WO2016159707A1 - 증류 장치 - Google Patents
증류 장치 Download PDFInfo
- Publication number
- WO2016159707A1 WO2016159707A1 PCT/KR2016/003387 KR2016003387W WO2016159707A1 WO 2016159707 A1 WO2016159707 A1 WO 2016159707A1 KR 2016003387 W KR2016003387 W KR 2016003387W WO 2016159707 A1 WO2016159707 A1 WO 2016159707A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- region
- stripper
- dividing wall
- mmhg
- column
- Prior art date
Links
- 238000004821 distillation Methods 0.000 title claims abstract description 253
- 239000002994 raw material Substances 0.000 claims abstract description 80
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 74
- 239000002699 waste material Substances 0.000 claims abstract description 53
- 239000011347 resin Substances 0.000 claims abstract description 31
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000009835 boiling Methods 0.000 claims description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 239000003960 organic solvent Substances 0.000 claims description 33
- -1 amine compound Chemical class 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 18
- 239000002798 polar solvent Substances 0.000 claims description 15
- 238000005192 partition Methods 0.000 claims description 7
- 238000000746 purification Methods 0.000 abstract description 11
- 238000009434 installation Methods 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 46
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
- 238000010992 reflux Methods 0.000 description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000000926 separation method Methods 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 13
- 239000012535 impurity Substances 0.000 description 11
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 7
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 2
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- QZXIXSZVEYUCGM-UHFFFAOYSA-N 2-aminopropan-2-ol Chemical compound CC(C)(N)O QZXIXSZVEYUCGM-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- VMLCXHOZGAIVPC-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;ethanol Chemical compound CCO.C1CN=CN1 VMLCXHOZGAIVPC-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/02—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in boilers or stills
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/141—Fractional distillation or use of a fractionation or rectification column where at least one distillation column contains at least one dividing wall
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/42—Regulation; Control
- B01D3/4211—Regulation; Control of columns
- B01D3/4261—Side stream
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D5/00—Condensation of vapours; Recovering volatile solvents by condensation
- B01D5/0057—Condensation of vapours; Recovering volatile solvents by condensation in combination with other processes
- B01D5/006—Condensation of vapours; Recovering volatile solvents by condensation in combination with other processes with evaporation or distillation
- B01D5/0063—Reflux condensation
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers
- H01L27/12—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body
- H01L27/1214—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs
- H01L27/1259—Multistep manufacturing methods
- H01L27/1288—Multistep manufacturing methods employing particular masking sequences or specially adapted masks, e.g. half-tone mask
Definitions
- the present application relates to a distillation apparatus and method.
- a photoresist stripper In order to remove photoresist, particulate residue, foreign matter, and denatured material remaining after gate pattern formation and metal film etching in the photoresist stripping process during the TFT-LCD array substrate manufacturing process, a photoresist stripper, Hereinafter, a 'striper') solution is used.
- the amount of organic solvent used in the stripper is about 30,000 tons per year, and accounts for the highest proportion of raw material purchase costs. Accordingly, there is an increasing need for recycling waste stripper solutions.
- the waste stripper solution used in the manufacturing process contains impurities such as photoresist resin, water, heavy metal, etc. in addition to the organic amine compound and the organic solvent, the organic solvent and the photoresist resin are removed from the waste stripper solution.
- impurities such as photoresist resin, water, heavy metal, etc.
- the organic solvent and the photoresist resin are removed from the waste stripper solution.
- the organic solvent and the organic amine compound were recovered from the waste stripper solution including water, the organic amine compound, the organic solvent and the exfoliated photoresist resin using a distillation apparatus in which two distillation columns were sequentially connected. The problem is that a large amount of energy is consumed in.
- the present application is to provide a distillation apparatus for separating the waste stripper solution used in the process of peeling the photoresist with high efficiency and low cost.
- the present application relates to a distillation apparatus.
- Exemplary distillation apparatus according to embodiments of the present application, to minimize the energy loss generated during the purification of the waste stripper solution containing the stripper and the exfoliated photoresist resin used in the process of peeling the photoresist, Separation with high purity can improve the economics of the process.
- temperature and pressure conditions optimized for separation of the waste stripper solution using the dividing wall distillation column are provided, and thus, the stripper and the peeled photoresist resin are separated using the distillation apparatus of the present application. In this case, the stripper can be separated and reused with high efficiency.
- FIG. 1 exemplarily shows a distillation apparatus according to an embodiment of the present application.
- the distillation apparatus of the present application includes a condenser 102, a reboiler 103, and a distillation column 100 having a dividing wall 101 therein.
- the distillation column 100 having the dividing wall 101 therein may be a dividing wall type distillation column 100.
- the dividing wall distillation column 100 is a device designed for the distillation of the raw material F 1-1 including low boiling point, middle boiling point and high boiling point components, and a similar device in terms of thermodynamic distillation column (Petlyuk column). to be.
- the heat-comprising distillation column primarily separates low boiling point and high boiling point materials from the preliminary separator, and the top and bottom portions of the preliminary separator are introduced into the feed stage of the main separator, respectively. It is designed to separate each one.
- the dividing wall distillation column 100 is a form in which the preliminary separator is integrated into the main separator by installing the dividing wall 101 in the tower.
- the design structure and operating conditions of the distillation column such as the position of the feed stage, the dividing wall section, the production stage position of the middle boiling point material, the total theoretical stage, the distillation temperature, and the distillation pressure are very limited.
- the design structure such as the number of stages of the distillation column, the positions of the feed stage and the outlet stage, and the operating conditions such as the distillation temperature, the distillation pressure and the reflux ratio should be specially changed.
- the distillation apparatus of the present application separates the waste stripper solution including the stripper and the exfoliated photoresist resin with high purity and high efficiency so as to reduce the energy required for purification of the waste stripper and reduce the equipment cost of the distillation apparatus. It is possible to provide operating conditions of the dividing wall distillation column 100 designed to be suitable below.
- the specific kind of the dividing wall distillation column 100 that can be used in the distillation apparatus of the present application is not particularly limited.
- a dividing wall distillation column 100 having a general structure as shown in FIG. 1 may be used, or a distillation column in which the position or design of the dividing wall 101 in the distillation column is modified in consideration of purification efficiency may be used.
- the number of stages and the inner diameter of the distillation column are not particularly limited, and for example, the number of stages inferred from the distillation curve in consideration of the composition of the raw material F 1-1 may be set.
- the dividing wall distillation column 100 of the present application may have a structure as shown in FIG. 1.
- the exemplary dividing wall distillation column 100 is divided by a dividing wall 101.
- the interior of the dividing wall distillation column 100 is divided into a top dotted region 110, a bottom region 130, and between the top region 110 and the bottom region 130, as shown in FIG. 1. It may be divided into a top wall region 110 and a partition wall region 120 in contact with the top bottom region 130.
- the dividing wall 101 may be located in the dividing wall area 120.
- the inside of the distillation column 100 may include a dividing wall area 120 in which the dividing wall 101 is located.
- the partition wall 101 may be divided into a top region 110 and a bottom region 130 where the separation wall 101 is not located.
- the dividing wall region 120 may be divided into a raw material supply region 121 and a product outlet region 122 divided by the dividing wall 101.
- the dividing wall distillation column 100 may include a top region 110 through which a low boiling point flow is discharged, a bottom region 130 through which a high boiling point flow is discharged, and a raw material supply region through which a raw material F 1-1 flows in ( 121) and the product outlet region 122 from which the product flows out.
- “Top column” of the dividing wall distillation column 100 refers to the top portion of the dividing wall distillation column 100, and may be included in the top region 110 of the dividing wall distillation column 100 described above.
- “Top bottom” of 100 means the bottom portion of the dividing wall distillation column 100, and may be included in the top bottom region 130 of the dividing wall distillation column 100 described above.
- the "condenser” is a device installed separately from the distillation column, and may mean an apparatus for cooling the material flowing out of the main body in contact with the cooling water introduced from the outside.
- the condenser 102 of the distillation apparatus may be a device for condensing the overhead stream (F 1-2 ) flowing out of the overhead region 110 of the dividing wall distillation column (100).
- the "reboiler” is a heating device installed on the outside of the distillation column, it may mean a device for heating and evaporating again the high boiling point flow.
- the reboiler 103 of the distillation apparatus may be a device for heating the top flow (F 1-2 ) flowing out from the bottom region 130 of the dividing wall distillation column (100).
- the raw material supply region 121 and the product outlet region 122 may be separated or isolated from each other by the dividing wall 101. Accordingly, it is possible to prevent the flow in the raw material supply region 121 and the flow in the product outlet region 122 from mixing with each other.
- the term "separation or isolation” means that the flow in each region flows or exists independently in the region divided by the separating wall 101.
- the dividing wall 101 of the dividing wall distillation column 100 is 5 to 95% of the total theoretical number calculated based on the top of the dividing wall distillation column 100 based on the column top. , From 10 to 90%, preferably from 15 to 85%, more preferably from 20 to 80%.
- theoretical stage number means the number of virtual regions or stages in which the two phases, such as gaseous phase and liquid phase, are balanced with each other in the dividing wall distillation column 100.
- the dividing wall 101 is located in the dividing wall region 120 of the dividing wall distillation column 100 within the theoretical number of stages, so that the flow in the raw material supply region 121 and the flow in the product outlet region 122 are mixed. You can effectively block yourself from becoming. In addition, low-boiling components may be prevented from being mixed and mixed in the product flow F 1-4 flowing out of the product outflow region 122.
- the raw material F 1-1 of the waste stripper solution including the stripper and exfoliated photoresist resin may be introduced into the raw material supply region 121 of the dividing wall distillation column 100 as shown in FIG. 1. have.
- the raw material (F 1-1 ) of the waste stripper solution flows into the raw material supply region 121 of the dividing wall distillation column 100
- the raw material (F 1-1 ) in the column bottom region 130 It is separated into the outflow bottom stream (F 1-3 ), the top stream (F 1-2 ) flowing out from the top region 110, and the product flow (F 1-4 ) flowing out of the product outlet region 122, respectively.
- a column top flow F 1-2 which is a flow of a relatively low boiling point component, from the components contained in the waste stripper solution as the raw material F 1-1 may flow out.
- a product flow F 1-4 which is a flow of a relatively middle boiling point component, is included in the waste stripper solution that is a raw material F 1-1 .
- the term “low boiling point flow” refers to a stream in which a relatively low boiling point component is rich among raw material streams F 1-1 including low boiling point, middle boiling point, and high boiling point components.
- high boiling point flow refers to a stream in which a relatively high boiling point component is rich among raw material streams F 1-1 including low boiling point, middle boiling point, and high boiling point components.
- a relatively high boiling point component flowing out of the bottom region 130 of the dividing wall distillation column 100 means a rich flow.
- the "medium boiling point flow” means a rich flow of a component having a boiling point between the low boiling point component and the high boiling point component in the raw material stream F 1-1 including the low boiling point, the middle boiling point and the high boiling point component.
- the middle boiling point flow refers to, for example, a flow flowing out of the product outlet region 122 of the dividing wall distillation column 100.
- the term "rich flow” refers to flow out from the top region 110 of the dividing wall distillation column 100 rather than the content of the low boiling point component, the high boiling point component and the middle boiling point component contained in the raw material F 1-1 .
- the lower boiling point component included in the stream, the high boiling point component included in the stream flowing out of the bottom region 130, and the middle boiling point component included in the stream flowing out of the product outlet region 122 mean higher flows.
- the low boiling point component included in the column top flow (F 1-2 ) of the dividing wall distillation column 100 the high boiling point component included in the column bottom stream (F 1-3 ) and the product stream (F 1-4 ).
- Each content represented by the middle boiling point component included may mean a flow of 50% by weight, 80% by weight, 90% by weight, 95% by weight or 99% by weight or more.
- the top boiling flow (F 1-2 ) of the low boiling point stream and the dividing wall distillation column 100 may be used in the same sense, and the high boiling point flow and the bottom bottom flow (F 1-3 ) of the dividing wall distillation column 100. ) May be used in the same sense, and the product boiling point F 1-4 of the middle boiling point stream and the dividing wall distillation column 100 may be used in the same sense.
- the stripper included in the raw material F 1-1 of the waste stripper solution may be a stripper used in the peeling process of the photoresist.
- the stripper may be a non-aqueous stripper or an aqueous stripper.
- the aqueous stripper means a stripper in which each component is dissolved in water
- the non-aqueous stripper means a stripper that does not contain water.
- the waste stripper solution (F 1-1 ) includes, for example, water or a low boiling point component such as isopropyl alcohol (IPA), methanol, diethylamine (DEA); Organoamine compounds; Organic solvents; And exfoliated photoresist, such as a non-volatile material generated by heating and decomposition of the photoresist, for example, a modified polymer or a metal component.
- IPA isopropyl alcohol
- DEA diethylamine
- Organoamine compounds Organoamine compounds
- Organic solvents Organic solvents
- exfoliated photoresist such as a non-volatile material generated by heating and decomposition of the photoresist, for example, a modified polymer or a metal component.
- the organic amine compound dissolves the photoresist by infiltrating the polymer structure of the photoresist deteriorated or crosslinked in various processes such as etching, incineration, ion implantation, and the like, thereby destroying the attractive force present in or between the molecules. It is included in the stripper for easy removal of the photoresist.
- examples of the organic amine compound may include alkylamine, alkanol amine, tertiary ammonium, tertiary cyclic amine, alkoxy amine, oxymethyl amine, and the like, but are not limited thereto.
- the organic amine compound may be exemplified by one or more from the group consisting of a primary amino alcohol compound, a secondary amino alcohol compound and a tertiary amino alcohol compound.
- the amino alcohol compounds include monoethanol amine (MEA), 1-aminoisopropanol (AIP), 2-amino-1-propanol, N-methylaminoethanol (N-MAE), and 3-amino-1.
- -Propanol 4-amino-1-butanol, 2- (2-aminoethoxy) -1-ethanol (AEE), 2- (2-aminoethylamino) -1-ethanol, triethanol amine (TEA), hydroxy Ethyl piperazine (HEP), aniline, phenylenediamine (PPD), aminobiphenyl (ABP) and 2-aminonaphthalene, 1-amino-2-propanol (AIP2), 1-imidazoline ethanol At least one selected from the group consisting of, but is not limited thereto.
- the organic solvent may include a protic organic solvent and an aprotic polar solvent.
- the proton organic solvent is a compound having a low vapor pressure and has a low loss due to heating or evaporation.
- the quantum organic solvent is included in the stripper so that the oxide ions which can be generated in the alkali compound effectively penetrate into the space between the photoresist and the glass substrate and have a dissolving and peeling action. That is, the quantum organic solvent can dissolve the photoresist peeled off by the alkali compound better.
- a quantum glycol ether type organic solvent can be used, and as the quantum glycol ether type organic solvent, for example, diethylene glycol monoether (DGME), diethylene glycol monobutyl ether (BDG), diethylene glycol monoethyl ether (EDG), diethylene glycol monomethyl ether (MDG), triethylene glycol (TEG), propylene glycol monoether (PGME), propylene glycol monoether acetate (PGMEA), diethylene One or more selected from the group consisting of glycol (DEG), ethylene glycol (EG), and mixtures thereof, but is not limited thereto.
- DGME diethylene glycol monoether
- BDG diethylene glycol monobutyl ether
- EDG diethylene glycol monoethyl ether
- MDG diethylene glycol monomethyl ether
- TEG triethylene glycol
- PGME propylene glycol monoether
- PMEA propylene glycol monoether acetate
- DEG glycol
- EG ethylene glycol
- the aprotic polar solvent has high solubility in photoresist, in order to dissolve the photoresist peeled off by the organic amine compound to prevent reattachment of the photoresist mainly generated during the cleaning process and to maximize the cleaning effect. It is included in the stripper.
- aprotic polar solvent examples include dimethyl sulfoxide (DMSO), N-methyl pyrrolidone (NMP), N, N-dimethylacetamide (DMAc), and N, N-dimethylformamide (DMF).
- DMSO dimethyl sulfoxide
- NMP N-methyl pyrrolidone
- DMAc N, N-dimethylacetamide
- DMF N, N-dimethylformamide
- N, N-dimethylimidazole, ⁇ -butyrolactone, sulfolane, diethylformamide (DEF) and mixtures thereof may be exemplified, preferably, 2 Mixtures of more than one species may be used, but are not limited thereto.
- the stripper may further include a regulator or an additive for improving the characteristics of the stripper, such as preventing corrosion of the TFT wiring, adjusting contact resistance and enhancing peeling ability.
- the stripper may be a non-aqueous stripper.
- the waste stripper solution may include the organic amine compound, the organic solvent and the exfoliated photoresist.
- water may be included in the waste stripper solution including the non-aqueous stripper.
- specific control conditions are required to separate only the non-aqueous stripper containing no water in the product stream F 1-4 .
- the temperature of the top region 110 of the dividing wall distillation column 100 is within the lower and upper temperature ranges calculated by the following general formulas (1) and (2). Can be.
- T top .lower represents the lower limit temperature of the top region
- T top .upper represents the upper limit temperature of the top region
- P represents the pressure in the top region and is 20 mmHg to 300 mmHg.
- the water content in the product stream (F 1-4) May be adjusted to 0.001 parts by weight or less based on the total components included in the product stream (F 1-4 ).
- the water content can be adjusted to 500 ppm or less, thereby separating the high purity non-aqueous stripper with excellent efficiency. That is, in the distillation apparatus, by controlling the temperature of the top region 110 within the lower limit temperature and the upper limit temperature range calculated by the general formulas (1) and (2), it is possible to maximize the energy saving effect.
- the top region of the dividing wall distillation column 100 ( The temperature of 110) is not particularly limited as long as it is within the lower limit temperature and the upper limit temperature range calculated by the general formulas (1) and (2), for example, 14 to 92 ° C, for example, 14 to 47 ° C and 19 to 51 ° C. , 44 to 70 ° C, 66 to 87 ° C, or 70 to 92 ° C.
- the temperature of the column bottom region 130 of the dividing wall distillation column 100 is 100 to 250 °C, for example, 100 to 130 °C, 130 to 150 °C, 150 to 180 °C, 180 to 210 °C, or 210 To 250 ° C., but is not limited thereto.
- the pressure of the top region 110 of the dividing wall distillation column 100 is 20 mmHg to 300 mmHg, for example, 20 mmHg to 30 mmHg, 30 mmHg to 50 mmHg, 100 mmHg to 120 mmHg, 200 mmHg to 220 mmHg, or 270 mmHg to 300mmHg
- the pressure of the bottom region 130 of the dividing wall distillation column 100 is 50 mmHg to 400 mmHg, for example, 50 mmHg to 100 mmHg, 150 mmHg to 180 mmHg, 250 mmHg to 270 mmHg, or 350 mmHg to 400 mmHg, but is not limited thereto.
- the reflux ratio of the overhead flow (F 1-2 ) refluxed to the overhead region 110 of the separation wall distillation column 100 of the overhead flow (F 1-2 ) of the dividing wall distillation column 100 is 0.01 to 50.
- Reflux ratio of the bottom stream (F 1-3 ) to be refluxed to the bottom region 130 of) may be 1 to 200, preferably 10 to 180, 20 to 160, or 30 to 150 from a thermodynamic point of view. .
- the term "reflux ratio" as used herein refers to the ratio of the flow rate refluxed with respect to the outflow flow rate flowing out of the distillation column (100).
- the overhead flow (F 1-2 ) flowing out of the top region of the distillation column is water and atmospheric pressure.
- it may include one or more selected from the group consisting of materials having a boiling point at 1 atm below 100 ° C. Examples of the material having a boiling point of less than 100 ° C. at atmospheric pressure include methanol, isopropyl alcohol (IPA), diethylamine (DEA), and the like.
- the product stream (F 1-4 ) flowing out of the product outlet region 122 of the distillation column may include a proton organic solvent, an aprotic polar solvent, and an organic amine compound.
- the content of water in the product stream F 1-4 can be adjusted to within 500 ppm, for example up to 100 ppm, up to 10 ppm or up to 1 ppm.
- the bottom streams F 1-3 flowing out from the bottom region 130 of the distillation column may include a peeled photoresist resin.
- the stripper may be an aqueous stripper.
- the waste stripper solution may include water, an organic amine compound, an organic solvent, and a peeled photoresist, and in the case of separating the aqueous stripper by the distillation apparatus of the present application, in the product flow F 1-4 Specific control conditions are required to separate water so that it does not contain materials with boiling points below 100 ° C at atmospheric pressure.
- the temperature of the top region 110 of the dividing wall distillation column 100 may be within the lower and upper temperature ranges calculated by the following general formulas (3) and (4). Can be.
- T top .lower represents the lower limit temperature of the top region
- T top .upper represents the upper limit temperature of the top region
- P represents the pressure in the top region and is 20 mmHg to 300 mmHg.
- water is included in the product stream (F 1-4 ), so as not to include substances having a boiling point below 100 ° C. at atmospheric pressure, for example the content of the product stream (F 1-4) the atmospheric pressure boiling point less than 100 °C materials in within can be controlled to less than 0.001 part by weight relative to the total components contained in the product stream (F 1-4).
- the content of the material having a boiling point below 100 ° C. at atmospheric pressure may be adjusted to 500 ppm or less, thereby separating the high purity aqueous stripper with excellent efficiency. That is, in the distillation apparatus, by controlling the temperature of the top region 110 within the lower and upper temperature ranges calculated by the general formulas (3) and (4), it is possible to maximize the energy saving effect.
- the top region 110 of the dividing wall distillation column 100 is not particularly limited as long as it is within the lower and upper temperature ranges calculated by the general formulas (3) and (4), for example, 4 to 74 °C, for example, 4 to 24 °C, 8 to 29 °C, 28 to 50 ° C, 46 to 69 ° C, or 50 to 74 ° C.
- the temperature of the bottom region 130 of the dividing wall distillation column 100 is 150 to 300 ° C, for example, 150 to 180 ° C, 180 to 200 ° C, 210 to 240 ° C, 250 to 280 ° C, or 280 to 300 ° C. °C may be, but is not limited thereto.
- the pressure of the top region 110 of the dividing wall distillation column 100 is 20 mmHg to 300 mmHg, for example, 20 mmHg to 30 mmHg, 30 mmHg to 50 mmHg, 100 mmHg to 120 mmHg, 200 mmHg to 220 mmHg, or 270 mmHg to 300 mmHg
- the pressure of the bottom region 130 of the dividing wall distillation column 100 is 50 mmHg to 400 mmHg, for example, 50 mmHg to 100 mmHg, 150 mmHg to 180 mmHg, 250 mmHg to 270 mmHg, or 350 mmHg to 400 mmHg.
- the reflux ratio of the overhead flow (F 1-2 ) refluxed to the overhead region 110 of the separation wall distillation column 100 of the overhead flow (F 1-2 ) of the dividing wall distillation column 100 is 1 to 100. It may be, preferably from 5 to 90, 10 to 80, or 20 to 60 from the thermodynamic point of view, the dividing wall distillation column 100 of the bottom stream (F 1-3 ) of the dividing wall distillation column 100
- the reflux ratio of the bottom stream (F 1-3 ) to be refluxed to the bottom region 130 of) may be 1 to 300, preferably 10 to 280, 30 to 260, or 50 to 250 from the thermodynamic point of view. .
- the overhead stream (F 1-2 ) flowing out of the column top region of the distillation column has a boiling point of 100 ° C. It may include one or more selected from the group consisting of less than. Examples of the material having a boiling point of less than 100 ° C. at atmospheric pressure include methanol, isopropyl alcohol (IPA), diethylamine (DEA), and the like.
- the product stream (F 1-4 ) flowing out of the product outlet region 122 of the distillation column may include water, a protic organic solvent, an aprotic polar solvent, and an organic amine compound.
- the content of the substance whose boiling point at atmospheric pressure in the stream F 1-4 is less than 100 ° C. is within 0.001 parts by weight, for example, 0.0001 parts by weight or less based on the total components included in the product stream F 1-4 , It may be adjusted to 0.00001 parts by weight or less or 0.000005 parts by weight or less.
- the content of low boiling point components having a lower boiling point than water in the product stream F 1-4 may be adjusted to 500 ppm or less, for example 100 ppm or less, 10 ppm or less or 5 ppm or less.
- the bottom streams F 1-3 flowing out from the bottom region 130 of the distillation column may include a peeled photoresist resin.
- the raw material of the waste stripper solution comprising a non-aqueous stripper and exfoliated photoresist (F 1-1 ) to perform a separation process from the raw material (F 1-1 ) including low boiling point, middle boiling point and high boiling point (F) 1-1 may be introduced into the raw material supply region 121 of the dividing wall distillation column 100 as shown in FIG.
- the raw material F 1-1 introduced into the raw material supply region 121 includes a bottom stream F 1-3 including a peeled photoresist resin, an organic amine compound contained in the non-aqueous stripper, and a quantum glycol.
- the product stream (F 1-4 ) comprising an etheric organic solvent and an aprotic polar solvent and the overhead stream (F 1-2 ) comprising water and / or a substance having a boiling point below 100 ° C. at atmospheric pressure are separated and discharged.
- the organic amine compound included in the product stream (F 1-4 ) may be, for example, 2- (2-aminoethoxy) -1-ethanol (AEE), proton glycol ether
- the organic solvent may be, for example, diethylene glycol monobutyl ether (BDG), and the aprotic polar solvent may be, for example, N-methyl pyrrolidone (NMP) and dimethylacetamide (DMAc).
- the material having a boiling point of less than 100 ° C. at atmospheric pressure included in the overhead stream F 1-2 may include, for example, methanol.
- low boiling point components of water and / or methanol Middle boiling point components 2- (2-aminoethoxy) -1-ethanol (AEE), diethylene glycol monobutyl ether (BDG), N-methyl pyrrolidone (NMP) and dimethylacetamide (DMAc);
- AEE 2- (2-aminoethoxy) -1-ethanol
- BDG diethylene glycol monobutyl ether
- NMP N-methyl pyrrolidone
- DMAc dimethylacetamide
- the raw material (F 1-1 ) of the waste stripper solution containing a high-resistance photoresist flows into the raw material supply region 121 of the dividing wall distillation column 100, in this case, the dividing wall distillation column (100)
- the top stream F 1-2 which is a flow containing a relatively low boiling point component among the components of the raw material F 1-1 , for example, is rich in water and / or methanol.
- the flow can be outflowed, the outflowed overhead stream (F 1-2 ) is passed through the condenser 102, some of it is refluxed to the overhead zone 110 of the dividing wall distillation column 100, the other portion is stored as a product Can be.
- a bottom bottom flow F 1-3 including a component having a relatively high boiling point among the components of the raw material F 1-1 , for example, peeling off.
- the flow of the rich photoresist may flow out, and the bottom streams F 1-3 flowed out through the reboiler 103 and a part thereof is returned to the bottom region 130 of the dividing wall distillation column 100. And the rest can be stored as a product.
- the product flow F 1-4 including the middle boiling point component among the components of the raw material F 1-1 for example, 2- ( A rich stream of 2-aminoethoxy) -1-ethanol (AEE), diethylene glycol monobutyl ether (BDG), N-methyl pyrrolidone (NMP) and dimethylacetamide (DMAc) can be separated and spilled.
- AEE 2-aminoethoxy-1-ethanol
- BDG diethylene glycol monobutyl ether
- NMP N-methyl pyrrolidone
- DMAc dimethylacetamide
- the raw material of the waste stripper solution comprising an aqueous stripper and exfoliated photoresist to perform a separation process from the raw material (F 1-1 ) comprising low boiling point, middle boiling point and high boiling point components.
- F 1-1 may flow into the raw material supply region 121 of the dividing wall distillation column 100 as shown in FIG. 1.
- the raw material (F 1-1 ) introduced into the raw material supply region (121) is a bottom stream (F 1-3 ) including a peeled photoresist resin, the organic amine compound, a proton glycol ether-based organic solvent, aprotic
- the product stream (F 1-4 ) comprising a polar solvent and water and the overhead stream (F 1-2 ) comprising a substance having a boiling point of less than 100 ° C. at atmospheric pressure may be separated out.
- the organic amine compound included in the product stream (F 1-4 ) is, for example, 2- (2-aminoethoxy) -1-ethanol (AEE) and / or monoethanolamine (MEA
- Proton glycol ether-based organic solvent may be, for example, diethylene glycol monoethyl ether (EDG) and / or ethylene glycol (EG), aprotic polar solvent, for example, N -Methyl pyrrolidone (NMP).
- the material having a boiling point of less than 100 ° C. at atmospheric pressure included in the overhead stream F 1-2 may include, for example, methanol.
- methanol is a low boiling point component
- the raw material F 1-1 including the high boiling point photoresist resin is introduced into the raw material supply region 121 of the dividing wall distillation column 100, in this case, the top region of the dividing wall distillation column 100.
- a top stream (F 1-2 ) may flow out of a component including the low boiling point component among the components of the raw material (F 1-1 ) at 110.
- the outflowed overhead stream (F 1-2 ) may be returned to the overhead region 110 of the dividing wall distillation column 100 through the condenser 102, and the other portion may be stored as a product.
- the flow of the rich photoresist may flow out, and the bottom streams F 1-3 flowed out through the reboiler 103 and a part thereof is returned to the bottom region 130 of the dividing wall distillation column 100. And the rest can be stored as a product.
- the product flow F 1-4 including the middle boiling point component among the components of the raw material F 1-1 for example, 2- ( 2-aminoethoxy) -1-ethanol (AEE), monoethanolamine (MEA), diethylene glycol monoethyl ether (EDG), ethylene glycol (EG), N-methyl pyrrolidone (NMP) and water are rich
- AEE 2- ( 2-aminoethoxy) -1-ethanol
- MEA monoethanolamine
- EDG diethylene glycol monoethyl ether
- EG ethylene glycol
- NMP N-methyl pyrrolidone
- the bottom stream F 1-3 flowing out from the bottom region 130 of the dividing wall distillation column 100 passes through the reboiler 103 and the bottom stream F 1-3 passed through the reboiler 103. Some or all of) may be introduced into the bottom region 130 to be refluxed into the dividing wall distillation column 100 or may be stored as a product.
- the overhead flow (F 1-2 ) flowing out of the overhead region 110 of the dividing wall distillation column 100 passes through the condenser 102 and the overhead flow (F 1-2 ) passed through the condenser 102.
- Some or all of) may be introduced into the column top region 110 to be refluxed to the dividing wall distillation column 100, or stored as a product, and the product flowing out of the product outlet region 122 of the dividing wall distillation column 100 Flows F 1-4 may be stored as products.
- the present application also relates to a distillation method for separating waste stripper solution.
- Exemplary distillation method of the present application may be carried out using the above-described distillation apparatus, and therefore, descriptions overlapping with those described in the above-described distillation apparatus will be omitted.
- One embodiment of the distillation method of the present application includes introducing a raw material (F 1-1 ) of the waste stripper solution and separating the raw material (F 1-1 ) of the waste stripper solution.
- the method comprising introducing the raw material (F 1-1) of the waste stripper solution is a step of introducing the raw material (F 1-1) of the waste stripper solution containing a stripper and stripping the photoresist by separation Wall Distillation Column 100,
- the distillation apparatus of the present application for example, a partition wall 101 is provided inside, and the top region 110 and the bottom region 130 in which the partition wall 101 is not located. ), And the dividing wall area 120 in which the dividing wall is located, and the dividing wall area 120 is divided into the raw material supply area 121 and the product outlet area 122 divided by the dividing wall 101.
- the step of introducing into the dividing wall distillation column 100 is divided into.
- the raw material F 1-1 of the waste stripper solution is introduced into the raw material supply region 121 of the dividing wall distillation column.
- the raw material F 1-1 of the waste stripper solution flowing into the dividing wall distillation column 100 may include a stripper and a peeled photoresist, and the stripper may be a non-aqueous stripper or an aqueous stripper.
- Description of the raw material (F 1-1 ) of the waste stripper solution is the same as described above will be omitted.
- the material (F 1-1) For example, separating the material (F 1-1), the material (F 1-1) a relatively low boiling point of the flow from the tower top region 110 of the separation Wall Distillation Column 100 overhead stream ( F 1-2 ) and the relatively high boiling point flows from the bottom region 130 of the dividing wall distillation column 100 to the bottom bottom flow (F 1-3 ), and the relatively middle boiling point flows the And may flow out of the product outlet region 122 of the dividing wall distillation column 100.
- the stripper is a non-aqueous stripper including water, an organic amine compound, an organic solvent, and a peeled photoresist resin
- the step of separating the raw material (F 1-1 ), the raw material (F 1 -1 ) the bottom stream (F 1-3 ) comprising the photoresist resin peeled off, the product stream (F 1-4 ) comprising the organic amine compound and the organic solvent and the boiling point at water and / or atmospheric pressure is 100 It may include separating and distilling into a top stream (F 1-2 ) containing a material that is less than °C.
- T top .lower represents the lower limit temperature of the top region
- T top .upper represents the upper limit temperature of the top region
- P represents the pressure in the top region and is 20 mmHg to 300 mmHg.
- the stripper is an aqueous stripper including water, an organic amine compound, an organic solvent, and a peeled photoresist resin
- the raw material F 1-1 may be separated from the raw material F 1-1 .
- a bottom stream (F 1-3 ) comprising the exfoliated photoresist resin, a product stream (F 1-4 ) comprising the organic amine compound, an organic solvent and water, and a substance having a boiling point of less than 100 ° C. at atmospheric pressure. Separation into the overhead stream (F 1-2 ) may include the outflow.
- Separation into the overhead stream (F 1-2 ) may include the outflow.
- T top .lower represents the lower limit temperature of the top region
- T top .upper represents the upper limit temperature of the top region
- P represents the pressure in the top region and is 20 mmHg to 300 mmHg.
- Detailed description of the pressure, temperature and reflux ratio of the product stream (F 1-4 ) is the same as described above in the dividing wall distillation column 100, and will be omitted.
- each of the steps is organically combined independently, each boundary is not clearly divided according to the order of time, and thus, each of the above steps may be performed sequentially or independently of each other.
- each step may further include a process step that can be conventionally performed in the art, the manufacturing method is not limited to the above steps.
- the economical efficiency of the process can be improved by reducing the energy consumption and minimizing the size of the distillation apparatus used for the purification of the raw materials.
- distillation apparatus of the present application it is possible to minimize the energy required in the purification process of the waste stripper solution including the stripper used in the photoresist stripping process and the peeled photoresist resin, and purification using two distillation columns Since the installation cost of a distillation apparatus can be reduced rather than the case, the economics of a process can be improved.
- FIG. 1 exemplarily shows a distillation apparatus according to an embodiment and example of the present application.
- FIG. 2 is a diagram schematically showing a distillation apparatus used in Comparative Examples 1 and 3.
- FIG. 2 is a diagram schematically showing a distillation apparatus used in Comparative Examples 1 and 3.
- a non-aqueous stripper comprising an organic amine compound, a proton glycol ether-based organic solvent and an aprotic polar solvent using the distillation apparatus of FIG. 1;
- the waste stripper solution containing the peeled photoresist and water was separated. Specifically, 47 wt% of dimethylacetamide (DMAc), 14 wt% of N-methylpyrrolidone (NMP), 5 wt% of 2- (2-aminoethoxy) -1-ethanol (AEE), diethylene glycol A raw material at 25 ° C.
- DMAc dimethylacetamide
- NMP N-methylpyrrolidone
- AEE 2- (2-aminoethoxy) -1-ethanol
- BDG monobutyl ether
- photoresist 1 wt% of photoresist
- 14 wt% of water located at 11 stages of a dividing wall distillation column having 24 theoretical stages at a flow rate of 1500 kg / hr.
- a separation process was performed by entering the feed zone, and the respective flows were discharged from the top region, the product outlet region, and the bottom region of the dividing wall distillation column.
- the product stream flowing out of the product outlet region was separated by distillation from the product outlet region of the dividing wall distillation column, dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), and 2- (2-aminoethoxy ) -1-ethanol (AEE) and diethylene glycol monobutyl ether (BDG) were stored as separate products.
- DMAc dimethylacetamide
- NMP N-methylpyrrolidone
- AEE 2- (2-aminoethoxy ) -1-ethanol
- BDG diethylene glycol monobutyl ether
- the operating pressure of the column top region of the dividing wall distillation column was adjusted to 200 mmHg
- the operating temperature was adjusted to 65 to 70 °C
- the operating pressure of the column bottom region was adjusted to 260 to 270 mmHg
- the operating temperature is 190 To 195 ° C.
- the operating pressure of the product outlet region was adjusted to 230 to 240 mmHg
- the operating temperature was adjusted to 135 to 140 ° C.
- the reflux ratio of the column top region of the dividing wall distillation column was set to 2 to 2.5
- the reflux ratio of the column bottom region was set to 57.2 to 57.7.
- the operating pressure of the column top region of the dividing wall distillation column was adjusted to 100 mmHg, the operating temperature to 50 to 55 °C, the operating pressure of the column bottom region to 160 to 170 mmHg, operating temperature was adjusted to 175 to 180 °C, product outlet area
- the waste stripper solution containing the non-aqueous stripper and the peeled photoresist resin was separated in the same manner as in Example 1 except that the operating pressure of 130 to 140 mmHg and the operating temperature were adjusted to 120 to 125 ° C.
- the reflux ratio of the column top region of the dividing wall distillation column was set to 2 to 2.5
- the reflux ratio of the column bottom region was set to 57.2 to 57.5
- the content of water in the product stream is 1 ppm
- the high boiling point impurities in the column bottom stream The content of photoresist was 2 ppb.
- An aqueous stripper comprising an organic amine compound, a protic glycol ether based organic solvent, an aprotic polar solvent and water using the distillation apparatus of FIG. 1; And a waste stripper solution including the exfoliated photoresist.
- MEA monoethanolamine
- EG ethylene glycol
- EDG diethylene glycol monoethyl ether
- NMP N-methylpyrrolidone
- the product stream flowing out of the product outlet region was separated by distillation from the product outlet region of the dividing wall distillation column, and monoethanolamine (MEA), ethylene glycol (EG), diethylene glycol monoethyl ether (EDG), and N- Separately stored products containing methylpyrrolidone (NMP) and water.
- MEA monoethanolamine
- EG ethylene glycol
- EDG diethylene glycol monoethyl ether
- NMP N- Separately stored products containing methylpyrrolidone
- the content of methanol, the low boiling point impurity in the product stream was 5 ppm
- the content of the photoresist, the high boiling point impurity in the bottom stream was 1 ppb.
- the operating pressure of the column top region of the dividing wall distillation column was adjusted to 250 mmHg
- the operating temperature was adjusted to 60 to 65 °C
- the operating pressure of the column bottom region was adjusted to 310 mmHg to 320 mmHg
- the operating temperature is It was adjusted to 185-190 degreeC.
- the operating pressure of the product outlet region was adjusted to 285 to 290 mmHg
- the operating temperature was adjusted to 85 to 90 °C.
- the reflux ratio of the column top region of the dividing wall distillation column was set to 33 to 33.5
- the reflux ratio of the column bottom region was set to 228.5 to 229.
- the operating pressure of the column top region of the dividing wall distillation column was adjusted to 100 mmHg, the operating temperature to 40 to 45 °C, the operating pressure of the column bottom region was adjusted to 160 to 170 mmHg, operating temperature to 160 to 165 °C, product outlet area
- the waste stripper solution including the aqueous stripper and the exfoliated photoresist resin was separated in the same manner as in Example 3 except that the operating pressure was adjusted to 130 to 140 mmHg and the operating temperature was adjusted to 70 to 75 ° C.
- the reflux ratio of the column top region of the dividing wall distillation column was set to 31 to 31.5
- the reflux ratio of the column bottom region was set to 207 to 207.5
- the content of the methanol of the low boiling point impurities in the product stream is 5 ppm
- DMAc dimethylacetamide
- NMP N-methylpyrrolidone
- AEE 2- (2-aminoethoxy) -1-ethanol
- a separation process was performed by introducing a 25 ° C. raw material containing 19 wt% monobutyl ether (BDG), 1 wt% photoresist, and 14 wt% water into the first distillation column at a flow rate of 1500 kg / hr.
- the low-boiling stream discharged from the top column of the first distillation column was passed through the condenser and partly refluxed to the first distillation column, the remaining 210 kg / hr was stored as product, and some of the flow from the bottom of the first distillation column was partially recycled. Was again refluxed to the bottom region of the first distillation column and the remaining 1290 kg / hr were introduced into the second distillation column.
- the middle boiling point stream discharged from the top of the second distillation column was condensed using a condenser, partly refluxed to the top of the second distillation column, the remaining 1227 kg / hr separated into the product, the high boiling point discharged from the bottom of the second distillation column
- the flow was recirculated using a reboiler, some of which was refluxed to the bottom of the second distillation column and the other 63 kg / hr were separated into product.
- the temperature of the top of the first distillation column was adjusted to 70 to 75 °C
- the pressure was 250 mmHg
- the temperature of the tower bottom was adjusted to 140 to 145 °C
- the pressure was 300 to 310 mmHg
- the temperature of the top of the second distillation column is 120 To 125 °C
- the pressure was adjusted to 65 mmHg
- the bottom temperature was adjusted to 165 to 170 °C
- pressure was 130 to 140 mmHg.
- the reflux ratio of the column top region of the first distillation column was set to 1.5 to 2.0
- the reflux ratio of the column top region of the second distillation column was set to 0.01 to 0.5.
- the water content in the product stream was 1 ppm and the content of high boiling point photoresist in the bottom stream was 2 ppb.
- the operating pressure of the column top region of the dividing wall distillation column was adjusted to 760 mmHg, the operating temperature to 100 to 105 °C, the operating pressure of the column bottom region was adjusted to 820 to 830 mmHg, operating temperature to 240 to 245 °C, product outlet area
- a waste stripper solution including a non-aqueous waste stripper and a peeled photoresist resin was separated in the same manner as in Example 1 except that the operating pressure of 790 to 800 mmHg and the operating temperature were adjusted to 180 to 185 ° C.
- the reflux ratio of the column top region of the dividing wall distillation column was set to 2.5 to 3
- the reflux ratio of the column bottom region was set to 77.5 to 78
- the water content in the product stream is 1 ppm
- the high boiling point impurities in the column bottom stream The resist content was 18 ppb.
- an aqueous stripper including an organic amine compound, a proton glycol ether-based organic solvent, an aprotic polar solvent, and water using a distillation apparatus connected to two distillation columns; And a waste stripper solution including the exfoliated photoresist resin.
- MEA monoethanolamine
- EG ethylene glycol
- EDG diethylene glycol monoethyl ether
- NMP N-methylpyrrolidone
- the low-boiling stream from the top of the first distillation column was passed through the condenser and partly refluxed to the first distillation column, the remaining 20 kg / hr flow rate was stored as product, and a portion of the flow from the bottom of the first distillation column was recycled. Some were returned to the bottom region of the first distillation column and the remaining 1380 kg / hr flow rate was introduced into the second distillation column.
- the middle boiling point stream discharged from the top of the second distillation column was condensed using a condenser, partly refluxed to the top of the second distillation column, and the remaining flow rate of 1344 kg / hr was separated into the product, and discharged from the bottom of the second distillation column.
- the high boiling point flow was recirculated using a reboiler, some of which was refluxed to the bottom of the second distillation column, and the remaining 36 kg / hr of flow was separated into the product.
- the temperature of the top of the first distillation column was adjusted to 90 to 95 °C
- the pressure was 760 mmHg
- the temperature of the tower bottom was adjusted to 100 to 105 °C
- the pressure was 810 to 820 mmHg
- the temperature of the top of the second distillation column is 110
- the pressure was adjusted to 65 mmHg
- the bottom temperature of the column was 155 to 160 °C
- the pressure was adjusted to 130 to 140 mmHg.
- the reflux ratio of the column top region of the first distillation column was set to 15.5 to 16
- the reflux ratio of the column top region of the second distillation column was set to 0.01 to 0.5.
- the content of methanol, the low boiling impurity in the product stream, was 5 ppm
- the content of the photoresist, the high boiling impurity in the bottom stream was 7 ppb.
- the operating pressure of the column top region of the dividing wall distillation column was adjusted to 760 mmHg, the operating temperature to 85 to 90 °C, the operating pressure of the column bottom region was adjusted to 820 to 830 mmHg, operating temperature to 220 to 225 °C, product outlet area
- the waste stripper solution containing the aqueous waste stripper and the exfoliated photoresist resin was separated in the same manner as in Example 3 except that the operating pressure of 790 to 800 mmHg and the operating temperature were adjusted to 115 to 120 ° C.
- the reflux ratio of the column top region of the dividing wall distillation column was set to 43 to 43.5
- the reflux ratio of the column bottom region was set to 303.5 to 304
- the methanol content of the low boiling point impurities in the product stream is 5 ppm
- the high ratio in the column bottom stream was 7 ppb.
- Example 1 Example 2 Comparative Example 1 Comparative Example 2 Water content in the product stream (ppm) 1 ppm 1 ppm 1 ppm 1 ppm 1 ppm Energy saving rate (%) 16 20 - One % Recovery of product (striper) 96.5 96.5 96.5 96.5
- Example 3 Example 4 Comparative Example 3 Comparative Example 4 Water content in the product stream (ppm) 5 ppm 5 ppm 5 ppm 5 ppm Energy saving rate (%) 30 34 - 11 % Recovery of product (striper) 96.5 96.5 92.4 96.5
- the energy consumption of the reboiler used in the purification process using the distillation apparatus of Examples 1 to 4 of the present application is the ash used in the purification process using the distillation apparatus of Comparative Examples 1 to 4 It can be seen that compared to the energy consumption of the non-significantly. That is, when separating the waste stripper and the peeled photoresist resin by the distillation apparatus according to the embodiment of the present application, it is possible to obtain an energy saving effect of up to 34% compared to the case of Comparative Examples 1 and 3.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Coating Apparatus (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
Description
실시예 1 | 실시예 2 | 비교예 1 | 비교예 2 | |
생성물 흐름 내의 물의 함량(ppm) | 1 ppm | 1 ppm | 1 ppm | 1 ppm |
에너지 절감율(%) | 16 | 20 | - | 1 |
제품(스트리퍼)의 회수율(%) | 96.5 | 96.5 | 96.5 | 96.5 |
실시예 3 | 실시예 4 | 비교예 3 | 비교예 4 | |
생성물 흐름 내의 물의 함량(ppm) | 5 ppm | 5 ppm | 5 ppm | 5 ppm |
에너지 절감율(%) | 30 | 34 | - | 11 |
제품(스트리퍼)의 회수율(%) | 96.5 | 96.5 | 92.4 | 96.5 |
Claims (21)
- 응축기, 재비기 및 내부에 분리벽이 구비된 증류탑을 포함하고,상기 증류탑의 상기 내부가, 탑정 영역; 탑저 영역; 및 상기 탑정 영역과 탑저 영역 사이에서 상기 탑정 영역 및 탑저 영역과 접해있는 분리벽 영역으로 구분되고, 상기 분리벽은 상기 분리벽 영역에 위치하며, 상기 분리벽 영역은 상기 분리벽에 의하여 나뉘어지는 원료 공급 영역 및 생성물 유출 영역으로 구분되고,스트리퍼 및 박리된 포토레지스트 수지를 포함하는 폐스트리퍼 용액의 원료가 상기 원료 공급 영역으로 유입되며, 유입된 상기 원료는 생성물 흐름, 탑저 흐름 및 탑정 흐름으로 각각 분리되어 유출되고,상기 탑저 흐름은 상기 탑저 영역에서 유출되며, 상기 탑저 흐름 중 일부는 상기 재비기를 통과하여 상기 탑저 영역으로 환류되고,상기 탑정 흐름은 상기 탑정 영역에서 유출되며, 탑정 흐름 중 일부는 상기 응축기를 통과하여 상기 탑정 영역으로 환류되고,상기 생성물 흐름은 상기 생성물 유출 영역에서 유출되는 증류 장치.
- 제 1 항에 있어서, 탑저 흐름은 박리된 포토레지스트 수지를 포함하는 증류 장치.
- 제 1 항에 있어서, 스트리퍼는 비수계 스트리퍼 또는 수계 스트리퍼인 증류 장치.
- 제 3 항에 있어서, 스트리퍼는 비수계 스트리퍼이고, 탑정 흐름은 물 및 대기압에서의 비점이 100℃ 미만인 물질로 이루어진 군으로부터 선택된 1종 이상을 포함하는 증류 장치.
- 제 3 항에 있어서, 스트리퍼는 비수계 스트리퍼이고, 생성물 흐름은 양자성 유기용매, 비양자성 극성 용매 및 유기 아민 화합물을 포함하는 증류 장치.
- 제 3 항에 있어서, 스트리퍼는 비수계 스트리퍼이고, 탑정 영역의 온도가 하기 일반식 1 및 일반식 2에 의하여 계산되는 하한온도 및 상한온도 범위 이내인 증류 장치:[일반식 1]P = 0.00126 × Ttop . lower 3 - 0.07051 × Ttop . lower 2 + 3.17767 × Ttop .lower - 15.01040[일반식 2]P = 0.00150 × Ttop . upper 3 - 0.18493 × Ttop .upper 2 + 9.56742 × Ttop .upper - 176.07273상기 일반식 1 및 일반식 2에서,Ttop .lower는 상기 탑정 영역의 하한온도를 나타내고,Ttop .upper는 상기 탑정 영역의 상한온도를 나타내며,P는 상기 탑정 영역의 압력을 나타내고, 20 mmHg 내지 300 mmHg이다.
- 제 6 항에 있어서, 탑저 영역의 온도는 100℃ 내지 250℃인 증류 장치.
- 제 6 항에 있어서, 탑정 영역의 온도는 14℃ 내지 92℃인 증류 장치.
- 제 6 항에 있어서, 탑저 영역의 압력은 50 내지 400 mmHg인 증류 장치.
- 제 6 항에 있어서, 탑정 영역의 압력은 20 내지 300 mmHg인 증류 장치.
- 제 3 항에 있어서, 스트리퍼는 수계 스트리퍼이고, 탑정 흐름은 대기압에서의 비점이 100℃ 미만인 물질을 포함하는 증류 장치.
- 제 3 항에 있어서, 스트리퍼는 수계 스트리퍼이고, 생성물 흐름은, 물, 양자성 유기용매, 비양자성 극성 용매 및 유기 아민 화합물을 포함하는 증류 장치.
- 제 3 항에 있어서, 스트리퍼가 수계 스트리퍼이고, 탑정 영역의 온도가 하기 일반식 3 및 일반식 4에 의하여 계산되는 하한온도 및 상한온도 범위 이내인 증류 장치:[일반식 3]P = 0.00177 × Ttop . lower 3 - 0.01645 × Ttop . lower 2 + 2.13532 × Ttop .lower + 12.36272[일반식 4]P = 0.00144 × Ttop . upper 3 - 0.10028 × Ttop .upper 2 + 4.27752 × Ttop .upper - 44.49051상기 일반식 3 및 일반식 4에서,Ttop .lower는 상기 탑정 영역의 하한온도를 나타내고,Ttop .upper는 상기 탑정 영역의 상한온도를 나타내며,P는 상기 탑정 영역의 압력을 나타내고, 20 mmHg 내지 300 mmHg이다.
- 제 13 항에 있어서, 탑저 영역의 온도는 150℃ 내지 300℃인 증류 장치.
- 제 13 항에 있어서, 탑정 영역의 온도는 4℃ 내지 74℃인 증류 장치.
- 제 13 항에 있어서, 탑저 영역의 압력은 50 내지 400 mmHg인 증류 장치.
- 제 13 항에 있어서, 탑정 영역의 압력은 20 내지 300 mmHg인 증류 장치.
- 내부에 분리벽이 구비되며, 상기 내부가 탑정 영역; 및 탑저 영역; 및 상기 탑정 영역과 탑저 영역 사이에서 상기 탑정 영역 및 탑저 영역과 접해있는 분리벽 영역으로 구분되고, 상기 분리벽은 상기 분리벽 영역에 위치하며, 상기 분리벽 영역은 상기 분리벽에 의해 나뉘어지는 원료 공급 영역 및 생성물 유출 영역으로 구분되는 분리벽형 증류탑의 상기 원료 공급 영역으로 스트리퍼 및 박리된 포토레지스트 수지를 포함하는 폐스트리퍼 용액의 원료를 유입하여 분리하는 것을 포함하는 증류 방법.
- 제 18 항에 있어서, 스트리퍼는 비수계 스트리퍼 또는 수계 스트리퍼인 증류 방법.
- 제 19 항에 있어서, 스트리퍼가 비수계 스트리퍼이고, 탑정 영역의 온도를 하기 일반식 1 및 일반식 2에 의하여 계산되는 하한온도 및 상한온도 범위 이내로 조절하는 것을 포함하는 증류 방법:[일반식 1]P = 0.00126 × Ttop . lower 3 - 0.07051 × Ttop . lower 2 + 3.17767 × Ttop .lower - 15.01040[일반식 2]P = 0.00150 × Ttop . upper 3 - 0.18493 × Ttop .upper 2 + 9.56742 × Ttop .upper - 176.07273상기 일반식 1 및 일반식 2에서,Ttop .lower는 상기 탑정 영역의 하한온도를 나타내고,Ttop .upper는 상기 탑정 영역의 상한온도를 나타내며,P는 상기 탑정 영역의 압력을 나타내고, 20 mmHg 내지 300 mmHg이다.
- 제 19 항에 있어서, 스트리퍼가 수계 스트리퍼이고, 탑정 영역의 온도를 하기 일반식 3 및 일반식 4에 의하여 계산되는 하한온도 및 상한온도 범위 이내로 조절하는 것을 포함하는 증류 방법:[일반식 3]P = 0.00177 × Ttop . lower 3 - 0.01645 × Ttop . lower 2 + 2.13532 × Ttop .lower + 12.36272[일반식 4]P = 0.00144 × Ttop . upper 3 - 0.10028 × Ttop .upper 2 + 4.27752 × Ttop .upper - 44.49051상기 일반식 3 및 일반식 4에서,Ttop .lower는 상기 탑정 영역의 하한온도를 나타내고,Ttop .upper는 상기 탑정 영역의 상한온도를 나타내며,P는 상기 탑정 영역의 압력을 나타내고, 20 mmHg 내지 300 mmHg이다.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201680020924.5A CN107438470A (zh) | 2015-04-03 | 2016-04-01 | 蒸馏装置 |
US15/563,772 US10556191B2 (en) | 2015-04-03 | 2016-04-01 | Distillation method |
JP2017550808A JP6450470B2 (ja) | 2015-04-03 | 2016-04-01 | 蒸留装置 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2015-0047681 | 2015-04-03 | ||
KR1020150047681A KR101819278B1 (ko) | 2015-04-03 | 2015-04-03 | 증류 장치 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2016159707A1 true WO2016159707A1 (ko) | 2016-10-06 |
Family
ID=57006242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2016/003387 WO2016159707A1 (ko) | 2015-04-03 | 2016-04-01 | 증류 장치 |
Country Status (5)
Country | Link |
---|---|
US (1) | US10556191B2 (ko) |
JP (1) | JP6450470B2 (ko) |
KR (1) | KR101819278B1 (ko) |
CN (1) | CN107438470A (ko) |
WO (1) | WO2016159707A1 (ko) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MY181298A (en) * | 2014-02-13 | 2020-12-21 | Bp Corp North America Inc | Energy efficient fractionation process for separating the reactor effluent from tol/ap+ transalkylation processes |
US11207611B1 (en) | 2018-07-03 | 2021-12-28 | Burns & Mcdonnell Engineering Company, Inc. | Process for separating hydrocarbons in a liquid feed utilizing an externally heated reboiler connected to a divided wall column as the primary source of heat energy |
KR102294876B1 (ko) | 2018-09-28 | 2021-08-27 | 주식회사 엘지화학 | 아미드계 화합물의 회수 방법 및 장치 |
JP6692029B1 (ja) * | 2019-03-25 | 2020-05-13 | パナソニックIpマネジメント株式会社 | レジスト剥離液 |
CN109925781A (zh) * | 2019-03-28 | 2019-06-25 | 武汉华星光电半导体显示技术有限公司 | 剥离液回收系统 |
CN111747856B (zh) * | 2020-07-17 | 2022-12-13 | 新中天环保股份有限公司 | 一种废溶剂的处理方法 |
CN112245949B (zh) * | 2020-09-17 | 2022-03-04 | 江阴丰力生化工程装备有限公司 | 一种环保高效反应及溶剂精馏回收系统 |
CN115531905A (zh) * | 2022-06-10 | 2022-12-30 | 宁夏福瑞硅烷材料有限公司 | 一种新型分隔壁精馏塔动态控制工艺 |
JP7290194B1 (ja) | 2022-10-19 | 2023-06-13 | Jsr株式会社 | 半導体処理用組成物及び処理方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20080099034A (ko) * | 2007-05-08 | 2008-11-12 | 주식회사 엘지화학 | 저비점, 중비점 및 고비점 물질을 포함하는 원료의 분리방법 |
KR101330653B1 (ko) * | 2013-02-25 | 2013-11-19 | 주식회사 코렉스 | 포토레지스트 고비점 박리 폐액 재생 방법 |
KR20140092785A (ko) * | 2013-01-16 | 2014-07-24 | 주식회사 엘지화학 | 알칸올의 제조 장치 |
KR20150010663A (ko) * | 2013-07-18 | 2015-01-28 | 주식회사 엘지화학 | 분리벽형 증류탑 |
KR20150016137A (ko) * | 2013-08-01 | 2015-02-11 | 주식회사 엘지화학 | 정제 장치 및 이를 이용한 정제 방법 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4230533A (en) * | 1978-06-19 | 1980-10-28 | Phillips Petroleum Company | Fractionation method and apparatus |
DE4328424A1 (de) * | 1993-08-24 | 1995-03-02 | Basf Ag | Destillationskolonne zur Trennung eines Flüssigkeitsgemisches in mehrere reine Fraktionen |
JP3409028B2 (ja) * | 2000-04-28 | 2003-05-19 | 松下環境空調エンジニアリング株式会社 | 溶剤の再生方法及び装置 |
JP4110451B2 (ja) * | 2002-04-08 | 2008-07-02 | ナガセケムテックス株式会社 | フォトレジスト剥離剤組成物及びその製造方法 |
JP4476356B2 (ja) * | 2007-09-05 | 2010-06-09 | コレックス コーポレーション | フォトレジストストリッパー廃液の再生方法及び再生装置、並びにその再生回収率の改善方法 |
KR101191122B1 (ko) | 2009-01-20 | 2012-10-15 | 주식회사 엘지화학 | 고순도 노르말 부탄올 생산용 분리벽형 증류탑, 및 노르말 부탄올 증류방법 |
BRPI1008753B1 (pt) * | 2009-02-12 | 2020-01-28 | Lg Chemical Ltd | coluna de destilação com parede divisória |
US8932434B2 (en) * | 2009-03-19 | 2015-01-13 | Lg Chem, Ltd. | Dividing wall distillation column for producing high purity acrylic acid and fractional distillation method using the same |
CN102188830B (zh) * | 2010-03-03 | 2013-12-25 | 中国石油化工股份有限公司 | 反应蒸馏的方法 |
KR101372712B1 (ko) * | 2011-11-11 | 2014-03-11 | 주식회사 엘지화학 | 트리할로실란의 정제 장치 |
KR101372791B1 (ko) * | 2011-11-11 | 2014-03-10 | 주식회사 엘지화학 | 트리할로실란의 정제 장치 |
EP2778133A4 (en) * | 2011-11-11 | 2015-07-15 | Lg Chemical Ltd | DEVICE FOR FINISHING TRIHALOSILANE |
CN102584576A (zh) * | 2012-01-06 | 2012-07-18 | 长岭炼化岳阳工程设计有限公司 | 利用分隔壁塔提纯醋酸叔丁酯的方法及其装置 |
US8961744B2 (en) * | 2013-02-25 | 2015-02-24 | Korex Corporation | System and method for recycling high-boiling-point waste photoresist stripper |
-
2015
- 2015-04-03 KR KR1020150047681A patent/KR101819278B1/ko active IP Right Grant
-
2016
- 2016-04-01 CN CN201680020924.5A patent/CN107438470A/zh active Pending
- 2016-04-01 WO PCT/KR2016/003387 patent/WO2016159707A1/ko active Application Filing
- 2016-04-01 JP JP2017550808A patent/JP6450470B2/ja active Active
- 2016-04-01 US US15/563,772 patent/US10556191B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20080099034A (ko) * | 2007-05-08 | 2008-11-12 | 주식회사 엘지화학 | 저비점, 중비점 및 고비점 물질을 포함하는 원료의 분리방법 |
KR20140092785A (ko) * | 2013-01-16 | 2014-07-24 | 주식회사 엘지화학 | 알칸올의 제조 장치 |
KR101330653B1 (ko) * | 2013-02-25 | 2013-11-19 | 주식회사 코렉스 | 포토레지스트 고비점 박리 폐액 재생 방법 |
KR20150010663A (ko) * | 2013-07-18 | 2015-01-28 | 주식회사 엘지화학 | 분리벽형 증류탑 |
KR20150016137A (ko) * | 2013-08-01 | 2015-02-11 | 주식회사 엘지화학 | 정제 장치 및 이를 이용한 정제 방법 |
Also Published As
Publication number | Publication date |
---|---|
KR20160118856A (ko) | 2016-10-12 |
CN107438470A (zh) | 2017-12-05 |
JP6450470B2 (ja) | 2019-01-09 |
KR101819278B1 (ko) | 2018-01-17 |
US10556191B2 (en) | 2020-02-11 |
JP2018512735A (ja) | 2018-05-17 |
US20180178141A1 (en) | 2018-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2016159707A1 (ko) | 증류 장치 | |
WO2010107284A2 (ko) | 고순도 아크릴산 생산을 위한 분리벽형 증류탑 및 이를 이용한 분별증류방법 | |
WO2010085072A2 (ko) | 고순도 노르말 부탄올 생산용 분리벽형 증류탑, 및 노르말 부탄올 증류방법 | |
WO2017003247A1 (ko) | 증류 장치 | |
WO2010107283A2 (ko) | 고순도 2-에틸헥산올 생산을 위한 분리벽형 증류탑 및 이를 이용한 분별증류방법 | |
WO2017026803A1 (ko) | Lcd 제조용 포토레지스트 박리액 조성물 | |
US7612028B2 (en) | Thinner composition, method of preparing the same and method of recovering the same | |
WO2022255586A1 (ko) | 초고순도 불화수소의 정제방법 및 장치 | |
WO2023177133A1 (ko) | Pgme, pgmea, 물의 혼합물로부터 물을 분리하는 방법 | |
WO2011037300A1 (ko) | 포토레지스트 스트리퍼 조성물 및 이를 이용한 포토레지스트 박리방법 | |
WO2020130367A1 (ko) | 아미드계 화합물의 회수 방법 | |
KR101266883B1 (ko) | 레지스트 박리페액 재생방법 및 재생장치 | |
WO2021101227A1 (ko) | 디스플레이 제조용 포토레지스트 박리액 조성물 | |
KR20150115457A (ko) | 포토레지스트용 스트리퍼 조성물의 회수 방법 | |
WO2018124579A1 (ko) | 부타디엔 제조방법 | |
WO2015009117A1 (ko) | 분리벽형 증류탑 | |
WO2015178717A1 (ko) | 큐멘의 정제 장치 및 정제 방법 | |
WO2015178718A1 (ko) | 큐멘의 정제 장치 및 정제 방법 | |
WO2018097690A1 (ko) | 메탄올 및 아세톤의 제거 유닛 및 이를 포함하는 페놀 및 비스페놀 a의 제조 시스템 | |
WO2021015541A1 (en) | Method of recovering unreacted ethylene in ethylene oligomerization process | |
WO2016068676A1 (ko) | 증류 장치 | |
WO2020130264A1 (ko) | 방향족 비닐 화합물-비닐시안 화합물 중합체의 제조방법 및 제조장치 | |
WO2020017780A1 (ko) | 포토레지스트 세정용 신너 조성물 | |
WO2023214694A1 (ko) | 압력스윙증류를 이용한 초산과 디메틸포름아미드의 회수 방법 | |
WO2015026194A1 (ko) | 신규한 중합체 및 이를 포함하는 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16773488 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2017550808 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15563772 Country of ref document: US |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 16773488 Country of ref document: EP Kind code of ref document: A1 |