JPS5824425B2 - Polyester material - Google Patents
Polyester materialInfo
- Publication number
- JPS5824425B2 JPS5824425B2 JP6252974A JP6252974A JPS5824425B2 JP S5824425 B2 JPS5824425 B2 JP S5824425B2 JP 6252974 A JP6252974 A JP 6252974A JP 6252974 A JP6252974 A JP 6252974A JP S5824425 B2 JPS5824425 B2 JP S5824425B2
- Authority
- JP
- Japan
- Prior art keywords
- polyester
- water
- present
- acid
- 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.)
- Expired
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
【発明の詳細な説明】
本発明はポリエステル糸条体層の解重合方法、特にポリ
エステルの製糸工程以降様々の油剤で処理された糸条体
層を簡単な方法で油剤除去を行ない、かつ熱安定性の優
れたポリエステルの中間生成物であるビスヒドロキシア
ルキルテレフタレートおよび／またはその低重合体（Ｂ
ＨＡＴ ）として再生する方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for depolymerizing a polyester filament layer, in particular, a simple method for removing oil from a filament layer that has been treated with various oils after the polyester spinning process, and for thermally stabilizing the filament layer. Bishydroxyalkyl terephthalate and/or its low polymer (B
HAT).
今日ポリエステルは繊維、フィルム、プラスチック等の
成型材料として多（の用途をもっているが、これらの製
造工程において繊維状、フィルム状あるいは樹脂状のポ
リエステル屑が発生する。Today, polyester has many uses as a molding material for fibers, films, plastics, etc., but polyester waste in the form of fibers, films, or resins is generated during these manufacturing processes.
これらの回収方法については従来様々の方法が提案され
、例えばポリエステル屑を過剰のエチレンクリコールで
解重合した後メタノールでエステル化しジメチルテレフ
タレートとして回収する方法、あるいはテレフタル酸と
エチレングリコールとの反応系に直接ポリエステル屑を
投入する方法等がある。Various methods have been proposed to recover these materials, including a method in which polyester waste is depolymerized with excess ethylene glycol and then esterified with methanol to be recovered as dimethyl terephthalate, or a method in which polyester waste is recovered as dimethyl terephthalate using a reaction system between terephthalic acid and ethylene glycol. There are methods such as directly adding polyester waste.
しかるに前者についてはエチレングリコールによる解重
合工程およびメタノールによるエステル化工程等回収工
程の迂回に伴なう多額の設備費、材料薬品費、人件費等
から経済的に不利であった。However, the former method was economically disadvantageous due to the large equipment costs, material and chemical costs, labor costs, etc. associated with bypassing recovery steps such as the depolymerization step using ethylene glycol and the esterification step using methanol.
また後者については前者のような迂回工程を必要としな
い反面、ポリエステル屑の添加によって反応速度が低下
し、特に製糸工程において発生するような油剤処理後の
糸条体層については油剤の混入によって生成するポリエ
ステルを著しく汚染し実用に供し得ないのが現状である
。In addition, while the latter does not require a bypass process like the former, the reaction rate is reduced by the addition of polyester waste, and in particular, the filament layer after oil treatment, which occurs in the silk spinning process, is formed due to the mixing of oil. At present, the polyester used in this process is severely contaminated and cannot be put to practical use.
本発明者等はかねてより油剤処理後のポリエステル糸条
体層の回収方法について研究中のところ該糸条体層をグ
リコール類で解重合するに際し、特定量の水を存在させ
ることが特に効果的であることを見出し、本発明に至っ
た。The present inventors have been researching a method for recovering the polyester filament layer after oil treatment, and found that it is particularly effective to have a specific amount of water present when depolymerizing the filament layer with glycols. It was discovered that this was the case, and the present invention was developed.
すなわち、本発明はポリアルキレンテレフタレートを主
たる成分とし、かつ油剤分０．０１重量％（対ポリマ）
以上を含有するポリエステル糸条体層をグリコール類で
解重合するに際し、該ポリエステル糸条体層に対して水
５〜７０重量％を存在させることを特徴とするポリエス
テル糸条体層の解重合方法を提供するものである。That is, the present invention has polyalkylene terephthalate as the main component, and has an oil content of 0.01% by weight (based on the polymer).
A method for depolymerizing a polyester thread layer comprising the steps of: when depolymerizing the polyester thread layer containing the above with glycols, 5 to 70% by weight of water is present in the polyester thread layer. It provides:
本発明におけるポリエステルとしては出発原料であるテ
レフタル酸もしくはその低級アルキルエステルとグリコ
ール類とから得られたポリアルキレンテレフタレートで
あるが、その酸成分およα／マタハクリコール成分の一
部をイソフタル酸、フタル酸、ジフェニルカルボン酸、
ナフタレンカルホン酸、コハク酸、グルタル酸、アジピ
ン酸、セパチン酸、ｐ−ヒドロキシ安息香酸、ω−ヒド
ロキシカブロン酸等の二官能性酸、およびトリメチレン
クリコール、テトラメチレンクリコール、ヘキサメチレ
ングリコール、シクロヘキサンジメタツール（１・４）
、２・２．４・４−テトラメチルシクロブタンジオール
（２・４）、ハイドロキノン等のジオール化合物の１種
または２種以上で置き換えたポリエステルであってもよ
い。The polyester used in the present invention is a polyalkylene terephthalate obtained from the starting materials terephthalic acid or its lower alkyl ester and glycols, but a part of the acid component and α/Mataha glycol component is added to isophthalic acid, phthalate, etc. acid, diphenylcarboxylic acid,
Difunctional acids such as naphthalenecarphonic acid, succinic acid, glutaric acid, adipic acid, sepatic acid, p-hydroxybenzoic acid, ω-hydroxycabronic acid, and trimethylene glycol, tetramethylene glycol, hexamethylene glycol, Cyclohexane dimetatool (1/4)
, 2.2.4.4-tetramethylcyclobutanediol (2.4), hydroquinone, and the like may be substituted with one or more diol compounds.
そして解重合の対象とするポリエステル糸条体層は前記
ポリエステルの例えば製糸過程で発生する未延伸糸屑あ
るいは延伸糸屑であって、特に油剤を含んだ状態の糸条
体層である。The polyester thread layer to be depolymerized is, for example, undrawn thread waste or drawn thread waste generated during the spinning process of the polyester, and is particularly a thread layer containing an oil agent.
この場合の油剤としてはアニオン系油剤、カチオン系油
剤、非イオン系油剤あるいはこれらの混合油剤等、いわ
ゆる通常ポリエステルの製糸工程で紡糸用油剤、延伸用
油剤または仕上用油剤として使用されているものである
。In this case, the oils include anionic oils, cationic oils, nonionic oils, or mixtures thereof, which are normally used as spinning oils, drawing oils, or finishing oils in the polyester spinning process. be.
またポリエステル糸条体に対する油剤付着量は０．０１
重量％（対ポリマ）以上であり、この付着量以下のとき
は本発明の効果が顕著でない。Also, the amount of oil attached to the polyester thread is 0.01
% by weight (based on the polymer) or more, and if the amount is less than this, the effect of the present invention is not significant.
本発明においては上記油剤処理後のポリエステル糸条体
層をグリコール類で解重合し、ポリエステルの中間生成
物であるＢＨＡＴとして再生するのであるが、特に要点
となるところはポリエステル糸条体層に対して５〜７０
重量％、好ましくは１０〜５０重量％の水を存在させる
ことである。In the present invention, the polyester thread layer after the oil treatment is depolymerized with glycols and recycled as BHAT, which is a polyester intermediate product. Te 5-70
% by weight of water, preferably 10-50% by weight.
ここにおける水の存在は解重合過程において分解する油
剤分を共に系外に留出させるべく作用するものと推定さ
れる。It is presumed that the presence of water here acts to distill out of the system the oil components that are decomposed during the depolymerization process.
したがってポリエステル糸条体層があらかじめ上記５〜
７０重量％の水を含んでいる場合は別として、５重量％
未滴の場合は水の添加が必要であり、一方７０重量％を
越える水があるとポリエステルの解重合反応を遅延させ
るという問題が生じ易い。Therefore, the polyester filament layer is preliminarily
5% by weight, unless it contains 70% water.
If there are no drops, it is necessary to add water; on the other hand, if the amount of water exceeds 70% by weight, the problem tends to occur that the depolymerization reaction of the polyester is delayed.
なお本発明方法であるポリエステル糸条体層のグリコー
ル類による解重合方法は特定量の水を存在させるほか更
にＢＲＡＴを存在させること、あるいは従来公知の解重
合条件もしくは操作が適用できるのはもちろんであり、
また得られ７’ｊＢＨＡＴは引きつづき通常の重縮合反
応によってポリエステルとなるが、この場合の反応条件
としては公知の条件がそのまま適用され、更に繊維ある
いはフィルムのような仕上製品に転換されるのである。It goes without saying that the method of depolymerizing a polyester thread layer using glycols, which is the method of the present invention, requires the presence of BRAT in addition to the presence of a specific amount of water, or that conventionally known depolymerization conditions or operations can be applied. can be,
The obtained 7'jBHAT is then converted into polyester by a conventional polycondensation reaction, using known reaction conditions, and further converted into finished products such as fibers or films. .
以上述べた様に本発明はポリエステル糸条体層をグリコ
ール類で解重合するに際し、特定量の水を存在させると
ころがその特徴であり、本発明方法に従えば例えばポリ
エステルの製糸工程で発生するような各種油剤を含んだ
状態の糸条体層を特別の工程を採ることなく簡単な方法
で油剤もしくはその分解物の残留しないＢＨＡＴとして
再生できる。As mentioned above, the present invention is characterized by the presence of a specific amount of water when depolymerizing the polyester thread layer with glycols. The filament layer containing various oils can be regenerated into BHAT without any oils or their decomposition products remaining by a simple method without any special steps.
そしてこのＢＨＡＴから得られたポリエステルは特に色
調が通常のポリエステルと比較して全く見劣りしない等
その効果は著しい。The polyester obtained from this BHAT has remarkable effects, especially in terms of color tone which is not inferior to that of ordinary polyester.
以下実施例を挙げて本発明を具体的に説明する。The present invention will be specifically explained below with reference to Examples.
なお、実施例中、ポリマ色調はポリマをいったんチップ
状とした後、色差計（東洋理化製）によるハンター値（
Ｌ、ａ、ｂ）で示し、Ｌは明度（値が大きい柱間るい）
、ａは赤−縁糸の色相（＋は赤味、−は緑味）、ｂは黄
−青光の色相（＋は黄味、−は青味）を表わす。In addition, in the examples, the color tone of the polymer was determined by the Hunter value (
L, a, b), where L is the lightness (larger value is Rui Hashirama)
, a represents the hue of red-edge yarn (+ means reddish, - means greenish), and b represents the hue of yellow-blue light (+ means yellowish, - means bluish).
実施例 １
油脂分０．２重量％および含水量０．２重量％（いずれ
も対ポリマ）を含むポリエチレンテレフタレート延伸糸
屑５ｋｇ、エチレングリコール３ｋｇ、および水１ｋｇ
（水存在量として）を解重合缶に仕込み、常圧下温度を
１５０℃から１時間かげて２１０°Ｃまで昇温し、更に
２１０℃で３時間解重合反応を継続した。Example 1 5 kg of polyethylene terephthalate drawn yarn waste containing 0.2% by weight of oil and fat and 0.2% by weight of water (all based on polymer), 3 kg of ethylene glycol, and 1 kg of water
(as the amount of water present) was charged into a depolymerization reactor, the temperature under normal pressure was raised from 150°C for 1 hour to 210°C, and the depolymerization reaction was further continued at 210°C for 3 hours.
この場合の反応生成物、すなわちビス−２−ヒドロキシ
エチルテレフタレートおよび／またはその低重合体（Ｂ
ＨＴ）を重合缶に移し、三酸化アンチモン１．０グ、リ
ン酸１．１’を加え０．４ｍ７／ＬＨｇの減圧下２８５
°Ｇで３時間重合反応を行なった。The reaction product in this case is bis-2-hydroxyethyl terephthalate and/or its oligomer (B
HT) was transferred to a polymerization tank, 1.0 g of antimony trioxide and 1.1' of phosphoric acid were added, and the mixture was heated to 285 ml under a reduced pressure of 0.4 m7/LHg.
The polymerization reaction was carried out at °G for 3 hours.
得られたポリマの色調はＬ６７．５、ａ−１，７、ｂｌ
、５であった。The color tone of the obtained polymer is L67.5, a-1,7, bl
, 5.
比較例 １
解重合缶に水を仕込まなかったほかは、実施例１と同様
にして解重合反応、重合反応を行なった。Comparative Example 1 A depolymerization reaction and a polymerization reaction were carried out in the same manner as in Example 1, except that water was not charged into the depolymerization tank.
得られたポリマの色調はＬ６６．７、ａ−１，７、ｂ３
．１であった。The color tone of the obtained polymer is L66.7, a-1,7, b3
．． It was 1.
実施例２、比較例２
実施例１において解重合缶への水仕込量を変え、ポリエ
チレンテレフタレート延伸糸屑に対する水の存在量を第
１表に示すとおり変更した場合のポリマ色調を調べた。Example 2, Comparative Example 2 In Example 1, the amount of water charged into the depolymerization tank was changed, and the color tone of the polymer was investigated when the amount of water present relative to the drawn polyethylene terephthalate yarn waste was changed as shown in Table 1.
その結果を第１表に示した。なお水存在量７５％（應７
）、１００％（煮８）の場合は解重合反応が２１０℃到
達後３時間では完結せず、更に完結までに０．５時間（
扁７）、１．５時間（Ａ８）を要した。The results are shown in Table 1. The amount of water present is 75% (75%)
), in the case of 100% (boiling 8), the depolymerization reaction was not completed within 3 hours after reaching 210°C, and it took an additional 0.5 hour (
It took 1.5 hours (A8).
実施例３、比較例３
実施例１において、含水量が０．２重量％であって油剤
量の異なる延伸糸屑を使用し、かつ水を添加（水の存在
量１ｋｙ）した場合、水を添加しない場合のポリマ色調
について比較した。Example 3, Comparative Example 3 In Example 1, when drawn yarn waste with a water content of 0.2% by weight and a different amount of oil agent was used, and water was added (the amount of water present was 1 ky), The color tone of the polymer without the addition was compared.
その結果を第２表に示した。The results are shown in Table 2.
Claims (1)
かつ油剤分０．０１重量％（対ポリマ）以上を含有する
ポリエステル糸条体層をグリコール類で解重合するに際
し、該ポリエステル糸条体層に対して水５〜７０重量％
を存在させることを特徴とするポリエステル糸条体層の
解重合方法。1 The main component is polyalkylene terephthalate,
When depolymerizing a polyester thread layer containing an oil component of 0.01% by weight or more (based on the polymer) with glycols, 5 to 70% by weight of water based on the polyester thread layer.
1. A method for depolymerizing a polyester thread layer, characterized by the presence of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6252974A JPS5824425B2 (en) | 1974-06-04 | 1974-06-04 | Polyester material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6252974A JPS5824425B2 (en) | 1974-06-04 | 1974-06-04 | Polyester material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50154215A JPS50154215A (en) | 1975-12-12 |
| JPS5824425B2 true JPS5824425B2 (en) | 1983-05-20 |
Family
ID=13202797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6252974A Expired JPS5824425B2 (en) | 1974-06-04 | 1974-06-04 | Polyester material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5824425B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0244022Y2 (en) * | 1983-05-02 | 1990-11-22 | ||
| JPH0433450Y2 (en) * | 1986-02-25 | 1992-08-11 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5553291Y2 (en) * | 1976-10-09 | 1980-12-10 | ||
| JP2006299143A (en) * | 2005-04-22 | 2006-11-02 | Teijin Fibers Ltd | Method for producing polyester resin |
-
1974
- 1974-06-04 JP JP6252974A patent/JPS5824425B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0244022Y2 (en) * | 1983-05-02 | 1990-11-22 | ||
| JPH0433450Y2 (en) * | 1986-02-25 | 1992-08-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50154215A (en) | 1975-12-12 |
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