetraethyl orthocarbonate to react in there-necked flask, add 2-4g molecular sieve, until solvent is micro-boil after, system temperature is down to room temperature, then adds tetraethyl orthocarbonate, the proportioning of tetraethyl orthocarbonate and dibasic alcohol should be 1:1-1:4; Add catalyzer and siccative, then mixed solution is filtered, leach anhydrous sodium carbonate solid matter, product is filtered and purifies, and final product is dried, obtain spiromonomer 3,8-dimethyl chloride-1,4,6,9-tetra-oxaspiro [4,4] nonane, be applied in the middle of epoxy resin modification, have expansion; Chlorine element is incorporated in the middle of spiro orthocarbonate, makes modified epoxy resin have flame retardant resistance.
Description
Technical field
The present invention relates to a kind of synthetic method of functional high molecule material orthocarbonic ester monomer, particularly relate to a kind of synthetic method of chloride screw ring orthocarbonicester monomer.
Background technology
Macromolecular material all can produce volumetric shrinkage phenomenon in processing preparation process, thus causes the decline of the strength of materials to bring very large impact to practical application, and therefore this phenomenon also result in showing great attention to of people.1972, Americanized scholar professor W.J.Bailey has found Expanding Monomer, after this chemists have synthesized again multiple volution Expanding Monomer in succession, and spiromonomer can reduce the volumetric shrinkage that macromolecular material produces, so spiromonomer is applied on the study on the modification of epoxy resin by chemists.
The Expanding Monomer of current discovery mainly contains spiro orthoester class, bicyclo orthoester class, spiro orthocarbonate class and ketal lactone class.Open loop approach is cationic and free radical type mainly.Its topmost application is and thermosetting resin copolymerization, reduces volumetric shrinkage, reduces string stress, thus resin property is improved.
Owing to there is volumetric expansion when volution Expanding Monomer is polymerized, if it is joined in epoxy resin-base, can effectively reduce or eliminate volumetric shrinkage during curable epoxide, reduce the internal stress in epoxy resin-base, the toughness of epoxy matrix is improved.Consequent pucker & bloat can regard partial offset as.Find under study for action, ring-opening polymerization volumetric shrinkage size is relevant with the quantity of ring with the size of ring.Along with the increase of ring, the nearly Fan Shi distance generated after open loop is more and more close to Fan Shi distance, and thus volumetric shrinkage reduces.Here the just monocyclic monomers said; If monomer is bicyclic monomer, there is two ring-opening polymerization, then have two singly-bounds fractures to become nearly Fan Shi distance, after likely making polymerization volumetric shrinkage less, do not shrink and even expand; Along with the increase of the quantity of ring, the chance of open loop is just more, and the quantity that singly-bound becomes nearly Van der Waals distance is just more, also just makes volumetric shrinkage will be less, and rate of expansion will be higher.The factor of another volume change is the change from monomer to polymkeric substance entropy in the course of the polymerization process, monomer is to the change of the free volume of phase emergencing copolymer in other words, the change of the tightness degree of namely piling up at monomer and polymkeric substance Atom, the change of entropy will cause volumetric expansion.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method of chloride screw ring orthocarbonicester monomer, the present invention with epoxy chloropropane hydrolysate for raw material, synthesize chloride element spiro orthocarbonate with ester-interchange method, the spiro orthocarbonate with the chloride element of symmetrical structure utilizing ester-interchange method to synthesize also has good swelling property.
The object of the invention is to be achieved through the following technical solutions:
A synthetic method for chloride screw ring orthocarbonicester monomer, described method with epoxy chloropropane hydrolysate for raw material ester-interchange method synthesizing spiro orthocarbonic ester, its process is: adding epoxy chloropropane hydrolysate is 3-chloro-1,2-propylene glycol, when utilizing the hydrolysate of epoxy chloropropane and tetraethyl orthocarbonate to react in there-necked flask, add 2-4g molecular sieve, until solvent is micro-boil after, system temperature is down to room temperature, then adds tetraethyl orthocarbonate, the proportioning of tetraethyl orthocarbonate and dibasic alcohol should be 1:1-1:4, add catalyzer and siccative, and join in reaction system according to the proportioning of orthocarbonic ester and 3-chlorine-1,2-propylene glycol, magnetic agitation, condensing reflux, treat that thermometer registration is stable and start timing, the reaction times of magnetic agitation condensing reflux should control at 4-8 hour, heating in water bath 40-60 DEG C, there-necked flask interpolation thermometer and dropping funnel, react under the condition of nitrogen protection, first process for mixed solution after reaction terminates should leave standstill 10-20 minute, then mixed solution is filtered, comprise and add dissolution with solvents product, leach anhydrous sodium carbonate solid matter, product is filtered and purifies, product filters to adopt and filter paper is converted into taper, be put among conical hopper and mixed solution is filtered, filter 2-4 time, obtain colourless transparent solution, colourless transparent solution is dry, drying temperature is 60-120 DEG C, the product obtained after drying is carried out purification processes, product is dissolved in sherwood oil, acetone, anhydrous diethyl ether, at least one solvent in ethyl acetate, employing sonic oscillation cleans, the sonic oscillation time is 5-20 minute, filter after vibration, and final product is dried, obtain spiromonomer 3, 8-dimethyl chloride-1, 4, 6, 9-tetra-oxaspiro [4, 4] nonane, its structural formula is as follows:
。
The synthetic method of described a kind of chloride screw ring orthocarbonicester monomer, the hydrolyzed reaction product of described epoxy chloropropane is tetraethyl orthocarbonate, or is the compounds of orthocarbonic ester of original methyl carbonate class.
The synthetic method of described a kind of chloride screw ring orthocarbonicester monomer, the solvent of described reaction system adopts the solvent of mixed solution as reaction system of a kind of or arbitrary proportion in sherwood oil, anhydrous diethyl ether, toluene.
Advantage of the present invention and effect are:
The method utilizes ester-interchange method, synthesizes containing chlorine element and has the spiro orthocarbonate of symmetrical structure; Be applied in the middle of epoxy resin modification, have expansion; Chlorine element is incorporated in the middle of spiro orthocarbonate, makes modified epoxy resin have flame retardant resistance.
Embodiment
Below in conjunction with embodiment, the invention will be further described.
The present invention is the spiro orthocarbonate with the chloride element of symmetrical structure that utilizes ester-interchange method to synthesize and has good swelling property, and structural formula is:
Synthetic product of the present invention can be used as a kind of intermediate, utilizes the active character of the chlorine element on spiromonomer, other element and functional groups can be incorporated in the middle of spiro orthocarbonate.
Synthetic route of the present invention is:
Following examples are only for the present invention is further described; limiting the scope of the invention can not be interpreted as; some nonessential remodeling and adjustment that the professional and technical personnel in this field makes according to the content of the invention described above, still belong to protection scope of the present invention.
Embodiment one:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol is about 100g, yield about 70%.
2. in the there-necked flask of 100ml, anhydrous sodium carbonate 0.082g is added; tosic acid 0.044g; 30ml sherwood oil is as solvent; 2g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.78g is added drop-wise in reaction system; reaction system is carried out under magnetic stirring; adopt nitrogen protection, condensing reflux under 60 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel.When thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 4 hours.
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution.Carry out rotary evaporation subsequently, solvent sherwood oil is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
Embodiment two:
1. the synthetic method of intermediate 3-chlorine-1,2-propylene glycol is identical with example one.
2. in the there-necked flask of 100ml, anhydrous sodium carbonate 0.082g is added; tosic acid 0.044g; 30ml anhydrous diethyl ether is as solvent; 2g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.78g is added drop-wise in reaction system; reaction system is carried out under magnetic stirring; adopt nitrogen protection, condensing reflux under 40 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel.When thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 4 hours.
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution.Carry out rotary evaporation subsequently, solvent anhydrous diethyl ether is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
Embodiment three:
1. the synthetic method of intermediate 3-chlorine-1,2-propylene glycol is identical with example one.
2. in the there-necked flask of 100ml, anhydrous sodium carbonate 0.082g is added; tosic acid 0.044g; 40ml sherwood oil is as solvent; 3g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.94g is added drop-wise in reaction system; reaction system is carried out under magnetic stirring; adopt nitrogen protection, condensing reflux under 60 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel.When thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 6 hours.
3., after reaction terminates, post processing mode is identical with example one.
Embodiment four:
1. the synthetic method of intermediate 3-chlorine-1,2-propylene glycol is identical with example one.
2. in the there-necked flask of 100ml, anhydrous sodium carbonate 0.082g is added; tosic acid 0.044g; 40ml anhydrous diethyl ether is as solvent; 4g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.94g is added drop-wise in reaction system; reaction system is carried out under magnetic stirring; adopt nitrogen protection, condensing reflux under 40 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel.When thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 6 hours.
3., after reaction terminates, post processing mode is identical with example two.
Embodiment five:
1. the synthetic method of intermediate 3-chlorine-1,2-propylene glycol is identical with example one.
2. in the there-necked flask of 100ml, anhydrous sodium carbonate 0.082g is added; tosic acid 0.044g; 40ml sherwood oil is as solvent; 4g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.94g is added drop-wise in reaction system; reaction system is carried out under magnetic stirring; adopt nitrogen protection, condensing reflux under 80 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel.When thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 8 hours.
3., after reaction terminates, post processing mode is identical with example one.
Embodiment six:
1. the synthetic method of intermediate 3-chlorine-1,2-propylene glycol is identical with example one.
2. in the there-necked flask of 100ml, anhydrous sodium carbonate 0.164g is added; tosic acid 0.088g; 40ml sherwood oil is as solvent; 4g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 3.56g is added drop-wise in reaction system; reaction system is carried out under magnetic stirring; adopt nitrogen protection, condensing reflux under 80 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel.When thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 8 hours.
3., after reaction terminates, post processing mode is identical with example one.
Claims (6)
1. a synthetic method for chloride screw ring orthocarbonicester monomer, is characterized in that, described method comprises:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol 100g,
2. in the there-necked flask of 100ml, add anhydrous sodium carbonate 0.082g, tosic acid 0.044g, 30ml sherwood oil is as solvent, 2g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.78g is added drop-wise in reaction system, reaction system is carried out under magnetic stirring, adopt nitrogen protection, condensing reflux under 60 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel, when thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 4 hours;
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution; Carry out rotary evaporation subsequently, solvent sherwood oil is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
2. a synthetic method for chloride screw ring orthocarbonicester monomer, is characterized in that, described method comprises:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol 100g,
2. in the there-necked flask of 100ml, add anhydrous sodium carbonate 0.082g, tosic acid 0.044g, 30ml anhydrous diethyl ether is as solvent, 2g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.78g is added drop-wise in reaction system, reaction system is carried out under magnetic stirring, adopt nitrogen protection, condensing reflux under 40 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel, when thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 4 hours;
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution; Carry out rotary evaporation subsequently, solvent anhydrous diethyl ether is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
3. a synthetic method for chloride screw ring orthocarbonicester monomer, is characterized in that, described method comprises:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol 100g,
2. in the there-necked flask of 100ml, add anhydrous sodium carbonate 0.082g, tosic acid 0.044g, 40ml sherwood oil is as solvent, 3g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.94g is added drop-wise in reaction system, reaction system is carried out under magnetic stirring, adopt nitrogen protection, condensing reflux under 60 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel, when thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 6 hours;
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution; Carry out rotary evaporation subsequently, solvent sherwood oil is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
4. a synthetic method for chloride screw ring orthocarbonicester monomer, is characterized in that, described method comprises:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol 100g,
2. in the there-necked flask of 100ml, add anhydrous sodium carbonate 0.082g, tosic acid 0.044g, 40ml anhydrous diethyl ether is as solvent, 4g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.94g is added drop-wise in reaction system, reaction system is carried out under magnetic stirring, adopt nitrogen protection, condensing reflux under 40 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel, when thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 6 hours;
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution; Carry out rotary evaporation subsequently, solvent anhydrous diethyl ether is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
5. a synthetic method for chloride screw ring orthocarbonicester monomer, is characterized in that, described method comprises:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol 100g,
2. in the there-necked flask of 100ml, add anhydrous sodium carbonate 0.082g, tosic acid 0.044g, 40ml sherwood oil is as solvent, 4g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 1.94g is added drop-wise in reaction system, reaction system is carried out under magnetic stirring, adopt nitrogen protection, condensing reflux under 80 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel, when thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 8 hours;
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution; Carry out rotary evaporation subsequently, solvent sherwood oil is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
6. a synthetic method for chloride screw ring orthocarbonicester monomer, is characterized in that, described method comprises:
1. by adding distilled water 120ml in the there-necked flask of 250ml, vitriol oil 1ml, magnetic agitation condensing reflux are in the oil bath pan of 80-90 DEG C, pear shape bottle is utilized slowly to be added drop-wise in the middle of reaction system by epoxy chloropropane 120g, after epoxy chloropropane all adds, by oil bath pan heating temperatures to 90-110 DEG C, reaction 2-6h, water white mixed solution is obtained after reaction terminates, the NaOH solution of 15% is utilized to adjust the pH value of mixed solution in 7-8, underpressure distillation steams the water in mixed solution, finally collect the cut of 140-150 DEG C/2.4KPa, obtain 3-chloro-1, 2-propylene glycol 100g,
2. in the there-necked flask of 100ml, add anhydrous sodium carbonate 0.164g, tosic acid 0.088g, 40ml sherwood oil is as solvent, 4g molecular sieve, the 3-chlorine-1,2-propylene glycol getting 3.56g is added drop-wise in reaction system, reaction system is carried out under magnetic stirring, adopt nitrogen protection, condensing reflux under 80 DEG C of water-baths, there-necked flask interpolation thermometer and dropping funnel, when thermometer registration is stablized, add tetraethyl orthocarbonate 1.35g, start timing and stir, react 8 hours;
3., after reaction terminates, there-necked flask cooling is left standstill, reacted mixed solution is filtered, filters molecular sieve and anhydrous sodium carbonate, obtain settled solution; Carry out rotary evaporation subsequently, solvent sherwood oil is removed, obtains reaction product, by purification of products, with anhydrous diethyl ether sonic oscillation washing 5 ~ 20 minutes, finally resultant product vacuum-drying is obtained product.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4849529A (en) * | 1983-02-21 | 1989-07-18 | Toagosei Chemical Industry, Ltd. | Method for production of spiro-orthocarbonate |
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| JPS5810582A (en) * | 1981-07-09 | 1983-01-21 | Toagosei Chem Ind Co Ltd | Preparation of spiroorthocarbonate |
| JPS59161382A (en) * | 1983-03-02 | 1984-09-12 | Toagosei Chem Ind Co Ltd | Spiro-orthocarbonate compound |
| JPS61171752A (en) * | 1985-01-24 | 1986-08-02 | Adeka Argus Chem Co Ltd | Halogen-containing resin composition |
| JPS63275585A (en) * | 1987-05-08 | 1988-11-14 | Showa Denko Kk | Sulfur-containing spiroorthocarbonate compound |
| JPH0684334A (en) * | 1992-09-01 | 1994-03-25 | Funai Electric Co Ltd | Information recording and reproducing device |
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| US4849529A (en) * | 1983-02-21 | 1989-07-18 | Toagosei Chemical Industry, Ltd. | Method for production of spiro-orthocarbonate |
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| Title |
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| Radical polymerization of unsaturated spiroorthocarbonate;Tagoshi, Hirotaka, 等;《Journal of Polymer Science, Part A: Polymer Chemistry》;19891231;第27卷(第4期);第1415页第16-23行 * |
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