JPS62201832A - Reaction product of phenolic compound and aromatic aldehyde and production thereof - Google Patents
Reaction product of phenolic compound and aromatic aldehyde and production thereofInfo
- Publication number
- JPS62201832A JPS62201832A JP28389986A JP28389986A JPS62201832A JP S62201832 A JPS62201832 A JP S62201832A JP 28389986 A JP28389986 A JP 28389986A JP 28389986 A JP28389986 A JP 28389986A JP S62201832 A JPS62201832 A JP S62201832A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic aldehyde
- polymerization
- pyrogallol
- hydroxyhydroquinone
- molecular weight
- 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
- 150000002989 phenols Chemical class 0.000 title claims abstract description 15
- 150000003934 aromatic aldehydes Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000007795 chemical reaction product Substances 0.000 title description 7
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims abstract description 25
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229940079877 pyrogallol Drugs 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract 2
- 238000009833 condensation Methods 0.000 claims abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 25
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 9
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract description 8
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 4
- -1 cresole Chemical compound 0.000 abstract description 2
- 230000008021 deposition Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000002265 prevention Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000007423 decrease Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- MPJLLBLFMGXUNW-UHFFFAOYSA-N 1,3,5-tribromocyclohexa-2,4-dien-1-ol Chemical compound OC1(Br)CC(Br)=CC(Br)=C1 MPJLLBLFMGXUNW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、フェノール性化合物と芳香族アルデヒドとの
反応物およびその製造方法に関するものである。この化
合物を、塩化ビニルの重合にあたり、予め重合器内各部
に塗布しておくことにより重合体スケールの発生を防止
することができる。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a reaction product of a phenolic compound and an aromatic aldehyde and a method for producing the same. By applying this compound to various parts of the polymerization vessel in advance during the polymerization of vinyl chloride, it is possible to prevent the formation of polymer scale.
（従来の技術と問題点）
塩化ビニルを分散剤および油醍性触媒の存在下に水性媒
体中で懸濁重合する場合、あるいは乳化剤と水溶性触媒
の存在下、乳化重合する場合、あるいは塊状重合する場
合、いずれの重合形式においても、重合器の内面に重合
体のスケールが付着するという問題がある。このスケー
ル付着の為に、重合器壁の伝熱効率の低下、製品収率の
低下、剥離スケールの製品への混入による品質の低下、
スケールの剥離に要する労力、および剥離に要する時間
がもたらす重合器の稼動率の低下など好ましくない多く
の不利益が生じる。これらの問題を解決する１こめに、
スケールの生成や付着を防止する多くの化合物が既に提
案されているが、一長一短があり、適当な解決方法は未
だ見い出さｎていない。(Prior art and problems) When vinyl chloride is subjected to suspension polymerization in an aqueous medium in the presence of a dispersant and an oil-soluble catalyst, when emulsion polymerization is performed in the presence of an emulsifier and a water-soluble catalyst, or when vinyl chloride is subjected to bulk polymerization. In either case, there is a problem in that polymer scale adheres to the inner surface of the polymerization vessel. Due to this scale adhesion, the heat transfer efficiency of the polymerization vessel wall decreases, the product yield decreases, and the quality decreases due to the contamination of peeled scale into the product.
Many undesirable disadvantages arise, such as the labor required for peeling off scale and the time required for peeling off, such as a reduction in the operating rate of the polymerization reactor. To solve these problems,
Many compounds that prevent scale formation and adhesion have already been proposed, but they have advantages and disadvantages, and no suitable solution has yet been found.
（問題点を解決するための手段及び作用効果）発明者ら
は、この問題を解決する為に、各種化合物を合成し、乳
化重合、懸濁重合、塊状重合におけるスケール防止効果
を検討した結果、次に示されるフェノール性化合物と芳
香族アルデヒドとの反応物が非常に有効であることを見
出し、本発明を完成した。(Means and effects for solving the problem) In order to solve this problem, the inventors synthesized various compounds and studied their scale prevention effects in emulsion polymerization, suspension polymerization, and bulk polymerization. The present invention was completed based on the discovery that the following reaction product of a phenolic compound and an aromatic aldehyde is very effective.
ここにフェノール性化合物と芳香族アルデヒドとの反応
物とは、ピロガロールあるいはヒドロキシヒドロキノン
単独又はこれを含む他のフェノール性化合物と芳香族ア
ルデヒドとの反応によって得られる分子量３０８から２
０００までの化合物をいう。該化合物としては、たとえ
ばピロガロールとベンズアルデヒドとの反応物、ヒドロ
キシヒドロキノンとベンズアルデヒドとの反応物があげ
られる。Here, the reaction product of a phenolic compound and an aromatic aldehyde refers to a product having a molecular weight of 308 to 2, which is obtained by reacting pyrogallol or hydroxyhydroquinone alone or other phenolic compound containing this with an aromatic aldehyde.
Refers to compounds up to 000. Examples of the compound include a reaction product of pyrogallol and benzaldehyde, and a reaction product of hydroxyhydroquinone and benzaldehyde.
本発明による化合物は、ピロガロールあるいはヒドロキ
シヒドロキノンを酸性条件下、水性媒体中あるいはアル
コール性媒体中で温度６０°Ｃから１２０°Ｃの範囲内
で芳香族アルデヒドと反応させることにより合成される
。さらに、他のフェノール性化合物をピロガロールある
いはヒドロキシヒドロキノンと共（ζ用いる場合も同様
な方法によって合成できる。The compounds according to the invention are synthesized by reacting pyrogallol or hydroxyhydroquinone with an aromatic aldehyde under acidic conditions in an aqueous or alcoholic medium at a temperature in the range from 60°C to 120°C. Furthermore, when other phenolic compounds are used together with pyrogallol or hydroxyhydroquinone (ζ), they can be synthesized by the same method.
他のフェノール性化合物とは、たとえばフェノール、ｐ
−ブロムフェノール、１，３．５−トリブロムフェノー
ル、２．６−シメチルフエノール、クレゾール、２価フ
ェノールとしてはカテコール、ヒドロキノン、レゾルシ
ン、４−ｔ−ブチル−１，２−ジヒドロキシベンゼンな
ど、３価フェノールとしてはフロログリシンなどが挙げ
られたが、これらに限定されるものではない。Other phenolic compounds include, for example, phenol, p
- Bromophenol, 1,3.5-tribromophenol, 2.6-dimethylphenol, cresol, dihydric phenols such as catechol, hydroquinone, resorcinol, 4-t-butyl-1,2-dihydroxybenzene, etc. Examples of the phenol include phloroglycin, but are not limited to these.
これらのフェノール性化合物もピロガロールあるいはヒ
ドロキシヒドロキノンと共に用いることができるが、顕
著なスケール防止効果を発現するのはピロガロールある
いはヒドロキシヒドロキノンの骨格であるので、他のフ
ェノール性化合物は５０モル％以下であることが好まし
い。These phenolic compounds can also be used together with pyrogallol or hydroxyhydroquinone, but since it is the skeleton of pyrogallol or hydroxyhydroquinone that exhibits a significant scale prevention effect, the content of other phenolic compounds should be 50 mol% or less. is preferred.
塩化ビニル重合用のスケール防止用塗布剤としては合成
上、水に対する溶解性が良いことや、コスト的にも安価
であること等によりピロガロール、あるいはヒドロキシ
ヒドロキノンのみが有利である。As a coating agent for preventing scale for vinyl chloride polymerization, only pyrogallol or hydroxyhydroquinone is advantageous due to its good solubility in water and low cost in terms of synthesis.
芳香族アルデヒドはベンゼン核置換体を有するアルデヒ
ドが使用できるが、塩化ビニル重合用のスケール防止用
塗布剤としては無置換ベンズアルデヒドの更用がコスト
的に最も有利である。用いるアルデヒドの量は、フェノ
ール性化合物１モルに対して０．１−１モルの範囲で使
用できる。As the aromatic aldehyde, an aldehyde having a substituted benzene nucleus can be used, but unsubstituted benzaldehyde is most advantageous in terms of cost as a scale prevention coating agent for vinyl chloride polymerization. The amount of aldehyde used can range from 0.1 to 1 mole per mole of the phenolic compound.
本発明の化合物は、塩化ビニルを主成分とするあらゆる
形態の重合法に適用でき、重合終了後、重合器内各部へ
のスケールの付着は全く認められない。これらの化合物
を使用するときには適当な浴剤で稀釈して重合器の内面
や攪拌翼、バッフルプレートなどスケールの付着しやす
い器内各部に塗布すればよい。溶剤としては、特に限定
するものではなく、テトラヒドロフラン、ジオキサン、
メタノール、エタノール、アセトン、ジメチルホルムア
ミド、ジメチルスルホキシド、クロロホルム、１．１．
１−１−リクロルエタン、水など及びこれらの混合物が
使用できる。The compound of the present invention can be applied to all types of polymerization methods in which vinyl chloride is the main component, and no scale is observed to adhere to any part of the polymerization vessel after completion of the polymerization. When using these compounds, they may be diluted with a suitable bath agent and applied to various parts of the vessel where scale tends to adhere, such as the inner surface of the polymerization vessel, stirring blades, and baffle plates. The solvent is not particularly limited, and may include tetrahydrofuran, dioxane,
Methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, chloroform, 1.1.
1-1-lichloroethane, water, etc. and mixtures thereof can be used.
前記化合物の塗布量は通常０．００１Ｆ／ｍから５ｆ／
ｄの範囲であるが、塗布量の上限については、特に悪影
響がない限り５ｆ／ｎ１以上での使用を妨げるものでは
ない。The coating amount of the above compound is usually from 0.001F/m to 5f/m.
d, but the upper limit of the coating amount does not preclude use at 5f/n1 or more unless there is any particular adverse effect.
（実施例）
次に、本発明を実施例により更に具体的に説明するが、
これらはいずれも本発明の範囲を限定するものではない
。(Example) Next, the present invention will be explained in more detail with reference to Examples.
None of these are intended to limit the scope of the invention.
実施例１
ピロガロール４７８ ｆ （８ｍｏｌ ）を２１の水に
溶解させ、ベンズアルデヒド２ Ｌ ２１ （２ｍｏｌ
）及びリン酸５８８ｆ（６ｍｏｌ）を添加し、油浴の
温度１２０°Ｃに設定し、４時間反応させた所、水に不
溶の生成物が得られた。Example 1 Pyrogallol 478 f (8 mol) was dissolved in 21 water, and benzaldehyde 2 L 21 (2 mol
) and 588f (6 mol) of phosphoric acid were added, the temperature of the oil bath was set to 120°C, and the reaction was carried out for 4 hours to obtain a water-insoluble product.
この生成物は、ＧＰＯの測定からいくつかの成分が含ま
れていることが認められた。次いで、該生成物をエーテ
ルにより分離した。生成物のうちエーテルに可癖なもの
を、さらにカラムクロマトグラフィーによって分離した
ところ、次の特性値を与える生成物を得た。This product was found to contain several components from GPO measurements. The products were then separated with ether. The ether-prone product was further separated by column chromatography to obtain a product with the following characteristics.
（ａ） 赤外線吸収 ３４００ｃ１！ｔ（ＯＨ）７６
０画 、６９５１（ベンゼン核
Ｉ置換）
８１０劇 （ベンゼン核４置換）
元素分析 計算値 ０ ６９．８２％Ｈ４，６１％０
２５．６７％
理論値 Ｃ７０，３１％Ｈ４，６９％
０ ２５．００％
分子量 ７７４（ＶＰＯ分子量測定法による）理論値
７６８
■）赤外線吸収 （ａ）と同様
元素分析 計算値 Ｃ７０，０３％Ｈ４，２５％０ ２
４．９９％
理論値 Ｃ７０，８８％Ｈ４，６８％
０ ２４．４Ｂ％
分子量 １０１３（ＶＰＯによる）
理論値 ９８２
反応温度の低い場合には、以下の特性値を与える生成物
も多量に得られた。(a) Infrared absorption 3400c1! t(OH)76
0 stroke, 6951 (Benzene nucleus I substitution) 810 play (Benzene nucleus 4 substitution) Elemental analysis Calculated value 0 69.82%H4, 61%0
25.67% Theoretical value C70, 31% H4, 69% 0 25.00% Molecular weight 774 (by VPO molecular weight measurement method) Theoretical value
768 ■) Infrared absorption Same elemental analysis as in (a) Calculated value C70,03%H4,25%0 2
4.99% Theoretical value C70, 88% H4, 68% 0 24.4B% Molecular weight 1013 (by VPO) Theoretical value 982 When the reaction temperature was low, a large amount of products giving the following characteristic values were also obtained. .
（Ｃ） 赤外線吸収 （ａ）と同様
元素分析 計算値 Ｃ６６，７１％１４ ４．８９％０
２８．４８％
理論値 Ｃ６７，０６％ｉ−Ｉ ４．７１％０ ２８
．２３％
分子ｉ ３４０（マススペクトルによる）理論値
３４０
（ｄ） 赤外線吸収 （ａ）と同様
分子ｔ ５５４（マススペクトルにょる）理論値
５５４
元素分析 計算値 Ｃ６９゜７５％Ｈ４，５２％０ ２
５．７８％
理論値 Ｃ８９，３１％１■ ４．６９％０ ２５．９
９％
さらに、エーテル不溶のものを溶剤により、１ことえば
メタノールで分別し、以下の特性値を有する生成物を得
た。(C) Infrared absorption Elemental analysis same as (a) Calculated value C66,71%14 4.89%0
28.48% Theoretical value C67,06%i-I 4.71%0 28
．． 23% Molecule i 340 (based on mass spectrum) theoretical value
340 (d) Infrared absorption Similar to (a), molecule t 554 (mass spectrum) theoretical value
554 Elemental analysis Calculated value C69゜75%H4,52%0 2
5.78% Theoretical value C89, 31%1■ 4.69%0 25.9
9% The ether-insoluble material was further fractionated with a solvent, for example methanol, to obtain a product having the following characteristic values.
（ｅ） 赤外線吸収 ８４００ ａｓ−’ （０Ｈ）
７６０ｏｚ 、６９５Ｌ：ｒｌｌ（ベンゼン核１置換
）
元素分析 計算値 ０ ７２．４４％Ｈ４，４２％０
２Ｂ、１４％
理論値 Ｃ７２，０６％Ｈ４，９６％
０ ２２．９８％
分子量 ７７ＢＣＶＰＯによる）
理論値 ７６６
（０赤外線吸収 （ｅ）と同様
元素分析 計算値 ０ ７１．９８％Ｈ４，４２％０
２８．６０％
理論値 Ｇ！ ７１．４０％Ｈ４−８１％０ ２Ｂ、
８０％
分子量 ８５２（ｖＰＯによる）
理論値 ８７４
以北の生成物の溝造式は、以下の如くなる。(e) Infrared absorption 8400 as-' (0H)
760oz, 695L:rll (one benzene nucleus substituted) Elemental analysis Calculated value 0 72.44%H4, 42%0
2B, 14% Theoretical value C72,06%H4,96% 0 22.98% Molecular weight 77BCVPO) Theoretical value 766 (0 Infrared absorption Same elemental analysis as (e) Calculated value 0 71.98%H4,42%0
28.60% Theoretical value G! 71.40%H4-81%0 2B,
80% Molecular weight 852 (according to vPO) Theoretical value 874 The formula for products north of this is as follows.
（ｆ）
なお、更に（ｂ）よりも昼分子量の存在もＧＰＯで確認
される。(f) Furthermore, the presence of diurnal molecular weight is further confirmed by GPO than in (b).
（ａ）から（ｆ）までの赤外線吸収スペクトルは図１に
記しである。The infrared absorption spectra from (a) to (f) are shown in FIG.
容［１０００１のステンレス製重合器の内面に、反応に
よって得られた水不溶物を混合物のまま、アセトンに芯
、＠シ塗布した。その時の塗布量は３．０５ ｆ／ｐｎ
’、 １．２０ ｆ／ｖｌ、 ０．０７ ！／ｙｎ’
であった。The water-insoluble material obtained by the reaction was coated as a mixture with acetone on the inner surface of a stainless steel polymerization vessel having a volume of 10001. The amount of coating at that time was 3.05 f/pn
', 1.20 f/vl, 0.07! /yn'
Met.
溶剤のアセトンを乾燥後、重合器に塩化ビニル２００ｋ
Ｑ、純水４５０ｋｑ、ポリ酢酸ビニル部分ケン化物１８
０ ｆ 、アゾビスジメチルバレロニトリル５０ｆを加
えて５０〜６０°Ｃで１３〜１５時間重合を行なった。After drying the solvent acetone, add 200k of vinyl chloride to the polymerization vessel.
Q, 450 kq of pure water, partially saponified polyvinyl acetate 18
0 f and 50 f of azobisdimethylvaleronitrile were added and polymerization was carried out at 50 to 60°C for 13 to 15 hours.
重合終了後、重合体をとり出した所、いずれの塗布量の
場合でも重合器内面へのスケールの付着は皆無であった
。After the polymerization was completed, when the polymer was taken out, there was no scale attached to the inner surface of the polymerization vessel regardless of the coating amount.
これに対し、何も塗布しないで上記の重合条件下、重合
した場合には２２５ ｆ ／ｎｌのスケールの付着が観
察された。On the other hand, when polymerization was carried out under the above polymerization conditions without coating anything, scale adhesion of 225 f/nl was observed.
さらに、上記の反応において、分離した各成分について
、上記と同様な方法で塗布し、塗布量についても０．１
ｇ／Ｗｌのオーダーで実施した所、いずれの場合でも
スケールの付着防止効果は充分にみられた。Furthermore, in the above reaction, each separated component was coated in the same manner as above, and the coating amount was also 0.1.
When it was carried out on the order of g/Wl, a sufficient effect of preventing scale adhesion was observed in all cases.
しかしながら、低分子量成分である生成物（Ｃ）は、よ
り分子世の萬い生成物に比べ、スケール付着防止効果は
、わずかに劣る。生成物（Ｃ）は実施例１の方法によっ
て合成する際には、わずかの量しか含まれていないので
、該化合物をスケール付着防止用塗布剤として用いる場
合ζこは、混合物のままで充分に使用でき、操作上も極
めて有利である。However, the product (C), which is a low molecular weight component, has a slightly inferior scale adhesion prevention effect compared to a more molecular weight product. Since the product (C) is only contained in a small amount when synthesized by the method of Example 1, when the compound is used as a coating agent for preventing scale adhesion, the mixture as it is is sufficient. It is very convenient to use and operationally.
実施例２
ピロガロールのかわりにヒドロキシヒドロキノンを用い
て実施例１と同様に反応を行なった所、いくつかの成分
が混ざった生成物が得らｎた。そｎらの成分の分子量は
、ＶＰＯにより実施例１に示された構造式（ａ）（ｂ）
（ｃ）（ｄ）（ｅ）（ｆｌに対応するものとして、それ
ぞれ７７０，１００５，３４０，５５４゜７７３．８５
０であった。それらの１凡スペクトルの特性値は、３２
００傷 （ＯＨ）、 ７４０ｃｙｔｔ 。Example 2 A reaction was carried out in the same manner as in Example 1 using hydroxyhydroquinone instead of pyrogallol, and a product containing several components was obtained. The molecular weights of these components are based on the structural formulas (a) and (b) shown in Example 1 by VPO.
(c) (d) (e) (770, 1005, 340, 554°773.85 respectively as corresponding to fl
It was 0. The characteristic value of their one-dimensional spectrum is 32
00 wounds (OH), 740cytt.
６９０備 （ベンゼン核１置換体）、８６（ｌｌ！−’
（ベンゼン核４＠換体）である。690bi (one-substituted benzene nucleus), 86 (ll!-'
(benzene nucleus 4@conversion).
容積ｔｏｏ０６のステンレス製重合器の内面に、上記で
得られた生成物を、混合物のままアセトンに溶解し、塗
布し１こ後、乾燥によりｇ剤を除去しｔこ。このときの
塗布量は１．８２１／ｄであった。The product obtained above was dissolved as a mixture in acetone and coated on the inner surface of a stainless steel polymerization vessel having a volume of 0.6 mm, and then the g agent was removed by drying. The coating amount at this time was 1.821/d.
次に、実施例１と同様に重合を行なった。重合終了後、
重合体をとり出しｆこ所、重合器内壁および重合器付帯
機器へのスケールの付着は全く見らｔ′Ｌなかった。Next, polymerization was carried out in the same manner as in Example 1. After polymerization,
When the polymer was taken out, no scale was observed at all on the inner walls of the polymerization vessel and on equipment attached to the polymerization vessel.
図１−１は実施例１で得られ１こ反応生成物、即ち実施
例１に記載した化合物ａ、ｂ、ｃ、ａ、ｅ。
ｆの混合物の赤外吸収スペクトル、図１−２は上記化合
物ａ、ｂ、ｃ、ｄの赤外吸収スペクトルであり、何れも
同じ吸収スペクトルを示す。図１−３は上記化合物ｅ、
ｆの赤外吸収スペクトルであり、何れも同じ吸収スペク
トルを示す。Figure 1-1 shows the reaction products obtained in Example 1, namely compounds a, b, c, a, and e described in Example 1. The infrared absorption spectrum of the mixture of f and FIGS. 1-2 are the infrared absorption spectra of the above compounds a, b, c, and d, all of which show the same absorption spectra. Figure 1-3 shows the above compound e,
These are the infrared absorption spectra of f, and both exhibit the same absorption spectra.
Claims (2)
又はこれを含む他のフエノール性化合物と芳香族アルデ
ヒドとの反応によつて得られ、前記フエノール残基と前
記芳香族アルデヒドの反応残基とを繰り返し単位として
含み、且つ分子量が３０８から２０００までである化合
物。(1) obtained by the reaction of pyrogallol or hydroxyhydroquinone alone or other phenolic compound containing it with an aromatic aldehyde, and containing the phenol residue and the reactive residue of the aromatic aldehyde as a repeating unit; and a compound having a molecular weight of 308 to 2000.
ン単独又はこれを含む他のフエノール性化合物と、（Ｂ
）芳香族アルデヒドとを反応させることにより、分子量
が３０８から２０００である（Ａ）と（Ｂ）との縮合化
合物を製造する方法。(2) (A) pyrogallol or hydroxyhydroquinone alone or other phenolic compound containing this, and (B
) A method for producing a condensation compound of (A) and (B) having a molecular weight of 308 to 2000 by reacting with an aromatic aldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28389986A JPS62201832A (en) | 1978-10-17 | 1986-11-28 | Reaction product of phenolic compound and aromatic aldehyde and production thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12768278A JPS5554317A (en) | 1978-10-17 | 1978-10-17 | Reaction product of phenolic compound with aromatic aldehyde and polymerization of vinyl chloride with it |
| JP28389986A JPS62201832A (en) | 1978-10-17 | 1986-11-28 | Reaction product of phenolic compound and aromatic aldehyde and production thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12768278A Division JPS5554317A (en) | 1978-10-17 | 1978-10-17 | Reaction product of phenolic compound with aromatic aldehyde and polymerization of vinyl chloride with it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62201832A true JPS62201832A (en) | 1987-09-05 |
Family
ID=26463578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28389986A Pending JPS62201832A (en) | 1978-10-17 | 1986-11-28 | Reaction product of phenolic compound and aromatic aldehyde and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62201832A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6894125B2 (en) | 2001-12-12 | 2005-05-17 | Tokuyama Corporation | Scale deposit inhibitor, process for its production, polymerizer whose inside wall is covered with the inhibitor, and process for production of vinylic polymers by the use of the polymerizer |
| JPWO2005087815A1 (en) * | 2004-03-11 | 2008-01-24 | 株式会社クラレ | Scale adhesion inhibitor |
| JP2016060751A (en) * | 2014-09-12 | 2016-04-25 | 群栄化学工業株式会社 | Polyhydric hydroxy resin and method for producing the same |
-
1986
- 1986-11-28 JP JP28389986A patent/JPS62201832A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6894125B2 (en) | 2001-12-12 | 2005-05-17 | Tokuyama Corporation | Scale deposit inhibitor, process for its production, polymerizer whose inside wall is covered with the inhibitor, and process for production of vinylic polymers by the use of the polymerizer |
| JPWO2005087815A1 (en) * | 2004-03-11 | 2008-01-24 | 株式会社クラレ | Scale adhesion inhibitor |
| JP2016060751A (en) * | 2014-09-12 | 2016-04-25 | 群栄化学工業株式会社 | Polyhydric hydroxy resin and method for producing the same |
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