JP3430373B2 - 乳酸でエステル化したポリビニルアルコール類およびそれらの製造方法 - Google Patents
乳酸でエステル化したポリビニルアルコール類およびそれらの製造方法Info
- Publication number
- JP3430373B2 JP3430373B2 JP51809294A JP51809294A JP3430373B2 JP 3430373 B2 JP3430373 B2 JP 3430373B2 JP 51809294 A JP51809294 A JP 51809294A JP 51809294 A JP51809294 A JP 51809294A JP 3430373 B2 JP3430373 B2 JP 3430373B2
- Authority
- JP
- Japan
- Prior art keywords
- lactic acid
- polyvinyl alcohol
- water
- esterified
- hours
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 229920002451 polyvinyl alcohol Polymers 0.000 title claims abstract description 47
- 239000004310 lactic acid Substances 0.000 title claims abstract description 31
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 18
- 235000019422 polyvinyl alcohol Nutrition 0.000 title description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 2
- 229920000578 graft copolymer Polymers 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 6
- 230000001070 adhesive effect Effects 0.000 abstract description 6
- 239000000835 fiber Substances 0.000 abstract description 3
- 238000000465 moulding Methods 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000010408 film Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 229920000642 polymer Polymers 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- -1 aliphatic amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 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
- C08F8/14—Esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/017,234 | 1993-02-12 | ||
| US08/017,234 US5331045A (en) | 1993-02-12 | 1993-02-12 | Polyvinyl alcohol esterified with lactic acid and process therefor |
| PCT/US1994/000936 WO1994018243A2 (en) | 1993-02-12 | 1994-02-03 | Polyvinyl alcohol esterified with lactic acid and process therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08506605A JPH08506605A (ja) | 1996-07-16 |
| JP3430373B2 true JP3430373B2 (ja) | 2003-07-28 |
Family
ID=21781489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51809294A Expired - Fee Related JP3430373B2 (ja) | 1993-02-12 | 1994-02-03 | 乳酸でエステル化したポリビニルアルコール類およびそれらの製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5331045A (enExample) |
| EP (1) | EP0683794B1 (enExample) |
| JP (1) | JP3430373B2 (enExample) |
| AT (1) | ATE152738T1 (enExample) |
| CA (1) | CA2155115C (enExample) |
| DE (1) | DE69403067T2 (enExample) |
| DK (1) | DK0683794T3 (enExample) |
| ES (1) | ES2101509T3 (enExample) |
| GR (1) | GR3024118T3 (enExample) |
| WO (1) | WO1994018243A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3301506B2 (ja) * | 1993-09-20 | 2002-07-15 | 大日本インキ化学工業株式会社 | ラクタイド系共重合体の製造方法 |
| US5612412A (en) * | 1994-09-30 | 1997-03-18 | Daicel Chemical Industries, Ltd. | Lactone-modified polyvinyl alcohol, a process for the preparation thereof |
| DE10140597A1 (de) * | 2001-08-18 | 2003-03-06 | Kuraray Specialities Europe | Teilvernetzter Polyvinylalkohol |
| DE112006002190T5 (de) * | 2005-08-22 | 2008-06-12 | Japan VAM & POVAL Co., Ltd., Sakai | Verfahren zur Veresterung eines auf Polyvinylalkohol basierenden Harzes, daraus resultierendes modifiziertes auf Polyvinylalkohol basierendes Harz, und Verfahren zu dessen Herstellung |
| CN100406498C (zh) * | 2006-03-09 | 2008-07-30 | 四川大学 | 聚乙烯醇/聚乳酸接枝共聚物及其与淀粉的共混材料和它们的制备方法、用途 |
| DE102006047617B4 (de) | 2006-10-09 | 2008-11-27 | Clariant International Limited | Verfahren zur Herstellung basischer (Meth)acrylamide |
| DE102008017216B4 (de) | 2008-04-04 | 2013-08-14 | Clariant International Ltd. | Kontinuierliches Verfahren zur Herstellung von Fettsäureamiden |
| DE102009031059A1 (de) | 2009-06-30 | 2011-01-05 | Clariant International Ltd. | Vorrichtung zur kontinuierlichen Durchführung chemischer Reaktionen bei hohen Temperaturen |
| DE102009042522A1 (de) | 2009-09-22 | 2011-04-07 | Clariant International Ltd. | Kontinuierliches Umesterungsverfahren |
| DE102009042523B4 (de) | 2009-09-22 | 2012-02-16 | Clariant International Ltd. | Vorrichtung und Verfahren zur kontinuierlichen Durchführung heterogen katalysierter chemischer Reaktionen bei hohen Temperaturen |
| DE102010056565A1 (de) | 2010-12-30 | 2012-07-05 | Clariant International Ltd. | Verfahren zur Modifizierung Hydroxylgruppen tragender Polymere |
| DE102010056564A1 (de) * | 2010-12-30 | 2012-07-05 | Clariant International Limited | Hydroxylgruppen und Estergruppen tragende Polymere und Verfahren zu ihrer Herstellung |
| DE112018008121T5 (de) * | 2018-11-08 | 2021-07-22 | Hunan Xinjinfu Medical Technology Co., Ltd. | Gepfropfte Polyvinylalkoholfaser und deren Verfahren zur Herstellung sowie mit dieser gepfropften Polyvinylalkoholfaser hergestelltes Textil |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL123810C (enExample) * | 1963-12-24 | 1900-01-01 | ||
| JPS4944601B1 (enExample) * | 1970-05-15 | 1974-11-29 | ||
| US3749699A (en) * | 1971-01-07 | 1973-07-31 | Power Chemco Inc | Light-sensitive mixed esters of polyvinyl alcohol |
| CH645391A5 (de) * | 1978-02-21 | 1984-09-28 | Ciba Geigy Ag | Polymere mit succinylobernsteinsaeureester-resten. |
| JPS5917550A (ja) * | 1982-07-21 | 1984-01-28 | Mitsubishi Chem Ind Ltd | 光架橋性感光材料 |
| JP2657109B2 (ja) * | 1990-08-03 | 1997-09-24 | 東洋インキ製造株式会社 | 樹脂の製造方法，水性樹脂組成物の製造方法および樹脂組成物の製造方法 |
-
1993
- 1993-02-12 US US08/017,234 patent/US5331045A/en not_active Expired - Lifetime
-
1994
- 1994-02-03 WO PCT/US1994/000936 patent/WO1994018243A2/en not_active Ceased
- 1994-02-03 DE DE69403067T patent/DE69403067T2/de not_active Expired - Fee Related
- 1994-02-03 EP EP94906713A patent/EP0683794B1/en not_active Expired - Lifetime
- 1994-02-03 AT AT94906713T patent/ATE152738T1/de not_active IP Right Cessation
- 1994-02-03 DK DK94906713.6T patent/DK0683794T3/da active
- 1994-02-03 JP JP51809294A patent/JP3430373B2/ja not_active Expired - Fee Related
- 1994-02-03 ES ES94906713T patent/ES2101509T3/es not_active Expired - Lifetime
- 1994-02-03 CA CA002155115A patent/CA2155115C/en not_active Expired - Fee Related
-
1997
- 1997-07-16 GR GR970401768T patent/GR3024118T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69403067T2 (de) | 1997-08-21 |
| DE69403067D1 (de) | 1997-06-12 |
| CA2155115C (en) | 2004-06-22 |
| DK0683794T3 (enExample) | 1997-06-02 |
| EP0683794A1 (en) | 1995-11-29 |
| US5331045A (en) | 1994-07-19 |
| WO1994018243A3 (en) | 1994-10-27 |
| JPH08506605A (ja) | 1996-07-16 |
| GR3024118T3 (en) | 1997-10-31 |
| ES2101509T3 (es) | 1997-07-01 |
| EP0683794B1 (en) | 1997-05-07 |
| CA2155115A1 (en) | 1994-08-18 |
| WO1994018243A2 (en) | 1994-08-18 |
| ATE152738T1 (de) | 1997-05-15 |
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