JP2009030051A - カーボネートコポリマー - Google Patents
カーボネートコポリマー Download PDFInfo
- Publication number
- JP2009030051A JP2009030051A JP2008181457A JP2008181457A JP2009030051A JP 2009030051 A JP2009030051 A JP 2009030051A JP 2008181457 A JP2008181457 A JP 2008181457A JP 2008181457 A JP2008181457 A JP 2008181457A JP 2009030051 A JP2009030051 A JP 2009030051A
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- JP
- Japan
- Prior art keywords
- copolymer
- carbonate
- cyclic
- aromatic
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 167
- -1 aromatic cyclic carbonate Chemical class 0.000 claims abstract description 91
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000000178 monomer Substances 0.000 claims abstract description 50
- 238000000576 coating method Methods 0.000 claims abstract description 35
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 15
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 13
- 238000012377 drug delivery Methods 0.000 claims description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 12
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 12
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims description 11
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical group O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
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- 238000010438 heat treatment Methods 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 10
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- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 8
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 6
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- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims description 5
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 claims description 5
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims description 5
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Abstract
【解決手段】少なくとも1種の環状モノマーを芳香族環状カーボネートの存在下で重合させてコポリマーを形成する工程;および得られたコポリマーを回収する工程を包含する、方法。上記方法により生成されたコポリマー、上記コポリマーを含有する医療デバイス、薬物送達デバイス、およびデバイスのコーティング。
【選択図】なし
Description
(項目1)
方法であって、
少なくとも1種の環状モノマーを芳香族環状カーボネートの存在下で重合させて、コポリマーを形成する工程;および
得られたコポリマーを回収する工程、
を包含する、方法。
上記少なくとも1種の環状モノマーが、環状エステルおよび環状カーボネートからなる群より選択される、項目1に記載の方法。
上記少なくとも1種の環状モノマーが、グリコリド、L(−)−ラクチド、D(+)−ラクチド、メソ−ラクチド、p−ジオキサノン、1,4−ジオキサン−2−オン、1,5−ジオキセパン−2−オン、ε−カプロラクトン、δ−バレロラクトン、γ−ブチロラクトン、β−プロピオラクトン、およびこれらの組み合わせからなる群より選択される環状エステルを含有する、項目1に記載の方法。
上記少なくとも1種の環状モノマーが、エチレンカーボネート、トリメチレンカーボネート、ジメチルトリメチレンカーボネート、3−エチル−3−ヒドロキシメチルトリメチレンカーボネート、プロピレンカーボネート、トリメチロールプロパンモノカーボネート、4,6−ジメチル−1,3−プロピレンカーボネート、2,2−ジメチルトリメチレンカーボネート、および1,3−ジオキセパン−2−オン、ならびにこれらの組み合わせからなる群より選択される環状カーボネートを含有する、項目1に記載の方法。
上記芳香族環状カーボネートが、式
上記芳香族環状カーボネートが、式
上記芳香族環状カーボネートが、式
上記少なくとも1種の環状モノマーを上記芳香族環状カーボネートの存在下で重合させる工程が、該環状モノマーおよび該芳香族環状カーボネートを、約170℃〜約185℃の温度まで、約4時間〜約6時間にわたって加熱する工程を包含する、項目1に記載の方法。
上記少なくとも1種の環状モノマーを上記芳香族環状カーボネートの存在下で重合させる工程が、該環状モノマーおよび該芳香族環状カーボネートを、約175℃〜約180℃の温度まで、約4.25時間〜約4.75時間にわたって加熱する工程を包含する、項目1に記載の方法。
上記コポリマーを、約100℃〜約120℃の温度まで、約25時間〜約35時間の範囲の時間にわたって加熱する工程をさらに包含する、項目1に記載の方法。
上記コポリマーを、約107℃〜約113℃の温度まで、約28時間〜約32時間の範囲の時間にわたって加熱する工程をさらに包含する、項目1に記載の方法。
項目1に記載の方法によって生成されたコポリマー。
式
Wは、エステルおよびカーボネートからなる群より選択される環状モノマーから得られる誘導体であり、
Aは、芳香族環状オリゴマーカーボネートから得られる芳香族カーボネート誘導体であり、
xは、約1〜約200の数であり、そして
yは、約1〜約200の数である、
コポリマー。
Wが、上記コポリマーの総重量の約15重量%〜約75重量%を構成し、そして
Aが、該コポリマーの総重量の約20重量%〜約75重量%を構成する、
項目13に記載のコポリマー。
式
Wは、エステルおよびカーボネートからなる群より選択される環状モノマーから得られる誘導体であり、
xは、約1〜約200の数であり、そして
yは、約1〜約200の数である、
コポリマー。
式
Wは、エステルおよびカーボネートからなる群より選択される環状モノマーから得られる誘導体であり、
xは、約50〜約150の数であり、そして
yは、約50〜約150の数である、
コポリマー。
項目1に記載の方法によって生成されたコポリマーを含有する、医療デバイス。
項目1に記載の方法によって生成されたコポリマーを含有する、薬物送達デバイス。
項目1に記載の方法によって生成されたコポリマーを含有する、医療デバイスのためのコーティング。
式
Wは、環状エステルおよび環状カーボネートからなる群より選択される環状モノマーから得られる誘導体であり、
xは、約1〜約200の数であり、
yは、約1〜約200の数であり、そして
Aは、式
コポリマー。
Wが、グリコリド、L(−)−ラクチド、D(+)−ラクチド、メソ−ラクチド、p−ジオキサノン、1,4−ジオキサン−2−オン、1,5−ジオキセパン−2−オン、ε−カプロラクトン、δ−バレロラクトン、γ−ブチロラクトン、β−プロピオラクトン、エチレンカーボネート、トリメチレンカーボネート、ジメチルトリメチレンカーボネート、3−エチル−3−ヒドロキシメチルトリメチレンカーボネート、プロピレンカーボネート、トリメチロールプロパンモノカーボネート、4,6−ジメチル−1,3−プロピレンカーボネート、2,2−ジメチルトリメチレンカーボネート、および1,3−ジオキセパン−2−オン、ならびにこれらの組み合わせからなる群より選択される環状モノマーから得られる誘導体であり、そして
Aが、式
Wが、上記コポリマーの総重量の約15重量%〜約75重量%を構成し、そしてAが、該コポリマーの総重量の約20重量%〜約75重量%を構成する、項目20に記載のコポリマー。
環状モノマーおよび芳香族環状カーボネートを含有する、コポリマー組成物が提供される。このコポリマーは、ある実施形態において、芳香族環状カーボネートにより開始される開環重合反応によって、生成され得る。ある実施形態において、このようなコポリマーを生成するための方法は、少なくとも1種の環状モノマーを芳香族環状カーボネートの存在下で重合させてコポリマーを形成する工程、および得られたコポリマーを回収する工程を包含する。
本明細書中に記載される組成物は、医療デバイス、薬物送達デバイス、および/または医療デバイスのコーティングの形成のために有用である。これらの組成物は、環状モノマーを、環内に芳香族基を有する環状カーボネートの存在下で重合させることによって形成される、コポリマーを含有する。本開示のコポリマーを形成する際に使用するために適切な環状モノマーは、望ましい特性(適切な反応条件下での合理的な反応速度が挙げられる)を有する。得られるコポリマーは、生体適合性であり、これらのコポリマーを、医療デバイスおよびそのコーティング、ならびに薬物送達デバイスの製造のために適切にする。
Claims (22)
- 方法であって、
少なくとも1種の環状モノマーを芳香族環状カーボネートの存在下で重合させて、コポリマーを形成する工程;および
得られたコポリマーを回収する工程、
を包含する、方法。 - 前記少なくとも1種の環状モノマーが、環状エステルおよび環状カーボネートからなる群より選択される、請求項1に記載の方法。
- 前記少なくとも1種の環状モノマーが、グリコリド、L(−)−ラクチド、D(+)−ラクチド、メソ−ラクチド、p−ジオキサノン、1,4−ジオキサン−2−オン、1,5−ジオキセパン−2−オン、ε−カプロラクトン、δ−バレロラクトン、γ−ブチロラクトン、β−プロピオラクトン、およびこれらの組み合わせからなる群より選択される環状エステルを含有する、請求項1に記載の方法。
- 前記少なくとも1種の環状モノマーが、エチレンカーボネート、トリメチレンカーボネート、ジメチルトリメチレンカーボネート、3−エチル−3−ヒドロキシメチルトリメチレンカーボネート、プロピレンカーボネート、トリメチロールプロパンモノカーボネート、4,6−ジメチル−1,3−プロピレンカーボネート、2,2−ジメチルトリメチレンカーボネート、および1,3−ジオキセパン−2−オン、ならびにこれらの組み合わせからなる群より選択される環状カーボネートを含有する、請求項1に記載の方法。
- 前記少なくとも1種の環状モノマーを前記芳香族環状カーボネートの存在下で重合させる工程が、該環状モノマーおよび該芳香族環状カーボネートを、約170℃〜約185℃の温度まで、約4時間〜約6時間にわたって加熱する工程を包含する、請求項1に記載の方法。
- 前記少なくとも1種の環状モノマーを前記芳香族環状カーボネートの存在下で重合させる工程が、該環状モノマーおよび該芳香族環状カーボネートを、約175℃〜約180℃の温度まで、約4.25時間〜約4.75時間にわたって加熱する工程を包含する、請求項1に記載の方法。
- 前記コポリマーを、約100℃〜約120℃の温度まで、約25時間〜約35時間の範囲の時間にわたって加熱する工程をさらに包含する、請求項1に記載の方法。
- 前記コポリマーを、約107℃〜約113℃の温度まで、約28時間〜約32時間の範囲の時間にわたって加熱する工程をさらに包含する、請求項1に記載の方法。
- 請求項1に記載の方法によって生成されたコポリマー。
- Wが、前記コポリマーの総重量の約15重量%〜約75重量%を構成し、そして
Aが、該コポリマーの総重量の約20重量%〜約75重量%を構成する、
請求項13に記載のコポリマー。 - 請求項1に記載の方法によって生成されたコポリマーを含有する、医療デバイス。
- 請求項1に記載の方法によって生成されたコポリマーを含有する、薬物送達デバイス。
- 請求項1に記載の方法によって生成されたコポリマーを含有する、医療デバイスのためのコーティング。
- Wが、グリコリド、L(−)−ラクチド、D(+)−ラクチド、メソ−ラクチド、p−ジオキサノン、1,4−ジオキサン−2−オン、1,5−ジオキセパン−2−オン、ε−カプロラクトン、δ−バレロラクトン、γ−ブチロラクトン、β−プロピオラクトン、エチレンカーボネート、トリメチレンカーボネート、ジメチルトリメチレンカーボネート、3−エチル−3−ヒドロキシメチルトリメチレンカーボネート、プロピレンカーボネート、トリメチロールプロパンモノカーボネート、4,6−ジメチル−1,3−プロピレンカーボネート、2,2−ジメチルトリメチレンカーボネート、および1,3−ジオキセパン−2−オン、ならびにこれらの組み合わせからなる群より選択される環状モノマーから得られる誘導体であり、そして
Aが、式
からなる群より選択される芳香族環状カーボネートから得られる芳香族カーボネート誘導体であり、該式において、mは、約1〜約30の数である、
請求項20に記載のコポリマー。 - Wが、前記コポリマーの総重量の約15重量%〜約75重量%を構成し、そしてAが、該コポリマーの総重量の約20重量%〜約75重量%を構成する、請求項20に記載のコポリマー。
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| Application Number | Priority Date | Filing Date | Title |
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| US11/881,851 US7666973B2 (en) | 2007-07-30 | 2007-07-30 | Carbonate copolymers |
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| EP (1) | EP2028210B1 (ja) |
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| JP2013515816A (ja) * | 2009-12-23 | 2013-05-09 | インターナショナル・ビジネス・マシーンズ・コーポレーション | 生分解性ポリマ、遺伝子治療および薬物送達のためのその複合体、ならびにそれに関連する方法 |
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| US8709466B2 (en) | 2011-03-31 | 2014-04-29 | International Business Machines Corporation | Cationic polymers for antimicrobial applications and delivery of bioactive materials |
| US8487017B2 (en) * | 2011-06-27 | 2013-07-16 | Covidien Lp | Biodegradable materials for orthopedic devices based on polymer stereocomplexes |
| WO2015164703A1 (en) | 2014-04-25 | 2015-10-29 | Valspar Sourcing, Inc. | Polycyclocarbonate compounds and polymers and compositions formed therefrom |
| CN106459658B (zh) | 2014-04-25 | 2019-04-23 | 宣伟投资管理有限公司 | 多环碳酸酯化合物以及由其形成的聚合物 |
| US11986568B2 (en) * | 2018-10-05 | 2024-05-21 | Prevent-Plus, Llc | Method for the reduction of fixation pin track infections |
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| JP2013515816A (ja) * | 2009-12-23 | 2013-05-09 | インターナショナル・ビジネス・マシーンズ・コーポレーション | 生分解性ポリマ、遺伝子治療および薬物送達のためのその複合体、ならびにそれに関連する方法 |
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| US11180608B2 (en) | 2009-12-23 | 2021-11-23 | International Business Machines Corporation | Biodegradable polymers, complexes thereof for gene therapeutics and drug delivery, and methods related thereto |
Also Published As
| Publication number | Publication date |
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| US20090036645A1 (en) | 2009-02-05 |
| EP2028210A1 (en) | 2009-02-25 |
| AU2008202998B2 (en) | 2014-01-23 |
| US7666973B2 (en) | 2010-02-23 |
| CA2635243A1 (en) | 2009-01-30 |
| EP2028210B1 (en) | 2016-08-31 |
| AU2008202998A1 (en) | 2009-02-19 |
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