JP2020176258A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020176258A5 JP2020176258A5 JP2020019175A JP2020019175A JP2020176258A5 JP 2020176258 A5 JP2020176258 A5 JP 2020176258A5 JP 2020019175 A JP2020019175 A JP 2020019175A JP 2020019175 A JP2020019175 A JP 2020019175A JP 2020176258 A5 JP2020176258 A5 JP 2020176258A5
- Authority
- JP
- Japan
- Prior art keywords
- polyester
- dye
- polyethylene terephthalate
- terephthalate
- dyed
- 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.)
- Granted
Links
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims 16
- -1 polyethylene terephthalate Polymers 0.000 claims 11
- 229920000139 polyethylene terephthalate Polymers 0.000 claims 7
- 239000005020 polyethylene terephthalate Substances 0.000 claims 7
- 239000000975 dye Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 1
- 239000000986 disperse dye Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 claims 1
- 229920001707 polybutylene terephthalate Polymers 0.000 claims 1
- 239000011112 polyethylene naphthalate Substances 0.000 claims 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims 1
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
Description
（実施例８）
脱色剤として、ジエチレングリコールモノヘキシルエーテルに代えて、エチレングリコールモノブチルエーテル（炭素原子数：６）を使用し、脱色剤の加熱温度を１７０℃に変更した以外は、実施例１と同様にして、晶析乾燥ＢＨＥＴおよび再生ＰＥＴを得た。
（実施例９）
脱色剤として、ジエチレングリコールモノヘキシルエーテルに代えて、９０質量部のジエチレングリコールモノメチルエーテル（炭素原子数：５）と１０質量部のジエチレングリコールジエチルエーテル（炭素原子数：８）とを含有する混合液を使用した以外は、実施例１と同様にして、晶析乾燥ＢＨＥＴおよび再生ＰＥＴを得た。
(Example 8)
As the decolorizing agent, ethylene glycol monobutyl ether (number of carbon atoms: 6) was used instead of diethylene glycol monohexyl ether, and the crystal was formed in the same manner as in Example 1 except that the heating temperature of the decolorizing agent was changed to 170 ° C. Derivation-dried BHET and regenerated PET were obtained.
(Example 9)
As the decolorizing agent, a mixed solution containing 90 parts by mass of diethylene glycol monomethyl ether (carbon atom number: 5) and 10 parts by mass of diethylene glycol diethyl ether (carbon atom number: 8) was used instead of diethylene glycol monohexyl ether. Except for the above, crystallization dry BHET and regenerated PET were obtained in the same manner as in Example 1.
（参考例１）
脱色剤の加熱温度を１６５℃とし、着色衣料と加熱脱色剤との接触時間を２０分間とした以外は、実施例１と同様にして、晶析乾燥ＢＨＥＴおよび再生ＰＥＴを得た。
（参考例２）
脱色剤として、ジエチレングリコールモノヘキシルエーテルに代えて、８０質量部のエチレングリコールモノヘキシルエーテル（炭素原子数：８）と２０質量部のモノエチレングリコール（ＥＧ）とを含有する混合液を使用した以外は、実施例１と同様にして、晶析乾燥ＢＨＥＴおよび再生ＰＥＴを得た。
(Reference example 1)
Crystallizing-dried BHET and regenerated PET were obtained in the same manner as in Example 1 except that the heating temperature of the decolorizing agent was 165 ° C. and the contact time between the colored clothing and the heating decolorizing agent was 20 minutes.
(Reference example 2)
As a desiccant, a mixed solution containing 80 parts by mass of ethylene glycol monohexyl ether (carbon atom number: 8) and 20 parts by mass of monoethylene glycol (EG) was used instead of diethylene glycol monohexyl ether. , Crystallized and dried BHET and regenerated PET were obtained in the same manner as in Example 1.
（比較例１）
脱色剤として、ジエチレングリコールモノヘキシルエーテルに代えて、モノエチレングリコール（炭素原子数：２）を使用した以外は、実施例１と同様にして、晶析乾燥ＢＨＥＴおよび再生ＰＥＴを得た。
(Comparative Example 1)
Crystalline-dried BHET and regenerated PET were obtained in the same manner as in Example 1 except that monoethylene glycol (number of carbon atoms: 2) was used instead of diethylene glycol monohexyl ether as the decolorizing agent.
（比較例２）
脱色剤の加熱温度を１９５℃とし、着色衣料と加熱脱色剤との接触時間を３０分間とした以外は、比較例１と同様にして、晶析乾燥ＢＨＥＴおよび再生ＰＥＴを得た。
(Comparative Example 2)
Crystallized dry BHET and regenerated PET were obtained in the same manner as in Comparative Example 1 except that the heating temperature of the decolorizing agent was 195 ° C. and the contact time between the colored clothing and the heating decolorizing agent was 30 minutes.
Claims (7)
前記脱色剤を前記ポリエステルの融点以下、かつ１７０～２１０℃の温度に加熱するとともに、前記着色されたポリエステルに少なくとも１回接触させることにより、前記色素を除去して脱色されたポリエステルを得る工程とを有することを特徴とする脱色ポリエステルの製造方法。 A step of preparing a polyester colored with a dye and a decolorizing agent containing 90% by mass or more of glycol monoether having a boiling point of 160 ° C. or higher under atmospheric pressure.
A step of heating the decolorizing agent to a temperature equal to or lower than the melting point of the polyester and at a temperature of 170 to 210 ° C. and contacting the colored polyester at least once to remove the dye to obtain a decolorized polyester. A method for producing a decolorized polyester, which comprises.
大気圧下での沸点が１６０℃以上であるグリコールモノエーテルを９０質量％以上で含有することを特徴とする脱色剤。 A decolorizing agent used to remove and decolorize the dye from polyester colored with a dye.
A decolorizing agent containing 90% by mass or more of glycol monoether having a boiling point of 160 ° C. or higher under atmospheric pressure.
前記ポリエステルは、ポリエチレンテレフテレート、ポリトリメチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレートまたはポリブチレンナフタレートを含み、
前記色素付きポリエステルに含まれる前記窒素原子の量は、３０ｐｐｍ以下であることを特徴とする色素付きポリエステル。 A dyed polyester comprising a polyester and a dye that colors the polyester and has a chromophore containing nitrogen atoms.
The polyester comprises polyethylene terephthalate, polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate or polybutylene naphthalate.
The dyed polyester is characterized in that the amount of the nitrogen atom contained in the dyed polyester is 30 ppm or less.
得られた前記ビス－２－ヒドロキシエチルテレフタレートを重縮合させて、再生ポリエチレンテレフテレートを得る工程とを有する再生ポリエチレンテレフテレートの製造方法。 A step of depolymerizing the polyethylene terephthalate contained in the dyed polyester according to claim 5 to obtain bis-2-hydroxyethyl terephthalate.
A method for producing a regenerated polyethylene terephthalate, which comprises a step of polycondensing the obtained bis-2-hydroxyethyl terephthalate to obtain a regenerated polyethylene terephthalate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020019175A JP7177449B2 (en) | 2020-02-06 | 2020-02-06 | Method for producing decolorized polyester, method for producing decolorant and recycled polyethylene terephthalate |
| JP2022158524A JP7402456B2 (en) | 2020-02-06 | 2022-09-30 | bleached polyester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020019175A JP7177449B2 (en) | 2020-02-06 | 2020-02-06 | Method for producing decolorized polyester, method for producing decolorant and recycled polyethylene terephthalate |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019542486A Division JP6659919B1 (en) | 2019-04-15 | 2019-04-15 | Method for producing bleached polyester, bleached polyester and bleaching agent |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022158524A Division JP7402456B2 (en) | 2020-02-06 | 2022-09-30 | bleached polyester |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020176258A JP2020176258A (en) | 2020-10-29 |
| JP2020176258A5 true JP2020176258A5 (en) | 2022-04-25 |
| JP7177449B2 JP7177449B2 (en) | 2022-11-24 |
Family
ID=72916340
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020019175A Active JP7177449B2 (en) | 2020-02-06 | 2020-02-06 | Method for producing decolorized polyester, method for producing decolorant and recycled polyethylene terephthalate |
| JP2022158524A Active JP7402456B2 (en) | 2020-02-06 | 2022-09-30 | bleached polyester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022158524A Active JP7402456B2 (en) | 2020-02-06 | 2022-09-30 | bleached polyester |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP7177449B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI752829B (en) * | 2021-02-24 | 2022-01-11 | 南亞塑膠工業股份有限公司 | Decolorization method for dyed fiber cloth |
| TW202311400A (en) * | 2021-09-13 | 2023-03-16 | 南亞塑膠工業股份有限公司 | Method for improving the hue of recycled bhet |
| FR3130804A1 (en) * | 2021-12-17 | 2023-06-23 | IFP Energies Nouvelles | BIS(2-HYDROXYETHYL)TEREPHTHALATE WITH A LOW NITROGEN CONTENT |
| WO2023176649A1 (en) * | 2022-03-15 | 2023-09-21 | 東レ株式会社 | Recycled polyester resin obtained by using colored pet fabric as material, and method for obtaining ester monomer from colored pet fabric |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5226549B2 (en) * | 1973-08-10 | 1977-07-14 | ||
| JP2003238673A (en) | 2002-02-19 | 2003-08-27 | Toray Ind Inc | Method for producing polyester |
| JP2004217871A (en) | 2003-01-17 | 2004-08-05 | Teijin Fibers Ltd | Method of recovering useful components from dyed polyester fiber |
| JP2007254904A (en) | 2006-03-22 | 2007-10-04 | Komatsu Seiren Co Ltd | Polyester-based textile product for recycling, method for decoloring polyester-based textile product for recycling, and method for recycling polyester-based textile product |
-
2020
- 2020-02-06 JP JP2020019175A patent/JP7177449B2/en active Active
-
2022
- 2022-09-30 JP JP2022158524A patent/JP7402456B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020176258A5 (en) | ||
| JP6659919B1 (en) | Method for producing bleached polyester, bleached polyester and bleaching agent | |
| EP3583162B1 (en) | Polyester textile waste recycling | |
| KR20200061948A (en) | Purification of bis-2-hydroxyethyl terephthalate and preparation of polyester by using the same | |
| JP7177449B2 (en) | Method for producing decolorized polyester, method for producing decolorant and recycled polyethylene terephthalate | |
| US11802190B2 (en) | Polyester textile waste recycling | |
| JPH04261497A (en) | Purification of oil and fat rich in diglyceride | |
| US1883182A (en) | Esterification product of dicarboxylic acids and their production | |
| JPS62241919A (en) | Improvement in color of polyester by oxygen desorption | |
| JP2023041599A (en) | Method for producing recycled polyester chips from recycled polyester fabric | |
| US1864893A (en) | Process for making esters of butyl alcohol | |
| CN110041194A (en) | The preparation method of phthalic acid two (2- ethyl hexyl) ester | |
| CN115807336A (en) | Method for recovering polyester cotton blended fabric | |
| WO2023121411A1 (en) | Eco-friendly method for decolorization and depolymerization of colored polymer containing ester functional group | |
| KR0174826B1 (en) | Replacements of fatty acid alkaline salts | |
| US3120560A (en) | purification of bis beta hydroxyethyl terephtalate | |
| CN108191650A (en) | A kind of preparation method of pentaerythrite tetra-acetate | |
| US3840574A (en) | Process for the preparation of heatresistant and lightfast fatty acids | |
| JP2023041608A (en) | Method for improving hue of recycled bis(2-hydroxyethyl) terephthalate | |
| CN108129642B (en) | Method for preventing polyester polyol from acid reversion | |
| CN106748920A (en) | A kind of Florfenicol raw material DL ethyl ester preparation methods | |
| JP4794081B2 (en) | Method for producing high purity terephthalic acid | |
| CN114539175A (en) | Synthetic method of ultraviolet absorbent UV-384-2 | |
| CN117624091A (en) | Crystallization purification method for improving stability of 3-o-ethyl ascorbic acid | |
| US3012066A (en) | Production of dimethyl terephthalate |