CN101896427A - 包含热解制备的二氧化硅的片 - Google Patents
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- CN101896427A CN101896427A CN2008801204687A CN200880120468A CN101896427A CN 101896427 A CN101896427 A CN 101896427A CN 2008801204687 A CN2008801204687 A CN 2008801204687A CN 200880120468 A CN200880120468 A CN 200880120468A CN 101896427 A CN101896427 A CN 101896427A
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000000377 silicon dioxide Substances 0.000 title claims abstract description 22
- 235000012239 silicon dioxide Nutrition 0.000 title claims abstract description 19
- 244000043261 Hevea brasiliensis Species 0.000 claims abstract 2
- 229920003052 natural elastomer Polymers 0.000 claims abstract 2
- 229920001194 natural rubber Polymers 0.000 claims abstract 2
- 238000010090 natural rubber production Methods 0.000 claims abstract 2
- 238000010091 synthetic rubber production Methods 0.000 claims abstract 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000000197 pyrolysis Methods 0.000 claims description 15
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000137 annealing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002940 repellent Effects 0.000 abstract 1
- 239000005871 repellent Substances 0.000 abstract 1
- -1 methyl- Chemical group 0.000 description 62
- 125000000217 alkyl group Chemical group 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 150000001282 organosilanes Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010334 sieve classification Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
- C09C1/30—Silicic acid
- C09C1/309—Combinations of treatments provided for in groups C09C1/3009 - C09C1/3081
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/18—Preparation of finely divided silica neither in sol nor in gel form; After-treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
- C09C1/30—Silicic acid
- C09C1/3081—Treatment with organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/11—Powder tap density
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/19—Oil-absorption capacity, e.g. DBP values
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Silicon Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本申请公开了包含热解制备的二氧化硅的片，其经压实后呈现疏水性。所述片可用于天然橡胶和合成橡胶的生产中。
Description
本发明涉及包含热解制备的二氧化硅的片(flake)、其制备方法及其用途。
众所周知，可以通过使以纳米级的高团聚颗粒的松散堆呈现的热解制备二氧化硅部分脱气由热解制备的二氧化硅来制备片，通过降低的大气压、机械预压所述二氧化硅并最终将其压实以获得片。随后可以将这些片压碎并任选地将碎片分级(EP1813574A1)。
可以采用亲水的和也可以是疏水的、热解制备的二氧化硅颗粒作为起始原料。还可以用
型硅氮烷使二氧化硅呈现疏水性。
发现已知方法的一个缺点是在颗粒通过氮气吸附(BET)测量具有高比表面积，并且通过用甲醇含量级的甲醇-水混合物(康宁玻璃)湿润测量同时具有高疏水性的情况下，由于这些颗粒具有很高的流动性，因此按照EP1813574A1的方法压实这样的颗粒是非常不经济的。
流动性理解为是指由高度聚合的颗粒通过团聚形成，并且由占其体积95％以上的空气和仅占其体积5％以下的固体组成的松散堆在从外界施加压力的作用下发生正交偏离，所述的堆也可以以与低粘度液体同样的方式通过很小的缝隙脱离。因而，通过EP1813574A1描述的方法制备疏水二氧化硅片是困难的。
在很多情况下，压实疏水二氧化硅需要实施非常高的压力、非常长的保压时间以及往往众多的压实周期。因此通过已知的方法不能经济地压缩由非常细微的颗粒组成同时强烈疏水的二氧化硅以得到压实材料。
因此，本发明的目的是由通过不具有这些缺点的方法制备包含热解制备的二氧化硅的疏水片。
本发明涉及包含热解制备的二氧化硅的片，其特征在于该片经压实呈现疏水性。
采用选自下面组中的一种或多种化合物可以实现赋予疏水性：
a)(RO)3Si(CnH2n+1)和(RO)3Si(CnH2n-1)型有机硅烷
R＝烷基，例如甲基-、乙基-、正丙基-、异丙基-、丁基-
n＝1-20
b)R’x(RO)ySi(CnH2n+1)和R’x(RO)ySi(CnH2n-1)型有机硅烷
R＝烷基，例如甲基-、乙基-、正丙基-、异丙基-、丁基-
R’＝烷基，例如甲基-、乙基-、正丙基-、异丙基-、丁基-
R’＝环烷基
n＝1-20
x+y＝3
x＝1，2
y＝1，2
c)X3Si(CnH2n+1)和X3Si(CnH2n-1)型卤代有机硅烷
X＝Cl，Br
n＝1-20
d)X2(R’)Si(CnH2n+1)和X2(R’)Si(CnH2n-1)型卤代有机硅烷
X＝Cl，Br
R’＝烷基，例如甲基-、乙基-、正丙基-、异丙基-、丁基-
R’＝环烷基
n＝1-20
e)X(R’)2Si(CnH2n+1)和X(R’)2Si(CnH2n-1)型卤代有机硅烷
X＝Cl，Br
R’＝烷基，例如甲基-、乙基-、正丙基-、异丙基-、丁基-
R’＝环烷基
n＝1-20
f)(RO)3Si(CH2)m-R’型有机硅烷
R＝烷基，例如甲基-，乙基-，丙基-
m＝0，1-20
R’＝甲基-、芳基(例如-C6H5、取代的苯基)
-C4F9，OCF2-CHF-CF3，-C6F13，-O-CF2-CHF2
-NH2，-N3，-SCN，-CH＝CH2，-NH-CH2-CH2-NH2，
-N-(CH2-CH2-NH2)2
-OOC(CH3)C＝CH2
-OCH2-CH(O)CH2
-NH-CO-N-CO-(CH2)5
-NH-COO-CH3，-NH-COO-CH2-CH3，-NH-(CH2)3Si(OR)3
-SX-(CH2)3Si(OR)3，其中X＝1-10并且R可以是烷基，例如甲基-、
乙基-、丙基-、丁基-
-SH
-NR’R”R”’(R＝烷基、芳基；R”＝H、烷基、芳基；R”’＝H、烷基、芳基、苯甲基、C2H4NR””R””’其中R””＝A、烷基，R””’＝H、烷基)
g)(R”)x(RO)ySi(CH2)m-R’型有机硅烷
R”＝烷基 x+y＝2
＝环烷基 x＝1，2
y＝1，2
m＝0，1-20
R’＝甲基-、芳基(例如-C6H5、取代的苯基)
-C4F9，OCF2-CHF-CF3，-C6F13，-O-CF2-CHF2
-NH2，-N3，-SCN，-CH＝CH2，-NH-CH2-CH2-NH2，
-N-(CH2-CH2-NH2)2
-OOC(CH3)C＝CH2
-OCH2-CH(O)CH2
-NH-CO-N-CO-(CH2)5
-NH-COO-CH3，-NH-COO-CH2-CH3，-NH-(CH2)3Si(OR)3
-SX-(CH2)3Si(OR)3，其中X＝1-10并且R可以是甲基-、乙基-、丙基-、丁基-
-SH
-NR’R”R”’(R＝烷基、芳基；R”＝H、烷基、芳基；R”’＝H、烷基、芳基、苯甲基、C2H4NR””R””’其中R””＝A、烷基，R””’＝H、烷基)
h)X3Si(CH2)m-R’型卤代有机硅烷
X＝Cl，Br
m＝0，1-20
R’＝甲基-、芳基(例如-C6H5、取代的苯基)
-C4F9，OCF2-CHF-CF3，-C6F13，-O-CF2-CHF2
-NH2，-N3，-SCN，-CH＝CH2，
-NH-CH2-CH2-NH2，
-N-(CH2-CH2-NH2)2
-OOC(CH3)C＝CH2
-OCH2-CH(O)CH2
-NH-CO-N-CO-(CH2)5
-NH-COO-CH3，-NH-COO-CH2-CH3，-NH-(CH2)3Si(OR)3
-SX-(CH2)3Si(OR)3，其中X＝1-10并且R可以是甲基-、乙基-、丙基-、丁基-
-SH
i)(R)X2Si(CH2)m-R’型卤代有机硅烷
X＝Cl，Br
R＝烷基，例如甲基-，乙基-，丙基-
m＝0，1-20
R’＝甲基-、芳基(例如-C6H5、取代的苯基)
-C4F9，OCF2-CHF-CF3，-C6F13，-O-CF2-CHF2
-NH2，-N3，-SCN，-CH＝CH2，-NH-CH2-CH2-NH2，
-N-(CH2-CH2-NH2)2
-OOC(CH3)C＝CH2
-OCH2-CH(O)CH2
-NH-CO-N-CO-(CH2)5
-NH-COO-CH3，-NH-COO-CH2-CH3，-NH-(CH2)3Si(OR)3，其中
R可以是甲基-、乙基-、丙基-、丁基-
-SX-(CH2)3Si(OR)3，其中R可以是甲基-、乙基-、丙基-、丁基-，并且X可以是1-10
-SH
j)(R)2XSi(CH2)m-R’型卤代有机硅烷
X＝Cl，Br
R＝烷基，例如甲基-、乙基-、丙基-、丁基-
m＝0，1-20
R’＝甲基-、芳基(例如-C6H5、取代的苯基)
-C4F9，OCF2-CHF-CF3，-C6F13，-O-CF2-CHF2
-NH2，-N3，-SCN，-CH＝CH2，-NH-CH2-CH2-NH2，
-N-(CH2-CH2-NH2)2
-OOC(CH3)C＝CH2
-OCH2-CH(O)CH2
-NH-CO-N-CO-(CH2)5
-NH-COO-CH3，-NH-COO-CH2-CH3，-NH-(CH2)3Si(OR)3
-SX-(CH2)3Si(OR)3，其中X＝1-10并且R可以是甲基-、乙基-、丙基-、丁基-
-SH
k)
型硅氮烷
R＝烷基
R’＝烷基、乙烯基
1)D3、D4、D5型环状聚硅氧烷，其中D3、D4、D5理解为具有3、4或5个-O-Si(CH3)2-型单元的环状聚硅氧烷，
例如，八甲基环四硅氧烷＝D4
m)下面类型的聚硅氧烷或硅油
R＝烷基，例如CnH2n+1，其中n为1-20，芳基，例如苯基和取代的苯基，(CH2)n-NH2，H
R’＝烷基，例如CnH2n+1，其中n为1-20，芳基，例如苯基和取代的苯基，(CH2)n-NH2，H
R”＝烷基，例如CnH2n+1，其中n为1-20，芳基，例如苯基和取代的苯基，(CH2)n-NH2，H
R”’＝烷基，例如CnH2n+1，其中n为1-20，芳基，例如苯基和取代的苯基，(CH2)n-NH2，H
在本发明的优选实施方案中，可以使用HMDS(六甲基二硅氮烷)为所述片赋予疏水性。
可以使用具有以下物理化学特性的亲水的、热解制备的二氧化硅作为起始原料：
BET表面积： 30-400m2/g
夯实密度： 40-200g/l
平均初级颗粒尺寸：5-50nm
本发明还涉及制备疏水片的方法，其特征在于将亲水的、热解制备的二氧化硅压实以获得片，然后任选地将所述片粉碎并通过筛分分级，随后任选地用水或催化剂或反应辅助剂(例如，稀酸或碱溶液，例如，盐酸或氨水)喷雾所述片，然后用疏水剂喷雾，使混合物在10-80℃的温度下熟化，然后在80-140℃优选100-130℃的温度下退火0.5-8小时。
根据本发明包含热解制备的二氧化硅的疏水片具有以下优点：
该片表现为低粉尘量到无粉尘量形式的疏水二氧化硅。根据本发明的片的特征还在于夯实密度大幅提高，这与小的装填体积相关。
实施例：
使用亲水的、热解制备的二氧化硅
作为起始原料。
具有以下的物理化学特性：
| 性质 | 单位 | 参考值 |
| 比表面积(BET) | m2/g | 300±30 |
| 初级颗粒的平均粒径 | nm | 7 |
| 夯实密度(近似值)*基于DIN EN ISO 787/11，1983年8月 | g/l | 约50 |
| 干燥失重*在105℃下2h | 重量％ | ＜1.5 |
| 在1000℃下2h的烧失量，基于干燥物(在105℃下2h) | 重量％ | ＜2.0 |
| pH值浓度4％的分散液 | 3.7-4.7 | |
| SiO2含量，基于燃烧后的物质 | 重量％ | ＞99.8 |
根据EP1813574压实
以获得片。
将所述片通过破碎筛分并分级。
然后用HMDS(六甲基二硅氮烷)喷雾所述片。
随后使混合物在10-50℃的温度下熟化最多3周。
随后混合物在130℃下退火5小时。
表1概述了制备条件。
表2显示了得到的片的物理化学数据。
表1制备条件：
表2获得的包含热解制备的二氧化硅的表面改性的片
具有以下物理化学参数：
| 实施例 | 夯实密度[g/l] | 干燥失重[％] | 烧失量[％] | pHDIN | DBP数[％] | 碳含量[％] |
| 1 | 298 | 0.7 | 4.1 | 7.0 | 128 | 3.4 |
| 2 | 293 | 0.5 | 3.4 | 8.3 | 125 | 3.3 |
Claims (3)
1.包含热解制备的二氧化硅的片，其特征在于：所述片经压实后呈现疏水性。
2.制备根据权利要求1所述的片的方法，其特征在于将亲水的、热解制备的二氧化硅压实以获得片，用疏水剂喷雾所述片，使该混合物在10-80℃的温度下熟化，并随后在80-140℃，优选100-130℃的温度下退火O.5-8小时。
3.包含热解制备的二氧化硅的疏水片在天然橡胶和合成橡胶生产中的用途。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007059860.4 | 2007-12-12 | ||
| DE102007059860A DE102007059860A1 (de) | 2007-12-12 | 2007-12-12 | Schülpen aus pyrogen hergestelltem Siliziumdioxid |
| PCT/EP2008/065775 WO2009074432A1 (en) | 2007-12-12 | 2008-11-18 | Flakes comprising pyrogenically prepared silicon dioxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101896427A true CN101896427A (zh) | 2010-11-24 |
Family
ID=40292466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008801204687A Pending CN101896427A (zh) | 2007-12-12 | 2008-11-18 | 包含热解制备的二氧化硅的片 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100261823A1 (zh) |
| EP (1) | EP2244974B1 (zh) |
| JP (1) | JP2011506243A (zh) |
| CN (1) | CN101896427A (zh) |
| DE (1) | DE102007059860A1 (zh) |
| WO (1) | WO2009074432A1 (zh) |
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| WO2020038581A1 (de) * | 2018-08-23 | 2020-02-27 | Wacker Chemie Ag | Homogen hydrophobierte formkörper aus kieselsäuren |
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| IN186494B (zh) * | 1995-02-04 | 2001-09-15 | Degussa | |
| US5959005A (en) * | 1996-04-26 | 1999-09-28 | Degussa-Huls Aktiengesellschaft | Silanized silica |
| US6156285A (en) * | 1998-11-12 | 2000-12-05 | Dow Corning Corporation | Method for densifying particulate silica |
| GB2357497A (en) * | 1999-12-22 | 2001-06-27 | Degussa | Hydrophobic silica |
| EP1199336B1 (de) * | 2000-10-21 | 2014-01-15 | Evonik Degussa GmbH | Funktionalisierte, strukturmodifizierte Kieselsäuren |
| WO2003068868A2 (en) * | 2002-02-18 | 2003-08-21 | Ciba Specialty Chemicals Holding Inc. | Method of producing plane-parallel structures of silicon suboxide, silicon dioxide and/or silicon carbide, plane-parallel structures obtainable by such methods, and the use thereof |
| JP4799830B2 (ja) * | 2003-05-06 | 2011-10-26 | 株式会社トクヤマ | 疎水性ヒュームドシリカ |
| DE102004010756A1 (de) * | 2004-03-05 | 2005-09-22 | Degussa Ag | Silanisierte Kieselsäuren |
| EP1813574A1 (de) * | 2006-01-25 | 2007-08-01 | Degussa GmbH | Zu Schülpen kompaktiertes pyrogen hergestelltes Siliciumdioxid |
| EP1813573A1 (de) * | 2006-01-25 | 2007-08-01 | Degussa GmbH | Verfahren zur Herstellung von Gummimischungen |
| JP2009536164A (ja) * | 2006-05-10 | 2009-10-08 | エボニック デグサ ゲーエムベーハー | ロール圧密成形した熱分解法二酸化ケイ素の医薬組成物での使用 |
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2007
- 2007-12-12 DE DE102007059860A patent/DE102007059860A1/de not_active Withdrawn
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2008
- 2008-11-18 US US12/742,518 patent/US20100261823A1/en not_active Abandoned
- 2008-11-18 JP JP2010537359A patent/JP2011506243A/ja not_active Withdrawn
- 2008-11-18 WO PCT/EP2008/065775 patent/WO2009074432A1/en active Application Filing
- 2008-11-18 EP EP08859885A patent/EP2244974B1/en not_active Not-in-force
- 2008-11-18 CN CN2008801204687A patent/CN101896427A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009074432A1 (en) | 2009-06-18 |
| JP2011506243A (ja) | 2011-03-03 |
| DE102007059860A1 (de) | 2009-06-18 |
| EP2244974A1 (en) | 2010-11-03 |
| US20100261823A1 (en) | 2010-10-14 |
| EP2244974B1 (en) | 2012-10-31 |
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