JP5752603B2 - 耐衝撃性改良ポリカーボネート組成物 - Google Patents
耐衝撃性改良ポリカーボネート組成物 Download PDFInfo
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- JP5752603B2 JP5752603B2 JP2011542694A JP2011542694A JP5752603B2 JP 5752603 B2 JP5752603 B2 JP 5752603B2 JP 2011542694 A JP2011542694 A JP 2011542694A JP 2011542694 A JP2011542694 A JP 2011542694A JP 5752603 B2 JP5752603 B2 JP 5752603B2
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- WIJVUKXVPNVPAQ-UHFFFAOYSA-N silyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)O[SiH3] WIJVUKXVPNVPAQ-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 238000009757 thermoplastic moulding Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
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Description
A)芳香族ポリカーボネートおよび/または芳香族ポリエステルカーボネート:いずれの場合も成分A+B+C+Dの総重量部に基づき、40〜99重量部、好ましくは50〜90重量部、特に好ましくは60〜80重量部、
B)シリコーンアクリレート複合ゴム、好ましい実施態様においては、シリコーンゴムおよびポリアルキル(メタ)アクリレートゴムの相互侵入ゴムをグラフトベースとする第1グラフトポリマーであって、シリコーンゴムの量がグラフトベースに基づき、65〜95重量%、好ましくは75〜95重量%、特に80〜95重量%である該第1グラフトポリマー:いずれの場合も成分A+B+C+Dの総重量部に基づき、0.5〜20重量部、好ましくは3〜13重量部、特に好ましくは8〜13重量部、
C)遊離コポリマー(すなわちゴムに対して化学的に結合しないコポリマー)を含有し、60000〜150000g/モル、好ましくは70000〜130000g/モル、特に好ましくは70000〜90000g/モルの重量平均分子量を有する第2グラフトポリマー:成分A+B+C+Dの総重量部に基づき、0.5〜40重量部、好ましくは3〜20重量部、特に好ましくは3〜7重量部、
D)ゴム不含ビニル(コ)ポリマーおよびポリアルキレンテレフタレートから成る群から選択される1または複数のポリマー:成分A+B+C+Dの総重量部に基づき、0〜20重量部、好ましくは0〜16重量部、特に好ましくは3〜16重量部、
E)添加剤:いずれの場合も成分A+B+C+Dの総重量部に基づき、0〜50重量部、好ましくは0.5〜25重量部、特に好ましくは0.5〜5重量部、
ただし、該組成物は防炎加工剤を含有せず、および
本明細書における全ての重量部は、組成物中の成分A+B+C+Dの総重量部が100となるように標準化される。
本発明において適する成分Aに係る芳香族ポリカーボネートおよび/または芳香族ポリエステルカーボネートは、関連文献に記載されており、または関連文献において記載されている方法により調製してもよい。芳香族ポリカーボネートの調製に関しては、例えば、シュネル著「ポリカーボネートの化学と物理」、インターサイエンスパブリッシャーズ、1964年、ならびに独国特許(DE−AS)1495626号明細書、独国特許出願公開第2232877号A明細書、および同2703376号A明細書、同2714544号A明細書、同3000610号A明細書および同3832396号A明細書を参照されたい。また、芳香族ポリエステルカーボネートの調製に関しては、例えば同3077934号A明細書が参照されたい。
Bは、いずれの場合もC1-C12-アルキル(好ましくはメチル)、ハロゲン(好ましくは塩素および/または臭素)を示し、
xは、いずれの場合も相互に独立して0、1または2を示し、
pは、1または0を示し、および
R5およびR6は、各X1に対して独立して選択され、相互に独立してハロゲンまたはC1−C6-アルキル、好ましくはハロゲン、メチル若しくはエチルから選択され、
X1は炭素原子を示し、ならびに
mは、4〜7の整数、好ましくは4または5を示す、但し、少なくとも1つのX1原子上においては、R5およびR6は同時にアルキルを示す。
好ましくは、成分Bは、以下の成分B.1およびB.2から成る:
B.1 5〜95重量%、好ましくは10〜90重量%、特に10〜50重量%の1種または複数種のビニルモノマー、
B.2 95〜5重量%、好ましくは90〜10重量%、特に50〜90重量%の、グラフトベースとしての1種または複数種のシリコーン-アクリレート複合ゴムであって、該シリコーン-アクリレートゴムは、以下の成分B.2.1およびB.2.2を含有する:
B.2.1 65〜95重量%、好ましくは75〜95重量%、特に80〜95重量%のシリコーンゴムおよび、
B.2.2 5〜35重量%、好ましくは5〜25重量%、特に5〜20重量%のポリアルキル(メタ)アクリレートゴム、
なお、好ましい実施態様において、上記ゴム成分B.2.1およびB.2.2は、複合ゴム中において相互侵入することにより、実質的に相互に分離できない状態となる。
アリルメタクリレート)、アクリル酸(C1-C8)-アルキルエステル(例えばメチルアクリレート、エチルアクリレート、n-ブチルアクリレート、tert-ブチルアクリレートなど)、有機酸(例えばアクリル酸、メタクリル酸など)および/またはシアン化ビニル(例えばアクリロニトリルおよびメタアクリロニトリル)および/または不飽和カルボン酸の誘導体(例えば無水物およびイミド)(例えば無水マレイン酸およびN-フェニル-マレイミドなど)である。これらのビニルモノマーを単独で使用してもよく、あるいは、少なくとも2種類のモノマーの混合物として使用してもよい。
R1 は、C1〜C4−アルキル、好ましくはメチル、エチルもしくはプロピル、あるいはフェニルを示し、
R2 は、水素原子またはメチルを示し、
n は、0、1または2であり、および
p は、1〜6の整数である。
ラジカルにより開始される単段式または多段式の乳化重合の場合、水性ラテックス形態で存在するグラフトベースに、所望のビニルモノマーB.1を重合させる。グラフト効率は、可能な限り高くすべきであり、好ましくは10%以上である。グラフト効率は、使用されるグラフト剤(V)または(VII)に大きく依存する。シリコーン-アクリレートグラフトゴムに対する重合の後、水性ラッテクスを、例えば、金属塩(例えば塩化カルシウムまたは硫酸マグネシウム)を予め溶解させた温水に添加する。このようにして、シリコーン-アクリレートグラフトゴムを凝固させて、その後、分離させる。次いで、好ましい実施態様においては、所望により洗浄する。
成分Cは、以下の成分C.1)およびC.2)から成る1または複数のグラフトポリマーである:
C.1)成分Cに基づき5〜95重量%、好ましくは30〜90重量%、特に好ましくは80〜90重量%、特に85〜90重量%の、以下の成分C.1.1)および成分C.1.2)からなる混合物:
C.1.1)C.1に基づき、65〜85重量%、好ましくは70〜80重量%の少なくとも1種のモノマーであって、該モノマーは、ビニル芳香族化合物(例えばスチレン、α-メチルスチレン)、環置換ビニル芳香族化合物(例えば、p-メチルスチレン、p-クロロスチレン)およびメタクリル酸(C1-C8)-アルキルエステル(例えば、メチルメタクリレート、エチルメタクリレート)から成る群から選択され、および、
C.1.2)C.1に基づき、15〜35重量%、好ましくは20〜30重量%の、少なくとも1種のモノマーであって、該モノマーは、シアン化ビニル(例えば、不飽和ニトリル、例えばアクリロニトリルおよびメタクリロニトリル)、(メタ)アクリル酸(C1-C8)-アルキルエステル(例えば、メチルメタクリレート、n-ブチルアクリレート、tert-ブチルアクリレート)および不飽和カルボン酸の誘導体(例えば、無水物およびイミド)(例えば無水マレイン酸、およびN-フェニル-マレイミド)、
C.2)成分Cに基づき95〜5重量%、好ましくは70〜10重量%、特に好ましくは20〜10重量%、特に15〜10重量%の含有量であり、0℃未満、好ましくは−20℃未満のガラス転移温度を有する少なくとも1種のグラフトベースであって、一般に、該グラフトベースC.2)は、0.05〜10μm、好ましくは0.1〜5μm、特に好ましくは0.15〜2μm、特に0.5〜1.5μmの平均粒度(d50値)を有する。
成分Dは、1種または複数種の熱可塑性ビニル(コ)ポリマーD.1および/またはポリアルキレンテレフタレートD.2を含有する。
D.1.1) ビニル芳香族化合物および/または環置換ビニル芳香族化合物(例えばスチレン、α-メチルスチレン、p-メチルスチレン、p-クロロスチレンなど)、および/または(メタ)アクリル酸(C1-C8)-アルキルエステル(例えばメチルメタクリレート、エチルメタクリレートなど);50〜99重量部、好ましくは60〜80重量部、特に70〜80重量部、および
D.1.2) シアン化ビニル(不飽和ニトリル)(例えばアクリロニトリルおよびメタアクリロニトリルなど)および/または(メタ)アクリル酸(C1-C8)-アルキルエステル(例えばメチルメタクリレート、n-ブチルアクリレート、tert-ブチルアクリレートなど)および/または不飽和カルボン酸(例えば、マレイン酸など)、および/または無水物およびイミドのような不飽和カルボン酸の誘導体、例えば無水マレイン酸およびN-マレイミドなど;1〜50重量部、好ましくは20〜40重量部、特に20〜30重量部。
組成物は、商業的に入手可能な添加剤を更に含有でき、該成分Eには以下のものが含まれる:滑剤、離型剤(例えば、ペンタエリトリトールテトラステアレート)、核形成剤、安定剤、耐電防止剤(例えば導電性ブラック、カーボン繊維カーボンナノチューブおよび有機耐電防止剤、例えばポリアルキレンエーテル、アルキルスルホネートまたはポリアミド含有ポリマー)、酸、充填剤、および強化材料(例えば、ガラスまたはカーボン繊維、マイカ、カオリン、タルク、CaCO3およびガラスフレーク)、並びに着色剤および顔料。
本発明に係る熱可塑性成形組成物は、既知の方法で各成分を混合し、常套の装置、例えば内部ニーダー、押出機および二軸押出し機などで220℃〜320℃、好ましくは240℃〜300℃で、該混合物を溶融配合および溶融押出しすることによって調製される。
25℃および0.5g/100mlの濃度で、溶媒としてCH2Cl2を用いて測定した相対溶液粘度ηrel=1.28を有するビスフェノールAに基づく非分岐鎖状ポリカーボネート。
耐衝撃性改良剤、以下の成分B-1.1およびB-1.2から成るグラフトポリマー:
B-1.1 11重量%のメチルメタクリレート、
B-1.2 89重量%の、グラフトベースとしてのシリコーンアクリレート複合ゴム、該シリコーンアクリレートゴムは、以下の成分B-1.2.1およびB-1.2.2を含有する;
B-1.2.1 92重量%のシリコーンゴム、および
B-1.2.2 8重量%のポリブチルアクリレートゴム、
なお、2つの上述したゴム成分B-1.2.1およびB-1.2.2は、該複合ゴム中において相互侵入することにより、実質的に相互に分離できない。
耐衝撃性改良剤、以下の成分B-2.1およびB-2.2から成るグラフトポリマー:
B-2.1 17重量%のメチルメタクリレート、
B-2.2 83重量%の、グラフトベースとしてのシリコーンアクリレート複合ゴム、該シリコーンアクリレートゴムは、以下の成分B-2.2.1およびB-2.2.2を含有する;
B-2.2.1 11重量%のシリコーンゴム、および
B-2.2.2 89重量%のポリブチルアクリレートゴム、
なお、2つの上述したゴム成分B-2.2.1およびB-2.2.2は、該複合ゴム中において相互侵入することにより、実質的に相互に分離できない。
スチレン含有量が26重量%のポリブタジエン-スチレンブロックコポリマーゴムを、ABSポリマーに基づき18重量%存在させた条件下で、24重量%のアクリロニトリルと76重量%のスチレンとの混合物を、ABSポリマーに基づき82重量%用いて塊状重合によって調製したABSポリマー。ABSポリマー中の遊離SANコポリマー成分の重量平均分子量Mwは、80000g/モルである(THF溶媒、GPCを用いて測定した)。ABSポリマーのゲル含有量は、24重量%である(アセトンを用いて測定した)。
塊状重合によってABSポリマーを調製した。アクリロニトリル:ブタジエン:スチレンの重量比は20:16:64である。ABSポリマー中の遊離SANコポリマー成分の重量平均分子量Mwは、168000g/モルである(THF溶媒、GPCを用いて測定した)。ABSポリマーのゲル含有量は、30重量%である(アセトンを用いて測定した)。
塊状法によって調製した、重量平均分子量Mwが130kg/モル(GPCを用いて測定)である、77重量%のスチレンと23重量%のアクリロニトリルから成るコポリマー。
成分E-1:ペンタエリトリトールテトラステアレート
成分E-2:Irganox(登録商標)B900(製造者:チバ・スペシャリティケミカルズ社、バーゼル、スイス)。
表1〜表2に記載した各物質を、2軸押出機(ZSK-25)(Werner und Pfleiderer社)を用いて、装置温度260℃にて、225rpmの速度で配合し、20kg/hの量で押出し、次いで粒状化した。
Claims (6)
- 以下の成分A)〜D)を含有し、防炎加工剤を含有しない組成物:
A)芳香族ポリカーボネートおよび/または芳香族ポリエステルカーボネート:
成分A+B+C+Dの合計100重量部に対して、40〜99重量部、
B)以下の成分B.1およびB.2から成る第1グラフトポリマー:
B.1 5〜95重量%の1種または複数種のビニルモノマー、
B.2 95〜5重量%の、グラフトベースとしての1種または複数種のシリコーン-アクリレート複合ゴムであって、該シリコーン-アクリレートゴムは、以下の成分B.2.1およびB.2.2を含有する:
B.2.1 65〜95重量%のシリコーンゴム、および、
B.2.2 35〜5重量%のポリアルキル(メタ)アクリレートゴム;
ただし、上記2種類のゴム成分B.2.1およびB.2.2は複合ゴム中において相互侵入することにより、相互に分離できない:
成分A+B+C+Dの合計100重量部に対して、0.5〜20重量部、
C)以下の成分C.1)およびC.2)から成る第2グラフトポリマーを成分Cとして含有し、第2グラフトポリマーが、該ゴムに対して化学的に結合しない遊離コポリマーを含有し、該遊離コポリマーは、60000〜150000g/モルの重量平均分子量を有し、以下の成分C.1.1)およびC.1.2)から成る:
C.1)以下の成分C.1.1)および成分C.1.2)から成る混合物:成分Cに基づき5〜95重量%:
C.1.1)ビニル芳香族化合物、環置換ビニル芳香族化合物およびメタクリル酸(C 1 -C 8 )-アルキルエステルから成る群から選択される少なくとも1種のモノマー:C.1に基づき65〜85重量%、および
C.1.2)シアン化ビニル、(メタ)アクリル酸(C 1 -C 8 )-アルキルエステルおよび不飽和カルボン酸の誘導体からなる群から選択される少なくとも1種のモノマー:C.1に基づき15〜35重量%、
C.2)0.05〜10μmの平均粒度(d 50 値)を有し、0℃未満のガラス転移温度を有する少なくとも1種のグラフトベースC.2):成分Cに基づき95〜5重量%:
成分A+B+C+Dの合計100重量部に対して、0.5〜40重量部、
D)ゴム不含ビニル(コ)ポリマーおよびポリアルキレンテレフタレートから成る群から選択される1種または複数種のポリマーであって、ゴム不含ビニル(コ)ポリマーが、ビニル芳香族化合物、シアン化ビニル(不飽和ニトリル)、(メタ)アクリル酸(C1-C8)-アルキルエステル、不飽和カルボン酸および不飽和カルボン酸の誘導体から成る群から選択される少なくとも1種のモノマーのポリマーである:
成分A+B+C+Dの合計100重量部に対して、0〜20重量部。 - 塊状重合法、溶液重合法または塊状-懸濁重合法によって調製されたグラフトポリマー
を成分Cとして含有する請求項1に記載の組成物であって、
成分C.1.1に係るモノマーのうちの少なくとも1種を、グラフトシェルのモノマーに基
づき70〜80重量%と、
成分C.1.2に係るモノマーのうちの少なくとも1種を、グラフトシェルのモノマーに基
づき20〜30重量%含有するグラフトシェルを有すると共に、
10〜20重量%のゴム含有量(グラフトポリマーC中の成分C.2の含有量)を示す該
組成物。 - 以下の成分A)〜E)から成る組成物:
A)芳香族ポリカーボネートおよび/または芳香族ポリエステルカーボネート;
成分A+B+C+Dの合計100重量部に対して40〜99重量部、
B)以下の成分B.1およびB.2から成る第1グラフトポリマー:
B.1 5〜95重量%の1種または複数種のビニルモノマー、
B.2 95〜5重量%の、グラフトベースとしての1種または複数種のシリコーン-アクリレート複合ゴムであって、該シリコーン-アクリレートゴムは、以下の成分B.2.1およびB.2.2を含有する:
B.2.1 65〜95重量%のシリコーンゴム、および、
B.2.2 35〜5重量%のポリアルキル(メタ)アクリレートゴム;
ただし、上記2種類のゴム成分B.2.1およびB.2.2は複合ゴム中において相互侵入す
ることにより、相互に分離できない:
成分A+B+C+Dの合計100重量部に対して0.5〜20重量部、
C)以下の成分C.1)およびC.2)から成る第2グラフトポリマーを成分Cとして含有し、第2グラフトポリマーが、該ゴムに対して化学的に結合しない遊離コポリマーを含有し、該遊離ポリマーは、60000〜150000g/モルの重量平均分子量を有し、以下の成分C.1.1)およびC.1.2)から成る:
C.1)以下の成分C.1.1)および成分C.1.2)から成る混合物:成分Cに基づき5〜95重量%:
C.1.1)ビニル芳香族化合物、環置換ビニル芳香族化合物およびメタクリル酸(C 1 -C 8 )-アルキルエステルから成る群から選択される少なくとも1種のモノマー:C.1に基づき65〜85重量%、および
C.1.2)シアン化ビニル、(メタ)アクリル酸(C 1 -C 8 )-アルキルエステルおよび不飽和カルボン酸の誘導体からなる群から選択される少なくとも1種のモノマー:C.1に基づき15〜35重量%、
C.2)0.05〜10μmの平均粒度(d 50 値)を有し、0℃未満のガラス転移温度を有する少なくとも1種のグラフトベースC.2):成分Cに基づき95〜5重量%:
成分A+B+C+Dの合計100重量部に対して0.5〜20重量部、
D)ゴム不含ビニル(コ)ポリマーおよびポリアルキレンテレフタレートから成る群から
選択される1種または複数種のポリマーであって、ゴム不含ビニル(コ)ポリマーが、ビニル芳香族化合物、シアン化ビニル(不飽和ニトリル)、(メタ)アクリル酸(C1-C8)-アルキルエステル、不飽和カルボン酸および不飽和カルボン酸の誘導体から成る群から選択される少なくとも1種のモノマーのポリマーである:
成分A+B+C+Dの合計100重量部に対して、3〜16重量部、および
E)滑剤、離型剤、核形成剤、安定剤、耐電防止剤、酸、充填剤、および強化材料、並び
に着色剤および顔料から成る群から選択される1種または複数種の添加剤:
A+B+C+Dの合計100重量部に対して0.5〜25重量部。 - 成分Bの量が、成分A+B+C+Dの合計100重量部に対して8〜13重量部であり、
成分Cの量が、成分A+B+C+Dの合計100重量部に対して7〜16重量部である請求項3に記載の組成物。 - 成形品の製造における請求項1に記載の組成物の使用。
- 請求項1〜4のいずれかに記載の組成物を含有する成形品。
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- 2009-01-23 DE DE102009005762A patent/DE102009005762A1/de not_active Withdrawn
- 2009-12-10 MX MX2011006318A patent/MX2011006318A/es active IP Right Grant
- 2009-12-10 EP EP09767987.2A patent/EP2382266B1/de active Active
- 2009-12-10 KR KR1020117014359A patent/KR101703364B1/ko active IP Right Grant
- 2009-12-10 JP JP2011542694A patent/JP5752603B2/ja active Active
- 2009-12-10 CN CN200980151970.9A patent/CN102264830B/zh active Active
- 2009-12-10 WO PCT/EP2009/008817 patent/WO2010072335A1/de active Application Filing
- 2009-12-10 ES ES09767987.2T patent/ES2440749T3/es active Active
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- 2009-12-10 CA CA2748221A patent/CA2748221A1/en not_active Abandoned
- 2009-12-17 US US12/640,328 patent/US8461260B2/en active Active
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Also Published As
Publication number | Publication date |
---|---|
DE102009005762A1 (de) | 2010-06-24 |
US8461260B2 (en) | 2013-06-11 |
TWI466944B (zh) | 2015-01-01 |
MX2011006318A (es) | 2011-06-24 |
US20100160534A1 (en) | 2010-06-24 |
JP2012513503A (ja) | 2012-06-14 |
EP2382266B1 (de) | 2013-11-27 |
ES2440749T3 (es) | 2014-01-30 |
KR101703364B1 (ko) | 2017-02-06 |
BRPI0923590A2 (pt) | 2016-01-26 |
CN102264830A (zh) | 2011-11-30 |
EP2382266A1 (de) | 2011-11-02 |
TW201035234A (en) | 2010-10-01 |
CA2748221A1 (en) | 2010-07-01 |
WO2010072335A1 (de) | 2010-07-01 |
CN102264830B (zh) | 2014-08-06 |
KR20110103399A (ko) | 2011-09-20 |
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