CN1176890C - 双酚在制备聚碳酸酯和环氧树脂方面的用途 - Google Patents
双酚在制备聚碳酸酯和环氧树脂方面的用途Info
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- 229920005989 resin Polymers 0.000 title claims description 5
- 239000011347 resin Substances 0.000 title claims description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title abstract description 8
- 229930185605 Bisphenol Natural products 0.000 title description 3
- 150000002148 esters Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000004417 polycarbonate Substances 0.000 claims abstract description 6
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 28
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- ZLDADNIBRBDHQW-UHFFFAOYSA-N 4-propylcyclohexa-1,5-diene-1,4-diol Chemical compound C(CC)C1(O)CC=C(O)C=C1 ZLDADNIBRBDHQW-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
- 241001550224 Apha Species 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 2
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 2
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 claims 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 6
- PQPVYEDTTQIKIA-UHFFFAOYSA-N 1,2-dimethyl-9h-xanthene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3OC2=C1 PQPVYEDTTQIKIA-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- -1 83.7%p Chemical compound 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Epoxy Resins (AREA)
Abstract
本发明涉及制备具有至少99.95%(重量)p，p-双酚A(BPA)的纯度的双酚A的方法。按照本发明纯化的热稳定和色稳定的双酚A在聚合物如用其制备的聚碳酸酯中表现出改善的热和颜色稳定性和改善的透光性。
Description
本申请是申请日为1996年8月14日，申请号为96111820.2，发明名称为“双酚的纯化方法”的发明专利申请的分案申请。
本发明涉及制备含至少99.95％(重量)p，p-双酚A(BPA)的双酚A的方法。按照本发明纯化的热稳定和颜色稳定的双酚A在聚合物如用其制备的聚碳酸酯中展现了改善的热和颜色稳定性和改善的透光性。
p，p-双酚A(BPA)例如通过已知方法在可选地改性的离子交换树脂的存在下用丙酮和苯酚来制备(例如DE-A-3727641，相应于US-A-4912263)。
高纯双酚A的制备是已知的。DE-A-4213827描述了如何能制备纯度为99.91％(重量)的双酚A。纯化是通过将双酚A/苯酚加合物结晶然后将加合物过滤并解吸出苯酚来进行。
DE-A-4413396描述了如何通过分二阶段蒸馏含至少90％(重量)的双酚A熔体并分离难/易挥发和不挥发的组分来得到高纯双酚A。氮气流被用来从所用的熔化物去除苯酚并使熔化物惰性。双酚A的初纯化通过结晶，过滤和解吸来实现。
业已发现，大量使用的酚的双酚A溶液的纯化步骤如双酚A/苯酚加合物的结晶、过滤和解吸在含p，p-双酚的酚溶液如用苯酚和丙酮进行双酚A的制备时制出的酚溶液以顺序连接的蒸馏阶段的顺序纯化时可以省去。
因此本发明提供从在可选地用巯基胺和/或噻唑烷和/或硫代羧酸改性的磺酸离子交换剂的存在下用丙酮和苯酚制备双酚A时得到的反应溶液获得纯度大于99.95％(重量)且哈曾(Hazen)(APHA)比色指数小于5的双酚A的方法，其中
a)将酚溶液在60-80℃温度下调节到含p，p-双酚A 10-40％(重量)的浓度，
b)然后将这样制备的溶液供到串联的系列塔中，其中
c)在第一蒸馏步骤中，将水和残存的丙酮及可选的苯酚从反应器排出的反应溶液中除去，然后
d)在第二蒸馏步骤中，将以这种方式制备的元水溶液在塔的底部调节到含p，p-双酚A 70-97％(重量)的浓度，
e)在第三蒸馏步骤中，将难挥发和不挥发组分从这样获得的溶液中去除，然后
f)在第四蒸馏步骤中，除去蒸馏于p，p-双酚A中的易挥发组分和残余的苯酚，然后
g)按常规方式处理从塔的底部获得的p，p-双酚A熔体。
如此制备的p，p-双酚A被用作制备聚合物如聚碳酸酯或环氧树脂的原料。
不可能预测酚的双酚A溶液可简单地通过串联排布的系列蒸馏步骤来纯化，因为正如所知，双酚A和其中所含的异构体在非常高温度下异构化并且这对双酚A熔体和双酚A固态产物来说导致了非常差的比色指数。
本发明的酚的双酚A溶液的蒸馏方法也具有不需容易失败的复杂的多级结晶过程、旋转滤机和离心机的使用和解吸设备的使用的优点。因此避免了处理设备技术复杂的高维护强度的操作并提高了设备的可得性。
实施例1 制备反应溶液
开始时将81苯酚润湿的磺化聚苯乙烯树脂(Lewatit SC 102，BayerAG)导到装填在维持于80℃的双壁玻璃反应器(10l)的玻璃丝上。通过导入氮气使其保护惰性。然后从上连接将已预热至70℃的含95.5％苯酚和4.5％丙酮的溶液(1 l/h)导入到反应器中。
在反应器较低的排放口得到下列组成的酚溶液：苯酚84％；丙酮1％；水1.2％；p，p-双酚A 11.6％；o，p双酚A1.6％；二甲基呫吨(dimethylxanthen，DMX)24ppm；色满3700ppm；茚满42ppm；三酚1780ppm；分子量402，410ppm；其它110ppm。
实施例2 从反应溶液蒸馏丙酮/水
最初得101具上面组成的酚溶液(从反应器排出)置于3-颈烧瓶中并在具10分离级的双板塔上于惰性条件下蒸馏。蒸馏在150毫巴塔底部温度为126℃的情况下进行。
获得具有下面组成的馏出物：丙酮37.5％；水58.5％；苯酚4％；1，3，5-三甲基苯25ppm；茴香醚10ppm；甲醇300ppm。
在塔底部的产物具有下面组成：酚85.9％；p，p-双酚A11.9％；o，p-双酚A1.6％；二甲基呫吨25ppm；色满3765ppm；茚满43ppm；三酚1820ppm；分子量402，420ppm；其它102ppm。
实施例3 从无水溶液中蒸馏掉苯酚
酚蒸馏在100毫巴、塔顶温度120℃的条件下进行。馏出物含99.95％苯酚和50ppm邻甲酚。在塔底部的产物含：4400ppm苯酚，83.7％p，p-双酚A；11.4％o，p-双酚A；173ppm二甲基呫吨；2.7％色满；303ppm茚满；1.3％三酚；3000ppm分子量402和700ppm残面异构物。
实施例4 除去难挥发和易挥发组分
将上述溶液在2毫巴和底部温度为226℃的条件下蒸馏。首先难挥发组分富集于塔底部并被除去。
将在塔顶蒸馏出的易挥发组分和双酚A送到第二塔。在那里易挥发组分和残留酚在2毫巴下从塔顶分离出来。底部产物含高纯p，p-双酚A(大于99.95(重量％))。
所述蒸馏例如按照DE-A-4413396中所述的进行双酚A熔体蒸馏的已知方法来进行。得到99.98％(重量)p，p-双酚A纯度的双酚A。
从质量平衡知道，p，p-双酚A的损失低于2％。
Claims (1)
1.制备聚碳酸酯或环氧树脂的方法，该方法包括步骤：
A)从在可选地用巯基胺和/或噻唑烷和/或硫代羧酸改性的磺酸离子交换剂的存在下用丙酮和苯酚制备双酚A时得到的反应溶液中获得纯度大于99.95重量％且哈曾APHA比色指数小于5的双酚A，其中
a)将酚溶液在60-80℃温度下调节到含p，p-双酚A 10-40重量％的浓度，
b)然后将这样制备的溶液供到串联的系列塔中，其中
c)在第一蒸馏步骤中，将水和残存的丙酮及可选的苯酚从反应器排出的反应溶液中除去，然后
d)在第二蒸馏步骤中，将以这种方式制备的无水溶液在塔的底部调节到含p，p-双酚A 70-97重量％的浓度，
e)在第三蒸馏步骤中，将难挥发和不挥发组分从这样获得的溶液中去除，然后
f)在第四蒸馏步骤中，除去蒸馏后p，p-双酚A中的易挥发组分和残余的苯酚，然后
g)按常规方式处理从塔的底部获得的p，p-双酚A熔体；和
B)由步骤A)中获得的双酚A制备聚碳酸酯或环氧树脂。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19529855A DE19529855A1 (de) | 1995-08-14 | 1995-08-14 | Verfahren zur Reinigung von Bisphenol |
| DE19529855.1 | 1995-08-14 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96111820A Division CN1066705C (zh) | 1995-08-14 | 1996-08-14 | 双酚的纯化方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1290683A CN1290683A (zh) | 2001-04-11 |
| CN1176890C true CN1176890C (zh) | 2004-11-24 |
Family
ID=7769440
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96111820A Expired - Fee Related CN1066705C (zh) | 1995-08-14 | 1996-08-14 | 双酚的纯化方法 |
| CNB001069209A Expired - Fee Related CN1176890C (zh) | 1995-08-14 | 1996-08-14 | 双酚在制备聚碳酸酯和环氧树脂方面的用途 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96111820A Expired - Fee Related CN1066705C (zh) | 1995-08-14 | 1996-08-14 | 双酚的纯化方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5785823A (zh) |
| EP (1) | EP0758637B1 (zh) |
| JP (1) | JP3810147B2 (zh) |
| KR (1) | KR100435021B1 (zh) |
| CN (2) | CN1066705C (zh) |
| DE (2) | DE19529855A1 (zh) |
| ES (1) | ES2139997T3 (zh) |
| TW (1) | TW358804B (zh) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19860144C1 (de) * | 1998-12-24 | 2000-09-14 | Bayer Ag | Verfahren zur Herstellung von Bisphenol A |
| DE19954311A1 (de) | 1999-11-11 | 2001-05-17 | Bayer Ag | Bisphenol-Herstellung |
| DE19954786A1 (de) * | 1999-11-15 | 2001-05-17 | Bayer Ag | Schmelzkristallisation |
| DE10015864A1 (de) * | 2000-03-30 | 2001-10-11 | Bayer Ag | Stoffgemisch enthaltend Bisphenol A |
| TW583266B (en) * | 2000-04-27 | 2004-04-11 | Idemitsu Petrochemical Co | Polycarbonate resin composition for optical disk substrate |
| US6620939B2 (en) * | 2001-09-18 | 2003-09-16 | General Electric Company | Method for producing bisphenol catalysts and bisphenols |
| US6703530B2 (en) * | 2002-02-28 | 2004-03-09 | General Electric Company | Chemical reactor system and process |
| US6960697B2 (en) * | 2002-03-13 | 2005-11-01 | Mitsubishi Chemical Corporation | System and method of producing bisphenol-A (BPA) |
| US7112702B2 (en) * | 2002-12-12 | 2006-09-26 | General Electric Company | Process for the synthesis of bisphenol |
| US7132575B2 (en) | 2003-07-01 | 2006-11-07 | General Electric Company | Process for the synthesis of bisphenol |
| DE102004005726A1 (de) * | 2004-02-05 | 2005-08-25 | Bayer Materialscience Ag | Entwässerung von Kreislaufströmen bei der Herstellung von Bisphenol A |
| JP5226172B2 (ja) * | 2004-05-27 | 2013-07-03 | 帝人化成株式会社 | 分岐状ポリカーボネート樹脂の製造方法 |
| DE102004032232A1 (de) * | 2004-07-02 | 2006-01-19 | Bayer Materialscience Ag | Verfahren zur Abtrennung von Phenol aus phenolhaltigen Strömen aus der Herstellung von Bisphenol A |
| US7371902B2 (en) * | 2004-09-29 | 2008-05-13 | General Electric Company | Methods for purifying p,p-bisphenol-A |
| CN100387564C (zh) * | 2006-09-26 | 2008-05-14 | 蓝星化工新材料股份有限公司无锡树脂厂 | 两步结晶提纯法中调节二酚基丙烷浓度的方法及装置 |
| EP3383833B1 (en) * | 2015-12-03 | 2020-11-11 | SABIC Global Technologies B.V. | Method of recovering phenol from a bpa production facility and the facility for recovering the same |
| KR102441561B1 (ko) * | 2018-12-20 | 2022-09-06 | 주식회사 엘지화학 | 페놀계 부산물의 분해 방법 및 이의 분해 장치 |
| JP7273603B2 (ja) * | 2019-04-19 | 2023-05-15 | 株式会社ダイセル | 脂環式エポキシ化合物製品 |
| CN112409573B (zh) * | 2019-08-23 | 2023-06-20 | 南通星辰合成材料有限公司 | 一种副产多元酚环氧树脂及其制造方法与应用 |
| CN116874355A (zh) * | 2023-06-25 | 2023-10-13 | 浙江工业大学 | 一种降低苯酚/双酚a产品色度的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BE678415A (zh) * | 1963-12-31 | 1966-09-01 | ||
| GB1574420A (en) * | 1976-12-18 | 1980-09-03 | Bp Chem Int Ltd | Process for recovering crude phenol from catalyst-free cumene hydroperoxide cleavage reaction products |
| DE2918990A1 (de) * | 1979-05-11 | 1980-11-20 | Gen Electric | Verfahren zur stabilisierung von bisphenolen unter schmelz- oder destillationsbedingungen |
| DE2935316A1 (de) * | 1979-08-31 | 1981-03-26 | Bayer Ag, 51373 Leverkusen | Verfahren zur herstellung reiner 4,4'-dihydroxydiphenylalkane bzw. -cycloalkane |
| US4400553A (en) * | 1981-06-24 | 1983-08-23 | General Electric Company | Recovery of BPA and phenol from aqueous effluent streams |
| US4400555A (en) * | 1981-10-06 | 1983-08-23 | General Electric Company | Ion exchange catalyzed bisphenol synethesis |
| DE4105428A1 (de) * | 1991-02-21 | 1992-08-27 | Bayer Ag | Verfahren zur reinigung von bisphenolen |
| EP0552518B1 (en) * | 1992-01-14 | 1995-09-13 | General Electric Company | Method of recovering bisphenol-A from preparative process efluent streams |
| DE4413396A1 (de) * | 1994-04-18 | 1995-10-19 | Bayer Ag | Verfahren zur Herstellung von ultrareinem Bisphenol-A und dessen Verwendung |
-
1995
- 1995-08-14 DE DE19529855A patent/DE19529855A1/de not_active Withdrawn
-
1996
- 1996-08-01 ES ES96112425T patent/ES2139997T3/es not_active Expired - Lifetime
- 1996-08-01 DE DE59603541T patent/DE59603541D1/de not_active Expired - Fee Related
- 1996-08-01 EP EP96112425A patent/EP0758637B1/de not_active Expired - Lifetime
- 1996-08-02 US US08/691,402 patent/US5785823A/en not_active Expired - Fee Related
- 1996-08-09 TW TW085109649A patent/TW358804B/zh active
- 1996-08-09 JP JP22615696A patent/JP3810147B2/ja not_active Expired - Fee Related
- 1996-08-13 KR KR1019960033581A patent/KR100435021B1/ko not_active IP Right Cessation
- 1996-08-14 CN CN96111820A patent/CN1066705C/zh not_active Expired - Fee Related
- 1996-08-14 CN CNB001069209A patent/CN1176890C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1066705C (zh) | 2001-06-06 |
| CN1290683A (zh) | 2001-04-11 |
| KR970010722A (ko) | 1997-03-27 |
| DE59603541D1 (de) | 1999-12-09 |
| JP3810147B2 (ja) | 2006-08-16 |
| CN1145352A (zh) | 1997-03-19 |
| KR100435021B1 (ko) | 2004-08-16 |
| EP0758637B1 (de) | 1999-11-03 |
| US5785823A (en) | 1998-07-28 |
| DE19529855A1 (de) | 1997-02-20 |
| JPH0959195A (ja) | 1997-03-04 |
| TW358804B (en) | 1999-05-21 |
| ES2139997T3 (es) | 2000-02-16 |
| EP0758637A1 (de) | 1997-02-19 |
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