JPH05295107A - Production of copolymer - Google Patents
Production of copolymerInfo
- Publication number
- JPH05295107A JPH05295107A JP9683492A JP9683492A JPH05295107A JP H05295107 A JPH05295107 A JP H05295107A JP 9683492 A JP9683492 A JP 9683492A JP 9683492 A JP9683492 A JP 9683492A JP H05295107 A JPH05295107 A JP H05295107A
- Authority
- JP
- Japan
- Prior art keywords
- ethylene
- carbon monoxide
- carbon
- group
- copolymer
- 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.)
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はエンジニアリング樹脂と
して有用なエチレン−一酸化炭素共重合体の製造方法に
関する。TECHNICAL FIELD The present invention relates to a method for producing an ethylene-carbon monoxide copolymer useful as an engineering resin.
【０００２】[0002]
【従来の技術】エチレン−一酸化炭素共重合体を有機過
酸化物の存在下で製造する方法は、米国特許第２４９５
２８６号、第３６８９４６０号および第３６９４４１２
号各明細書に開示されている。また、特開昭５３−１２
８６９０号、特開昭５３−１２８６９１号各公報には開
始剤としてペルオキシジカーボネートおよびペルオキシ
エステルを用いることにより、高融点のエチレン−一酸
化炭素共重合体を得る方法が開示されている。2. Description of the Prior Art A method for producing an ethylene-carbon monoxide copolymer in the presence of an organic peroxide is disclosed in US Pat.
No. 286, No. 3689460 and No. 3694412
No. disclosed in each specification. In addition, JP-A-53-12
Japanese Patent No. 8690 and Japanese Patent Laid-Open No. 53-128691 disclose a method of obtaining a high melting point ethylene-carbon monoxide copolymer by using peroxydicarbonate and peroxyester as an initiator.
【０００３】[0003]
【発明が解決しようとする課題】この発明の目的は、高
重合度のエチレン−一酸化炭素共重合体を提供すること
にある。SUMMARY OF THE INVENTION An object of the present invention is to provide an ethylene-carbon monoxide copolymer having a high degree of polymerization.
【０００４】[0004]
【課題を解決するための手段】この発明の特徴は、特定
の開始剤の存在下にエチレンと一酸化炭素を共重合させ
る点にある。すなわちこの発明は、エチレンと一酸化炭
素を一般式（Ｉ）で表わされるポリペルオキシジカーボ
ネートの存在下に重合させるエチレン−一酸化炭素共重
合体の製造方法である。A feature of the present invention is that ethylene and carbon monoxide are copolymerized in the presence of a specific initiator. That is, the present invention is a method for producing an ethylene-carbon monoxide copolymer in which ethylene and carbon monoxide are polymerized in the presence of the polyperoxydicarbonate represented by the general formula (I).
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】ここで、ｎは３〜２００の自然数、Ｒ1 は
エーテル基、カーボネート基、エステル基、飽和炭素環
または芳香族環を含んでいてもよい炭素数３〜５０の両
端がそれぞれ１級、２級または３級炭素である炭化水素
基を表わす。この発明に用いられる開始剤は、式（Ｉ）
に示される構造を有するものでなければならない。
（Ｉ）式において、ｎは３〜１００の範囲が好ましい。
ｎが３未満では高重合度の共重合体が得られず、２００
を超えると溶媒への溶解度が低下するので好ましくな
い。Here, n is a natural number of 3 to 200, R 1 is an ether group, a carbonate group, an ester group, a saturated carbon ring or an aromatic ring, and both ends of which have 3 to 50 carbon atoms are primary. It represents a hydrocarbon group which is a secondary or tertiary carbon. The initiator used in this invention has the formula (I)
It must have the structure shown in.
In the formula (I), n is preferably in the range of 3-100.
When n is less than 3, a copolymer having a high degree of polymerization cannot be obtained,
If it exceeds, the solubility in the solvent decreases, which is not preferable.
【０００７】Ｒ1 は炭素数３〜５０、好ましくは３〜２
０の炭化水素基である。Ｒ1 の炭素数が３未満の物質は
不安定であり、取扱いが困難であることから好ましくな
く、一方、炭素数が５０を超えると開始剤の使用量を増
加しなければならず好ましくない。Ｒ1 は、酸素原子と
結合する両端の基が１級、２級または３級炭素である炭
化水素基からなる。この炭化水素基は、エーテル基、カ
ーボネート基、エステル基、飽和炭素環または芳香族環
を含んでいてもよい。このようなＲ1 の例としては以下
の式（ＩＩ）〜（ＶＩ）のものがあげられる。R 1 has 3 to 50 carbon atoms, preferably 3 to 2 carbon atoms.
It is a hydrocarbon group of 0. A substance having a carbon number of R 1 of less than 3 is unstable and difficult to handle, while a substance having a carbon number of more than 50 is not preferable because the amount of the initiator used must be increased. R 1 is composed of a hydrocarbon group in which groups at both ends bonded to an oxygen atom are primary, secondary or tertiary carbons. This hydrocarbon group may contain an ether group, a carbonate group, an ester group, a saturated carbocycle or an aromatic ring. Examples of such R 1 include those of the following formulas (II) to (VI).
【０００８】 −Ｃ2 Ｈ4 −（Ｏ−Ｃ2 Ｈ4 ）1 − （ｌは１または２） （ＩＩ） −（ＣＨ2 ）6 −Ｏ−ＣＯ−Ｏ−（ＣＨ2 ）6 − （ＩＩＩ） −（ＣＨ2 ）2 −Ｏ−ＣＯ−（ＣＨ2 ）4 −ＣＯＯ−（ＣＨ2 ）2 −（ＩＶ）[0008] -C 2 H 4 - (O- C 2 H 4) 1 - (l is 1 or 2) (II) - (CH 2) 6 -O-CO-O- (CH 2) 6 - (III ) - (CH 2) 2 -O -CO- (CH 2) 4 -COO- (CH 2) 2 - (IV)
【０００９】[0009]
【化３】 [Chemical 3]
【００１０】[0010]
【化４】 [Chemical 4]
【００１１】好ましいＲ1 としては、−（ＣＨ2 ）m −
（ｍは３〜１０の自然数）、−ＣＨ 2 −Ｃ（ＣＨ3 ）2
−ＣＨ2 −および−Ｃ（ＣＨ3 ）2 −ＣＨ2 −ＣＨ（Ｃ
Ｈ3）−などの炭素数３〜１０の直鎖状脂肪族炭化水素
基や分岐状脂肪族炭化水素基、シクロヘキサジメチレン
基などの飽和炭素環を含む脂肪族炭化水素基、および−
Ｃ2 Ｈ4 −（ＯＣ2 Ｈ4 ）1 −（ｌは１または２）など
のエーテル基を含む脂肪族炭化水素基などがあげられ
る。これらのＲ1 を有するポリペルオキシジカーボネー
トは、合成時に原料ジオールが入手しやすい、安全性が
高いなどの点で好適である。Preferred R1As-(CH2)m−
(M is a natural number of 3 to 10), -CH 2-C (CH3)2
-CH2-And-C (CH3)2-CH2-CH (C
H3)-And other straight-chain aliphatic hydrocarbons having 3 to 10 carbon atoms
Groups and branched aliphatic hydrocarbon groups, cyclohexadimethylene
An aliphatic hydrocarbon group containing a saturated carbocycle such as a group, and-
C2HFour-(OC2HFour)1-(L is 1 or 2) etc.
Examples include aliphatic hydrocarbon groups containing ether groups
It These R1With polyperoxydicarbonate
The raw material diol is easy to obtain at the time of synthesis and is safe.
It is suitable in terms of high price.
【００１２】本発明で用いられる式（Ｉ）のポリペルオ
キシジカーボネートは、ＨＯ−Ｒ1−ＯＨで表わされる
ジオールを原料として公知の方法によりＣｌ−ＣＯ−Ｏ
−Ｒ 1 −Ｏ−ＣＯ−Ｃｌで表わされるビスクロロホ−メ
ートをまず得、つぎに水／有機溶媒二相系で過酸化水素
と苛性アルカリの存在下に常法でペルオキシ化すること
により得られる。The polyperuvium of formula (I) used in the present invention
Xydicarbonate is HO-R1Represented by -OH
Cl-CO-O by a known method using diol as a raw material
-R 1Bischlorohome represented by --O--CO--Cl
First, and then hydrogen peroxide in a water / organic solvent two-phase system.
And peroxidation in the presence of caustic and alkali
Is obtained by
【００１３】本発明において、エチレンと一酸化炭素の
重合は、開始剤を溶解する溶媒の存在下で行うのが好ま
しい。好ましい溶媒の例としては、ベンゼンがあげられ
る。エチレンと一酸化炭素の反応混合物中の比率は１対
４ないし４対１であり、１対３ないし３対１が好まし
い。また、重合は、使用する開始剤によって異なるが、
５０〜９０℃の範囲で行われる。In the present invention, the polymerization of ethylene and carbon monoxide is preferably carried out in the presence of a solvent which dissolves the initiator. An example of a preferable solvent is benzene. The ratio of ethylene to carbon monoxide in the reaction mixture is from 1 to 4 to 4 to 1, preferably from 1 to 3 to 3 to 1. Also, the polymerization depends on the initiator used,
It is performed in the range of 50 to 90 ° C.
【００１４】[0014]
【実施例】以下に実施例で本発明を説明する。EXAMPLES The present invention will be described below with reference to examples.
【００１５】[0015]
（１）ポリペルオキシジカーボネートの合成 １０重量％の水酸化ナトリウム水溶液９６ｇ（０．２４
モル）に３０重量％の過酸化水素水１２．５ｇ（０．１
１モル）を加えた溶液Ａと、１，６−ヘキサンジオール
ビスクロロホーメート２４．３ｇ（０．１モル）をシク
ロヘキサン１００ｇに溶解した溶液Ｂを調製した。強攪
拌し、氷冷にて１〜４℃に保った１リットル４つ口フラ
スコの中に、Ａ、Ｂ両液を添加した。生じた析出物をろ
別し、水で洗浄後５〜１０℃で減圧乾燥し、粉末状のポ
リ（ヘキサメチレンペルオキシジカーボネート）１９．
４ｇを得た。(1) Synthesis of polyperoxydicarbonate 96 g (0.24%) of a 10 wt% sodium hydroxide aqueous solution.
12.5 g (0.1 mol) of 30 wt% hydrogen peroxide solution (0.1 mol)
A solution A containing 1 mol) and a solution B containing 24.3 g (0.1 mol) of 1,6-hexanediol bischloroformate dissolved in 100 g of cyclohexane were prepared. Both solutions A and B were added to a 1 liter four-necked flask which was vigorously stirred and kept at 1 to 4 ° C. by ice cooling. The resulting precipitate was filtered off, washed with water and dried under reduced pressure at 5 to 10 ° C. to obtain powdery poly (hexamethylene peroxydicarbonate) 19.
4 g was obtained.
【００１６】この粉末をＧＰＣで分析した結果、ポリス
チレン換算の重量平均分子量で１．３×１０4 であっ
た。これは式（Ｉ）で表わされる繰返し単位においてｎ
＝６４に相当する。また、ＫＩ法により求めた活性酸素
は理論値の９４％であった。同様の方法にて、式（Ｉ）
におけるＲ1 が、式（Ｖ）、−ＣＨ2 −Ｃ（ＣＨ3）2
−ＣＨ2 −、−（ＣＨ2 ）4 −、−Ｃ2 Ｈ4 −Ｏ−Ｃ2
Ｈ4 −、および−Ｃ 2 Ｈ4 −（Ｏ−Ｃ2 Ｈ4 ）2 −であ
るポリペルオキシジカーボネートを合成した。Analysis of this powder by GPC revealed that
1.3 × 10 in terms of weight average molecular weight in terms of ethyleneFourAnd
It was This is n in the repeating unit represented by the formula (I).
= 64. In addition, active oxygen determined by the KI method
Was 94% of theory. In the same manner, the formula (I)
R in1Is the formula (V), -CH2-C (CH3)2
-CH2-,-(CH2)Four-, -C2HFour-OC2
HFour-, And -C 2HFour-(O-C2HFour)2−
Polyperoxydicarbonate was synthesized.
【００１７】[0017]
【実施例１】容量１リットルの攪拌機付ＳＵＳオートク
レーブに溶媒のベンゼン８００ｍｌ及び参考例により合
成した、ｎ＝６４のポリ（ヘキサメチレンペルオキシジ
カーボネート）１．６ｇを仕込み、続いてＣＯ／エチレ
ン圧力比１の混合ガスを室温で気相圧４５ｋｇ／ｃｍＧ
となるよう仕込んだ。１００ｒｐｍで攪拌しつつ熱媒に
てオートクレーブを加熱し６０℃に昇温した。気相圧力
を５０ｋｇ／ｃｍ2 に保つよう混合ガスを追加しながら
６時間反応させた後、オートクレーブを４０℃以下に冷
却し、大気圧まで落圧した。内容物にアセトンを加え、
固形物をろ別し、室温で減圧乾燥して白色の粉末を得
た。この粉末の０．５ｇ／ｄｌ ｍ−クレゾール溶液の
粘度を６０℃にてウベローデ粘度管を用いて測定し、以
下に定義する還元粘度ηｓｐ／ｃ値を得た。Example 1 A SUS autoclave equipped with a stirrer having a capacity of 1 liter was charged with 800 ml of benzene as a solvent and 1.6 g of poly (hexamethylene peroxydicarbonate) of n = 64, which was synthesized according to the reference example, followed by CO / ethylene pressure ratio. Gas phase pressure of 45 kg / cmG for 1 mixed gas at room temperature
I prepared to become. While stirring at 100 rpm, the autoclave was heated with a heat medium to raise the temperature to 60 ° C. After reacting for 6 hours while adding a mixed gas so as to keep the gas phase pressure at 50 kg / cm 2 , the autoclave was cooled to 40 ° C. or lower, and the pressure was reduced to atmospheric pressure. Add acetone to the contents,
The solid matter was filtered off and dried under reduced pressure at room temperature to obtain a white powder. The viscosity of a 0.5 g / dl m-cresol solution of this powder was measured at 60 ° C. using an Ubbelohde viscosity tube to obtain a reduced viscosity ηsp / c value defined below.
【００１８】[0018]
【数１】 [Equation 1]
【００１９】結果を表１に示す。The results are shown in Table 1.
【００２０】[0020]
【実施例２〜７】開始剤として参考例で合成した表１に
示すものを用い、仕込量を変えた以外は、実施例１と同
じ条件でエチレンと−酸化炭素の共重合を行った。結果
を表１に示した。Examples 2 to 7 Copolymerization of ethylene and carbon oxide was carried out under the same conditions as in Example 1 except that the initiator shown in Table 1 synthesized in Reference Example was used and the charged amount was changed. The results are shown in Table 1.
【００２１】[0021]
【比較例１】ラジカル開始剤としてジ−２−エチルヘキ
シルペルオキシジカーボネート（日本油脂（株）製 商
品名パーロイルＯＰＰ、７０％炭化水素溶液）４．０ｇ
を用いた以外は実施例１と同じ条件にて重合を行った結
果共重合体の還元粘度はηｓｐ／ｃ＝０．１８ｄｌ／ｇ
にとどまった。Comparative Example 1 4.0 g of di-2-ethylhexyl peroxydicarbonate (trade name Perloyl OPP, manufactured by NOF CORPORATION, 70% hydrocarbon solution) as a radical initiator
Polymerization was carried out under the same conditions as in Example 1 except that the copolymer had a reduced viscosity of ηsp / c = 0.18dl / g.
Stayed in.
【００２２】[0022]
【比較例２】ラジカル開始剤としてｔ−ブチルペルオキ
シピバレート（日本油脂（株）製商品名パーブチルＰ
Ｖ、７０％炭化水素溶液）２．０ｇを用いた以外は実施
例１と同じ条件にて重合を行った結果、共重合体の還元
粘度はηｓｐ／ｃ＝０．２２にとどまった。[Comparative Example 2] t-butyl peroxypivalate (trade name Perbutyl P manufactured by NOF CORPORATION) as a radical initiator
As a result of carrying out the polymerization under the same conditions as in Example 1 except that 2.0 g of V, 70% hydrocarbon solution) was used, the reduced viscosity of the copolymer remained at ηsp / c = 0.22.
【００２３】[0023]
【表１】 [Table 1]
【００２４】[0024]
【発明の効果】本発明によれば高重合度のエチレン−一
酸化炭素共重合体を得ることができる。According to the present invention, an ethylene-carbon monoxide copolymer having a high degree of polymerization can be obtained.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成４年６月９日[Submission date] June 9, 1992
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００２[Name of item to be corrected] 0002
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【０００２】[0002]
【従来の技術】エチレン−一酸化炭素共重合体を有機過
酸化物の存在下で製造する方法は、米国特許第２４９５
２８６号明細書に開示されている。また、特開昭５３−
１２８６９０号、特開昭５３−１２８６９１号各公報に
は開始剤としてペルオキシジカーボネートおよびペルオ
キシエステルを用いることにより、高融点のエチレン−
一酸化炭素共重合体を得る方法が開示されている。2. Description of the Prior Art A method for producing an ethylene-carbon monoxide copolymer in the presence of an organic peroxide is disclosed in US Pat.
No. 286. In addition, JP-A-53-
No. 128690 and JP-A No. 53-128691, the use of peroxydicarbonate and peroxyester as an initiator results in high melting point ethylene-
A method of obtaining a carbon monoxide copolymer is disclosed.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１７[Correction target item name] 0017
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１７】[0017]
【実施例１】容量１リットルの攪拌機付ＳＵＳオートク
レーブに溶媒のベンゼン８００ｍｌ及び参考例により合
成した、ｎ＝６４のポリ（ヘキサメチレンペルオキシジ
カーボネート）１．６ｇを仕込み、続いてＣＯ／エチレ
ン圧力比１の混合ガスを室温で気相圧４５ｋｇ／ｃｍＧ
となるよう仕込んだ。１００ｒｐｍで攪拌しつつ熱媒に
てオートクレーブを加熱し６０℃に昇温した。気相圧力
を５０ｋｇ／ｃｍ 2 Ｇに保つよう混合ガスを追加しなが
ら６時間反応させた後、オートクレーブを４０℃以下に
冷却し、大気圧まで落圧した。内容物にアセトンを加
え、固形物をろ別し、室温で減圧乾燥して白色の粉末を
得た。この粉末の０．５ｇ／ｄ１ ｍ−クレゾール溶液
の粘度を６０℃にてウベローデ粘度管を用いて測定し、
以下に定義する還元粘度ηｓｐ／ｃ値を得た。Example 1 A SUS autoclave equipped with a stirrer having a capacity of 1 liter was charged with 800 ml of benzene as a solvent and 1.6 g of poly (hexamethylene peroxydicarbonate) of n = 64, which was synthesized according to the reference example, followed by CO / ethylene pressure ratio. Gas phase pressure of 45 kg / cmG for 1 mixed gas at room temperature
I prepared to become. While stirring at 100 rpm, the autoclave was heated with a heat medium to raise the temperature to 60 ° C. After reacting for 6 hours while adding a mixed gas so as to keep the gas phase pressure at 50 kg / cm 2 G , the autoclave was cooled to 40 ° C. or lower, and the pressure was reduced to atmospheric pressure. Acetone was added to the content, the solid was filtered off, and dried under reduced pressure at room temperature to obtain a white powder. The viscosity of a 0.5 g / d1 m-cresol solution of this powder was measured at 60 ° C. using an Ubbelohde viscosity tube,
The reduced viscosity ηsp / c value defined below was obtained.
Claims (1)
（Ｉ）で表されるポリペルオキシジカーボネートの存在
下に重合させることを特徴とするエチレン−一酸化炭素
共重合体の製造方法。 【化１】 ここで、ｎは３〜２００の自然数、Ｒ1 はエーテル基、
カーボネート基、エステル基、飽和炭素環または芳香族
環を含んでいてもよい炭素数３〜５０の両端がそれぞれ
１級、２級または３級炭素である炭化水素基を表わす。1. A method for producing an ethylene-carbon monoxide copolymer, which comprises polymerizing a mixture of ethylene and carbon monoxide in the presence of the polyperoxydicarbonate represented by the general formula (I). [Chemical 1] Here, n is a natural number of 3 to 200, R 1 is an ether group,
A hydrocarbon group having a carbon number of 3 to 50, which may contain a carbonate group, an ester group, a saturated carbon ring or an aromatic ring, is a primary, secondary or tertiary carbon atom respectively.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9683492A JPH05295107A (en) | 1992-04-16 | 1992-04-16 | Production of copolymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9683492A JPH05295107A (en) | 1992-04-16 | 1992-04-16 | Production of copolymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05295107A true JPH05295107A (en) | 1993-11-09 |
Family
ID=14175568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9683492A Withdrawn JPH05295107A (en) | 1992-04-16 | 1992-04-16 | Production of copolymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05295107A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0830932A2 (en) | 1996-09-18 | 1998-03-25 | Kuraray Co., Ltd. | Blow molded polyalcohol container |
| WO2006095452A1 (en) * | 2005-03-08 | 2006-09-14 | Asahi Kasei Chemicals Corporation | Aliphatic ketone polymer |
-
1992
- 1992-04-16 JP JP9683492A patent/JPH05295107A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0830932A2 (en) | 1996-09-18 | 1998-03-25 | Kuraray Co., Ltd. | Blow molded polyalcohol container |
| WO2006095452A1 (en) * | 2005-03-08 | 2006-09-14 | Asahi Kasei Chemicals Corporation | Aliphatic ketone polymer |
| JP2006249121A (en) * | 2005-03-08 | 2006-09-21 | Asahi Kasei Chemicals Corp | Aliphatic ketone-based polymer |
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