JP4808401B2 - エチレン性不飽和化合物のカルボニル化の方法 - Google Patents
エチレン性不飽和化合物のカルボニル化の方法 Download PDFInfo
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- JP4808401B2 JP4808401B2 JP2004527015A JP2004527015A JP4808401B2 JP 4808401 B2 JP4808401 B2 JP 4808401B2 JP 2004527015 A JP2004527015 A JP 2004527015A JP 2004527015 A JP2004527015 A JP 2004527015A JP 4808401 B2 JP4808401 B2 JP 4808401B2
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- Prior art keywords
- carbonylation
- compound
- ethylenically unsaturated
- acid
- group
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- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 39
- 230000006315 carbonylation Effects 0.000 title claims abstract description 33
- 230000008569 process Effects 0.000 title claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 21
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- -1 di -t- butyl phosphino Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 229910052763 palladium Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000000010 aprotic solvent Substances 0.000 claims description 16
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- 239000007864 aqueous solution Substances 0.000 claims description 3
- MLGAABBOPODCFY-UHFFFAOYSA-N bis(1-adamantyl)-[[1-[bis(1-adamantyl)phosphanylmethyl]naphthalen-2-yl]methyl]phosphane Chemical compound C1C(C2)CC(C3)CC2CC13P(C12CC3CC(CC(C3)C1)C2)CC1=C2C=CC=CC2=CC=C1CP(C12CC3CC(CC(C3)C1)C2)C1(C2)CC(C3)CC2CC3C1 MLGAABBOPODCFY-UHFFFAOYSA-N 0.000 claims description 3
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- VYDCOISSDUAOOB-UHFFFAOYSA-N [3,3,5,5-tetramethyl-4-[2-(3,3,5,5-tetramethyl-4-phosphanylheptan-4-yl)phenyl]heptan-4-yl]phosphane Chemical compound CCC(C)(C)C(P)(C(C)(C)CC)C1=CC=CC=C1C(P)(C(C)(C)CC)C(C)(C)CC VYDCOISSDUAOOB-UHFFFAOYSA-N 0.000 claims description 2
- OLKBKESDJCCXEI-UHFFFAOYSA-N [6-[bis(2-methylbutan-2-yl)phosphanyl]-1,6-dimethylcyclohexa-2,4-dien-1-yl]-bis(2-methylbutan-2-yl)phosphane Chemical group CCC(C)(C)P(C(C)(C)CC)C1(C)C=CC=CC1(C)P(C(C)(C)CC)C(C)(C)CC OLKBKESDJCCXEI-UHFFFAOYSA-N 0.000 claims description 2
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- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- BDIOXGVXNCWLPL-UHFFFAOYSA-N thiolane;thiolane 1,1-dioxide Chemical compound C1CCSC1.O=S1(=O)CCCC1 BDIOXGVXNCWLPL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
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Description
国際公開第96/19434号パンフレットには、特定の群の二座ホスフィン化合物が、補充がほとんど又は全く不要である著しく安定な触媒を提供することが可能であり、そのような二座触媒の使用により、すでに開示されているものより著しく高い反応速度が得られ、高転化率で不純物がほとんど又は全く形成されないことが開示されている。
国際公開第01/68583号パンフレットは、外部から加えられた非プロトン性溶媒が存在する場合に、C3以上の炭素原子を有する高級アルケンに対して利用された同じ方法の速度を開示している。国際公開第96/19434号パンフレットは、実施例において30×105N・m-2及び100℃の反応条件を利用している。同様に、国際公開第01/68583号パンフレットは、30及び60barの一酸化炭素及びやはり100℃を開示している。国際公開第96/19434号パンフレットにおける最も好ましい温度範囲は70〜120℃であり、最も好ましい圧力は5×105から50×105N・m-2である。同様に、国際公開第01/68583号パンフレットにおいて、最も好ましい温度範囲は80〜120℃であり、最も好ましい分圧は5から65barの範囲である。
(a)VIII族の金属又はその化合物と、
(b)一般式(I)の二座ホスフィンと
Arは、リン原子が利用可能な隣接炭素原子に結合され、任意に置換されるアリール部分を含む架橋基であり、
A及びBは、それぞれ独立して低級アルキレンを表し、
K、D、E及びZはアリール部分(Ar)の置換基であり、それぞれ独立して水素、低級アルキル、アリール、Het、ハロ、シアノ、ニトロ、OR19、OC(O)R20、C(O)R21、C(O)OR22、NR23R24、C(O)NR25R26、C(S)R25R26、SR27、C(O)SR27又は−J−Q3(CR13(R14)(R15))CR16(R17)(R18)
を表し、Jは低級アルキレンを表し、又はK、Z、D及びEから選択される2つの隣接基が、それらが結合されたアリール環の炭素原子と共に、更なるフェニル環を形成し、該フェニル環は、水素、低級アルキル、ハロ、シアノ、ニトロ、OR19、OC(O)R20、C(O)R21、C(O)OR22、NR23R24、C(O)NR25R26、C(S)R25R26、SR27又はC(O)SR27から選択される一種以上の置換基で任意に置換され、
R1からR18は、それぞれ独立して低級アルキル、アリール又はHetを表し、
R19からR27は、それぞれ独立して水素、低級アルキル、アリール又はHetを表し、
Q1、Q2及びQ3(存在する場合)は、それぞれ独立してリン、ヒ素又はアンチモンを表し、後者2つの場合は、上記ホスフィン又はリンへの言及は適宜に修正され、
前記カルボニル化反応は、−30℃から49℃の間の温度、及び30×105N・m-2未満のCO分圧下で実施される方法が提供される。
より具体的には、水及び分岐又は直鎖のアルカノール(ここで、前記アルカノールはアリールアルカノールを含むとともに特にC1〜C30アルカノールであり、C1〜C10アルキル、アリール、ハロ、シアノ、ニトロ、OR19、OC(O)R20、C(O)R21、C(O)OR22、NR23R24、C(O)NR25R26、C(S)R25R26、SR27又はC(O)SR27から選択される一種以上の置換基によって任意に置換されてもよい)からなる水酸基含有化合物から選択される水酸基の供給源及び触媒系の存在下で、プロペン、1−ブテン、2−ブテン、イソブテン、1−ペンテン、2−ペンテン、3−ペンテン及びそれらの分岐異性体、1−ヘキセン及びその異性体、1−ヘプテン及びその異性体、1−オクテン及びその異性体、1−ノネン及びその異性体、1−デセン及びその異性体、C11〜C20アルケン及びそれらの異性体、3−ペンテンニトリル、メチル−3−ペンテノエート、1,3−ブタジエン、1,3−ペンタジエン、1,3−ヘキサジエン、1,3−シクロヘキサジエン、2,4−ヘプタジエン及び2−メチル1,3−ブタジエンから独立して選択されるC3〜C20エチレン性不飽和化合物と一酸化炭素とを反応させる工程を含むC3〜C20エチレン性不飽和化合物のカルボニル化の方法であって、前記触媒系が、
(c)パラジウム又はその化合物と、
(d)ビス(ジ−t−ブチルホスフィノ)−o−キシレン(1,2ビス(ジ−t−ブチルホスフィノメチル)ベンゼンとしても知られる)、1,2ビス(ジアダマンチルホスフィノメチル)ベンゼン、1,2ビス(ジアダマンチルホスフィノメチル)ナフタレン、1,2ビス(ジ−t−ペンチルホスフィノ)−o−キシレン(1,2ビス(ジ−t−ペンチル−ホスフィノメチル)ベンゼンとしても知られる)、及びビス1,2(ジ−t−ブチルホスフィノ)ナフタレンからなる群から選択される二座ホスフィンと
の組み合わせにより得られ、ここで、
R19からR27は、それぞれ独立して水素、C1〜C10アルキル又はアリールを表し、
前記カルボニル化は、−30℃から49℃の間の温度、及び30×105N・m−2未満のCO分圧下で実施される方法が提供される。
ここに使用する用語「低級アルキル基」は、C1からC10アルキル基を意味し、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル及びヘプチル基を含む。別段の定めがない限り、十分な数の炭素原子がある場合には、アルキル基は直鎖でも分岐でもよく、飽和でも不飽和でもよく、環式、非環式、又は部分的に環式及び非環式でもよく、及び/又はハロ、シアノ、ニトロ、OR19、OC(O)R20、C(O)R21、C(O)OR22、NR23R24、C(O)NR25R26、SR27、C(O)SR27、C(S)NR25R26、アリール又はHetから選択される一種以上の置換基によって置換されてもよいし末端処理されてもよい。ここで、R19からR27は、それぞれ独立して水素、アリール若しくは低級アルキルを表し、及び/又は一つ以上の酸素若しくは硫黄原子、又はシラノ若しくはジアルキルシリコン基に割り込まれてもよい。
式(I)の化合物がアルケニル基を含んでいる場合、シス(E)及びトランス(Z)異性をさらに生じてもよい。本発明は、式(I)の化合物の個々の立体異性体を含み、適切である場合は、その個々の互変異性体、その混合物をも含む。ジアステレオ異性体、又はシス及びトランス異性体の分離は、従来の技術、すなわち式(I)の化合物又はその適切な塩若しくは誘導体の立体異性の混合物の分別結晶化、クロマトグラフィ又はH.P.L.C.等によって行ってもよい。式(I)の化合物の個々の鏡像異性体は、対応する光学的に純粋な中間物から調製してもよく、適切なキラル担体を用いて、対応するラセミ化合物からH.P.L.C.等の分割によって調製してもよく、又は光学活性を有する適切な酸若しくは塩基と対応するラセミ化合物の反応によって生成されたジアステレオマーの塩類の分別結晶化によって調製してもよい。
式I(b)の化合物は、VIIIB族の金属又はその化合物(a)に配位する配位子として機能して、本発明で使用される化合物を生成してもよいことは当業者には理解されよう。一般的に、VIIIB族の金属又はその化合物(a)は、式Iの化合物の一つ以上のリン、ヒ素及び/又はアンチモン原子に配位する。
A及びBは、それぞれ独立して非置換のC1からC6アルキレンを表し、K、D、Z及びEは、それぞれ独立して水素、C1〜C6アルキル、フェニル、C1〜C6アルキルフェニル又は−J−Q3(CR13(R14)(R15))CR16(R17)(R18)を表し、ここで、Jは非置換のC1からC6アルキレンを表し、又はK、D、Z及びEのうちの2つが、それらが結合しているアリール環の炭素原子と共にフェニル環を形成し、該フェニル環は、低級アルキル、フェニル又は低級アルキルフェニルから選択された一種以上の置換基によって任意に置換されている。
式Iのさらに好ましい化合物としては、以下のものを含む。
R1からR18はそれぞれ同一であり、かつC1からC6アルキル、特にメチルを表す。
式Iのさらに一層好ましい化合物としては、以下のものを含む。
R1からR12はそれぞれ同一であり、かつメチル基を表し、A及びBは同一であり、かつ−CH2−を表し、K、D、Z及びEは同一であり、かつ水素を表す。
好ましくは、エチレン性不飽和化合物は1分子当たり1つから3つの炭素−炭素2重結合、特に1分子当たり1つ又は2つのみの炭素−炭素2重結合を有し、一般には、1分子当たり1つのみの炭素−炭素2重結合を有する。
本発明の触媒化合物は、「不均一系」触媒又は「均一系」触媒として作用してもよい。
従って、さらなる態様によれば、本発明は、ここに定義されているように、エチレン性不飽和化合物のカルボニル化の方法を提供し、この方法は、担体、好ましくは不溶性担体を含む触媒を用いて行われる。好ましくは、担体は、ポリオレフィン、ポリスチレン又はジビニルベンゼン共重合体等のポリスチレン共重合体、あるいは当業者に知られている他の適切なポリマー又は共重合体、すなわち、機能性シリカ、シリコーン又はシリコーンゴム等のシリコン誘導体、又は例えば無機酸化物及び無機塩化物等の他の多孔性粒子材料等が挙げられる。
あるいは、本発明の方法の化合物は、不溶性担体の表面へ任意に共有結合を介して固定されるが、その配置は二官能性スペーサー分子を含み、不溶性担体から化合物を隔てることもある。
有機基R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11及びR12は、それぞれの炭素原子と結合するとき、t−ブチルと少なくとも同程度の立体障害を示す複合基を形成することが特に好ましい。この点で立体障害は、「均質な遷移金属の触媒作用−温和な技術」Chapman and Hallから1981年出版、14頁以降で、C Mastersによって論じられている。
式Iの化合物と組み合わせ得る適切なVIIIB族の金属又はその化合物は、コバルト、ニッケル、パラジウム、ロジウム及びプラチナを含む。好ましくは、VIIIB族の金属はパラジウム又はその化合物である。前記VIII族の金属の適切な化合物は、硝酸;硫酸;酢酸及びプロピオン酸等の低級アルカン(C12まで)酸類;メタンスルホン酸、クロロスルホン酸、フルオロスルホン酸、トリフルオロメタンスルホン酸、ベンゼンスルホン酸、ナフタレンスルホン酸、トルエンスルホン酸、例えばp−トルエンスルホン酸、t−ブチルスルホン酸及び2−ヒドロキシプロパンスルホン酸等のスルホン酸類;スルホン化イオン交換樹脂類;過塩素酸等の過ハロゲン酸;トリクロロ酢酸及びトリフルオロ酢酸等のハロゲン化カルボン酸類;オルトリン酸;ベンゼンホスホン酸等のホスホン酸類;及びルイス酸とブレンステッド酸の間の相互作用に由来する酸から誘導される弱配位陰イオンと前記金属との塩、又は該弱配位陰イオンを含む化合物を含む。適切な陰イオンを与える他の供給源は、例えばパーフルオロテトラフェニルホウ酸塩のような、任意にハロゲン化されたテトラフェニルホウ酸誘導体類を含む。さらに、ゼロ価のパラジウム錯体類、特に、例えばトリフェニルホスフィン又はジベンジリデンアセトン若しくはスチレン等のアルケンのような置換活性配位子を有するゼロ価パラジウム錯体類、又はトリ(ジベンジリデンアセトン)ジパラジウムが使用可能である。
反応中で使用されるエチレン性不飽和化合物の量の、水酸基供与化合物の量に対するモル比は重要ではなく、例えば0.001:1から100:1モル/モルでの広範囲で変え得る。
好ましくは、重合体分散剤は、十分に酸性又は塩基性の官能性を有し、該VI族若しくはVIIIB族の金属、又は金属化合物のコロイド懸濁液を実質的に安定させる。
この目的のための特に好ましい分散剤は、カルボン酸、スルホン酸、アミン、及びポリアクル酸又は複素環、特に、前述の共重合体又はポリビニルピロリドン等の置換ポリビニルポリマーで置換した窒素複素環等のアミドを含む酸性又は塩基性ポリマーを含んでもよい。
分散されたVI族又はVIIIB族の金属は、反応器から取り出した液体流から濾過等によって回収可能であり、その後、処分されるか、又は触媒若しくは他の用途として再使用される。連続法では、液体流は外部熱交換器を通って循環してもよく、このような場合には、この循環装置にパラジウム粒子用のフィルターを設置することは好都合である。
実施例中で、水酸基の供給源としてメタノールを用い、様々な直鎖のエステルを、一酸化炭素及び適切なアルケンから調製した。
1−オクテンを分子ふるいで乾燥し、アルゴンでバブリングして脱気した。1−ドデセン(Aldrich製)を蒸留によって精製した。メタノール及び重水素化メタノール(Aldrich製)を分子ふるいで乾燥した。トルエンをナトリウムジフェニルケチル(sodium diphenyl ketyl)により蒸留した。アニソール(Aldrich製)は乾燥しなかったが、注射器を介してアルゴンをバブリングして脱気した。1,2−ビス(ジ−tertブチルホスフィノ)キシレン(Lucite International製)は空気に敏感な性質があるため、グローブボックスに収納して扱った。トリス(ジベンジリデンアセトン)ジパラジウム(Pd2(dba)3)(Aldrich製)を金属前駆体として使用した。トリス(ジベンジリデンアセトン)ジパラジウムは安定であり、空気中で計量することができた。
触媒溶液は、以下のようにして調製した。
Claims (7)
- 水及び分岐又は直鎖のアルカノール(ここで、前記アルカノールはアリールアルカノールを含むC1〜C30アルカノールであり、C1〜C10アルキル、アリール、ハロ、シアノ、ニトロ、OR19、OC(O)R20、C(O)R21、C(O)OR22、NR23R24、C(O)NR25R26、C(S)R25R26、SR27又はC(O)SR27から選択される一種以上の置換基によって任意に置換されてもよい)からなる水酸基含有化合物から選択される水酸基の供給源及び触媒系の存在下で、プロペン、1−ブテン、2−ブテン、イソブテン、1−ペンテン、2−ペンテン、3−ペンテン及びそれらの分岐異性体、1−ヘキセン及びその異性体、1−ヘプテン及びその異性体、1−オクテン及びその異性体、1−ノネン及びその異性体、1−デセン及びその異性体、C11〜C20アルケン及びそれらの異性体、3−ペンテンニトリル、メチル−3−ペンテノエート、1,3−ブタジエン、1,3−ペンタジエン、1,3−ヘキサジエン、1,3−シクロヘキサジエン、2,4−ヘプタジエン及び2−メチル1,3−ブタジエンから独立して選択されるC3〜C20エチレン性不飽和化合物と一酸化炭素とを反応させる工程を含むC3〜C20エチレン性不飽和化合物のカルボニル化の方法であって、前記触媒系が、
(c)パラジウム又はその化合物と、
(d)ビス(ジ−t−ブチルホスフィノ)−o−キシレン(1,2ビス(ジ−t−ブチルホスフィノメチル)ベンゼンとしても知られる)、1,2ビス(ジアダマンチルホスフィノメチル)ベンゼン、1,2ビス(ジアダマンチルホスフィノメチル)ナフタレン、1,2ビス(ジ−t−ペンチルホスフィノ)−o−キシレン(1,2ビス(ジ−t−ペンチル−ホスフィノメチル)ベンゼンとしても知られる)、及びビス1,2(ジ−t−ブチルホスフィノ)ナフタレンからなる群から選択される二座ホスフィンと
の組み合わせにより得られ、ここで、
R19からR27は、それぞれ独立して水素、C1〜C10アルキル又はアリールを表し、
前記カルボニル化は、−30℃から49℃の間の温度、及び30×105N・m−2未満のCO分圧下で実施される方法。 - エチレン性不飽和化合物のカルボニル化が、一種以上の非プロトン性溶媒中で行われる請求項1に記載の方法。
- 前記反応が、外部の非プロトン性溶媒、すなわち反応自体によって生成されたものでない非プロトン性溶媒のない状態で実施される請求項1に記載の方法。
- 前記パラジウムの化合物は、
硝酸;硫酸;低級アルカン(C12まで)酸類;スルホン酸類;スルホン化イオン交換樹脂類;過ハロゲン酸;ハロゲン化カルボン酸類;オルトリン酸;ホスホン酸類;及びルイス酸とブレンステッド酸との相互作用に由来する酸から誘導される弱配位陰イオンと前記パラジウムとの塩、又は該弱配位陰イオンを含む化合物、
ハロゲン化され又はハロゲン化されないテトラフェニルホウ酸塩誘導体類、ゼロ価パラジウム錯体類、又はトリ(ジベンジリデンアセトン)ジパラジウムから選択される請求項1に記載の方法。 - 前記陰イオンが、18℃の水溶液中で測定されたpKaが4未満である一種以上の酸から誘導される、又は該酸として導入される請求項4に記載の方法。
- 前記カルボニル化が−10から45℃の間の温度で実施される請求項1〜5のいずれか一項に記載の方法。
- 前記カルボニル化が15×105N・m−2未満のCO分圧で実施される請求項1〜6のいずれか一項に記載の方法。
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- 2003-08-04 AU AU2003255748A patent/AU2003255748A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
ZA200500674B (en) | 2006-08-30 |
ZA200500678B (en) | 2006-08-30 |
KR20050055709A (ko) | 2005-06-13 |
JP2005535695A (ja) | 2005-11-24 |
ATE461167T1 (de) | 2010-04-15 |
EP1527038A1 (en) | 2005-05-04 |
WO2004014834A1 (en) | 2004-02-19 |
CN1675160A (zh) | 2005-09-28 |
AU2003255748A1 (en) | 2004-02-25 |
TW200404773A (en) | 2004-04-01 |
EP1527038B1 (en) | 2010-03-17 |
US20060122435A1 (en) | 2006-06-08 |
US7265240B2 (en) | 2007-09-04 |
CN1301955C (zh) | 2007-02-28 |
TWI322802B (en) | 2010-04-01 |
MY142606A (en) | 2010-12-15 |
DE60331736D1 (de) | 2010-04-29 |
GB0218613D0 (en) | 2002-09-18 |
ES2341853T3 (es) | 2010-06-29 |
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