TWI396702B - 生醫材料之預聚物 - Google Patents
生醫材料之預聚物 Download PDFInfo
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- TWI396702B TWI396702B TW098115239A TW98115239A TWI396702B TW I396702 B TWI396702 B TW I396702B TW 098115239 A TW098115239 A TW 098115239A TW 98115239 A TW98115239 A TW 98115239A TW I396702 B TWI396702 B TW I396702B
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- 239000000463 material Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003519 biomedical and dental material Substances 0.000 claims description 25
- 150000001336 alkenes Chemical group 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- 150000007824 aliphatic compounds Chemical group 0.000 claims description 9
- 150000001491 aromatic compounds Chemical group 0.000 claims description 9
- -1 siloxane compound Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 230000035699 permeability Effects 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 125000001033 ether group Chemical group 0.000 description 8
- 229910052732 germanium Inorganic materials 0.000 description 8
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 230000003020 moisturizing effect Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 150000002433 hydrophilic molecules Chemical class 0.000 description 5
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 4
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 3
- 206010052428 Wound Diseases 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFVPJMZRRXCXAO-UHFFFAOYSA-N [He].[O] Chemical compound [He].[O] KFVPJMZRRXCXAO-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- YQTUWVDYKNJLCE-UHFFFAOYSA-N 1,4-diisocyanatobutane;1,6-diisocyanatohexane Chemical compound O=C=NCCCCN=C=O.O=C=NCCCCCCN=C=O YQTUWVDYKNJLCE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5096—Polyethers having heteroatoms other than oxygen containing silicon
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
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- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
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Description
本發明係關於一種生醫材料之預聚物，特別係關於一種可透氣、透氧及保濕之生醫材料之預聚物。
材料適用於生物醫藥裝置係依一些因素而定，這些因素包含材料的保濕性、透氧性、粘著性或與其他生物材料例如蛋白質及脂質之反應特性等。一般而言，目前醫療人員使用紗布做為傷口敷料之預聚物，以避免傷口暴露感染。然而，紗布之缺點為無法防止水分自傷口表面揮發，且更新傷口之敷藥時易於破壞口之結痂。近來，研發人員開發高分子材料製成之敷材(例如含有矽氧烷之高分子材料)，其可改善紗布之缺點。另在眼科的應用方面，例如隱形眼鏡及眼內植入物，透氧性亦為一重要的考量，透氧性高通常為較佳，因為其具有良好保濕性及抗粘著或抗生物材料之反應。
矽氧烷高分子材料因可克服先前技術之缺點並具有上述生醫材料之優點，因而研發人員亦嘗試矽氧烷高分子材料之多方應用。
本發明提供一種生醫材料之預聚物，其可藉由改變分子基團之數量而調整其透氣、透氧、保濕及提高與其他親水分子相容特性。
本發明之生醫材料之預聚物之一實施例，具有下列化學式：
其中X1係脂肪族化合物或芳香族化合物，X3係含烯官能基化合物(作為該預聚物後續製備生醫材料之反應端點)，X2係具有下列化學式之矽氧烷化合物。在本發明之一實施例中，n係介於1至20之間，m係介於10至20之間，y係介於1至7之間。
上文已相當廣泛地概述本發明之技術特徵及優點，俾使下文之本發明詳細描述得以獲得較佳瞭解。構成本發明之申請專利範圍標的之其它技術特徵及優點將描述於下文。本發明所屬技術領域中具有通常知識者應瞭解，可相當容易地利用下文揭示之概念與特定實施例可作為修改或設計其它結構或製程而實現與本發明相同之目的。本發明所屬技術領域中具有通常知識者亦應瞭解，這類等效建構無法脫離後附之申請專利範圍所界定之本發明的精神和範圍。
本發明第一實施例之生醫材料之預聚物，具有下列化學式：
其中X1係脂肪族化合物(例如，butane、octane、hexane)或芳香族化合物(例如，Phenylene)。X3係含烯官能基化合物，係作為該預聚物後續製備生醫材料之反應端點。X2係具有下列化學式之矽氧烷化合物。
藉由改變X2之m值，可調整該預聚物之透氣/透氧特性，而改變X2之n值則可調整該預聚物之保濕及與其他親水分子相容特性，俾便製備需要高透氧及高保濕之材料(例如人體敷材、隱形眼鏡)。在本發明之一實施例中，n係介於1至20之間，m係介於10至20之間。
此外，X2的矽原子與醚基間之碳數(即y值)可予以調整，增加碳數可增加延展性，縮短則可增加強度。在本發明之一實施例中，X2的矽原子與醚基間之碳數(即y值)係介於1至7之間。
將含有二個異氰酸基團之化合物(例如，1,3-Phenylene diisocyanate、1,4-Diisocyanatobutane、1,6-Diisocyanatohexane、1,4-Phenylene diisocyanate、1,8-Diisocyanatooctane、Toluene 2,4-diisocyanate)與含有矽氧烷及二個羥基(hydroxy)之化合物(例如下式之化合物)反應，其中羥基與異氰酸基團反應鍵結。
接著，將包含異氰酸基團及丙烯酸基團(acrylate)或丙烯酸甲酯基團(methacrylate)之含烯官能基化合物加入反應，即可製備第一實施例之生醫材料之預聚物。之後，含烯官能基即可作為此預聚物後續製備生醫材料之反應端點。
本發明第二實施例之生醫材料之預聚物，具有下列化學式：
其中X1係脂肪族化合物(例如，butane、octane、hexane)或芳香族化合物(例如，Phenylene)。X3係含烯官能基化合物，係作為該預聚物後續製備生醫材料之反應端點。X2係具有下列化學式之矽氧烷化合物。
藉由改變X2之m值，可調整該預聚物之透氣/透氧特性，而改變X2之n值則可調整該預聚物之保濕及與其他親水分子相容特性，俾便製備需要高透氧及高保濕之材料(例如人體敷材、隱形眼鏡)。在本發明之一實施例中，n係介於1至20之間，m係介於10至20之間。
此外，X2的矽原子與醚基間之碳數(即y值)可予以調整，增加碳數可增加延展性，縮短則可增加強度。在本發明之一實施例中，X2的矽原子與醚基間之碳數(即y值)係介於1至7之間。
將含有二個異氰酸基團之化合物(例如，1,3-Phenylene diisocyanate、1,4-Diisocyanatobutane 1,6-Diisocyanatohexane、1,4-Phenylene diisocyanate、1,8-Diisocyanatooctane、Toluene 2,4-diisocyanate)與含有矽氧烷及二個胺基(amine)之化合物(例如下式之化合物)反應，其中胺基與異氰酸基團反應鍵結。
接著，將包含異氰酸基團及丙烯酸基團(或丙烯酸甲酯基團)之含烯官能基化合物加入反應，即可製備第二實施例之生醫材料之預聚物。之後，含烯官能基即可作為此預聚物後續製備生醫材料之反應端點。
本發明第三實施例之生醫材料之預聚物，具有下列化學式：
其中X1係脂肪族化合物(例如，butane、octane、hexane)或芳香族化合物(例如，Phenylene)。X3係含烯官能基化合物，係作為該預聚物後續製備生醫材料之反應端點。X2係具有下列化學式之矽氧烷化合物。
藉由改變X2之m值，可調整該預聚物之透氣/透氧特性，而改變X2之n值則可調整該預聚物之保濕及與其他親水分子相容特性，俾便製備需要高透氧及高保濕之材料(例如人體敷材、隱形眼鏡)。在本發明之一實施例中，n係介於1至20之間，m係介於10至20之間。
此外，X2的矽原子與醚基間之碳數(即y值)可予以調整，增加碳數可增加延展性，縮短則可增加強度。在本發明之一實施例中，X2的矽原子與醚基間之碳數(即y值)係介於1至7之間。
將含有二個異氰酸基團之化合物(例如，1,3-Phenylene diisocyanate、1,4-Diisocyanatobutane、1,6-Diisocyanatohexane、1,4-Phenylene diisocyanate、1,8-Diisocyanatooctane、Toluene 2,4-diisocyanate)與含有矽氧烷及二個羥基之化合物(例如下式之化合物)反應，其中羥基與異氰酸基團反應鍵結。
接著，將包含氯及丙烯酸基團(或丙烯酸甲酯基團)之含烯官能基化合物(例如，methacryloyl chloride、acryloyl chloride)加入反應，即可製備第三實施例之生醫材料之預聚物。之後，含烯官能基即可作為此預聚物後續製備生醫材料之反應端點。
本發明第四實施例之生醫材料之預聚物，具有下列化學式：
其中X1係脂肪族化合物(例如，butane、octane、hexane)或芳香族化合物(例如，Phenylene)。X3係含烯官能基化合物，係作為該預聚物後續製備生醫材料之反應端點。X2係具有下列化學式之矽氧烷化合物。
藉由改變X2之m值，可調整該預聚物之透氣/透氧特性，而改變X2之n值則可調整該預聚物之保濕及與其他親水分子相容特性，俾便製備需要高透氧及高保濕之材料(例如人體敷材、隱形眼鏡)。在本發明之一實施例中，n係介於1至20之間，m係介於10至20之間。
此外，X2的矽原子與醚基間之碳數(即y值)可予以調整，增加碳數可增加延展性，縮短則可增加強度。在本發明之一實施例中，X2的矽原子與醚基間之碳數(即y值)係介於1至7之間。
將含有二個異氰酸基團之化合物(例如，1,3-Phenylene diisocyanate、1,4-Diisocyanatobutane、1,6-Diisocyanatohexane、1,4-Phenylene diisocyanate、1,8-Diisocyanatooctane、Toluene 2,4-diisocyanate)與含有矽氧烷及二個胺基(amine)之化合物(例如下式之化合物)反應，其中胺基與異氰酸基團反應鍵結。
接著，將包含氯及丙烯酸基團(或丙烯酸甲酯基團)之含烯官能基化合物(例如，methacryloyl chloride、acryloyl chloride)加入反應，即可製備第四實施例之生醫材料之預聚物。之後，含烯官能基即可作為此預聚物後續製備生醫材料之反應端點。
本發明之技術內容及技術特點已揭示如上，然而本發明所屬技術領域中具有通常知識者應瞭解，在不背離後附申請專利範圍所界定之本發明精神和範圍內，本發明之教示及揭示可作種種之替換及修飾。例如，上文揭示之許多製程可以不同之方法實施或以其它製程予以取代，或者採用上述二種方式之組合。
此外，本案之權利範圍並不侷限於上文揭示之特定實施例的製程、機台、製造、物質之成份、裝置、方法或步驟。本發明所屬技術領域中具有通常知識者應瞭解，基於本發明教示及揭示製程、機台、製造、物質之成份、裝置、方法或步驟，無論現在已存在或日後開發者，其與本案實施例揭示者係以實質相同的方式執行實質相同的功能，而達到實質相同的結果，亦可使用於本發明。因此，以下之申請專利範圍係用以涵蓋用以此類製程、機台、製造、物質之成份、裝置、方法或步驟。
Claims (4)
- 一種生醫材料之預聚物，包含具有下列化學式之化合物：
- 一種生醫材料之預聚物，包含具有下列化學式之化合物：
- 一種生醫材料之預聚物，包含具有下列化學式之化合物：
- 一種生醫材料之預聚物，包含具有下列化學式之化合物：
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| TW098115239A TWI396702B (zh) | 2009-05-08 | 2009-05-08 | 生醫材料之預聚物 |
| US12/704,731 US8304570B2 (en) | 2009-05-08 | 2010-02-12 | Prepolymer for biomedical materials |
| EP10156845.9A EP2248836B1 (en) | 2009-05-08 | 2010-03-18 | Prepolymer for biomedical materials |
| KR1020100041993A KR101207656B1 (ko) | 2009-05-08 | 2010-05-04 | 의용재료용 프리폴리머 |
| JP2010107183A JP5551505B2 (ja) | 2009-05-08 | 2010-05-07 | バイオメディカルマテリアルのプレポリマー |
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| US (1) | US8304570B2 (zh) |
| EP (1) | EP2248836B1 (zh) |
| JP (1) | JP5551505B2 (zh) |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0519214A (ja) * | 1991-07-15 | 1993-01-29 | Asahi Chem Ind Co Ltd | 汚染性の少ないコンタクトレンズ |
| JP2002327063A (ja) * | 2001-05-01 | 2002-11-15 | Asahi Kasei Aimii Kk | 親水性ポリシロキサンモノマーおよびその共重合体からなるコンタクトレンズ材料、およびコンタクトレンズ |
| US6524564B1 (en) * | 1998-08-26 | 2003-02-25 | Basf Aktiengesellschaft | Urethane(meth)acrylates containing siloxane groups and able to undergo free-radical polymerization |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136250A (en) | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
| US4605712A (en) | 1984-09-24 | 1986-08-12 | Ciba-Geigy Corporation | Unsaturated polysiloxanes and polymers thereof |
| CA2218363A1 (en) | 1995-04-25 | 1996-10-31 | Constance J. Nelson | Polydiorganosiloxane oligourea segmented copolymers and a process for making same |
| JPH11228643A (ja) * | 1998-02-17 | 1999-08-24 | Menicon Co Ltd | 眼用レンズ材料およびその製法 |
| US6809169B2 (en) | 2002-06-07 | 2004-10-26 | The Boeing Company | Polysiloxane coatings for surfaces |
| US7691917B2 (en) | 2007-06-14 | 2010-04-06 | Bausch & Lomb Incorporated | Silcone-containing prepolymers |
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- 2010-03-18 EP EP10156845.9A patent/EP2248836B1/en not_active Ceased
- 2010-05-04 KR KR1020100041993A patent/KR101207656B1/ko not_active Expired - Fee Related
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0519214A (ja) * | 1991-07-15 | 1993-01-29 | Asahi Chem Ind Co Ltd | 汚染性の少ないコンタクトレンズ |
| US6524564B1 (en) * | 1998-08-26 | 2003-02-25 | Basf Aktiengesellschaft | Urethane(meth)acrylates containing siloxane groups and able to undergo free-radical polymerization |
| JP2002327063A (ja) * | 2001-05-01 | 2002-11-15 | Asahi Kasei Aimii Kk | 親水性ポリシロキサンモノマーおよびその共重合体からなるコンタクトレンズ材料、およびコンタクトレンズ |
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| Publication number | Publication date |
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| EP2248836A3 (en) | 2012-09-05 |
| US20100286428A1 (en) | 2010-11-11 |
| KR101207656B1 (ko) | 2012-12-03 |
| JP2010261041A (ja) | 2010-11-18 |
| EP2248836A2 (en) | 2010-11-10 |
| JP5551505B2 (ja) | 2014-07-16 |
| EP2248836B1 (en) | 2014-06-11 |
| TW201040207A (en) | 2010-11-16 |
| US8304570B2 (en) | 2012-11-06 |
| KR20100121422A (ko) | 2010-11-17 |
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