JPH0291121A - Preparation of aromatic polyformal resin - Google Patents
Preparation of aromatic polyformal resinInfo
- Publication number
- JPH0291121A JPH0291121A JP24261388A JP24261388A JPH0291121A JP H0291121 A JPH0291121 A JP H0291121A JP 24261388 A JP24261388 A JP 24261388A JP 24261388 A JP24261388 A JP 24261388A JP H0291121 A JPH0291121 A JP H0291121A
- Authority
- JP
- Japan
- Prior art keywords
- water
- resin
- solvent
- polyformal
- polyformal resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 27
- 239000011347 resin Substances 0.000 title claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 title claims description 6
- 239000002904 solvent Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 abstract description 4
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYVUZHAPQWPWKJ-UHFFFAOYSA-N 2-(2-phenylpropyl)phenol Chemical compound C=1C=CC=CC=1C(C)CC1=CC=CC=C1O TYVUZHAPQWPWKJ-UHFFFAOYSA-N 0.000 description 1
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical group OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- -1 3-dihydroxybenzene Chemical class 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- BKTRENAPTCBBFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)propan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 BKTRENAPTCBBFA-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、機械、電気・電子機器、光学機器等の素材と
して有用な高重合度のポリホルマール樹脂を短時間で合
成することができる芳香族ポリホルマール樹脂の製造方
法に関する。[Detailed Description of the Invention] [Field of Industrial Application] The present invention is an aromatic resin that can be synthesized in a short time into a polyformal resin with a high degree of polymerization, which is useful as a material for machines, electrical/electronic equipment, optical equipment, etc. The present invention relates to a method for producing a group polyformal resin.
光学材料、特に光学機器用素材としてポリホルマール樹
脂を利用する研究が近年数多くなされるようになってき
た。これはポリホルマール樹脂がポリカーボネート樹脂
のように有毒なホスゲンを使用せずに製造できることが
製造上の大きな長所となっているためである。In recent years, much research has been conducted on the use of polyformal resins as optical materials, particularly as materials for optical devices. This is because polyformal resin has a major manufacturing advantage in that it can be manufactured without using toxic phosgene, unlike polycarbonate resin.
しかしながら、例えば米国特許第４２６０７３３号明細
書に記載されているように、従来のポリホルマール樹脂
は、二価フェノール類と塩化メチレンを非プロトン性極
性溶媒中でアルカリ金属水酸化物の存在下で反応させる
ことにより合成しているが１．アルカリ金属水酸化物が
溶媒に溶けにくく、そのため二価フェノール類の七ツマ
−が塩を形成するのに長時間を要し、重合速度が遅いと
いう欠点があった。However, as described for example in U.S. Pat. No. 4,260,733, conventional polyformal resins are produced by reacting dihydric phenols and methylene chloride in an aprotic polar solvent in the presence of an alkali metal hydroxide. It is synthesized by 1. The alkali metal hydroxide is difficult to dissolve in a solvent, so it takes a long time for the dihydric phenols to form a salt, resulting in a slow polymerization rate.
本発明は、前記事情に基づいてなされたもので、その目
的とするところは、短時間で高重合度のポリホルマール
樹脂を製造することができる生産性に優れた芳香族ポリ
ホルマール樹脂の製造方法を提供することにある。The present invention has been made based on the above-mentioned circumstances, and its purpose is to produce an aromatic polyformal resin with excellent productivity by which a polyformal resin with a high degree of polymerization can be produced in a short period of time. Our goal is to provide the following.
本発明者らは、前記課題を解決するために鋭意研究を重
ねた結果、樹脂の合成の際、反応系に少量の水を添加す
るとにより、前記目的を満足する製造法が得られること
を見出し、この知見に基づいて本発明を完成するに至っ
た。As a result of extensive research in order to solve the above-mentioned problems, the present inventors have discovered that a manufacturing method that satisfies the above-mentioned objectives can be obtained by adding a small amount of water to the reaction system during resin synthesis. Based on this knowledge, the present invention was completed.
すなわち、本発明は、弐〇〇−Ａｒ−ＯＨ（但し、Ａｒ
は芳香族基である）で表される二価フェノールとメチレ
ンジハライドとの反応を、溶媒中で、アルカリ金属水酸
化物と水の存在下におこなうことを特徴とする芳香族ポ
リホルマール樹脂の製造方法を提供するものである。That is, the present invention provides 2〇〇-Ar-OH (however, Ar
is an aromatic group) and methylene dihalide in a solvent in the presence of an alkali metal hydroxide and water. A manufacturing method is provided.
本発明で用いられる前記二価フェノールとしては特に制
限はないが、通常、１．４−ジヒドロキシベンゼン、１
．３−ジヒドロキシベンゼン、１゜２−ジヒドロキシベ
ンゼン、２，５−ジヒドロキシビフェニル等のジヒドロ
キシベンゼン化合物、４．４′−ジヒドロキシビフェニ
ル、ジヒドロキシナフタレン等のジヒドロキシ芳香族化
合物、２゜２−ビス（４−ヒドロキシフェニル）プロパ
ン、２．２−ビス（３−メチル−４−ヒドロキシフェニ
ル）プロパン、２，２−ビス（３−フェニル−４−ヒド
ロキシフェニル）プロパン、２．２−ビス（４−ヒドロ
キシフェニル）−２−フェニルエタン、４．４’−ジヒ
ドロキシテトラフェニルメタン等のビスフェノール類が
用いられる。The dihydric phenol used in the present invention is not particularly limited, but usually 1,4-dihydroxybenzene, 1
．． Dihydroxybenzene compounds such as 3-dihydroxybenzene, 1゜2-dihydroxybenzene, 2,5-dihydroxybiphenyl, dihydroxy aromatic compounds such as 4,4'-dihydroxybiphenyl, dihydroxynaphthalene, 2゜2-bis(4-hydroxy phenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)- Bisphenols such as 2-phenylethane and 4,4'-dihydroxytetraphenylmethane are used.
これらの二価フェノールは単独又は混合して用いられる
。These dihydric phenols may be used alone or in combination.
得られるポリホルマール樹脂を光学的材料として用いる
場合は、二価フェノールとしてビスフェノール類を用い
ることが好ましい。When using the obtained polyformal resin as an optical material, it is preferable to use bisphenols as the dihydric phenol.
メチレンジハライドとしては、塩化メチレン、臭化メチ
レンが用いられるが、好ましくは塩化メチレンが用いら
れる。As the methylene dihalide, methylene chloride and methylene bromide are used, and methylene chloride is preferably used.
また、アルカリ金属水酸化物としては、水酸化ナトリウ
ム、水酸化カリウム等が用いられるが、好ましくは水酸
化ナトリウムが用いられる。Further, as the alkali metal hydroxide, sodium hydroxide, potassium hydroxide, etc. are used, and sodium hydroxide is preferably used.
溶媒としては、好ましくは、Ｎ、Ｎ−ジメチルホルムア
ミド、ヘキサメチルホスホルアミド、Ｎ−メチル−２−
ピロリドン、ジメチルスルホキシド、ジメチルイミダゾ
リジノン等の非プロトン性極性溶媒が用いられ、特にジ
メチルイミダゾリジノンが好適に用いられる。As a solvent, preferably N,N-dimethylformamide, hexamethylphosphoramide, N-methyl-2-
Aprotic polar solvents such as pyrrolidone, dimethyl sulfoxide, and dimethylimidazolidinone are used, and dimethylimidazolidinone is particularly preferably used.
水は溶媒に対して通常１〜２０重量％、好ましくは５〜
１０重量％添加して用いられる。水の量が１重量％未満
であると重合速度はそれほど速くならず、また２０重量
％を超えると生成重合体が析出するため、いずれも好ま
しくない。Water is usually 1 to 20% by weight, preferably 5 to 20% by weight based on the solvent.
It is used by adding 10% by weight. If the amount of water is less than 1% by weight, the polymerization rate will not be very high, and if it exceeds 20% by weight, the produced polymer will precipitate, so both are not preferred.
各反応物の使用量は、二価フェノール１に対して重量比
でメチレンジハライドが好ましくは１．０５〜５となる
ように、アルカリ金属水酸化物が好ましくは２．１〜３
．０、さらに好ましくは２．２〜２゜８となるように用
いられ、溶媒は二価フェノールの濃度が好ましくは０．
１〜３モル／β、さらに好ましくは０．５〜２モル／ｌ
となるように用いられる。The amount of each reactant to be used is such that methylene dihalide is preferably used in a weight ratio of 1.05 to 5, and alkali metal hydroxide is preferably used in a weight ratio of 2.1 to 3.
．． The concentration of dihydric phenol in the solvent is preferably 0.0, more preferably 2.2 to 2.8.
1 to 3 mol/β, more preferably 0.5 to 2 mol/l
It is used as follows.
各反応物の反応器への投入順序は特に限定はされないが
、通常これらの反応物を同時に投入して撹拌下でハロゲ
ン化シバライドを還流させながら反応を行う。Although the order in which the reactants are introduced into the reactor is not particularly limited, these reactants are usually introduced at the same time and the reaction is carried out while stirring and refluxing the halogenated cybaride.
反応温度は好ましくは５０〜１００℃、さらに好ましく
は６０〜９０℃で、好ましくは５分〜２時間反応させる
。反応時間は添加する水の量、合成するポリホルマール
樹脂の分子量に応じて適宜決定すればよい。The reaction temperature is preferably 50 to 100°C, more preferably 60 to 90°C, and preferably 5 minutes to 2 hours. The reaction time may be appropriately determined depending on the amount of water added and the molecular weight of the polyformal resin to be synthesized.
また、反応に際し必要に応じ、フェノール、フェニルフ
ェノール、オクチルフェノール、ｐ−ｔ−プチルフェノ
ール、２−ヒドロキシフェニル２−フェニルプロパン等
の末端停止剤を反応系に加えて反応を行ってもよい。Further, during the reaction, if necessary, a terminal capping agent such as phenol, phenylphenol, octylphenol, pt-butylphenol, 2-hydroxyphenyl-2-phenylpropane, etc. may be added to the reaction system.
このようにして、反応を行い、０．５ ｇ ／ ｄｌ’
ＩＱ度の塩化メチレン溶液の２０℃における還元粘度（
７７ｓｌ）／Ｃ）が好ましくは０．２〜１．Ｏｊ／ｇの
ポリホルマール樹脂を得る。In this way, the reaction was carried out and 0.5 g/dl'
Reduced viscosity at 20°C of a methylene chloride solution of IQ degree (
77sl)/C) is preferably 0.2 to 1. Oj/g polyformal resin is obtained.
このようにして得られたポリホルマール樹脂には光学的
性質を損なわない範囲で、必要に応じ、酸化防止剤、紫
外線吸収剤、滑剤、着色剤等通常ポリホルマール樹脂に
添加される添加剤を配合することができる。The polyformal resin thus obtained is blended with additives that are normally added to polyformal resins, such as antioxidants, ultraviolet absorbers, lubricants, and colorants, as necessary, to the extent that optical properties are not impaired. can do.
以下、本発明を実施例に基づいて詳細に説明するが、本
発明はこれに限定されるものではない。Hereinafter, the present invention will be explained in detail based on Examples, but the present invention is not limited thereto.
０、２９ ｄｒｙ’ ｇであった。It was 0.29 dry'g.
実施例２
溶媒中の水の濃度を１０重貴簡にした他は実施例１と同
様の操作を行い、還元粘度〔ηｓｐ／ｃ） ０゜３１ａ
／ｇのポリホルマール樹脂を得た。Example 2 The same operation as in Example 1 was carried out except that the concentration of water in the solvent was changed to 10 times the concentration, and the reduced viscosity [ηsp/c) was 0°31a.
/g of polyformal resin was obtained.
実施例１
反応器に４，４′−ジヒドロキシテトラフェニルメタン
８８０ｇ（２，５モル）、水酸化ナトリウム２２０ｇ（
５，５モル）、塩化メチレン２５５ｇ（３，０モル）及
び水を１５重量％含有する溶媒のジメチルイミダゾリジ
ノン２５００−を入れ、撹拌下に塩化メチレンの還流温
度で６０分間反応させた。反応終了後、生成物を冷却し
て塩化メチレン１０βを加えて希釈し、０．０１規定の
塩酸及び水でそれぞれ洗浄し、有機層を分離してメタノ
ール中に注入してポリホルマール樹脂を析出回収した。Example 1 880 g (2.5 mol) of 4,4'-dihydroxytetraphenylmethane and 220 g (2.5 mol) of sodium hydroxide were placed in a reactor.
5.5 moles), 255 g (3.0 moles) of methylene chloride, and 2500 g of dimethylimidazolidinone, a solvent containing 15% by weight of water, were added, and the mixture was reacted for 60 minutes at the reflux temperature of methylene chloride while stirring. After the reaction, the product is cooled, diluted with methylene chloride 10β, washed with 0.01N hydrochloric acid and water, and the organic layer is separated and poured into methanol to precipitate and recover the polyformal resin. did.
ここで得られた重合体の還元粘度〔ηｓｐ／ｃ）（塩化
メチレン中０．５ｇ／ｄ！、２０℃で測定）は実施例３
溶媒中の水の濃度を５重量％にし、かつ反応時間を４５
分とした他は実施例１と同様の操作を行い、還元粘度〔
ηｓｐ／ｃ） ０．５４ ａ ／ ｇのポリホルマール
樹脂を得た。The reduced viscosity [ηsp/c] (0.5 g/d in methylene chloride!, measured at 20°C) of the polymer obtained here was determined in Example 3.The concentration of water in the solvent was 5% by weight, and the reaction time was 45
The same operation as in Example 1 was carried out except that the reduced viscosity [
A polyformal resin with a ηsp/c) of 0.54 a/g was obtained.
比較例１
水を含有しない溶媒を用い、かつ反応時間を４時間とし
た他は実施例１と同様の操作を行い、還元粘度〔ηｓｐ
／ｃ） ０．３２のポリホルマール樹脂を得た。Comparative Example 1 The same operation as in Example 1 was carried out except that a water-free solvent was used and the reaction time was 4 hours.
/c) 0.32 polyformal resin was obtained.
実施例４
二価フェノールとして、２．２−ビス（４−ヒドロキシ
フェニル）プロパン５７Ｑｇ（２，５−１−ル）を用い
、反応時間を５０分間としたほかは実施例１と同様の操
作を行い、還元粘度〔ηｓｐ／ｃ）０．３９ｄｌ／ｇの
ポリホルマール樹脂を得た。Example 4 The same procedure as in Example 1 was carried out except that 57Qg (2,5-1-l) of 2,2-bis(4-hydroxyphenyl)propane was used as the dihydric phenol and the reaction time was 50 minutes. A polyformal resin having a reduced viscosity [ηsp/c] of 0.39 dl/g was obtained.
還元粘度〔η３ｐ／ｃ） ０．３４ ａ ／ ｇのボ’
） ＊ ルマール樹脂を得た。Bo' with reduced viscosity [η3p/c) 0.34 a/g
) *Remarre resin was obtained.
以上の結果をまとめて第１表に示す。The above results are summarized in Table 1.
実施例５
溶媒中の水の濃度を１０重量％にしたほかは実施例４と
同様にして、還元粘度（ηｓｐ／ｃ） ０．４４ｄｉ／
ｇのポリホルマール樹脂を得た。Example 5 The same procedure as Example 4 was carried out except that the concentration of water in the solvent was 10% by weight, and the reduced viscosity (η sp/c) was 0.44 di/
A polyformal resin of g was obtained.
実施例６
溶媒中の水の濃度を５重量％とし、かつ反応時間を３５
分間としたほかは、実施例４と同様にして、還元粘度（
ηｓｐ／ｃ） ｏ、 ６７ ｄ１７ ｇのポリホルマー
ル樹脂を得た。Example 6 The concentration of water in the solvent was 5% by weight, and the reaction time was 35% by weight.
The reduced viscosity (
ηsp/c) o, 67 d17 g of polyformal resin was obtained.
比較例２
水を含有しない溶媒を用い、かつ反応時間を１８０分間
としたほかは、実施例４と同様にして、第１表
〔発明の効果〕
本発明によれば、水を添加するという極めて筒車な方法
によって、高重合度のポリホルマール樹脂を短時間で合
成することができ、本発明の工業的価値は極めて大であ
る。Comparative Example 2 The same procedure as in Example 4 was carried out except that a water-free solvent was used and the reaction time was 180 minutes. Polyformal resins with a high degree of polymerization can be synthesized in a short time by a simple method, and the industrial value of the present invention is extremely large.
Claims (1)
）で表される二価フェノールとメチレンジハライドとの
反応を、溶媒中で、アルカリ金属水酸化物と水の存在下
におこなうことを特徴とする芳香族ポリホルマール樹脂
の製造方法。1. Reacting the dihydric phenol represented by the formula HO-Ar-OH (where Ar is an aromatic group) with methylene dihalide in a solvent in the presence of an alkali metal hydroxide and water. A method for producing an aromatic polyformal resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24261388A JPH0291121A (en) | 1988-09-29 | 1988-09-29 | Preparation of aromatic polyformal resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24261388A JPH0291121A (en) | 1988-09-29 | 1988-09-29 | Preparation of aromatic polyformal resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0291121A true JPH0291121A (en) | 1990-03-30 |
Family
ID=17091658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24261388A Pending JPH0291121A (en) | 1988-09-29 | 1988-09-29 | Preparation of aromatic polyformal resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0291121A (en) |
-
1988
- 1988-09-29 JP JP24261388A patent/JPH0291121A/en active Pending
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