JP5630999B2 - 歯科用接着剤組成物 - Google Patents
歯科用接着剤組成物 Download PDFInfo
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- JP5630999B2 JP5630999B2 JP2009531760A JP2009531760A JP5630999B2 JP 5630999 B2 JP5630999 B2 JP 5630999B2 JP 2009531760 A JP2009531760 A JP 2009531760A JP 2009531760 A JP2009531760 A JP 2009531760A JP 5630999 B2 JP5630999 B2 JP 5630999B2
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
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- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
- C08F222/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
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- 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
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/125—Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
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- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dental Preparations (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
(i)下記式(A):
aは1〜10の整数であり、
R1は水素原子又は下記式(Y)の部位
Xは独立して、酸素原子、硫黄原子又はNR基(式中、Rは水素原子、C1−6アルキル基又はアシル基であり得る)を示し、
Lは、1個〜20個の炭素原子を含有し、且つエーテル、チオエーテル、アミノ基及び/若しくはケト基、並びに/又はさらなる酸性基を任意に含む(a+b)価の有機残基を示し、ここで、炭素原子は、第一級及び第二級脂肪族炭素原子、第二級脂環式炭素原子、及び芳香族炭素原子から選択される少なくともa+b個の炭素原子を含み、a+b個の炭素原子は各々リン酸誘導体基又は2−(オキサアリル)誘導体基と結合しており、
bは1〜10の整数である)を示し、
R2は、同じであっても異なっていてもよく、独立して水素、アリル基、又はbが1であるR1部位であるが、
但し、R1及びR2の少なくとも一方は水素でない)の重合性酸性リン酸エステルモノマーと、
(ii)1種以上の重合性N置換アルキルアクリルモノマー又はアクリル酸アミドモノマーと、
(iii)有機系水混和性溶媒及び/又は水と、
(iv)重合開始剤と、
(v)抑制剤及び/又は安定化剤と、
(vi)任意の有機酸又は無機酸と、
(vii)任意のフィラー及び/又はフッ化物放出化合物と、
を含有することを特徴とする水系歯科用組成物を提供する。
R3及びR4は独立して、
水素原子、
C1−18アルキル基、
任意に置換されたC3−8シクロアルキル基、
任意に置換されたC4−18アリール基又はヘテロアリール基、
任意に置換されたC5−18アルキルアリール基又はアルキルヘテロアリール基、又は
任意に置換されたC7−30アラルキル基を示し、
ここで、R1及びR2は、それらが結合する隣接する窒素原子及び炭素原子と一緒になって、さらに窒素原子又は酸素原子を含有し得る6員〜9員の複素環を形成してもよく、且つ任意に置換された基は、1個〜5個のC1−5アルキル基によって置換されてもよい。好ましくはR3及びR4は独立して、水素原子又はC1−6アルキル基を示す。
ペンタエリスリトールトリアリルエーテルモノホスフェートPETAP
乾燥ジエチルエーテル60mlに溶解させた、9.909gのペンタエリスリトールトリアリルエーテル(70%)及び3.809gのトリエチルアミンの溶液に、乾燥ジエチルエーテル60mlに溶解させた5.30g酸塩化リンの溶液を、攪拌しながら55分かけて添加し、反応混合物の温度を−5℃〜0℃に保った。添加を終了した後、懸濁液をさらに23時間室温で攪拌した。
nD 20=1.4690
η23℃=250.6±82.1mPa*s
IR(フィルム、cm−1)24864(CH2)、1477/1423/1308(CH2)、1087(CH2OCH2)、994(P=O)
1H−NMR(250MHz、DMSO、ppm)3.40〜3.34(m)、4.17〜3.80(m)、5.25〜5.10(m)、5.89〜5.77(m)。
7−ジハイドロジェンホスホリル−4,7−ジオキサヘプト−1−エン(AOEP) ジエチルエーテル250mlに溶解させた75.543g(0.490mol)のリン酸トリクロリドの攪拌溶液に、ジエチルエーテル150mlに溶解させた、50.002g(0.490mol)の2−アリルオキシエタノール及び49.590g(0.490mol)のトリエチルアミンの溶液を、0℃〜5℃に温度を維持しながら90分にわたって滴下した。その後、濾過前に反応混合物を23℃で16時間攪拌した。次に、温度を0℃に維持しながらこの溶液を水に滴下した。添加を終了した後、溶液をさらに0℃で0.5時間攪拌した。この層を分離し、水性画分を150mlのジエチルエーテルで一回洗浄した。水相の生成物をアセトン50ml中に溶解し、Na2SO4で16時間乾燥させた。濾過後、0.053g(0.05mol%)BHTを添加した。その後、溶媒を除去してわずかに黄色みがかった固体を得た。
収量:62.0g(Thの69.5%)
nD 20=1.4570
η23℃=745.2±31.2mPa*s
IR(フィルム、cm−1)2868(CH2)、2326(POH)、1646(C=C)、1457(CH2)、975(P=O)
1H−NMR(250MHz、CDCl3、ppm)3.63(s,2H,CH2OP)、3.99〜4.08(d,4H,CH2O)、5.12〜5.81(m,3H,CH2=CH)、10.53(s,2H,OP(OH)2)。
13C−NMR(63MHz、CDCl3、ppm)133.5(2)、1118.6(1)、72.1(3)、68.8(4)、66.1(5)
3,3−ビス(アリルオキシメチル)−5−ジハイドロジエンホスホリル−5−オキサペンタン(TMPDAP) ジエチルエーテル250mlに溶解させた35.775g(0.233mol)のリン酸トリクロリドの攪拌溶液に、ジエチルエーテル150mlに溶解させた、50.000g(0.233mol)の2,2−ビス(アリルオキシメチル)−1−ブタノール及び23.609g(0.233mol)のトリエチルアミンの溶液を、0℃〜5℃に温度を維持しながら90分にわたって滴下した。その後、濾過前に反応混合物を23℃で16時間攪拌した。次に、温度を0℃に維持しながらこの溶液を水に滴下した。添加を終了した後、溶液をさらに0℃で0.5時間攪拌した。この層を分離し、水性画分を150mlのジエチルエーテルで一回洗浄した。有機層をNa2SO4で16時間乾燥させた。濾過後、0.051g(0.05mol%)BHTを添加した。その後、溶媒を除去してわずかに黄色みがかった固体を得た。
収量:63.8g(Thの92.9%)
nD 20=1.4638
η23℃=858.8±47.6mPa*s
IR(フィルム、cm−1)2864(CH2)、2358(POH)、1646(C=C)、1465(CH2)、1024(CH2O)、924(P=O)
1H−NMR(250MHz、CDCl3、ppm)0.82(s,3H,CH3)、1.40(s,2H,CH2)、3.28〜3.30(d,2H,CH2OPO3H2)、3.91〜3.92(d,4H,CCH2O,OCH2CH=)、5.07〜5.23(m,2H,CH2=)、5.81〜5.82(d,1H,CH=)、10.21〜10.33(OP(OH)2)
13C−NMR(63MHz、CDCl3、ppm)134.2(2)、116.3(1)、71.8(3)、69.1(4)、65.5(8)、42.5(5)、21.7(6)、6.9(7)
2−(アリルオキシエチル)−2−エチル−2−ビス−[3−ジハイドロジェンホスホリル−3−オキサペンタン](TMPADP) ジエチルエーテル250mlに溶解させた88.000g(0.574mol)のリン酸トリクロリドの攪拌溶液に、ジエチルエーテル150mlに溶解させた、50.000g(0.574mol)の2−(アリルオキシメチル)−2エチルー1,3−プロパンジオールブタノール及び58.075g(0.574mol)のトリエチルアミンの溶液を、0℃〜5℃に温度を維持しながら90分にわたって滴下した。その後、濾過前に反応混合物を23℃で16時間攪拌した。次に、温度を0℃に維持しながらこの溶液を水に滴下した。添加を終了した後、溶液をさらに0℃で0.5時間攪拌した。この層を分離し、水性画分を150mlのジエチルエーテルで一回洗浄した。
収量:30.4g(Thの63.4%)
nD 20=1.4040
η23℃=241.4±63.9mPa*s
IR(フィルム、cm−1)2829(CH2)、2336(POH)、1632(C=C)、1457(CH2)、981(P=O)
13C−NMR(63MHz、D2O、ppm)133.6(2)、117.2(1)、74.3(3)、71.9(4)、66.5(8)、38.9(5)、22.2(6)、7.2(7)
PETAPを用いて、エタノールと水とから成る混合溶媒中にモノマーを溶解することによって下記式を調製した。
200グリット及び500グリットの研磨紙で歯を研磨、
歯を37℃で水中に保存、
樹脂製剤による処理:20秒、
空気流による蒸発:5秒、
光硬化:10秒、
Spectrum TPH(Dentsply)体の歯の上における20秒間の硬化を3回、
処理した歯を37℃で水中に24時間保存、及び測定前に1800サイクルの5℃〜55℃のヒートサイクル試験を用いた。
エナメル質:19.4±3.9MPa
象牙質:16.7±5.3MPa
溶媒として水、t−ブタノール及びアクリル酸を使用した応用例1と類似の製剤中に調製例2のAOEPを用いて、上記の手法に従い以下の接着力値が測定された。
エナメル質:15.1±2.2MPa
象牙質:18.2±2.4MPa
溶媒として水、t−ブタノール及びアクリル酸を使用した応用例1と類似の製剤中に調製例3のTMPDAPを用いて、上記の手法に従い以下の接着力値が測定された。
エナメル質:15.0±2.5MPa
象牙質:20.0±3.3MPa
N−ブチル−N−(エチルホスホン酸)アクリルアミドを用いて、このモノマーをエタノールと水とから成る混合溶媒に溶解させることによって比較用製剤を調製した:
エナメル質:9.4±3.0MPa
象牙質:19.4±1.8MPa
Claims (14)
- 水系混合物を含む歯科用組成物であって、該水系混合物が、
(i)下記各式:
(ii)1種以上の、該重合性酸性リン酸エステルモノマーとは異なる、重合性N置換アルキルアクリル酸モノマー又はアクリル酸アミドモノマーと、
(iii)有機系水混和性溶媒、水、又は有機系水混和性溶媒と水の双方と、
(iv)重合開始剤と、
(v)抑制剤及び/又は安定化剤と、
(vi)任意成分としての有機酸又は無機酸と、
(vii)任意成分としてのフィラー及び/又はフッ化物放出化合物と、
(viii)下記各式:
を含有することを特徴とする請求項1に記載の組成物。 - 60℃で少なくとも10日間貯蔵時に安定である請求項1に記載の組成物。
- 5以下のpHを有する請求項1に記載の組成物。
- 一液型自己エッチング自己プライマー処理の歯科用接着剤である請求項1に記載の組成物。
- 成分(ii)の前記1つ又は複数の重合性N置換アルキルアクリル酸モノマー又はアクリル酸アミドモノマーが、下記各式:
R5及びR6は独立して、
水素原子、又は
置換C1〜C18アルキル基、
任意に置換されたC3−18シクロアルキル基、
任意に置換されたC5−18アリール又はヘテロアリール基、
任意に置換されたC5−18アルキルアリール又はアルキルヘテロアリール基、
任意に置換されたC7−30アラルキル基を示し、
R7は、1個〜45個の炭素原子を有する二価の置換又は非置換の有機残基を示し、該有機残基は、1個〜14個の酸素原子及び/又は窒素原子を含有していてもよく、且つ、C1〜C18アルキレン基から選択され、1つ〜6つの−CH2−基は、−N−(C=O)−CR9=CH2基(式中、R9は水素原子又はC1〜C18アルキル基、二価の置換又は非置換のC3〜C18シクロアルキル又はシクロアルキレン基、二価の置換又は非置換のC4〜C18アリール又はヘテロアリール基、二価の置換又は非置換のC5〜C18アルキルアリール又はアルキルヘテロアリール基、二価の置換又は非置換のC7〜C30アラルキル基、及び1個〜14個の酸素原子を有する二価の置換又は非置換のC2〜C45モノ、ジ又はポリエーテル基である)で置換されていてもよく、
R8は、飽和二価又は多価の置換又は非置換のC2〜C18炭化水素基、飽和二価又は多価の置換又は非置換の環状C3〜C18炭化水素基、二価又は多価の置換又は非置換のC4〜C18アリール又はヘテロアリール基、二価又は多価の置換又は非置換のC5〜C18アルキルアリール又はアルキルヘテロアリール基、二価又は多価の置換又は非置換のC7〜C30アラルキル基、又は1個〜14個の酸素原子を有する二価又は多価の置換又は非置換のC2〜C45モノ、ジ又はポリエーテル残基を示し、
nは整数である)のうちの1つにより特徴付けられる請求項1又は2に記載の組成物。 - 前記重合性酸性リン酸エステルモノマーを0.5重量%〜20重量%の量で含有する請求項1に記載の組成物。
- 式(B)の前記重合性酸性モノマーを0.5重量%〜20重量%の量で含有する請求項3に記載の組成物。
- 成分(ii)の前記1つ又は複数の重合性N置換アルキルアクリル酸モノマー又はアクリル酸アミドモノマーを10重量%〜70重量%の量で含有する請求項1に記載の組成物。
- 前記重合開始剤が光開始剤である請求項1に記載の組成物。
- 少なくとも15MPaの、エナメル質及び象牙質に対する接着力をもたらす請求項4に記載の組成物。
- ナノフィラーを含有する請求項1に記載の組成物。
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EP06021540A EP1911434B1 (en) | 2006-10-13 | 2006-10-13 | Dental adhesive composition |
EP06021540.7 | 2006-10-13 | ||
PCT/EP2007/008764 WO2008043518A1 (en) | 2006-10-13 | 2007-10-09 | Dental adhesive composition |
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EP (1) | EP1911434B1 (ja) |
JP (1) | JP5630999B2 (ja) |
AT (1) | ATE504285T1 (ja) |
CA (1) | CA2665572C (ja) |
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ES2381500T3 (es) * | 2007-02-07 | 2012-05-28 | Dentsply Detrey Gmbh | Composición autoadhesiva para restauración dental |
EP2229930B1 (de) * | 2009-03-17 | 2012-12-12 | Ivoclar Vivadent AG | Dentale universelle Haftvermittlerzusammensetzung |
JP5416456B2 (ja) * | 2009-03-31 | 2014-02-12 | クラレノリタケデンタル株式会社 | リン酸エステル化合物及びそれを含む重合性組成物 |
EP2497454A1 (en) | 2011-03-10 | 2012-09-12 | Dentsply DeTrey GmbH | Dental composition |
EP3124477B1 (en) * | 2015-07-27 | 2019-07-17 | DENTSPLY DETREY GmbH | Dental adhesive |
EP3231412A3 (en) * | 2016-04-15 | 2017-10-25 | DENTSPLY DETREY GmbH | Aqueous dental glass ionomer composition |
EP3231411B1 (en) * | 2016-04-15 | 2021-11-10 | DENTSPLY DETREY GmbH | Aqueous dental glass ionomer composition |
EP3336092A1 (en) | 2016-12-14 | 2018-06-20 | DENTSPLY DETREY GmbH | Dental composition |
WO2018181710A1 (ja) | 2017-03-31 | 2018-10-04 | 三井化学株式会社 | 歯科材料用多官能モノマーおよび歯科材料用水酸基含有モノマー |
CN110938234B (zh) * | 2018-09-25 | 2021-06-08 | 中山台光电子材料有限公司 | 阻燃性化合物、其制造方法、树脂组合物及其制品 |
WO2020247565A1 (en) * | 2019-06-05 | 2020-12-10 | Rhodia Operations | Oral care composition |
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EP1105063A4 (en) * | 1998-08-18 | 2004-12-22 | Biomat Sciences Inc | ADHESIVE COMPOSITIONS FOR USE IN HARD TISSUES OF THE HUMAN BODY |
US6387982B1 (en) * | 1998-11-23 | 2002-05-14 | Dentsply Detrey G.M.B.H. | Self etching adhesive primer composition and polymerizable surfactants |
WO2003013444A1 (en) | 2001-08-10 | 2003-02-20 | Dentsply International Inc. | One-part self-priming dental adhesive |
KR100590132B1 (ko) * | 2003-03-04 | 2006-06-15 | 한국과학기술연구원 | 광중합성 치과용 접착제 조성물 |
EP1548021B1 (en) * | 2003-12-23 | 2007-03-21 | DENTSPLY DETREY GmbH | One-part self-etching, self-priming dental adhesive composition |
US7452925B2 (en) * | 2005-02-25 | 2008-11-18 | John A. Kanca, III | Three part dental bonding compositions and methods of use |
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2006
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CA2665572C (en) | 2014-12-30 |
EP1911434B1 (en) | 2011-04-06 |
EP1911434A1 (en) | 2008-04-16 |
WO2008043518A1 (en) | 2008-04-17 |
ATE504285T1 (de) | 2011-04-15 |
CA2665572A1 (en) | 2008-04-17 |
US20100022682A1 (en) | 2010-01-28 |
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