JP3709014B2 - Method for recovering monomer from waste acrylic resin - Google Patents
Method for recovering monomer from waste acrylic resin Download PDFInfo
- Publication number
- JP3709014B2 JP3709014B2 JP16360296A JP16360296A JP3709014B2 JP 3709014 B2 JP3709014 B2 JP 3709014B2 JP 16360296 A JP16360296 A JP 16360296A JP 16360296 A JP16360296 A JP 16360296A JP 3709014 B2 JP3709014 B2 JP 3709014B2
- Authority
- JP
- Japan
- Prior art keywords
- distillation
- acrylic resin
- monomer
- product
- liquefied
- 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 - Lifetime
Links
- 239000000178 monomer Substances 0.000 title claims description 17
- 239000004925 Acrylic resin Substances 0.000 title claims description 13
- 229920000178 Acrylic resin Polymers 0.000 title claims description 13
- 239000002699 waste material Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title description 12
- 238000004821 distillation Methods 0.000 claims description 19
- 238000000197 pyrolysis Methods 0.000 claims description 15
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 239000000047 product Substances 0.000 description 25
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 9
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 238000003763 carbonization Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- -1 alkyl methacrylate Chemical compound 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000013502 plastic waste Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Processing Of Solid Wastes (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【0001】
【発明の属する技術分野】
本発明は、アクリル系樹脂の廃材からモノマーを回収する方法に関する。
【0002】
【従来の技術】
近年、地球環境保護及び省資源の立場からプラスチック廃材の再利用が強く要請されている。プラスチック廃材の再利用は種々の方法により行われているが、特に有力な方法として乾留、すなわち、実質的に酸素の存在しない状態において、プラスチックを加熱分解し低分子量なモノマーに還元して再利用することが行われている。
【0003】
メチルメタクリレートを主成分とするアクリル系樹脂は、乾留によって樹脂を構成する原料モノマーを高収率で回収することが可能であり、従来から乾留によるモノマー回収が行われて来た。
【0004】
しかし、従来の方法によってアクリル系樹脂の廃材から回収されたモノマーを使用して製造されるプラスチック製品は、僅かながら黄帯色を有するため、極めて高度な透明性が要求される分野の製品向けには回収したモノマーを使用することは困難であった。
【0005】
【発明が解決しようとする課題】
本発明の目的は、メチルメタクリレートを主成分とするアクリル系樹脂廃材からモノマーを回収するに際して、上記従来技術の欠点を改良し、高度な透明性を有するプラスチック製品の製造を可能とするモノマーの回収方法を提供することにある。
【0006】
【課題を解決するための手段】
本発明の上記の目的は、アクリル系樹脂廃材を乾留によってガス状に加熱分解し、しかる後そのガス状加熱分解物を液化し、次いで、その液化した加熱分解物を蒸留精製してモノマーとして回収するに際し、液化した加熱分解物に多価アミンを予め添加するに際し5〜30重量%の水を添加して十分混合せしめしかる後に水層を分離除去し、油分層を蒸留精製することを特徴とするアクリル系樹脂廃材からモノマーを回収する方法によって達成される。
【0007】
【発明の実施の形態】
本発明において用いられるアクリル系樹脂廃材は、メチルメタクリレート単独重合体、又は80重量%以上のメチルメタクリレートと20重量%以下のアルキルメタクリレートもしくはアルキルアクリレートの共重合体より構成されるが、必要に応じて物性改良剤又は着色剤等が添加されたものも含まれる。
【0008】
本発明の原料となる上記のアクリル樹脂廃材は、乾留処理する前に必要に応じて適当な大きさに粉砕される。アクリル樹脂廃材に保護紙、保護フィルム等のマスキング材が貼り付けてある場合、本発明においては、そのまま乾留処理しても何ら問題はない。本発明によらない従来技術にて回収されたモノマーは、マスキング材の存在下に乾留処理された場合特に黄帯色を呈し透明性を損う。
【0009】
乾留は、一般的には、上記の原料を釜に投入し、必要に応じて不活性ガス雰囲気中で実質的に酸素の存在しない状態において350〜500℃の温度に加熱して行われる。ガス状の加熱分解物は釜から取り出した後、熱交換器タイプの冷却器等により凝縮液化される。
【0010】
次いで、その液化した加熱分解物に、多価アミンを予め添加し蒸留精製を行う。多価アミンの添加量は10〜10000ppmの範囲とするのが好ましい。使用される多価アミンとしては、例えば、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、テトラエチレンペンタミン、ペンタエチレンヘキサミン等が挙げられるが、このうちでもエチレンジアミン、ジエチレントリアミン及びトリエチレンテトラミンが好ましい。多価アミンの添加量が少なすぎると十分な効果が得られない。又、多すぎると蒸留精製時にモノマーからの分離除去が困難となる。
【0011】
液化した加熱分解物に多価アミンを添加する方法としては、蒸留する前に添加する。すなわち、蒸留塔内に添加する。好ましくは蒸留する前に予め多価アミンを添加する方法が採られる。この好ましい方法によって回収されるモノマーは透明性に関する品質が一層向上する。
【0012】
液化した加熱分解物に多価アミンを予め添加するには、液化した加熱分解物に5〜30重量%量の水を添加して十分混合せしめ、しかる後に水層をデカンター等にて分離除去し、残りの加熱分解物より成る油分層を蒸留精製することが望ましい。
【0013】
加熱分解物に多価アミンを添加すると沈殿物が生成するので、水を加えて溶解除去することで以降の運転操作が容易となる。加熱分解物に飽和状態で含まれる水分は蒸留精製時に除去される。
【0014】
蒸留精製は運転中の重合を防止するために、通常100〜500mmHgの減圧状態として沸点を下げて実施する。蒸留は回分的にも連続的にも実施することができる。蒸留精製に使用される装置としては、特に限定されないが、多段の蒸留塔を備えたものが好ましく使用される。
【0015】
【実施例】
以下、実施例により本発明を具体的に説明する。
【0016】
[参考例1]
クラフト保護紙が貼付けされたメチルメタクリレート95重量%及びn−ブチルアクリレート5重量%からなる3mm厚さのアクリル板と、ポリエチレンフィルムの貼付けされたメチルメタクリレート単独重合体からなる3mm厚さのアクリル板とを重量比で1:1の割合で粉砕混合した。次いで、その粉砕混合物を内径30cm、高さ50cmのステンレス製乾留釜に3kg仕込み、釜内部を十分窒素ガスにて置換した後、釜壁温度を430℃に昇温し、発生したガスを冷却液化して約2.8kgの乾留液を得た。
【0017】
次いで、その乾留液にトリエチレンテトラミンを5000ppm添加した後、内径46mmのガラス製オールダショ型30段の蒸留塔に仕込み300mmHgの減圧状態で蒸留を行った。還流比は3とした。初留分5重量%をカットした後、製品を採取し始め最終的に15重量%の高沸点物を残して蒸留を終了した。得られた製品をガスクロマトグラフィで分析したところ純度99.8%の高純度なメチルメタクリレートが得られた。この製品の色数(ハーゼン)をJIS−K−4101に従い測定したところ10と良好なものであった。
【0018】
[参考例2]
参考例1で使用したと同様の蒸留塔を2塔連結して連続蒸留置置を組み立てた。最初の低沸点物除去塔は下から20段目に原料(乾留液)を供給し、後の高沸点物除去塔は下から10段目に低沸点物除去塔の缶出液を供給するようにした。参考例1と同様にして得られた乾留液を1.2Kg/hの割合で低沸点物除去塔に供給し300mmHgで蒸留を行った。還流比は3とし、留出液カット率は5%とした。同時に10倍にメチルメタクリレートで希釈したジエチレントリアミンを乾留液に対し3000ppmの割合で乾留液の供給段に供給した。一方、低沸点物除去塔の缶出液はさらに高沸点物除去塔に供給し200mmHgで蒸留を行った。蒸留は連続3時間行った。還流比は2とし塔頂からは85%の収率で製品が得られた。この製品をガスクロマトグラフィーで分析したところ純度99.8%の高純度なメチルメタクリレートが得られた。この製品の色数(ハーゼン)を測定したところ8と良好なものであった。
【0019】
[参考例3]
多価アミンの添加方法を変えた他は、参考例2と同様にして行った。多価アミンの添加方法としては、トリエチレンテトラミンを予め乾留液に3000ppm添加し、さらに10倍にメチルメタクリレートで希釈したトリエチレンテトラミンを高沸点物除去塔のフィード供給段にフィード供給に対し200ppmの割合で供給した。蒸留を連続10時間実施した時に低沸点物除去塔への原料供給ポンプ出口に設けたフィルター詰りのために運転が停止した。このようにして得られた製品をガスクロマトグラフィで分析したところ純度99.8%の高純度なメチルメタクリレートが得られた。この製品の色数(ハーゼン)を測定したところ3と良好なものであった。
【0020】
[実施例1]
参考例3でトリエチレンテトラミンを予め乾留液に3000ppm添加した後15%の水を加えて十分混合し、静置後上層の油分層のみを低沸点物除去塔に供給した他は参考例3と同様にして行った。蒸留を連続30時間実施したがフィルターの詰りもなく順調に運転できた。このようにして得られた製品をガスクロマトグラフィで分析したところ純度99.8%の高純度なメチルメタクリレートが得られた。この製品の色数(ハーゼン)を測定したところ2と良好なものであった。
【0021】
【発明の効果】
本発明により、アクリル系樹脂廃材から極めて高度な透明性を有するプラスチック製品の製造を可能とするモノマーの回収が可能となり、工場等から排出する廃材の有効利用を促進し、且つ、省資源効果により地球環境の保護に資するものである。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for recovering a monomer from a waste material of an acrylic resin.
[0002]
[Prior art]
In recent years, there has been a strong demand for recycling plastic waste from the standpoints of global environmental protection and resource saving. Various methods are used to recycle plastic waste, but the most effective method is dry distillation, that is, in the absence of oxygen, the plastic is thermally decomposed and reduced to low molecular weight monomers for reuse. To be done.
[0003]
Acrylic resins mainly composed of methyl methacrylate can recover the raw material monomers constituting the resin by dry distillation in a high yield, and conventionally monomer recovery by dry distillation has been performed.
[0004]
However, plastic products manufactured using monomers recovered from acrylic resin waste by conventional methods have a slight yellowish color, so they are suitable for products in fields where extremely high transparency is required. It was difficult to use the recovered monomer.
[0005]
[Problems to be solved by the invention]
The object of the present invention is to recover the monomer which improves the drawbacks of the above prior art and enables the production of a highly transparent plastic product when recovering the monomer from the waste acrylic resin mainly composed of methyl methacrylate. It is to provide a method.
[0006]
[Means for Solving the Problems]
The above-mentioned object of the present invention is to thermally decompose acrylic resin waste into a gaseous state by dry distillation, then liquefy the gaseous thermally decomposed product, and then recover the liquefied thermally decomposed product as a monomer by distillation purification. In addition, when adding polyvalent amine to the liquefied thermal decomposition product in advance, 5 to 30% by weight of water is added and mixed thoroughly, and then the aqueous layer is separated and removed, and the oil layer is distilled and purified. This is achieved by a method of recovering monomers from waste acrylic resin.
[0007]
DETAILED DESCRIPTION OF THE INVENTION
The acrylic resin waste material used in the present invention is composed of a methyl methacrylate homopolymer or a copolymer of 80% by weight or more of methyl methacrylate and 20% by weight or less of alkyl methacrylate or alkyl acrylate. The thing to which the physical property improving agent or the coloring agent was added is also included.
[0008]
The acrylic resin waste material as a raw material of the present invention is pulverized to an appropriate size as necessary before the carbonization treatment. When a masking material such as protective paper or protective film is attached to the acrylic resin waste material, in the present invention, there is no problem even if the carbonization treatment is performed as it is. Monomers recovered by the prior art not according to the present invention exhibit a yellowish color particularly when subjected to dry distillation treatment in the presence of a masking material and impair transparency.
[0009]
In general, dry distillation is performed by charging the above-mentioned raw material into a kettle and heating to a temperature of 350 to 500 ° C. in an inert gas atmosphere in the absence of substantially oxygen as necessary. The gaseous thermal decomposition product is taken out from the kettle and then condensed and liquefied by a heat exchanger type cooler or the like.
[0010]
Then, on the liquefied thermal decomposition is carried out in advance added pressure Shi distillation purification polyamine. The amount of polyamine added is preferably in the range of 10 to 10,000 ppm. Examples of the polyvalent amine used include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and the like. Among these, ethylenediamine, diethylenetriamine and triethylenetetramine are preferable. If the amount of polyvalent amine added is too small, sufficient effects cannot be obtained. On the other hand, when the amount is too large, it is difficult to separate and remove from the monomer during distillation purification.
[0011]
As a method of adding a polyvalent amine to the liquefied thermal decomposition product, it is added before distillation . That is, it is added into the distillation column. Preferably, a method of adding a polyvalent amine in advance before distillation is employed. The monomer recovered by this preferred method is further improved in transparency quality.
[0012]
In order to add polyvalent amine to the liquefied pyrolysis product in advance, add 5 to 30% by weight of water to the liquefied thermolysis product and mix well, and then separate and remove the aqueous layer with a decanter or the like. It is desirable to purify the oil layer composed of the remaining thermal decomposition product by distillation.
[0013]
When a polyvalent amine is added to the thermally decomposed product, a precipitate is generated. Therefore, the subsequent operation is facilitated by dissolving and removing water by adding water. Moisture contained in the thermal decomposition product in a saturated state is removed during distillation purification.
[0014]
In order to prevent polymerization during operation, distillation purification is usually carried out at a reduced pressure in a reduced pressure state of 100 to 500 mmHg. The distillation can be carried out batchwise or continuously. The apparatus used for distillation purification is not particularly limited, but an apparatus equipped with a multistage distillation column is preferably used.
[0015]
【Example】
Hereinafter, the present invention will be described specifically by way of examples.
[0016]
[ Reference Example 1 ]
3 mm-thick acrylic plate consisting of 95% by weight methyl methacrylate and 5% by weight n-butyl acrylate with kraft protective paper affixed, and a 3 mm thick acrylic plate consisting of methyl methacrylate homopolymer with a polyethylene film affixed Were pulverized and mixed at a weight ratio of 1: 1. Next, 3 kg of the pulverized mixture was charged into a stainless steel dry distillation kettle with an inner diameter of 30 cm and a height of 50 cm, the inside of the kettle was sufficiently replaced with nitrogen gas, the kettle wall temperature was raised to 430 ° C., and the generated gas was cooled and liquefied. As a result, about 2.8 kg of a carbonized distillate was obtained.
[0017]
Next, after adding 5000 ppm of triethylenetetramine to the dry distillation liquid, it was charged in a glass old-type 30-stage distillation column having an inner diameter of 46 mm and distilled under reduced pressure of 300 mmHg. The reflux ratio was 3. After cutting 5% by weight of the first fraction, the product was collected and finally distillation was terminated leaving 15% by weight of high-boiling products. When the obtained product was analyzed by gas chromatography, high purity methyl methacrylate having a purity of 99.8% was obtained. When the number of colors (Hazen) of this product was measured according to JIS-K-4101, it was as good as 10.
[0018]
[ Reference Example 2 ]
Two distillation columns similar to those used in Reference Example 1 were connected to assemble a continuous distillation apparatus. The first low boiler removal tower supplies the raw material (dry distillation liquid) in the 20th stage from the bottom, and the subsequent high boiler removal tower supplies the bottoms of the low boiler removal tower in the 10th stage from the bottom. I made it. The dry distillation liquid obtained in the same manner as in Reference Example 1 was supplied to the low boiler removal column at a rate of 1.2 Kg / h and distilled at 300 mmHg. The reflux ratio was 3, and the distillate cut rate was 5%. At the same time, diethylenetriamine diluted 10-fold with methyl methacrylate was supplied to the dry distillation liquid supply stage at a ratio of 3000 ppm to the dry distillation liquid. On the other hand, the bottoms of the low boiler removal tower was further supplied to the high boiler removal tower and distilled at 200 mmHg. Distillation was continued for 3 hours. The reflux ratio was 2, and the product was obtained at a yield of 85% from the top of the column. When this product was analyzed by gas chromatography, high purity methyl methacrylate having a purity of 99.8% was obtained. When the number of colors (Hazen) of this product was measured, it was as good as 8.
[0019]
[ Reference Example 3 ]
The procedure was the same as in Reference Example 2 , except that the method for adding the polyvalent amine was changed. As a method for adding the polyvalent amine, 3000 ppm of triethylenetetramine was added to the dry distillation solution in advance, and triethylenetetramine diluted 10-fold with methyl methacrylate was added to the feed supply stage of the high boiler removal column at 200 ppm relative to the feed supply. Supplied in proportion. When the distillation was carried out continuously for 10 hours, the operation was stopped due to filter clogging provided at the outlet of the raw material supply pump to the low boiler removal column. When the product thus obtained was analyzed by gas chromatography, high purity methyl methacrylate having a purity of 99.8% was obtained. The number of colors (Hazen) of this product was measured and found to be 3 and good.
[0020]
[Example 1 ]
Thoroughly mixed with 15% water was added 3000ppm in advance carbonization solution triethylenetetramine in Reference Example 3, except that supply only after standing layer of the oil layer in low boilers removal column is as in Reference Example 3 The same was done. Distillation was carried out continuously for 30 hours, but it was able to operate smoothly without clogging the filter. When the product thus obtained was analyzed by gas chromatography, high purity methyl methacrylate having a purity of 99.8% was obtained. When the number of colors (Hazen) of this product was measured, it was as good as 2.
[0021]
【The invention's effect】
According to the present invention, it becomes possible to recover monomers that enable the production of plastic products having extremely high transparency from acrylic resin waste materials, promote the effective use of waste materials discharged from factories, etc. It contributes to the protection of the global environment.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16360296A JP3709014B2 (en) | 1996-06-05 | 1996-06-05 | Method for recovering monomer from waste acrylic resin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16360296A JP3709014B2 (en) | 1996-06-05 | 1996-06-05 | Method for recovering monomer from waste acrylic resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH09324068A JPH09324068A (en) | 1997-12-16 |
JP3709014B2 true JP3709014B2 (en) | 2005-10-19 |
Family
ID=15777052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16360296A Expired - Lifetime JP3709014B2 (en) | 1996-06-05 | 1996-06-05 | Method for recovering monomer from waste acrylic resin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3709014B2 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001288147A (en) * | 2000-04-11 | 2001-10-16 | Mitsubishi Rayon Co Ltd | Method for producing methyl methacrylate |
JP4733275B2 (en) * | 2001-01-10 | 2011-07-27 | 三菱レイヨン株式会社 | (Meth) acrylic acid ester purification method |
JP4942878B2 (en) * | 2001-02-07 | 2012-05-30 | 三菱レイヨン株式会社 | (Meth) acrylic acid ester purification method |
JP5083999B2 (en) * | 2001-09-28 | 2012-11-28 | 旭化成ケミカルズ株式会社 | Method for producing methyl methacrylate |
KR100883365B1 (en) * | 2007-10-12 | 2009-02-11 | 제일모직주식회사 | Recycling method of waste acrylic resin and a composition for acrylic artificial marble using recycled (meth)acrylic monomer |
KR101048268B1 (en) * | 2010-10-06 | 2011-07-08 | 최상근 | Recycling method of waste acrylic resin |
CN115516016A (en) * | 2020-05-15 | 2022-12-23 | Dic株式会社 | Regeneration method of waste polystyrene product |
-
1996
- 1996-06-05 JP JP16360296A patent/JP3709014B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPH09324068A (en) | 1997-12-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100733400B1 (en) | Azeotropic Distillation Process for Separating Acetic Acid, Methyl Acetate and Water | |
US4254246A (en) | Column system process for polyester plants | |
JPS6054939B2 (en) | Method for purifying crude acrylic acid | |
EP1301471B1 (en) | Process for the purification and recovery of acetonitrile | |
JP3709014B2 (en) | Method for recovering monomer from waste acrylic resin | |
EP0031097A1 (en) | Method for distilling ethyl alcohol | |
JPS5914018B2 (en) | Method for producing methacrylic acid ester | |
US6172258B1 (en) | Process for the production and purification of n-butyl acrylate | |
EP0601458A2 (en) | Separation process | |
US6264800B1 (en) | Purification process | |
US6494996B2 (en) | Process for removing water from aqueous methanol | |
EP0501374A1 (en) | Process for purifying dimethyl carbonate | |
WO2002076944A1 (en) | Method of purifying n-(2-hydroxyethyl)-2-pyrrolidone | |
KR100639475B1 (en) | Process for the production and purification of n-butyl acrylate | |
JPS6160624A (en) | Collection of sulfolane | |
CN1030909C (en) | Acetone removal process | |
CA2016347C (en) | Process for manufacturing high-purity o-toluic acid | |
JPH05230015A (en) | Purification of caprolactam | |
JPH02229182A (en) | Purification of tetrahydofuran | |
JP2003321571A (en) | Method for recovering monomer from acrylic resin | |
JP5194124B2 (en) | Method for removing heavy hydrocarbons from reaction products producing sec-butyl acetate | |
KR100225671B1 (en) | A waste water treating method from methylamine manufacturing process using organic compound separation method | |
WO2003057656A1 (en) | Acrylic acid recovery utilizing ethyl acrylate and selected co-solvents | |
SU923363A3 (en) | Method for inhibiting thermopolymerization | |
JP2005089359A (en) | [4-(hydroxymethyl)cyclohexyl]methyl acrylate |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20041028 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20050510 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050705 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20050802 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20050805 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080812 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090812 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100812 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100812 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110812 Year of fee payment: 6 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110812 Year of fee payment: 6 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110812 Year of fee payment: 6 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120812 Year of fee payment: 7 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120812 Year of fee payment: 7 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130812 Year of fee payment: 8 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |