bis(prop-2-enyl) benzene-1,2-dicarboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 1(A) was repeated, except that the diallyl phthalate crosslinking monomer was replaced by the aromatic diacrylate monomer available commercially as "Photomer" 4028 (Registered Trade Mark of Diamond Shamrock Co.) and which is believed to be essentially the diacrylate of bisphenol A. The amounts of the monomers were adjusted to give a polymer composition of ethyl acrylate 61.5%, methyl methacrylate 28%, 2-hydroxyethyl acrylate 10%, "Photomer" 4028 0.5%, and the amount of copolymer stabiliser solution in the main feed was increased from 294.9 parts to 368.6 parts. The final dispersion had a non-volatile content of 61.6%, a high-shear viscosity of 0.8 poise and a particle size ("Nanosizer" determination) of 0.25 μm. The gel content of the disperse phase was 89%. When the dispersion was applied to glass and allowed to dry, a good clear, flexible film was obtained; its extensibility was in excess of 1000%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Polyvinyl chloride resin of 54 mass % and carbon nanofibers of 1.4 mass % having an average grain diameter of 0.1 μm and a length of 5 μm as single-layer molded amorphous carbon source having a porosity of 50% and PMMA as a pore opening member to form pores were mixed together to form a composition and diallyl phthalate monomer as a plasticizer was added to this composition, the composition was then dispersed using a Henschel mixer, kneaded repeatedly a sufficient number of times using a pressure kneader to obtain a kneaded composition, which was then pelletized using a pelletizer to obtain a composition for molding. This pellet was used to perform extrusion molding for a film-like molded product having a thickness of 400 μm through extrusion molding. This film was processed in an air oven heated to 200° C. for five hours to be a carbon precursor. The film was then heated in a nitrogen gas at a temperature rising rate of 20° C./h and left for three hours at 1000° C. The film was naturally cooled and then kept under a vacuum at 1500° C. for three hours, naturally cooled, carbonization completed and a composite carbon vibration plate was thus obtained. to form pores were mixed together

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Polyvinyl chloride resin of 35 mass % and carbon nanofibers of 1.4 mass % having an average grain diameter of 0.1 μm and a length of 5 μm as amorphous carbon source and PMMA as a pore opening member to form pores were mixed together to form a composition and diallyl phthalate monomer as a plasticizer was added to this composition, the composition was then dispersed using a Henschel mixer, kneaded repeatedly a sufficient number of times using a pressure kneader to obtain a kneaded composition, which was then pelletized using a pelletizer to obtain a composition for molding. The pellet of this composition for molding was transformed into a sheet-like molded product having a thickness of 400 μm through extrusion molding, further graphite (SP270 manufactured by Nippon Graphite industries, ltd.) of 5 mass % and having an average grain diameter of on the order of 4 μm was dispersed on furan resin, both sides of which were coated with a liquid containing a hardener and hardened to be transformed into a multilayered sheet. The multilayered sheet was processed in an air oven of 200° C. for five hours to be a carbon precursor. The multilayered sheet was then heated in a nitrogen gas at a temperature rising rate of 20° C./h and left for three hours at 1000° C. The multilayered sheet was naturally cooled and then kept under a vacuum at 1500° C. for three hours, naturally cooled, carbonization completed and a composite carbon vibration plate was thus obtained. to form pores were mixed together

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.2 g of defoamer and 12 g of Fixapret COC were added to and mixed with a solution of 47 g of polyvinyl alcohol in 600 g of water. The mixture was heated to about 80° C. About 90% of a catalyst solution of 1.3 g of ammonium persulfate in 6 g of water were then added and the mixture was homogenized for about 5 minutes. A mixture of 460 g of vinyl acetate and 10 g of dibutyl phthalate was then added over a period of about 3.5 to 4 hours so that the temperature stayed between 82 and 88° C. After the monomer mixture had been added, the remaining catalyst solution was added and the reaction mixture was stirred for about 1 hour at a temperature of about 90° C. The solids content was then adjusted to about 55%. After the dispersion had cooled to a temperature of about 35 to about 40° C., 15 g of dibutyl phthalate were added. The product thus obtained had a pH of 4.2 and a viscosity (5/2120) of 44,000 cps. 0.2 g of defoamer and 12 g of Fixapret COC were added to and was then added over a period of about 3.5 to 4 hours so that the temperature stayed between 82 and 88° C After the monomer mixture had been added the remaining catalyst solution was added the reaction mixture was stirred for about 1 hour at a temperature of about 90° C were added The product thus obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using a method similar to the known preparation of diallyl phthalate by reacting allyl chloride with metal salts of phthalic acid, Matsumoto et al prepared DATCP by reacting disodium tetrachlorophthalate with 2 moles of allyl chloride in an aqueous solution containing cuprous ions. Diallyl tetrachlorophthalate was also produced by Guseinov et al who reacted the anhydride with 3 moles of allyl alcohol plus 1 mole of hydrochloric acid in a benzene solution (Azerbaizhan Chemical Journal, No. 6, (1964), 21-23). Nordlander et al also produced DATCP by reacting the tetrachlorophthalic anhydride with 2 moles of allyl alcohol using sulfuric acid as a catalyst and driving off the water of reaction by distillation as an azeotrope with benzene (Journal of the American Chemical Society, 69, Nov., (1947), 2679-2682). However, only a 10% to 15% yield of the DATCP was obtained because of dehydration and polymerization reactions of the allyl alcohol. prepared DATCP

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The term "addition-polymerizable unsaturated compound" as used herein is intended to indicate compounds having at least one carbon-carbon double bond capable of taking an active part in the addition polymerization reaction. Examples of such compounds include those having at least one group selected from a vinyl group, a vinylidene group, a fumaroyl group and a maleoyl group. Specific examples of such compounds include unsaturated monocarboxylic acids such as acrylic acid and methacrylic acid; esters of acrylic acid or methacrylic acid having as an ester-forming group an alkyl group, a cycloalkyl group, a halogenated alkyl group, an alkoxyalkyl group, a hydroxyalkyl group, an aminoalkyl group, a tetrahydrofurfuryl group, an allyl group, a glycidyl group, a benzyl group or a phenoxy group; mono- or di-acrylates and mono- or di-methacrylates of alkylene glycols or polyoxyalkylene glycols (number average molecular weight: up to 2,000); polyacrylates and polymethacrylates such as trimethylopropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetraacrylate and pentaerythritol tetramethacrylate; unsaturated monocarboxylic acid amides such as acrylamide and methacrylamide; derivatives of acrylamide or methacrylamide such as N-alkyl- or N,N-dialkyl-acrylamides, N-alkyl- or N,N-dialkyl-methacrylamides, N-hydroxyalkyl- or N,N-dihydroxyalkyl-acrylamide, N-hydroxyalkyl- or N,N-dihyroxyalkyl-methacrylamides, diacetone acrylamide, diacetone methacrylamide, N,N'-alkylenebisacrylamide and N,N'-alkylenebismethacrylamide; allyl compounds such as allyl alcohol, allyl isocianate, diallyl phthalate and triallyl cyanurate; unsaturated dicarboxylic acids and acid anhydrides such as maleic acid, maleic anhydride, fumaric acid and itaconic acid; monoesters and diesters of maleic acid, fumaric acid or itaconic acid having as an ester-forming group one or two groups selected from an alkyl group, a halogenated alkyl group and an alkoxy-alkyl group; acrylates and methacrylates of epoxy group-containing compounds obtained by esterifying acrylic acid or methacrylic acid with an epoxy group-containing compound which is obtained, for example, by the dehydrochlorination reaction of a polyhydric alcohol or a polyhydric phenol with epichlorohydrin; and other unsaturated compounds such as styrene, vinyltoluene, divinylbenzene, N-vinylcarbazole, and N-vinylpyrrolidone. Various resins and polymers may also be used as the addition-polymerizable unsaturated compound. Examples of such resins and polymers include unsaturated polyesters prepared from at least one unsaturated dicarboxylic acid, such as maleic acid, fumaric acid or itaconic acid, and/or its anhydride, and at least one polyhydric alcohol such as ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, glycerin, trimethylolpropane or penta-erythritol; unsaturated polyesters prepared from at least one unsaturated dicarboxylic acid or its anhydride as mentioned above, at least one polyhydric alcohol as mentioned above, and at least one saturated dicarboxylic acid or its anhydride such as succinic acid, adipic acid, phthalic acid, isophthalic acid, phthalic anhydride, trimellitic acid or trimellitic acid anhydride; alkyd resins prepared by using at least one drying oil and/or at least one semidrying oil as a modifier for polyesters; unsaturated polyurethanes having addition-polymerizable unsaturated groups derived from at least one unsaturated mono- or di-carboxylic acid or its ester derivative or an unsaturated polyester as mentioned above and introduced thereinto by utilizing terminal isocyanate and/or hydroxyl groups of a urethane compound or polyurethane having urethane groups derived from at least one polyol having two or more hydroxyl groups and at least one polyisocyanate, for example, unsaturated polyurethanes which are prepared from (1) a polyurethane having terminal isocyanate and/or hydroxyl groups and prepared from at least one polyol such as a polyhydric alcohol as mentioned above, a polyester polyol or a polyether polyol and at least one polyisocyanate such as tolylene diisocyanate, diphenylmethane-4,4'-diisocyanate or hexamethylene diisocyanate and (2) at least one unsaturated mono- or di-carboxylic acid as mentioned above or its ester or polyester having active hydrogen atoms derived from hydroxyl (reactive with the terminal isocyanate) and/or carboxyl (reactive with both of the terminal isocyanate and the terminal hydroxyl) and/or amino groups (reactive with the terminal isocyanate), if any; polyisocyanate-modified unsaturated polyester obtained by linking two or more molecules of an unsaturated polyester as mentioned above with a polyisocyanate; polymers having, in its side chains, carbon-carbon double bonds capable of taking an active part in the addition polymerization reaction, for example, polymers obtained by reacting an unsaturated carboxylic acid or its anhydride with a polymer having hydroxyl groups such as polyvinyl alcohol or cellulose, polymers obtained by esterifying a polymer or a copolymer of acrylic acid or methacrylic acid having carboxyl groups with an unsaturated alcohol such as allyl alcohol, glycidyl acrylate or glycidyl methacrylate, a polymer obtained by reacting a copolymer containing maleic anhydride monomer units with allyl alcohol, a hydroxyalkyl acrylate and/or a hydroxy-alkyl methacrylate, and a polymers obtained by reacting a copolymer having glycidyl acrylate and/or glycidyl methacrylate monomer units with acrylic acid and/or methacrylic acid. Various oligomers may also be used as the addition-polymerizable unsaturated compound. Examples of such oligomers include oligomers of an ester-acrylate type obtained by the co-condensation of an esterification reaction system composed of a polycarboxylic acid or its anhydride and a polyhydric alcohol with acrylic acid and/or methacrylic acid and having a number average molecular weight of about 200 to about 5,000, said molecular weight being controlled by choosing an appropriate molar ratio of the raw materials, examples of said polycarboxylic acid or its anhydride being adipic acid, isophthalic acid, phthalic acid and phthalic anhydride, examples of said polyhydric alcohol being ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, glycerin, trimethylolpropane and pentaerythritol. The above-enumerated addition-polymerizable unsaturated compounds may be used either alone or in combination. In the addition-polymerizable unsaturated compounds, by the alkyl is meant a straight chain or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms, by the cycloalkyl a group having 5 to 26 carbon atoms and consisting of a 5- or 6-membered alicyclic ring unsubstituted or substituted with alkyl, and by the alkylene a straight or branched hydrocarbon group having 2 to 6 carbon atoms. The number average molecular weight of a resin or polymer is desired to be up to 1,000,000, preferably 1,000 to 200,000. For the measurement of a number average molecular weight, there is adopted a gel permeation chromatography (GPC) method using, as a standard sample, a polystyrene manufactured by Pressure Chemical Co., U.S.A. and as an apparatus, WATERS 200 manufactured by Japan-Waters Co., Japan.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.68 kg of trimethylolpropane, 3.03 kg of acrylic acid, 0.5 kg of an acid ion exchanger (Lewatit 3333 of BAYER AG), 9 g of hydroquinone monomethyl ether and 1.5 liters of petroleum ether (boiling range 60° to 70° C) were heated under a water separator, whilst stirring, in a 10 liter three-necked flask equipped with a stirrer, water separator and gas inlet tube. At the same time, a constant stream of air was passed through the flask at about 2 liters/hour. Over the course of the entire reaction time of 72 hours, during which an acid number of 17 was reached, a total of 20 ml of diallyl phthalate was added dropwise to the reaction mixture. The petroleum ether was distilled off, remnants being removed by applying a vacuum of approx. 4 mm Hg at a product temperature of 40° C. The esterification catalyst was filtered off. The resulting trimethylolpropane diacrylate mixture was pale yellowish and clear. The viscosity corresponded to a time of outflow of 186 seconds, measured in a DIN cup 4, at 20° C. equipped with a stirrer Over the course of the entire reaction time of 72 hours The petroleum ether was distilled off remnants being removed at a product temperature of 40° C The esterification catalyst was filtered off corresponded to a time of outflow of 186 seconds measured in a DIN cup 4, at 20° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 1(A) was repeated, except that the diallyl phthalate crosslinking monomer was replaced by the aromatic diacrylate monomer available commercially as "Photomer" 4028 (Registered Trade Mark of Diamond Shamrock Co.) and which is believed to be essentially the diacrylate of bisphenol A. The amounts of the monomers were adjusted to give a polymer composition of ethyl acrylate 61.5%, methyl methacrylate 28%, 2-hydroxyethyl acrylate 10%, "Photomer" 4028 0.5%, and the amount of copolymer stabiliser solution in the main feed was increased from 294.9 parts to 368.6 parts. The final dispersion had a non-volatile content of 61.6%, a high-shear viscosity of 0.8 poise and a particle size ("Nanosizer" determination) of 0.25 μm. The gel content of the disperse phase was 89%. When the dispersion was applied to glass and allowed to dry, a good clear, flexible film was obtained; its extensibility was in excess of 1000%.