JPS6134023A - Production of novel polyhydroxyl compound - Google Patents
Production of novel polyhydroxyl compoundInfo
- Publication number
- JPS6134023A JPS6134023A JP15624384A JP15624384A JPS6134023A JP S6134023 A JPS6134023 A JP S6134023A JP 15624384 A JP15624384 A JP 15624384A JP 15624384 A JP15624384 A JP 15624384A JP S6134023 A JPS6134023 A JP S6134023A
- Authority
- JP
- Japan
- Prior art keywords
- glycidol
- compound
- addition reaction
- polyhydroxyl
- novel
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000007824 aliphatic compounds Chemical class 0.000 claims abstract description 12
- 238000007259 addition reaction Methods 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 6
- 238000005227 gel permeation chromatography Methods 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 abstract description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 abstract description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 abstract description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract description 2
- 229930006000 Sucrose Natural products 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000600 sorbitol Substances 0.000 abstract description 2
- 239000005720 sucrose Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- -1 α -Methyl glucodide Chemical compound 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は、新規なポリヒドロキシル化合物の製造方法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing polyhydroxyl compounds.
従来、ポリヒドロキシル化合物類は、ポリウレタン樹脂
、ポリエステル樹脂等の樹脂原料、又は可塑剤、化粧品
基剤、又は界面活性剤原料として利用されている。Conventionally, polyhydroxyl compounds have been used as raw materials for resins such as polyurethane resins and polyester resins, or as raw materials for plasticizers, cosmetic bases, or surfactants.
しかしながら、とりわけ１分子中に４個以上のヒドロキ
シル基を有する脂肪族化合物は、はとんどが、常温・固
体であるため、有用性に比べて、作業性に著しく問題が
ある。さらに、ノボラック類の場合、ヒドロキシル基が
フェノール性であり、ポリグリセリンの場合、一般に着
色が大きい等、いずれの場合も利用上制約を受けるのが
実状である。However, in particular, aliphatic compounds having four or more hydroxyl groups in one molecule are mostly solid at room temperature, and therefore have a significant problem in workability compared to their usefulness. Furthermore, in the case of novolaks, the hydroxyl group is phenolic, and in the case of polyglycerols, they are generally highly colored, and in reality, there are restrictions on their use in both cases.
本発明は、上鈑の如き従来の問題に鑑みなされたもので
あり、多くの用途に供しうる常温・液体の新規なポリヒ
ドロキシル化合物の製造方法を提供することを目的とす
る。すなわち、１分子中に４個以上のヒドロキシル基を
有する脂肪族化合物に、グリシドールを付加反応せしめ
ることを特徴とする新規なポリヒドロキシル化合物の製
造方法である。The present invention was made in view of the conventional problems such as the above-mentioned problems, and an object of the present invention is to provide a novel method for producing a polyhydroxyl compound that is liquid at room temperature and can be used in many applications. That is, this is a novel method for producing a polyhydroxyl compound, which is characterized by subjecting an aliphatic compound having four or more hydroxyl groups in one molecule to an addition reaction with glycidol.
本発明において使用する１分子中に４個以上のヒドロキ
シル基を有する脂肪族化合物（以下特定の脂肪族化合物
と言う）としては、例えば、ペンタエリスリット、ジペ
ンタエリスリット、ソルビトール、ショ糖、α−メチル
グルコジッド、ソルビタン等が挙げられる。Examples of aliphatic compounds having four or more hydroxyl groups in one molecule (hereinafter referred to as specific aliphatic compounds) used in the present invention include pentaerythritol, dipentaerythritol, sorbitol, sucrose, α -Methyl glucodide, sorbitan, etc.
本発明において使用するグリシドールとしては、公知の
ものが挙げられる。Glycidol used in the present invention includes publicly known glycidol.
本発明の目的とする新規なポリヒドロキシル化合物とし
ては、前記特定の脂肪族化合物に対して前記グリシドー
ルを付加反応せしめて得られるもので、好ましくは分子
量４００〜１００００、より好ましくは４００ 〜２０
００のものが挙げられる。尚１分子量は、ゲルパーミェ
ーションクロマトグラフによって、測定されるものであ
る。The novel polyhydroxyl compound targeted by the present invention is one obtained by subjecting the specific aliphatic compound to an addition reaction with the glycidol, and preferably has a molecular weight of 400 to 10,000, more preferably 400 to 20.
00 is mentioned. Note that the molecular weight is measured by gel permeation chromatography.
本発明の製造方法によれば、まず特定の脂肪族化合物１
モルにグリシドールｌ−１３０、好ましくは１〜２５モ
ルを付加反応せしめて新規なポリヒドロキシル化合物を
調製する。かかる付加反応は、塩基性触媒の存在下で、
約１００〜１５０℃の温度で約３０分〜４時間行なわれ
る。またかかる反応により得られる新規なポリヒドロキ
シル化合物の分子量は、ゲルパーミェーションクロマト
グラフによるピークトップ位置が４００〜１００００、
好ましくは４００〜２０００を示すように調製されたも
のである。According to the production method of the present invention, first, a specific aliphatic compound 1
The novel polyhydroxyl compounds are prepared by addition reaction of 1 to 25 moles of glycidol l-130, preferably 1 to 25 moles. Such an addition reaction is carried out in the presence of a basic catalyst,
The process is carried out at a temperature of about 100 to 150°C for about 30 minutes to 4 hours. In addition, the molecular weight of the novel polyhydroxyl compound obtained by this reaction is such that the peak top position measured by gel permeation chromatography is 400 to 10,000;
Preferably, it is prepared to have a molecular weight of 400 to 2,000.
上記塩基性触媒としては、例えば、苛性カリ、苛性ソー
ダ等のアルカリ金属水酸化物、またはそのアルコラード
化物、またはアルカリ金属およびアルカリ土金属等の塩
類が挙げられる。Examples of the above-mentioned basic catalyst include alkali metal hydroxides such as caustic potash and caustic soda, alcoholated products thereof, and salts of alkali metals and alkaline earth metals.
使用量は、全収量に対して、好ましイは０．１″ｌ・０
≠である・
前記の如く構成される本発明の製造方法には（１）高品
質で、かつ通常のものと比較した場合、優れた液状特性
を示す、新規なポリヒドロキシル化合物を提供すること
ができる（２）高官能基数と高活性を兼備する新規なポ
リヒドロキシル化合物を提供することができる、
（３）ポリウレタン樹脂、ポリエステル樹脂等の樹脂原
料、又は可塑剤、化粧品基剤、又は界面活性剤原料以外
の多くの用途に供しうる新規なポリヒドロキシル化合物
を提供することができる
等の特徴がある。The amount used is preferably 0.1″l・0 based on the total yield.
≠ The manufacturing method of the present invention configured as described above has the following advantages: (1) to provide a novel polyhydroxyl compound that is of high quality and exhibits excellent liquid properties when compared with ordinary polyhydroxyl compounds; (2) A novel polyhydroxyl compound having both a high number of functional groups and high activity can be provided. (3) A resin raw material such as a polyurethane resin or a polyester resin, or a plasticizer, a cosmetic base, or a surfactant. It has the characteristics of being able to provide a novel polyhydroxyl compound that can be used for many purposes other than as a raw material.
次に実施例を挙げて本発明を、より詳細に説明するが、
本発明はそれらの実施例のみに限定されるものではない
。Next, the present invention will be explained in more detail with reference to Examples.
The invention is not limited only to these examples.
尚、実施例中１部ｊは重量基準である。In the examples, 1 part j is based on weight.
実施例１
オートクレーブに特定の脂肪族化合物（以下出発物質と
言う）の水溶液を仕込み、塩基性触媒を入れて、加熱、
溶解させ、窒素でオートクレーブ内を置換したのち、ゲ
ージ圧 ｉｋｇ ／ ａｊで出発物質１モルに対してグ
リシドール３モルを導入し反応を完結せしめた。Example 1 An aqueous solution of a specific aliphatic compound (hereinafter referred to as starting material) was placed in an autoclave, a basic catalyst was added, and the mixture was heated.
After dissolving and purging the inside of the autoclave with nitrogen, 3 mol of glycidol was introduced per 1 mol of the starting material at a gauge pressure of ikg/aj to complete the reaction.
次に水を減圧留去し、同一条件で残量のグリシドールを
導入した。Next, water was distilled off under reduced pressure, and the remaining amount of glycidol was introduced under the same conditions.
次に反応を完結せしめ、未反応グリシドールを減圧蒸留
した。次に ６０”０に冷却して添加した塩基性触媒に
見合うモル比の酢酸を加えて中和し、ポリヒドロキシル
化合物を得た。同様にして各種ポリヒドロキシル化合物
を調製した。それらを第１表に示す。Next, the reaction was completed, and unreacted glycidol was distilled under reduced pressure. Next, it was cooled to 60"0 and neutralized by adding acetic acid in a molar ratio commensurate with the added basic catalyst to obtain polyhydroxyl compounds. Various polyhydroxyl compounds were prepared in the same manner. They are shown in Table 1. Shown below.
実施例−２
オートクレーブに出発物質を仕込み、塩基性触媒を入れ
て、加熱、溶解させ、窒素でオートクレーブ内を置換し
たのち、ゲージ圧０゜５ｋｇ／−でグリシドールを導入
した０次に反応を完結せしめ、未反応グリシドールを減
圧蒸留した０次に ８０℃に冷却した後、粒状活性炭と
合成珪酸アルミニウムを投入し、よく撹拌しながら、そ
のまま２４時間保った後、グラスフィルターで濾過を行
ないポリヒドロキシル化合物を得た。同様にして各種ポ
リヒドロキシル化合物を調製した。Example-2 The starting materials were placed in an autoclave, a basic catalyst was added, and the autoclave was heated and dissolved. After purging the inside of the autoclave with nitrogen, glycidol was introduced at a gauge pressure of 0.5 kg/- to complete the zero-order reaction. Then, unreacted glycidol was distilled under reduced pressure. After cooling to 80°C, granular activated carbon and synthetic aluminum silicate were added, and the mixture was kept as it was for 24 hours with thorough stirring. After that, it was filtered with a glass filter to obtain a polyhydroxyl compound. I got it. Various polyhydroxyl compounds were prepared in the same manner.
それらを第２表に示す。They are shown in Table 2.
実施例−３
実施例−１、実施例−２において得られたポリヒドロキ
シル化合物を用いてポリウレタンフォームを調整した。Example 3 Polyurethane foam was prepared using the polyhydroxyl compounds obtained in Examples 1 and 2.
それらを第３表に示す。They are shown in Table 3.
第３表
（注−１）；平均分子量５０００のポリエーテル（第−
工業製薬株式会社製）
（注−２）、ＭＤＩ （住友化学工業株式会社製）Table 3 (Note 1): Polyether with an average molecular weight of 5000 (No.
(manufactured by Kogyo Seiyaku Co., Ltd.) (Note 2), MDI (manufactured by Sumitomo Chemical Co., Ltd.)
Claims (1)
合物に、グリシドールを付加反応せしめることを特徴と
する新規なポリヒドロキシル化合物の製造方法。A novel method for producing a polyhydroxyl compound, which comprises subjecting an aliphatic compound having four or more hydroxyl groups in one molecule to an addition reaction with glycidol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15624384A JPS6134023A (en) | 1984-07-25 | 1984-07-25 | Production of novel polyhydroxyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15624384A JPS6134023A (en) | 1984-07-25 | 1984-07-25 | Production of novel polyhydroxyl compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6134023A true JPS6134023A (en) | 1986-02-18 |
Family
ID=15623502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15624384A Pending JPS6134023A (en) | 1984-07-25 | 1984-07-25 | Production of novel polyhydroxyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6134023A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01108471A (en) * | 1987-10-22 | 1989-04-25 | Ooe Kogyo Kk | Manhole for container, spherical surface in hand hole and tapered surface-like sealing structure |
| JPH01108472A (en) * | 1987-10-22 | 1989-04-25 | Ooe Kogyo Kk | Manhole for container, spherical surface in hand hole and tapered surface-like sealing structure |
| JPH01150072A (en) * | 1987-12-03 | 1989-06-13 | Meisei Electric Co Ltd | Sealing structure for pressure tight case |
-
1984
- 1984-07-25 JP JP15624384A patent/JPS6134023A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01108471A (en) * | 1987-10-22 | 1989-04-25 | Ooe Kogyo Kk | Manhole for container, spherical surface in hand hole and tapered surface-like sealing structure |
| JPH01108472A (en) * | 1987-10-22 | 1989-04-25 | Ooe Kogyo Kk | Manhole for container, spherical surface in hand hole and tapered surface-like sealing structure |
| JPH01150072A (en) * | 1987-12-03 | 1989-06-13 | Meisei Electric Co Ltd | Sealing structure for pressure tight case |
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