TWI487721B - 聚（乙烯丁醛）之連續製造 - Google Patents
聚（乙烯丁醛）之連續製造 Download PDFInfo
- Publication number
- TWI487721B TWI487721B TW099111748A TW99111748A TWI487721B TW I487721 B TWI487721 B TW I487721B TW 099111748 A TW099111748 A TW 099111748A TW 99111748 A TW99111748 A TW 99111748A TW I487721 B TWI487721 B TW I487721B
- Authority
- TW
- Taiwan
- Prior art keywords
- poly
- high shear
- stream
- vinyl butyral
- shear mixer
- Prior art date
Links
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 title claims description 52
- 238000010924 continuous production Methods 0.000 title description 5
- -1 poly(vinyl butyral) Polymers 0.000 claims description 105
- 238000000034 method Methods 0.000 claims description 40
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 40
- 238000002156 mixing Methods 0.000 claims description 34
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 31
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 16
- 239000003377 acid catalyst Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000005336 safety glass Substances 0.000 description 4
- 238000006359 acetalization reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- BJIUNQZHYLBUNL-UHFFFAOYSA-N 6-heptoxy-6-oxohexanoic acid Chemical compound CCCCCCCOC(=O)CCCCC(O)=O BJIUNQZHYLBUNL-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000005340 laminated glass Substances 0.000 description 2
- OJXOOFXUHZAXLO-UHFFFAOYSA-M magnesium;1-bromo-3-methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC(Br)=C1 OJXOOFXUHZAXLO-UHFFFAOYSA-M 0.000 description 2
- JOADGALWHMAAKM-UHFFFAOYSA-L magnesium;2-ethylbutanoate Chemical compound [Mg+2].CCC(CC)C([O-])=O.CCC(CC)C([O-])=O JOADGALWHMAAKM-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- OFYHGFUUNIWKQY-UHFFFAOYSA-N C(CCCCC(=O)O)(=O)O.C1(CCCCC1)CCCCCC Chemical compound C(CCCCC(=O)O)(=O)O.C1(CCCCC1)CCCCCC OFYHGFUUNIWKQY-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FRQDZJMEHSJOPU-UHFFFAOYSA-N Triethylene glycol bis(2-ethylhexanoate) Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CCCC FRQDZJMEHSJOPU-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- WMKJXMSCPRJMPV-UHFFFAOYSA-N [Mg].CCC(CC)C(O)=O.CCC(CC)C(O)=O Chemical compound [Mg].CCC(CC)C(O)=O.CCC(CC)C(O)=O WMKJXMSCPRJMPV-UHFFFAOYSA-N 0.000 description 1
- AQXKRWXRCJPTPV-UHFFFAOYSA-N [Mg].OC=1C(=CC2=CC=CC=C2C1)C(=O)O.OC=1C(=CC2=CC=CC=C2C1)C(=O)O Chemical compound [Mg].OC=1C(=CC2=CC=CC=C2C1)C(=O)O.OC=1C(=CC2=CC=CC=C2C1)C(=O)O AQXKRWXRCJPTPV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001535 azelaic acid derivatives Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical group CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZIKGDWWRHXYIQQ-UHFFFAOYSA-L magnesium;2-aminobenzoate Chemical compound [Mg+2].NC1=CC=CC=C1C([O-])=O.NC1=CC=CC=C1C([O-])=O ZIKGDWWRHXYIQQ-UHFFFAOYSA-L 0.000 description 1
- CGSNFLLWLBPMLH-UHFFFAOYSA-L magnesium;2-ethylhexanoate Chemical compound [Mg+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O CGSNFLLWLBPMLH-UHFFFAOYSA-L 0.000 description 1
- BJZBHTNKDCBDNQ-UHFFFAOYSA-L magnesium;dodecanoate Chemical compound [Mg+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BJZBHTNKDCBDNQ-UHFFFAOYSA-L 0.000 description 1
- PBXWVVFIFCYDDO-UHFFFAOYSA-N magnesium;pyridine-3-carboxylic acid Chemical compound [Mg].OC(=O)C1=CC=CN=C1 PBXWVVFIFCYDDO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/28—Condensation with aldehydes or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Joining Of Glass To Other Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/426,246 US9012570B2 (en) | 2009-04-18 | 2009-04-18 | Continuous production of poly(vinyl butyral) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201100452A TW201100452A (en) | 2011-01-01 |
| TWI487721B true TWI487721B (zh) | 2015-06-11 |
Family
ID=42167585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099111748A TWI487721B (zh) | 2009-04-18 | 2010-04-15 | 聚（乙烯丁醛）之連續製造 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9012570B2 (enExample) |
| EP (1) | EP2419460B1 (enExample) |
| JP (2) | JP2012524152A (enExample) |
| KR (1) | KR20140014351A (enExample) |
| CN (1) | CN102395609B (enExample) |
| AR (1) | AR076309A1 (enExample) |
| MY (1) | MY156571A (enExample) |
| RU (1) | RU2544533C2 (enExample) |
| SG (2) | SG174491A1 (enExample) |
| TW (1) | TWI487721B (enExample) |
| WO (1) | WO2010121105A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9012570B2 (en) * | 2009-04-18 | 2015-04-21 | Eastman Chemical Company | Continuous production of poly(vinyl butyral) |
| US7960503B2 (en) | 2009-05-26 | 2011-06-14 | Solutia, Inc. | Continuous washing of poly(vinyl butyral) |
| CN102702398B (zh) * | 2012-06-15 | 2014-02-19 | 浙江普利金塑胶有限责任公司 | 一种聚乙烯醇缩丁醛树脂的制备方法 |
| CN104098723B (zh) * | 2014-06-25 | 2016-08-24 | 四川东材科技集团股份有限公司 | 聚乙烯醇缩丁醛树脂的连续制备方法 |
| CN105399877B (zh) * | 2015-12-08 | 2018-02-16 | 清华大学 | 一种基于微分散技术的聚乙烯醇缩丁醛合成工艺 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0597918A (ja) * | 1991-10-04 | 1993-04-20 | Sekisui Chem Co Ltd | ポリビニルアセタール樹脂の製造方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2422754A (en) | 1943-03-13 | 1947-06-24 | Du Pont | Preparation of polyvinyl acetal resins |
| US2457261A (en) * | 1944-08-19 | 1948-12-28 | Shawinigan Chem Ltd | Polyvinyl acetal resins |
| US2720501A (en) | 1954-08-10 | 1955-10-11 | Du Pont | Aqueous condensation process for the preparation of polyvinyl acetal resins |
| DE1247663C2 (de) | 1961-02-24 | 1975-11-27 | E.I. Du Pont De Nemours And Company, Wilmington, Del. (V.St.A.) | Verfahren zur herstellung von polyvinylacetalen |
| GB2127834B (en) | 1982-09-27 | 1985-12-04 | Grace W R & Co | A continuous process for making solid free-flowing water dispersible pva-aldehyde reaction product |
| US5349014A (en) | 1984-08-02 | 1994-09-20 | E. I. Du Pont De Nemours And Company | Process for the production of polyvinyl butyral having improved properties |
| US5238994A (en) * | 1991-09-09 | 1993-08-24 | Monsanto Company | Forming polyvinyl butyral |
| US5137954A (en) * | 1991-09-30 | 1992-08-11 | Monsanto Company | Polyvinyl butyral sheet |
| JPH061853A (ja) * | 1992-06-18 | 1994-01-11 | Sekisui Chem Co Ltd | ポリビニルアルコール水溶液を得る方法及びポリビニルアセタール樹脂の製造方法 |
| DE19617893C1 (de) | 1996-05-04 | 1997-10-02 | Hoechst Ag | Verfahren zur Herstellung von Polyvinylacetalen und -ketalen |
| WO1999023118A1 (de) * | 1997-11-05 | 1999-05-14 | Bio-Tec Biologische Naturverpackungen Gmbh & Co.Kg | Umsetzung eines polyhydroxypolymeren bzw. eines derivates davon mit einem lacton |
| US6347934B1 (en) * | 2000-05-10 | 2002-02-19 | E. Khashoggi Industries, Llc. | System for metering and delivering a moldable composition into a mold |
| US6528025B1 (en) | 2000-06-26 | 2003-03-04 | Roche Vitamins Inc. | Process of manufacturing equipment for preparing acetals and ketals |
| JP4049595B2 (ja) * | 2002-02-07 | 2008-02-20 | 電気化学工業株式会社 | ポリビニルアセタール樹脂の製法 |
| US7385005B2 (en) | 2002-02-07 | 2008-06-10 | Denki Kagaku Kogyo Kabushiki Kaisha | Polyvinylacetal resin and process for producing the same |
| DE10319198A1 (de) * | 2002-07-04 | 2004-01-15 | Kuraray Specialities Europe Gmbh | Vernetzte Polyvinylacetale |
| DE10242417A1 (de) | 2002-09-12 | 2004-03-25 | Wacker Polymer Systems Gmbh & Co. Kg | Verfahren zur Herstellung von Polyvinylacetalen |
| JP4746290B2 (ja) * | 2004-06-17 | 2011-08-10 | 積水化学工業株式会社 | 変性エチレン−ビニルアルコール共重合体の製造方法 |
| WO2008096403A1 (ja) * | 2007-02-02 | 2008-08-14 | Kuraray Co., Ltd. | ポリビニルアセタール樹脂の製造方法 |
| US9012570B2 (en) * | 2009-04-18 | 2015-04-21 | Eastman Chemical Company | Continuous production of poly(vinyl butyral) |
-
2009
- 2009-04-18 US US12/426,246 patent/US9012570B2/en not_active Expired - Fee Related
-
2010
- 2010-04-15 TW TW099111748A patent/TWI487721B/zh not_active IP Right Cessation
- 2010-04-15 AR ARP100101262A patent/AR076309A1/es not_active Application Discontinuation
- 2010-04-16 MY MYPI2011004825A patent/MY156571A/en unknown
- 2010-04-16 EP EP10715428.8A patent/EP2419460B1/en not_active Not-in-force
- 2010-04-16 JP JP2012505952A patent/JP2012524152A/ja active Pending
- 2010-04-16 RU RU2011146828/04A patent/RU2544533C2/ru not_active IP Right Cessation
- 2010-04-16 CN CN201080017166.4A patent/CN102395609B/zh not_active Expired - Fee Related
- 2010-04-16 KR KR1020117024030A patent/KR20140014351A/ko not_active Ceased
- 2010-04-16 SG SG2011068111A patent/SG174491A1/en unknown
- 2010-04-16 WO PCT/US2010/031355 patent/WO2010121105A1/en not_active Ceased
- 2010-04-16 SG SG10201401619PA patent/SG10201401619PA/en unknown
-
2015
- 2015-05-07 JP JP2015094937A patent/JP2015180737A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0597918A (ja) * | 1991-10-04 | 1993-04-20 | Sekisui Chem Co Ltd | ポリビニルアセタール樹脂の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AR076309A1 (es) | 2011-06-01 |
| SG10201401619PA (en) | 2014-06-27 |
| US20100267921A1 (en) | 2010-10-21 |
| RU2011146828A (ru) | 2013-05-27 |
| EP2419460A1 (en) | 2012-02-22 |
| RU2544533C2 (ru) | 2015-03-20 |
| WO2010121105A1 (en) | 2010-10-21 |
| CN102395609B (zh) | 2014-08-20 |
| EP2419460B1 (en) | 2018-10-10 |
| JP2012524152A (ja) | 2012-10-11 |
| CN102395609A (zh) | 2012-03-28 |
| TW201100452A (en) | 2011-01-01 |
| US9012570B2 (en) | 2015-04-21 |
| KR20140014351A (ko) | 2014-02-06 |
| JP2015180737A (ja) | 2015-10-15 |
| MY156571A (en) | 2016-03-15 |
| SG174491A1 (en) | 2011-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |