CN110461379B - 硬组织修补用组合物及硬组织修补用套装 - Google Patents
硬组织修补用组合物及硬组织修补用套装 Download PDFInfo
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- CN110461379B CN110461379B CN201880021862.9A CN201880021862A CN110461379B CN 110461379 B CN110461379 B CN 110461379B CN 201880021862 A CN201880021862 A CN 201880021862A CN 110461379 B CN110461379 B CN 110461379B
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- XDSSGQHOYWGIKC-UHFFFAOYSA-N tris(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)CC(C)C XDSSGQHOYWGIKC-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Surgery (AREA)
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- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Composite Materials (AREA)
- Materials For Medical Uses (AREA)
Abstract
本发明公开了:硬组织修补用组合物,其包含单体(A)、聚合物(B)、聚合引发剂(C)、及体积平均粒径为3μm以上的造影剂(X),其向松质骨等被粘接物的侵入性优异,与被粘接物的密合性优异;以及,硬组织修补用套装,其具有将该硬组织修补用组合物中包含的单体(A)、聚合物(B)、聚合引发剂(C)、及造影剂(X)的各成分以任意的组合分成3部分以上而进行收纳的构件。
Description
技术领域
本发明涉及向松质骨等被粘接物的侵入性优异、与被粘接物的密合性优异的硬组织修补用组合物及硬组织修补用套装。
背景技术
以往,作为用于将骨、软骨等硬组织与人工关节固定的骨粘固剂、用于骨质疏松症治疗用途等的骨填充剂、人工骨材料等,对多种硬组织修补用组合物进行了研究。例如,对包含聚甲基丙烯酸甲酯、甲基丙烯酸甲酯、及过氧化苯甲酰(聚合引发剂)的组合物、包含(甲基)丙烯酸酯、磷酸钙等无机填料、及有机过氧化物的组合物等进行了研究(例如专利文献1)。然而,这样的组合物在固化时的发热大,对患部组织造成损伤的危险性高。
作为对这点进行了改良的硬组织修补用组合物,例如,专利文献2中,公开了包含(甲基)丙烯酸酯(A)、(甲基)丙烯酸酯聚合物(B)、特定的聚合引发剂(C)及造影剂(X)的硬组织修补用组合物。该组合物在固化时的发热小,而且操作性优异。
现有技术文献
专利文献
专利文献1:日本特开平8-224294号公报
专利文献2:国际公开第2011/062227号
发明内容
发明所要解决的课题
本申请的发明人认为在与骨组织的宏观密合性(macroscopic adhesion)方面,以往的硬组织修补用组合物存在改善空间。例如,骨粘固剂(硬组织修补用组合物)向松质骨的侵入性差时,在与骨的界面处产生缝隙,发生因骨溶解而导致的疼痛,如果恶化,则需要进行再置换术。这样的问题在该领域中非常重要。
即,本发明的目的在于提供向松质骨等被粘接物的侵入性优异、与被粘接物的密合性优异的硬组织修补用组合物及硬组织修补用套装。
用于解决课题的手段
本申请的发明人为了达成上述目的而进行了深入研究,结果发现,通过使用体积平均粒径在特定范围内的造影剂(X),由此使与骨组织的密合性提高,从而完成了本发明。即,本发明可通过下述项目确定。
[1]硬组织修补用组合物,其包含单体(A)、聚合物(B)、聚合引发剂(C)、及体积平均粒径为3μm以上的造影剂(X)。
[2]如[1]所述的硬组织修补用组合物,利用以下的方法测定的模拟骨侵入性为1.0mm以上。
[模拟骨侵入性的测定方法]
对于模拟骨侵入性而言,向具有连通的气泡的聚氨酯泡沫(孔隙率95%)中含浸生理盐水,在其上表面放置成为软块状且拉丝消失后5分钟后的组合物,以75kPa的压力施加30秒负荷,测定组合物侵入的深度(mm)。
[3]如[1]所述的硬组织修补用组合物,其中,造影剂(X)为硫酸钡或氧化锆。
[4]如[1]所述的硬组织修补用组合物,其中,单体(A)为(甲基)丙烯酸酯系单体。
[5]如[1]所述的硬组织修补用组合物,其中,聚合物(B)为(甲基)丙烯酸酯系聚合物。
[6]如[1]所述的硬组织修补用组合物,其包含单体(A)10~45质量份、聚合物(B)54.9~80质量份、聚合引发剂(C)0.1~10质量份(将成分(A)~(C)的合计作为100质量份)及造影剂(X)0.5~70质量份。
[7]如[1]所述的硬组织修补用组合物,其中,造影剂(X)的体积平均粒径为3.0~25.1μm。
[8]如[1]所述的硬组织修补用组合物,其中,硬组织修补用组合物中包含的粒子整体的体积平均粒径为32μm以下。
[9]硬组织修补用套装,其具有将[1]所述的硬组织修补用组合物中包含的单体(A)、聚合物(B)、聚合引发剂(C)、及造影剂(X)的各成分以任意的组合分成3部分以上而进行收纳的构件。
发明的效果
通过本发明,可提供向松质骨等被粘接物的侵入性优异、与被粘接物的密合性优异的硬组织修补用组合物及硬组织修补用套装。
根据一般常识,造影剂从缝隙通过时,理应粒径小的造影剂更容易从缝隙通过。然而,在本发明中,令人惊讶的是,通过使用粒径较大的造影剂(X),硬组织修补用组合物的模拟骨侵入性提高。其原因未必明确,但作为原因之一,推测可能是因为:造影剂(X)的粒径小的情况下,存在粉末彼此容易凝聚、容易变成大的凝聚体粒子的倾向,而造影剂(X)的粒径大的情况下,不易发生凝聚,因此,模拟骨侵入性提高。
具体实施方式
[单体(A)]
本发明中使用的单体(A)没有特别限制,只要是能利用后述的聚合引发剂(C)发生聚合的单体即可。关于单体(A),根据使用目的,单官能单体、多官能单体均可使用。
作为单体(A),例如,可使用(甲基)丙烯酸酯系单体及其他的乙烯基化合物。其中,从对人体的刺激较小的方面考虑,优选(甲基)丙烯酸酯系单体。本发明中,“(甲基)丙烯酸酯”是丙烯酸酯及甲基丙烯酸酯的统称。另外,通常,具有酸性基团的单体与硬组织的粘接性优异,而且作为后述的解络剂发挥作用,在使用烷基硼烷·胺络合物作为聚合引发剂(C)的情况下,通过使用具有酸性基团的单体,也能引发聚合反应。因此,例如,也可以将适量的具有酸性基团的单体与不具有酸性基团的(甲基)丙烯酸酯系单体并用来提高粘接性。
作为不具有酸性基团的单官能(甲基)丙烯酸酯系单体的具体例,可举出(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸月桂基酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸异冰片基酯等(甲基)丙烯酸烷基酯;(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸3-羟基丙酯、(甲基)丙烯酸4-羟基丁酯、(甲基)丙烯酸5-羟基戊酯、(甲基)丙烯酸6-羟基己酯、单(甲基)丙烯酸1,2-二羟基丙基酯、单(甲基)丙烯酸1,3-二羟基丙基酯、赤藓糖醇单(甲基)丙烯酸酯等(甲基)丙烯酸的羟基烷基酯;二乙二醇单(甲基)丙烯酸酯、三乙二醇单(甲基)丙烯酸酯、聚乙二醇单(甲基)丙烯酸酯、聚丙二醇单(甲基)丙烯酸酯等聚亚烷基二醇单(甲基)丙烯酸酯;乙二醇单甲基醚(甲基)丙烯酸酯、乙二醇单乙基醚(甲基)丙烯酸酯、二乙二醇单甲基醚(甲基)丙烯酸酯、三乙二醇单甲基醚(甲基)丙烯酸酯、聚乙二醇单甲基醚(甲基)丙烯酸酯、聚丙二醇单烷基醚(甲基)丙烯酸酯等(聚)亚烷基二醇单烷基醚(甲基)丙烯酸酯;(甲基)丙烯酸全氟辛酯、(甲基)丙烯酸六氟丁酯等(甲基)丙烯酸的氟烷基酯;γ-(甲基)丙烯酰氧基丙基三甲氧基硅烷、γ-(甲基)丙烯酰氧基丙基三(三甲基甲硅烷氧基)硅烷等具有(甲基)丙烯酰氧基烷基的硅烷化合物;(甲基)丙烯酸四氢糠基酯等具有杂环的(甲基)丙烯酸酯。
作为不具有酸性基团的多官能(甲基)丙烯酸酯系单体的具体例,可举出乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、丁二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、己二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯等烷烃多元醇的多(甲基)丙烯酸酯;二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、二丁二醇二(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯等多氧烷烃多元醇多(甲基)丙烯酸酯;下述通式(1)表示的脂环系或芳香族二(甲基)丙烯酸酯
[化学式1]
(式(1)中,R为氢原子或甲基,m及n各自独立地为0~10的数,R1为下述基团中的任一种,
[化学式2]
下述通式(2)表示的脂环系或芳香族环氧二(甲基)丙烯酸酯
[化学式3]
(式(2)中,R、n及R1与前述式(1)中的R、n及R1相同);
下述式(3)表示的在分子中具有氨基甲酸酯键的多官能(甲基)丙烯酸酯
[化学式4]
(式(3)中,R与前述式(1)中的R相同,R2为下述基团中的任一种,
[化学式5]
以上的示例化合物中,作为单官能(甲基)丙烯酸酯系单体,优选(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯等(甲基)丙烯酸烷基酯;(甲基)丙烯酸2-羟基乙酯、单(甲基)丙烯酸1,3-二羟基丙基酯、赤藓糖醇单(甲基)丙烯酸酯等(甲基)丙烯酸的羟基烷基酯;三乙二醇单甲基醚(甲基)丙烯酸酯、三乙二醇单(甲基)丙烯酸酯等聚乙二醇单(甲基)丙烯酸酯。
以上的示例化合物中,作为多官能(甲基)丙烯酸酯系单体,优选三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯等在分子内具有乙二醇链的二(甲基)丙烯酸酯;下述式(1)-a表示的化合物
[化学式6]
(式(1)-a中,R、m及n与前述式(1)中的R、m及n相同);
下述式(2)-a表示的化合物
[化学式7]
(式(2)-a中,R与前述式(1)中的R相同);
下述式(3)-a表示的化合物
[化学式8]
(式(3)-a中,R与前述式(1)中的R相同)。
这些(甲基)丙烯酸酯系单体可以并用2种以上。
作为具有酸性基团的单体的具体例,可举出(甲基)丙烯酸及其酐、1,4-二(甲基)丙烯酰氧基乙基均苯四甲酸、6-(甲基)丙烯酰氧基乙基萘1,2,6-三甲酸、N-(甲基)丙烯酰基对氨基苯甲酸、N-(甲基)丙烯酰基邻氨基苯甲酸、N-(甲基)丙烯酰基间氨基苯甲酸、N-(甲基)丙烯酰基-5-氨基水杨酸、N-(甲基)丙烯酰基-4-氨基水杨酸、4-(甲基)丙烯酰氧基乙基偏苯三甲酸及其酐、4-(甲基)丙烯酰氧基丁基偏苯三甲酸及其酐、4-(甲基)丙烯酰氧基己基偏苯三甲酸及其酐、4-(甲基)丙烯酰氧基癸基偏苯三甲酸及其酐、2-(甲基)丙烯酰基氧基苯甲酸、3-(甲基)丙烯酰基氧基苯甲酸、4-(甲基)丙烯酰基氧基苯甲酸、琥珀酸β-(甲基)丙烯酰基氧基乙酯、马来酸β-(甲基)丙烯酰基氧基乙酯、邻苯二甲酸β-(甲基)丙烯酰基氧基乙酯、11-(甲基)丙烯酰基氧基-1,1-十一烷二甲酸、对乙烯基苯甲酸等具有羧酸基或其酐基的单体;(2-(甲基)丙烯酰氧基乙基)磷酸、(2-(甲基)丙烯酰氧基乙基苯基)磷酸、10-(甲基)丙烯酰氧基癸基磷酸等具有磷酸基的单体;对苯乙烯磺酸、2-丙烯酰胺基-2-甲基丙磺酸等具有磺酸基的单体。其中,优选4-甲基丙烯酰氧基乙基偏苯三甲酸及其酐。
这些具有酸性基团的单体可以并用2种以上。另外,具有酸性基团的单体也可以以钙盐的形式使用。
单体(A)的配合量优选为10~45质量份,更优选为20~45质量份,特别优选为25~36质量份(将成分(A)~(C)的合计作为100质量份)。上述各范围的下限值在涂布的容易性、操作性、向骨组织内的侵入性等方面有意义。上限值在粘接强度、机械物性等方面有意义。单体(A)包含具有酸性基团的单体时,相对于单体(A)合计100质量%而言,具有酸性基团的单体的量优选为0.01~20质量%。
[聚合物(B)]
本发明中使用的聚合物(B)的种类没有特别限制,优选构成聚合物(B)的单体单元的一部分或全部为来源于与上文说明的单体(A)中的一部分单体或全部单体种类相同的单体的单体单元。本发明中,“聚合物”为均聚物及共聚物的统称。作为聚合物(B),例如可使用(甲基)丙烯酸酯系聚合物及其他的乙烯基系聚合物。其中,优选(甲基)丙烯酸酯系聚合物。
作为(甲基)丙烯酸酯系聚合物的具体例,可举出聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸乙酯、(甲基)丙烯酸甲酯·(甲基)丙烯酸乙酯共聚物、(甲基)丙烯酸甲酯·(甲基)丙烯酸丁酯共聚物、(甲基)丙烯酸甲酯·苯乙烯共聚物等非交联聚合物;(甲基)丙烯酸甲酯·乙二醇二(甲基)丙烯酸酯共聚物、(甲基)丙烯酸甲酯·三乙二醇二(甲基)丙烯酸酯共聚物、(甲基)丙烯酸甲酯与丁二烯系单体的共聚物等交联聚合物及部分地形成了钙盐的聚合物。另外,也可以是金属氧化物或金属盐被非交联聚合物或交联聚合物被覆而成的有机·无机复合体。
聚合物(B)的形态没有特别限制,优选为粉末状。关于聚合物粉末,可以单独使用1种聚合物粉末,也可使用多种聚合物粉末的混合物。其中,优选使用比表面积及/或体积平均粒径不同的2种以上聚合物粉末的混合物。
作为聚合物(B)使用的聚合物粉末的各粒子的形态可以是球形、不定形状中的任意形态,优选使用球形的聚合物粉末与不定形状的聚合物粉末的混合物。球形的粒子的比表面积较小,不定形状的粒子的比表面积较大,因此,两者可通过比表面积的差异来区分。本发明中,作为球形的聚合物粉末,优选使用比表面积为0.05~0.5m2/g的聚合物粉末(b1),作为不定形状的聚合物粉末,优选使用比表面积为1.5~4.5m2/g的聚合物粉末(b3)。此外,也优选并用具有球形的聚合物粉末(b1)与不定形状的聚合物粉末(b3)的中间形态的比表面积为0.51~1.2m2/g的聚合物粒子(b2)。比表面积的测定方法如后述的实施例一栏中所述。
聚合物粉末(b1)的比表面积为0.05~0.5m2/g,优选为0.1~0.4m2/g。聚合物粉末(b2)的比表面积为0.51~1.2m2/g,优选为0.7~1.1m2/g。聚合物粉末(b3)的比表面积为1.5~4.5m2/g,优选为2.5~3.5m2/g。
聚合物粉末(b1)的重均分子量优选为1万~500万,更优选为5万~154万,特别优选为10万~50万。聚合物粉末(b2)的重均分子量优选为1万~500万,更优选为5万~166万,特别优选为10万~50万。聚合物粉末(b3)的重均分子量优选为15万~500万,更优选为20万~115万,特别优选为24万~67万。重均分子量的测定方法如后述的实施例的栏中所述,是利用凝胶渗透色谱法(GPC)求出的按照标准聚苯乙烯换算的分子量。
聚合物粉末(b1)的体积平均粒径优选为12.7~77μm,更优选为15~45μm,特别优选为17.5~35μm。聚合物粉末(b2)的体积平均粒径优选为1~15μm,更优选为3.5~10μm。聚合物粉末(b3)的体积平均粒径优选为0.3~60μm,更优选为7.5~50μm,特别优选为15.7~40μm。体积平均粒径的测定方法如后述的实施例的栏中所述。
聚合物(B)的重均分子量(即,单独使用一种聚合物的情况下,为该聚合物的重均分子量,另外,使用2种以上聚合物的混合物的情况下,为混合物整体的重均分子量)优选为5万~500万,更优选为7.5万~200万,特别优选为7.5万~88万,最优选为10万~40万。聚合物(B)为粉末状时的体积平均粒径(即,单独使用一种聚合物粉末的情况下,为该聚合物粉末的体积平均粒径,另外,使用2种以上聚合物粉末的混合物的情况下,为混合物整体的体积平均粒径)优选为10~80μm,更优选为15~45μm,特别优选为15~30μm。
聚合物(B)的配合量优选为54.9~80质量份,更优选为56.7~73.7质量份,特别优选为59.7~70.7质量份(将成分(A)~(C)的合计作为100质量份)。聚合物(B)100质量%中的聚合物粉末(b1)的量优选为50.5~95质量%,更优选为53~85质量%。聚合物粉末(b2)的量优选为0~33.5质量%,更优选为0~25质量%。聚合物粉末(b3)的量优选为5~49.5质量%,更优选为15~47质量%。
聚合物(B)中,体积平均粒径大于2.0μm的聚合物粉末的含量优选大于70质量%,更优选为80质量%以上,特别优选为90质量%以上。
[聚合引发剂(C)]
作为本发明中使用的聚合引发剂(C),没有特别限制,可使用已知的各种化合物。其中,优选有机过氧化物、有机硼化合物,特别优选有机硼化合物。
作为有机过氧化物,可举出例如二乙酰基过氧化物、二异丁基过氧化物、二癸酰基过氧化物、过氧化苯甲酰(BPO)、琥珀酸过氧化物等二酰基过氧化物类;过氧二碳酸二异丙酯、过氧二碳酸二-2-乙基己酯、过氧二碳酸二烯丙酯等过氧二碳酸酯类;过氧异丁酸叔丁酯、过氧新癸酸叔丁酯、过氧新癸酸异丙苯酯等过氧酯类;乙酰基环己基磺酰基过氧化物等过氧化磺酸酯类。
有机过氧化物可与叔胺、或者亚磺酸或其碱金属盐类及叔胺组合而作为氧化还原引发剂使用。其中,优选过氧化苯甲酰(BPO)和N,N-二甲基对甲苯胺、过氧化苯甲酰(BPO)和N,N-二羟基乙基对甲苯胺。
N,N-二甲基对甲苯胺、N,N-二羟基乙基对甲苯胺等叔胺优选预先添加至单体(A)中而使用。其添加量优选为5.0质量份以下,更优选为0.1~3.0质量份,特别优选为0.25~2.6质量份(将单体(A)与叔胺的合计作为100质量份)。若使用叔胺,则即使在室温下也通过电子移动而产生自由基种,因此,即使不进行加热也能容易地引发聚合反应。
作为有机硼化合物,例如可使用三烷基硼、烷氧基烷基硼、二烷基硼烷、部分氧化三烷基硼、烷基硼烷·胺络合物。
作为三烷基硼的具体例,可举出三乙基硼、三丙基硼、三异丙基硼、三丁基硼、三仲丁基硼、三异丁基硼、三戊基硼、三己基硼、三庚基硼、三辛基硼、三环戊基硼、三环己基硼等具有碳原子数为2~8的烷基的三烷基硼。烷基可以为直链状烷基、支链状烷基、环烷基中的任何,三烷基硼中包含的3个烷基可以相同也可以不同。
作为烷氧基烷基硼的具体例,可举出丁氧基二丁基硼等单烷氧基二烷基硼、二烷氧基单烷基硼。烷氧基烷基硼所具有的烷基、与该烷氧基的烷基部可以相同也可以不同。
作为二烷基硼烷的具体例,可举出二环己基硼烷、二异戊基硼烷。二烷基硼烷所具有的2个烷基可以相同也可以不同。二烷基硼烷中包含的2个烷基可以键合而形成单环结构或双环结构。作为这样的化合物,例如有9-硼杂双环[3.3.1]壬烷(9-borabicyclo[3.3.1]nonane)。
部分氧化三烷基硼是指三烷基硼的部分氧化物。其中,优选部分氧化三丁基硼。相对于三烷基硼1摩尔而加成的氧的量优选为0.3~0.9摩尔,更优选为0.4~0.6摩尔。
作为烷基硼烷·胺络合物的具体例,可举出三乙基硼烷·二氨基丙烷(TEB-DAP)、三乙基硼烷·二亚乙基三胺(TEB-DETA)、三正丁基硼烷·3-甲氧基丙基胺(TnBB-MOPA)、三正丁基硼烷·二氨基丙烷(TnBB-DAP)、三仲丁基硼烷·二氨基丙烷(TsBB-DAP)、甲基氨基乙氧基二乙基硼烷(MAEDEB)、甲基氨基乙氧基二环己基硼烷(MAEDCB)及由它们衍生的衍生物。这些烷基硼烷·胺络合物可以单独使用或组合2种以上而使用。
在将烷基硼烷·胺络合物作为聚合引发剂(C)使用时,进一步优选与单体(A)一同使用解络剂。该“解络剂”是指能使烷基硼烷从烷基硼烷·胺络合物中游离出来的化合物,通过烷基硼烷的游离,能引发聚合反应。
作为适当的解络剂,例如可使用任意的酸、或具有酸性基团的单体(可作为前述的单体(A)使用的具有酸性基团的单体)。作为优选的酸,可举出路易斯酸(例如,SnCl4、TiCl4)、布朗斯台德酸(例如,羧酸类、HCl、H2SO4、H3PO4、膦酸、次膦酸、硅酸)等。作为优选的羧酸类,可举出通式R-COOH表示的物质。该式中,R表示氢原子、碳原子数为1~8的烷基(优选碳原子数为1~4的烷基)、碳原子数为2~8的链烯基(优选碳原子数为2~4的链烯基)、碳原子数为2~8的炔基(优选碳原子数为2~4的炔基)、或碳原子数为6~10的芳基(优选碳原子数为6~8的芳基)。R中的烷基、链烯基、炔基可以为直链状,也可以为支链状。R中的脂肪族基可以为饱和,也可以为不饱和。R中的芳基可以被烷基、烷氧基或卤素原子等取代基取代,也可以为未取代。作为上述通式表示的羧酸的具体例,可举出丙烯酸、甲基丙烯酸、乙酸、苯甲酸、对甲氧基苯甲酸。作为具有酸性基团的单体的具体例,前述的单体(A)中,优选4-甲基丙烯酰氧基乙基偏苯三甲酸及其酐。
有机硼化合物中,优选三丁基硼、部分氧化三丁基硼,尤其是更优选部分氧化三丁基硼。在使用三丁基硼、部分氧化三丁基硼作为有机硼化合物的情况下,不仅操作性变得良好,而且存在相对于具有水分的生物体而言具有适当的反应性的倾向。另外,在使用三丁基硼、部分氧化三丁基硼作为有机硼化合物的情况下,即使在如生物体那样水分多的场所,也会引发反应,使反应进行,因此,在粘接剂与生物体的界面处,单体不易残留,对生物体的危害性极小。这些有机硼化合物可以单独使用或组合2种以上而使用。
有机硼化合物可以还包含非质子性溶剂。若利用非质子性溶剂来稀释有机硼化合物,则具有起火性的有机硼化合物的发热性变得更稳定,抑制起火性,搬运时、保存时及混合时的处理变得容易。另外,能抑制剧烈的发热,因此,即使在使用极多的量的硬组织修补用组合物的情况下,也存在对与硬组织修补用组合物接触的组织的损伤变小的倾向。非质子性溶剂的1个大气压下的沸点通常为30℃~150℃,优选为50℃~120℃。沸点低于上述范围时,存在以下倾向:导致在搬运时或保存期间,非质子性溶剂从聚合引发剂中挥发、飞散等,导致有机硼化合物的起火抑制效果下降。另外,沸点高于上述范围时,存在以下倾向:非质子性溶剂在由本发明的硬组织修补用组合物形成的固化物中的残留变多,固化物相对于患部的粘接强度、和弯曲弹性模量、拉伸强度、压缩强度、弯曲强度等物性变得欠缺。
作为非质子性溶剂,优选不具有与有机硼化合物反应的羟基、巯基等含有活性氢的基团、可与有机硼化合物形成均匀的溶液的溶剂。
作为非质子性溶剂,可举出例如戊烷、己烷、环己烷、庚烷、苯、甲苯等烃;氟苯、1,1-二氯乙烷、1,2-二氯乙烷、氟利昂等卤代烃;***、二异丙基醚、乙二醇二甲基醚、四氢呋喃等醚;丙酮、甲基乙基酮、二乙基酮等酮;乙酸甲酯、乙酸乙酯、乙酸异丙酯等酯。其中,优选戊烷、己烷、庚烷等饱和脂肪族烃、醚、酯,更优选己烷、二异丙基醚、乙酸乙酯。这些非质子性溶剂可以单独使用或组合2种以上而使用。
相对于有机硼化合物100质量份而言,非质子性溶剂的含量优选为30~80质量份。非质子性溶剂的含量低于上述范围时,存在以下倾向:得不到充分的稀释效果,发热或起火的抑制效果不充分。另一方面,非质子性溶剂的含量高于上述范围时,存在使聚合引发剂(C)的聚合引发能力下降的倾向。
有机硼化合物可以除了非质子性溶剂之外还包含醇,或者也可包含醇来代替非质子性溶剂。通过向有机硼化合物中添加醇,存在以下倾向:基于有机硼化合物的反应在不降低聚合活性的情况下变得更稳定,能抑制在空气中与纸等构件接触时的烧焦、起火。
醇的1个大气压下的沸点通常为60℃~180℃,优选为60℃~120℃。沸点低于上述范围时,存在以下倾向:导致在搬运或保存期间,醇从聚合引发剂组合物中挥发、飞散,导致有机硼化合物的起火抑制效果下降。另一方面,沸点高于上述范围时,存在硬组织修补用组合物的固化时间变长的倾向,存在固化物相对于患部的粘接强度、和弯曲弹性模量、拉伸强度、压缩强度、弯曲强度等物性变得欠缺的倾向。
作为醇的具体例,可举出甲醇、乙醇、正丙醇及其异构体、正丁醇及其异构体、正戊醇及其异构体、正己醇及其异构体、正庚醇及其异构体。其中,优选碳原子数为4以下的醇、即甲醇、乙醇、正丙醇及其异构体、以及正丁醇及其异构体,更优选乙醇、正丙醇。这些醇可以单独使用或组合2种以上而使用。
相对于有机硼化合物100质量份而言,醇的含量通常为0.01~40质量份,优选为0.1~30质量份,更优选为0.5~20质量份。醇的含量低于上述范围时,存在以下倾向:得不到充分的稀释效果,发热或起火的抑制效果不充分。另一方面,高于上述范围时,存在使聚合引发剂的聚合引发能力超出必要地下降的倾向。
并用醇和非质子性溶剂时,相对于有机硼化合物100质量份而言,非质子性溶剂的含量优选为5~40质量份,更优选为10~30质量份,特别优选为10~25质量份。非质子性溶剂的含量低于上述范围时,存在发热或起火的抑制效果不充分的倾向。另一方面,高于上述范围时,存在使聚合引发剂(C)的聚合引发能力下降的倾向。
相对于单体(A)、聚合物(B)及聚合引发剂(C)的合计100质量份而言,聚合引发剂(C)的配合量优选为0.1~10质量份,更优选为1.0~7.0质量份,特别优选为2.1~4.3质量份。聚合引发剂(C)的配合量低于上述范围时,存在以下倾向:聚合变得难以进行,固化时间变慢。另一方面,高于上述范围时,由于稀释,可能使粘度下降,可能对安全性造成不良影响,另外,也推测聚合剧烈进行,快速形成聚合固化物。
[造影剂(X)]
本发明中使用的造影剂(X)的体积平均粒径为3μm以上,优选为3.0~25.1μm,更优选为3.0~18.0μm,特别优选为3.5~15.5μm,最优选为4.0~13.0μm。这样的较大的体积平均粒径的造影剂(X)不易凝聚,结果,认为组合物向松质骨的侵入性提高,与被粘接物的密合性优异。体积平均粒径的测定方法如后述的实施例的栏中所述。
造影剂(X)的种类没有特别限制。作为具体例,可举出硫酸钡、氧化锆、碳酸铋、钨酸钙、镱、碘化合物。其中,从硬组织用途、尤其是具有作为骨粘固剂的实际使用成绩方面考虑,优选硫酸钡、氧化锆。造影剂(X)优选单独形成粒子。另外,优选表面未被被覆(例如,未被二氧化钛等被覆)。
相对于单体(A)、聚合物(B)及聚合引发剂(C)的合计100质量份而言,造影剂(X)的配合量优选为0.5~70质量份,更优选为0.5~45质量份,特别优选为2.5~33.8质量份,最优选为4.5~22.5质量份。
优选造影剂(X)不被封入及/或吸附于聚合物(B)的内部,在制备硬组织修补用组合物时,被分散于固化前的液体成分中(单体(A)、聚合引发剂(C)等)中。造影剂(X)中,优选80质量%以上被分散于液体成分中,更优选90质量%以上被分散于液体成分中,特别优选95质量%以上被分散于液体成分中,最优选99质量%以上被分散于液体成分中。
优选造影剂(X)未被封入及/或吸附于聚合物(B)的内部。造影剂(X)中,被封入及/或吸附于聚合物(B)的内部的造影剂(X)的量优选为20质量%以下,更优选为10质量%以下,特别优选为1质量%以下,最优选为0.1质量%以下。
本发明的硬组织修补用组合物中包含的液体成分中,期望50质量%以上为单体(A),优选60质量%以上为单体(A),更优选70质量%以上为单体(A),特别优选80质量%以上为单体(A),最优选90质量%以上为单体(A)。
本发明的硬组织修补用组合物中包含的液体成分(其中,不包含存在于聚合物(B)内的液体)中,水的含量期望为20质量%以下,优选为10质量%以下,更优选为5.0质量%以下,特别优选为3.0质量%以下,最优选为1.5质量%以下。
本发明的硬组织修补用组合物中包含的全部液体成分中,水的含量期望为25质量%以下,优选为15质量%以下,更优选为10质量%以下,特别优选为5.0质量%以下,最优选为3.0质量%以下。
[其他成分]
本发明的硬组织修补用组合物根据需要可包含阻聚剂。作为阻聚剂的具体例,可举出对苯二酚、二丁基对苯二酚等对苯二酚化合物类、对苯二酚单甲基醚、2,6-二叔丁基苯酚、2,6-二叔丁基对甲酚等酚类、邻苯二酚、连苯三酚、苯醌、2-羟基苯醌、对甲氧基苯酚、叔丁基邻苯二酚、丁基化羟基苯甲醚、丁基化羟基甲苯、叔丁基氢醌。其中,优选对苯二酚单甲基醚与2,6-二叔丁基对甲酚的混合物。另外,从其自身的稳定性方面考虑,有时也优选对苯二酚单甲基醚。阻聚剂可以单独使用或组合2种以上而使用。
相对于硬组织修补用组合物总量而言,阻聚剂的添加量优选为1~1500ppm,更优选为5~1000ppm,特别优选为5~500ppm。另外,相对于单体(A)而言,阻聚剂(D)的添加量为10~5000ppm,更优选为25~1000ppm,特别优选为25~500ppm。
本发明的硬组织修补用组合物根据需要可包含紫外线吸收剂。作为紫外线吸收剂的具体例,可举出2-(2’-羟基-5’-甲基苯基)苯并***、2-(3’,5’-二叔丁基-2’-羟基苯基)苯并***、2-(5’-叔丁基-2’-羟基苯基)苯并***、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并***、2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并***、2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并***、2-(2’-羟基-4’-辛氧基苯基)苯并***、2-(3’,5’-二叔戊基-2’-羟基苯基)苯并***、2-(3’,5’-双(α,α-二甲基苄基)-2’-羟基苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛基氧基羰基乙基)苯基)-5-氯苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己基氧基)羰基乙基]-2’-羟基苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛基氧基羰基乙基)苯基)苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己基氧基)羰基乙基]-2’-羟基苯基)苯并***、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-异辛基氧基羰基乙基)苯基)苯并***与2,2’-亚甲基-双[4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基苯酚]的混合物、2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]苯并***与聚乙二醇300的酯交换反应产物、[[R-CH2CH2-COOCH2]3]2-(式中,R为3’-叔丁基-4’-羟基-5’-2H-苯并***-2-基苯基)等苯并***化合物;
2,4-二羟基二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2-羟基-4-辛氧基二苯甲酮、2-羟基-4-癸基氧基二苯甲酮、2-羟基-4-十二烷基氧基二苯甲酮、2-羟基-4-苄基氧基二苯甲酮、2,2’,4,4’-四羟基二苯甲酮、2,2’-二羟基-4,4’-二甲氧基二苯甲酮等二苯甲酮化合物;
水杨酸4-叔丁基苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰基间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯、3,5-二叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二叔丁基-4-羟基苯甲酸十八烷基酯、苯甲酸2-甲基-4,6-二叔丁基苯酯、苯甲酸3,5-二叔丁基-4-羟基酯;
癸二酸双(2,2,6,6-四甲基哌啶基)酯、琥珀酸双(2,2,6,6-四甲基哌啶基)酯、癸二酸双(1,2,2,6,6-五甲基哌啶基)酯、正丁基-3,5-二叔丁基-4-羟基苄基丙二酸双(1,2,2,6,6-五甲基哌啶基)酯、1-羟基乙基-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩合产物、N,N’-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺与4-叔辛基氨基-2,6-二氯-1,3,5-均三嗪的缩合产物、次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基)酯、1,2,3,4-丁烷四甲酸四(2,2,6,6-四甲基-4-哌啶基)酯、1,1’-(1,2-亚乙基)双(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-硬脂基氧基-2,2,6,6-四甲基哌啶、2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸双(1,2,2,6,6-五甲基-4-哌啶基)酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、癸二酸双(1-辛基氧基-2,2,6,6-四甲基哌啶基)酯、琥珀酸双(1-辛基氧基-2,2,6,6-四甲基哌啶基)酯、N,N’-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺与4-吗啉代-2,6-二氯-1,3,5-三嗪的缩合产物、2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪与1,2-双(3-氨基丙基氨基)乙烷的缩合产物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪与1,2-双(3-氨基丙基氨基)乙烷的缩合产物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮等受阻胺化合物;
4,4’-二辛基氧基草酰替苯胺、2,2’-二乙氧基草酰替苯胺、2,2’-二辛基氧基-5,5’-二叔丁基草酰替苯胺、2,2’-双十二烷基氧基-5,5’-二叔丁基草酰替苯胺、2-乙氧基-2’-乙基草酰替苯胺、N,N’-双(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙基草酰替苯胺与2-乙氧基-2’-乙基-5,4’-二叔丁基草酰替苯胺的混合物、邻及对甲氧基-、以及邻及对乙氧基-二取代草酰替苯胺的混合物等草酰胺化合物;
2,4,6-三(2-羟基-4-辛基氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙基氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛基氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁基氧基丙基氧基)苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛基氧基丙基氧基)苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[4-十二烷基/十三烷基氧基-(2-羟基丙基)氧基-2-羟基苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪等2-(2-羟基苯基)-1,3,5-三嗪化合物;
亚磷酸三苯酯、亚磷酸二苯基烷基酯、亚磷酸苯基二烷基酯、亚磷酸三(壬基苯基)酯、亚磷酸三月桂酯、亚磷酸三(十八烷基)酯、二硬脂基季戊四醇二亚磷酸酯、亚磷酸三(2,4-二叔丁基苯基)酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、双(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、双异癸基氧基季戊四醇二亚磷酸酯、双(2,4-二叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三叔丁基苯基)季戊四醇二亚磷酸酯、三硬脂基山梨糖醇三亚磷酸酯、四(2,4-二叔丁基苯基)4,4’-亚联苯基二亚膦酸酯、6-异辛基氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧磷杂八环、6-氟-2,4,8,10-四叔丁基-12H-甲基二苯并[d,g]-1,3,2-二氧磷杂八环、亚磷酸双(2,4-二叔丁基-6-甲基苯基)甲基酯、亚磷酸双(2,4-二叔丁基-6-甲基苯基)乙基酯等亚磷酸酯化合物或亚膦酸酯化合物。其中,优选苯并***化合物。
相对于单体(A)而言,紫外线吸收剂的添加量优选为10~1,000ppm,更优选为100~800ppm。通过添加紫外线吸收剂,能抑制包含单体的液体的着色,存在单体自身的保存稳定性提高的倾向。
作为其他成分的例子,还可举出软化剂、增塑剂。
作为软化剂,可举出例如天然橡胶、合成橡胶等橡胶、热塑性弹性体等弹性体。通过这样的软化剂,能提高硬组织修补用组合物的柔软性。作为合成橡胶的具体例,可举出EPT(乙烯·丙烯·三元共聚物)。作为热塑性弹性体的具体例,可举出苯乙烯系弹性体、氯乙烯系弹性体、烯烃系弹性体、聚酯系弹性体、聚酰胺系弹性体、聚氨酯系弹性体。弹性体的分子量通常为1000~100万,优选为2000~50万。弹性体的玻璃化转变温度(Tg)通常为20℃以下,优选为0℃以下。
作为增塑剂的具体例,可举出柠檬酸酯、异柠檬酸酯、酒石酸酯、苹果酸酯、乳酸酯、甘油酸酯、羟基乙酸酯等羟基羧酸酯、偏苯三甲酸三甲酯、二苯甲酸二乙二醇酯、丙二酸二乙酯、邻乙酰基柠檬酸三乙酯、邻苯二甲酸苄基丁酯、二苯甲酸二丙二醇酯、己二酸二乙酯、邻乙酰基柠檬酸三丁酯、癸二酸二甲酯、亚烷基二醇二酯。
软化剂及增塑剂的添加量根据其种类适当确定即可,在硬组织修补用组合物整体中,通常为0~30质量%,优选为0~20质量%,更优选为0~10质量%。
本发明的硬组织修补用组合物根据需要可包含保存剂。作为保存剂的具体例,可举出对羟基苯甲酸甲酯、对羟基苯甲酸甲酯钠、对羟基苯甲酸乙酯、对羟基苯甲酸丙酯、对羟基苯甲酸丙酯钠、对羟基苯甲酸丁酯、甲酚、氯甲酚、间苯二酚、4-正己基间苯二酚、3a,4,7,7a-四氢-2-((三氯甲基)硫基)-1H-异吲哚-1,3(2H)-二酮、苯扎氯铵、苯扎氯铵钠、苄索氯铵、苯甲酸、苯甲醇、西吡氯铵、氯丁醇、脱氢乙酸、邻苯基苯酚、苯酚、苯乙醇、苯甲酸钾、山梨酸钾、苯甲酸钠、脱氢乙酸钠、丙酸钠、山梨酸、硫柳汞、百里酚、硼酸苯汞、硝酸苯汞、乙酸苯汞等苯汞化合物、甲醛。
作为其他成分,还包括抗感染剂、抗生素、抗菌剂、抗病毒剂、镇痛药、镇痛药的配合物、食欲抑制药、抗蠕虫药、抗关节炎药、平喘药、抗惊厥药、抗抑郁药、抗利尿药、止泻药、抗组胺药、抗炎药、抗偏头痛药剂、止吐剂、抗肿瘤药、抗帕金森病药、止痒药、抗精神病药、解热药、解痉药、抗胆碱能药、交感神经***、心血管用药剂、抗心律失常药、抗高血压药、利尿药、血管扩张剂、免疫抑制药、肌肉松弛剂、副交感神经阻断药、***、镇静剂、精神稳定剂、胆碱能药、化疗药、放射性药物、骨诱导药、膀胱静止性的肝素中和剂(heparinneutralizer agents with bladder stand still)、促凝剂(procoagulant)、止血剂、黄嘌呤衍生物、激素、天然来源或通过基因工程而合成的蛋白质、多糖类、糖蛋白、脂蛋白、寡核苷酸、抗体、抗原、加压素、加压素类似物、肾上腺素、选择蛋白、促凝血毒素、纤溶酶原激活因子抑制剂、血小板激活剂、骨形成因子、骨生长因子、具有止血作用的合成肽、及其他的药学或治疗的成分。通过包含这些成分,本发明的硬组织修补用组合物也可用于药物传递***、再生医疗用途。
作为抗菌剂的具体例,可举出碘元素、固体聚乙烯吡咯烷酮碘、聚乙烯吡咯烷酮碘;三溴苯酚、三氯苯酚、四氯苯酚、硝基苯酚、3-甲基-4-氯苯酚、3,5-二甲基-4-氯苯酚、苯氧基乙醇、二氯酚、邻苯基苯酚、间苯基苯酚、对苯基苯酚、2-苄基-4-氯苯酚、2,4-二氯-3,5-二甲基苯酚、4-氯百里酚、苄氯酚、三氯生、芬替克洛、苯酚、2-甲基苯酚、3-甲基苯酚、4-甲基苯酚、4-乙基酚、2,4-二甲基苯酚、2,5-二甲基苯酚、3,4-二甲基苯酚、2,6-二甲基苯酚、4-正丙基苯酚、4-正丁基苯酚、4-正戊基苯酚、4-叔戊基苯酚、4-正己基苯酚、4-正庚基苯酚、单烷基卤代苯酚、多烷基卤代苯酚、芳香族卤代苯酚、以及它们的铵盐、碱金属盐及碱土金属盐等苯酚化合物;硝酸银、六氯酚、汞溴红。
作为抗生素的具体例,可举出庆大霉素、硫酸庆大霉素、妥布霉素、硫酸妥布霉素、阿米卡星、硫酸阿米卡星、地贝卡星、硫酸地贝卡星、万古霉素、盐酸万古霉素、磷霉素、头孢唑林、头孢唑林钠、米诺环素、克林霉素、粘菌素、利奈唑胺、盐酸四环素、四环素水合物、土霉素及红霉素。
抗生素的添加量根据其种类适当确定即可,相对于聚合物(B)、聚合引发剂(C)及造影剂(X)的合计100质量%而言,通常为0~30质量%,优选为0~20质量%,更优选为0~10质量%。
出于促进组织修复的目的,本发明的硬组织修补用组合物可包含骨形成因子、骨成长因子、及其他的药学的或治疗的成分。
作为其他成分,还包括香料。作为香料的具体例,可举出橙油、圆柚油、柠檬油、酸橙油、丁香油、冬青油、薄荷油、欧薄荷醑、香蕉馏出物、黄瓜馏出物、蜂蜜馏出物、玫瑰水、薄荷醇、茴香脑、水杨酸烷基酯、苯甲醛、谷氨酸一钠、乙基香草醛、百里酚、香草醛。
作为其他成分的例子,还包括以使与周边的骨组织的视觉上的区别明确化、提高密合性、增强压缩强度等物性、或降低因活性自由基种的补足而导致的对周边的骨组织的侵袭性为目的的无机填充剂(其中,不包含前述的X射线造影剂)、有机填充剂、有机复合填料、着色剂。
作为无机填充剂的具体例,可举出铋氧化物、钛氧化物、氧化锌、氧化铝粒子等金属氧化物粉末;磷酸锆等金属盐粉末;二氧化硅玻璃、含铝玻璃、含钡玻璃、含锶玻璃、硅酸锆玻璃等玻璃填料;具有银缓释性的填料、具有钙缓释性的填料;具有氟缓释性的填料。从在固化后的无机填充剂与单体(A)之间形成牢固的结合方面考虑,优选实施了硅烷处理、聚合物涂覆等表面处理的无机填充剂。这些无机填充剂可以单独使用或组合2种以上而使用。
作为着色剂的具体例,可举出红色2号及其铝色淀、红色3号及其铝色淀、红色102号及其铝色淀、红色104号的(1)及其铝色淀或钡色淀、红色105号的(1)及其铝色淀、红色106号及其铝色淀、黄色4号及其铝色淀或钡色淀或锆色淀、黄色5号及其铝色淀或钡色淀或锆色淀、绿色3号及其铝色淀、蓝色1号及其铝色淀或钡色淀或锆色淀、蓝色2号及其铝色淀、红色201号、红色202号、红色203号、红色204号、红色205号、红色206号、红色207号、红色208号、红色213号、红色214号、红色215号、红色218号、红色219号、红色220号、红色221号、红色223号、红色225号、红色226号、红色227号及其铝色淀、红色228号、红色230号的(1)及其铝色淀、红色230号的(2)及其铝色淀、红色231号及其铝色淀、红色232号及其铝色淀、橙色201号、橙色203号、橙色204号、橙色205号及其铝色淀或钡色淀或锆色淀、橙色206号、橙色207号及其铝色淀、黄色201号、黄色202号的(1)及其铝色淀、黄色202号的(2)及其铝色淀、黄色203号及其铝色淀或钡色淀或锆色淀、黄色204号、黄色205号、绿色201号及其铝色淀、绿色202号、绿色204号及其铝色淀、绿色205号及其铝色淀或锆色淀、蓝色201号、蓝色202号及其钡色淀、蓝色203号、蓝色204号、蓝色205号及其铝色淀、褐色201号及其铝色淀、紫色201号、红色401号及其铝色淀、红色404号、红色405号、红色501号、红色502号及其铝色淀、红色503号及其铝色淀、红色504号及其铝色淀、红色505号、红色506号及其铝色淀、橙色401号、橙色402号及其铝色淀或钡色淀、橙色403号、黄色401号、黄色402号及其铝色淀、黄色403号的(1)及其铝色淀、黄色404号、黄色405号、黄色406号及其铝色淀、黄色407号及其铝色淀、绿色401号、绿色402号及其铝色淀或钡色淀、蓝色403号、蓝色404号、紫色401号及其铝色淀、黑色401号及其铝色淀;叶绿素、叶绿酸、孔雀绿、结晶紫、亮绿、酞菁钴、胡萝卜素、维生素B12及由它们衍生的衍生物。这些着色剂可以单独使用或组合2种以上而使用。
着色剂的添加量根据其种类适当确定即可,相对于聚合物(B)、聚合引发剂(C)及造影剂(X)的合计100质量%而言,通常为0~5质量%,优选为0~2质量%,更优选为0~1质量%。
[硬组织修补用组合物]
本发明的硬组织修补用组合物是将单体(A)、聚合物(B)、聚合引发剂(C)、造影剂(X)及其他根据需要而包含的成分混合而制备的。该组合物例如可通过施用于患部而使用。需要说明的是,本发明中,“硬组织修补用组合物”用于硬组织彼此的粘接、向硬组织内的填充、硬组织与钛、陶瓷、不锈钢等人工物的粘接及/或密合、硬组织与软组织等其他组织的粘接及/或密合,不包含牙齿与填充物的粘接(即,牙科用途)。
在将这些各成分混合时,混合的顺序没有限制。从得到的硬组织修补用组合物的稳定性更优异这样的方面考虑,优选首先将单体(A)及聚合引发剂(C)混合,接下来混合配合有造影剂(X)的聚合物(B),更优选同时混合单体(A)、聚合引发剂(C)及配合有造影剂(X)的聚合物(B)。
本发明的硬组织修补用组合物包含阻聚剂时,从得到的组合物的稳定性更优异这样的方面考虑,优选首先将单体(A)与阻聚剂的混合物、及聚合引发剂(C)混合,然后混合配合有造影剂(X)的聚合物(B),更优选同时混合单体(A)与阻聚剂的混合物、聚合引发剂(C)、及配合有造影剂(X)的聚合物(B)。
本发明的硬组织修补用组合物的利用以下方法测定的模拟骨侵入性优选为1.0mm以上,更优选为1.0~6.0mm。由此,硬组织修补用组合物与骨组织的密合性变得更优异。
(模拟骨侵入性的测定方法)
对于模拟骨侵入性而言,向具有连通的气泡的聚氨酯泡沫(孔隙率95%)中含浸生理盐水(和光纯药工业制,商品名0.01mol/L磷酸缓冲生理盐水),在其上表面放置成为软块状且拉丝消失后5分钟后的组合物,以75kPa的压力施加30秒负荷,测定组合物侵入的深度(mm)。
本发明的硬组织修补用组合物中包含的粒子(具体而言,为粉末状时的聚合物(B)、造影剂(X)及其他粒子)整体的体积平均粒径优选为32μm以下,更优选为15~26μm。粒子整体的体积平均粒径大于26μm时,上述的模拟骨侵入性差。体积平均粒径的测定方法如后述的实施例一栏中所述。
本发明的硬组织修补用组合物中包含的粒子中,造影剂(X)的含量优选为1.0质量%以上且低于20质量%,更优选为1.5质量%以上且19质量%以下,特别优选为2.0质量%以上且18质量%以下。
可在将本发明的硬组织修补用组合物固化之前,例如,在将可通过干式加热处理、使用了蒸汽、环氧乙烷(EO)、过氧化氢等气体的处理、过滤处理、使用了液体的处理等处理进行灭菌的硬组织修补用组合物填充至患部之前,预先用乙醇等消毒液对患部表面进行消毒。此外,在将硬组织修补用组合物填充至患部之前,出于改善与患部的密合性的目的,可进行前处理。作为前处理用的液体,可举出例如生理盐水。
[硬组织修补用套装]
在担心本发明的硬组织修补用组合物由于经过长时间而导致形态、性能发生变化,可能损害本发明的效果的情况下,可将单体(A)、聚合物(B)、聚合引发剂(C)、造影剂(X)及其他根据需要而包含的全部成分以任意的组合分成3部分以上,将它们分别收纳于3个以上的构件,以硬组织修补用套装的形式保存。在即将使用之前将各成分混合而制成硬组织修补用组合物即可。作为用于收纳单体(A)、聚合引发剂(C)的构件,优选防止它们的挥散及飞散的构件,作为其具体例,可举出具有阻气性的可密闭的树脂容器、玻璃安瓿。作为用于收纳聚合物(B)的构件的具体例,可举出能防止吸湿的密闭性良好的树脂容器、玻璃容器、可进行基于环氧乙烷(EO)、过氧化氢等气体的灭菌的具有通气性的树脂制无纺布、灭菌纸。
作为硬组织修补用套装,优选下述硬组织修补用套装,其是分成单体(A)及其他根据需要而包含的成分的混合物、配合有造影剂(X)的聚合物(B)及其他根据需要而包含的成分的混合物、和聚合引发剂(C)及其他根据需要而包含的成分的混合物这3部分,将它们分别收纳于3个构件而成的。但硬组织修补用套装不限于此,例如,可以是分成单体(A)及其他根据需要而包含的成分的混合物、聚合物(B)及其他根据需要而包含的成分的混合物、造影剂(X)及其他根据需要而包含的成分的混合物、和聚合引发剂(C)及其他根据需要而包含的成分的混合物这4部分,将它们分别收纳于4个构件而成的硬组织修补用套装,也可以是分成单体(A)、造影剂(X)及其他根据需要而包含的成分的混合物、聚合物(B)及其他根据需要而包含的成分的混合物、和聚合引发剂(C)及其他根据需要而包含的成分的混合物这3部分,将它们分别收纳于3个构件而成的硬组织修补用套装。具有收纳有这些各成分的3个以上的构件的硬组织修补用套装可作为制品提供。
在使用硬组织修补用套装时,例如,优选将单体(A)及其他根据需要而包含的成分的混合物、与聚合引发剂(C)及其他根据需要而包含的成分的混合物混合,接下来混合配合有造影剂(X)的聚合物粉末(B)及其他根据需要而包含的成分的混合物。另外,也可将它们同时混合。通过按照上述方式混合,容易得到具有更稳定的性能的硬组织修补用组合物。
硬组织修补用套装可以不仅具有收纳各成分的构件(例如,树脂容器、玻璃安瓿),还具有用于将各成分取出并进行混合的构件(例如,粘固剂喷枪、混合容器、混合皿、粘固剂注入器、料筒)。
硬组织修补用套装中,1个处理室(混合容器)的内部被间隔壁或间隔物分成3部分以上,可在所述被分离的3个以上的位置收纳各成分。此外,硬组织修补用套装可具有:用于在通过该间隔壁的破坏、移动或间隔物的除去而使单体(A)及聚合引发剂(C)与配合有造影剂(X)的聚合物(B)接触后,操作搅拌叶片而将各成分混合的搅拌单元。这样的硬组织修补用套装与从各容器中取出各成分而进行混合的情况相比,容易操作。而且,从容易操作方面考虑,利用用于将组合物从处理室(混合容器)直接向患部填充的粘固剂喷枪等器具也是有用的。
对于在将硬组织修补用组合物涂布于骨、软骨等硬组织等的患部、软组织、以及钛、陶瓷、不锈钢等人工物时使用的器具,可预先含有聚合引发剂(C)成分的一部分或全部。这种情况下,在即将使用之前,使单体(A)、聚合物粉末(B)、及其他根据需要而包含的成分与器具接触,由此,制备硬组织修补用组合物,将其直接填充至患部。
作为向患部填充硬组织修补用组合物的器具,可举出例如粘固剂喷枪。
硬组织修补用套装例如可具有上文所述的醇等消毒液、用于以改善密合性为目的的前处理的溶液。
在将各成分收纳于硬组织修补用套装时,优选可在各成分不发生变质(例如单体不发生固化)的条件下,通过可见光等电磁波对各成分进行灭菌处理。
实施例
以下,基于实施例进一步具体地说明本发明,但本发明不受这些实施例的限制。
(1)比表面积
对于聚合物粉末的比表面积而言,作为前处理,于室温进行真空脱气,使用装置BELSORP-mini(Microtrack Bel公司制),利用液氮温度下的氮气吸附法进行测定。
(2)重均分子量(Mw)
将聚合物粉末溶解于试剂特级四氢呋喃(和光纯药工业公司制),用疏水性0.45μm聚四氟乙烯制过滤器对该溶液进行过滤。将该过滤后的溶液作为样品,利用高效液相色谱仪(岛津制作所制,LC-10AD)、分离柱(PLgel(10μm)MIXED-B×2)、检测器(Shodex公司制,RI-101),测定聚合物粉末的重均分子量(Mw)(按照标准聚苯乙烯换算)。
(3)体积平均粒径D50
作为分散溶剂,使用试剂特级甲醇(和光纯药工业公司制,溶剂折射率为1.33)或0.2质量%六偏磷酸钠水溶液(和光纯药工业公司制,溶剂折射率为1.33),用超声波均质机对聚合物粉末或造影剂进行5分钟(输出功率为25W)分散。将该分散液作为样品,使用粒度分布计(Microtrac公司制,Microtrac MT3300EXII),在装置装载指数(Loading Index)在适量范围内的浓度条件、且循环速度为50%(100%时、65mL/sec)的条件下,测定聚合物粉末、造影剂、及组合物中包含的粒子整体的体积平均粒径D50。
(4)模拟骨侵入性
关于模拟骨侵入性,向由具有连通的气泡的聚氨酯泡沫形成的松质模拟骨(HumanBody公司制,商品名为SAW 1522-507,孔隙率为95%)中含浸生理盐水(和光纯药工业制,商品名为0.01mol/L磷酸缓冲生理盐水),在其上表面放置成为软块状且拉丝消失后5分钟后的组合物,以75kPa的压力施加30秒负荷,测定组合物侵入的深度(mm)。
(5)与猪大腿骨的密合性
关于与猪大腿骨的密合性,向食用的猪大腿骨的髓腔内填充适量的成为软块状且拉丝消失后5分钟后的组合物,一边施加200g的负荷、一边在温度为37℃、相对湿度为95%RH的环境下使组合物进行24小时固化,对以5mm/分钟的速度从猪大腿骨中剜出上述固化后的组合物所需要的负荷的值(N)进行测定。评价方法参考了“Canadian Journal ofSurgery,54(2011)33-38,Stephen Hunt,Craig Stone,Shane Seal”。需要说明的是,对于食用的猪大腿骨而言,预先以10mm长度切断,用生理盐水(和光纯药工业制,商品名0.01mol/L磷酸缓冲生理盐水)将髓腔内充分洗涤,确认髓腔的内径(最小值与最大值的平均值)为10~25mm的范围、并且无损伤、破裂后使用。
[实施例1a~6a、比较例1a~6a]
实施例1a~6a、比较例1a~6a中,使用了作为单体(A)的甲基丙烯酸甲酯、作为球状的聚合物粉末(b1)的聚甲基丙烯酸甲酯(比表面积=0.32m2/g,Mw=12.1万,体积平均粒径D50=21.9μm)、作为不定形状的聚合物粉末(b3)的聚甲基丙烯酸甲酯(比表面积=2.9m2/g,Mw=44.2万,体积平均粒径D50=21.3μm)、作为聚合引发剂(C)的85质量%的部分氧化三丁基硼与15质量%的乙醇混合物(三井化学公司制,型号BC-Sli)(将聚合引发剂(C)的合计作为100质量%)、作为造影剂(X)的硫酸钡(Sakai Chemical Industry Co.,Ltd.制)。
首先,以表1及2所示的配合比,使聚合物(B)及造影剂(X)均匀分散,制备混合物,另外,另行地在5mL玻璃制样品管内制备单体(A)与聚合引发剂(C)的混合物。而后,使用聚丙烯制容器(松风公司制,商品名tray resin blender)及硅橡胶制的刮铲,于23℃对这2种混合物进行60秒混合。将得到的混合物静置适当时间,得到拉丝消失且成为软块状的硬组织修补用组合物。使用该组合物进行模拟骨侵入性及与猪大腿骨的密合性的评价。将结果示于表1及2。
需要说明的是,表中的各成分的以括号的形式表示的配合比为以成分(A)~(C)的合计100质量份为基准的比率(质量份)。另外,成分(b1)及(b3)的配合比为以聚合物粉末(B)100质量%为基准的比率(质量%)。
[表1]
表1
[表2]
表2
如表1及2所示,使用了作为造影剂(X)的体积平均粒径大的硫酸钡的实施例1a~6a的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性优异。将该硬组织修补用组合物作为骨粘固剂用于患者的治疗的情况下,可期待粘接性的提高。
另一方面,使用了作为造影剂(X)的体积平均粒径小的硫酸钡的比较例1a~6a的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性差。另外,在比较例1a~6a中,硬组织修补用组合物中包含的粒子整体的体积平均粒径最大的比较例6a的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性最差。由该结果可知,硬组织修补用组合物中包含的粒子整体的体积平均粒径过大时,反而存在模拟骨侵入性及与猪大腿骨的密合性下降的倾向。
[实施例1b及比较例1b]
除了作为造影剂(X)使用了表3所示的体积平均粒径的氧化锆(高纯度化学实验室公司制,商品名氧化锆(IV),及Aldrich公司制,商品名Zirconium(IV))来代替硫酸钡之外,与实施例4a同样地操作,制备硬组织修补用组合物,进行评价。将结果示于表3。
[表3]
表3
如表3所示,将造影剂(X)从硫酸钡变更为氧化锆的情况也同样,使用了作为造影剂(X)的体积平均粒径大的氧化锆的实施例1b的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性优异。另一方面,使用了作为造影剂(X)的体积平均粒径小的氧化锆的比较例1b的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性差。
[实施例1c~3c及比较例1c~3c]
作为聚合引发剂(C),代替烷基硼烷系聚合引发剂,以表4及表5所示的配合量使用过氧化苯甲酰(Aldrich公司制,商品名Luperox(注册商标)A75),向作为单体(A)的甲基丙烯酸甲酯中添加0.5质量%的N,N-二甲基对甲苯胺,并如表4及5所示那样地变更硫酸钡的体积平均粒径,除此之外,与实施例4a同样地操作,制备硬组织修补用组合物,进行评价。将结果示于表4及表5。
[表4]
表4
[表5]
表5
如表4及5所示,将聚合引发剂(C)从烷基硼烷系聚合引发剂变更为过氧化苯甲酰的情况也同样,使用了作为造影剂(X)的体积平均粒径大的硫酸钡的实施例1c~3c的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性优异。另一方面,使用了作为造影剂(X)的体积平均粒径小的硫酸钡的比较例1c~3c的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性差。
另外,对使用了过氧化苯甲酰作为聚合引发剂(C)的实施例1c~3c、与使用了烷基硼烷系聚合引发剂作为聚合引发剂(C)的实施例4a~6a分别进行比较时,实施例4a~6a的模拟骨侵入性及与猪大腿骨的密合性更优异。由该结果可知,作为聚合引发剂(C),与过氧化苯甲酰等有机过氧化物相比,从密合性方面考虑更优选烷基硼烷系聚合引发剂等有机硼化合物。
[实施例1d及比较例1d]
除了作为造影剂(X)使用了表6所示的体积平均粒径的氧化锆(高纯度化学公司制,商品名氧化锆(IV),及Aldrich公司制,商品名Zirconium(IV))来代替硫酸钡之外,与实施例1c同样地操作,制备硬组织修补用组合物,进行评价。将结果示于表6。
[表6]
表6
如表6所示,使用过氧化苯甲酰作为聚合引发剂(C)、并且使用氧化锆作为造影剂(X)的情况也同样,使用了作为造影剂(X)的体积平均粒径大的氧化锆的实施例1d的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性优异。另一方面,使用了作为造影剂(X)的体积平均粒径小的氧化锆的比较例1d的硬组织修补用组合物的模拟骨侵入性及与猪大腿骨的密合性差。
产业上的可利用性
本发明的硬组织修补用组合物在例如硬组织彼此的粘接、向硬组织内的填充、硬组织与钛、陶瓷、不锈钢等人工物的粘接、硬组织与软组织等其他组织的粘接的用途中有用。另外,本发明的硬组织修补用组合物例如作为用于骨、软骨等硬组织与人工关节的固定的骨粘固剂、向骨的缺损部的填充材料、骨填充材料、人工骨有用。
Claims (10)
1.硬组织修补用组合物,其包含单体(A)、聚合物(B)、聚合引发剂(C)、及体积平均粒径为3μm以上的造影剂(X),
并且,所述聚合物(B)包含:
比表面积为0.05~0.5m2/g的聚合物粉末(b1);和,
比表面积为0.51~1.2m2/g的聚合物粒子(b2)及/或比表面积为1.5~4.5m2/g的聚合物粉末(b3)。
2.如权利要求1所述的硬组织修补用组合物,利用以下的方法测定的模拟骨侵入性为1.0mm以上,
[模拟骨侵入性的测定方法]
对于模拟骨侵入性而言,向具有连通的气泡的孔隙率95%的聚氨酯泡沫中含浸生理盐水,在其上表面放置成为软块状且拉丝消失后5分钟后的组合物,以75kPa的压力施加30秒负荷,测定组合物侵入的深度(mm)。
3.如权利要求1所述的硬组织修补用组合物,其中,造影剂(X)为硫酸钡或氧化锆。
4.如权利要求1所述的硬组织修补用组合物,其中,单体(A)为(甲基)丙烯酸酯系单体。
5.如权利要求1所述的硬组织修补用组合物,其中,聚合物(B)为(甲基)丙烯酸酯系聚合物。
6.如权利要求1所述的硬组织修补用组合物,其中,相对于成分(A)~(C)的合计100质量份,所述硬组织修补用组合物包含单体(A)10~45质量份、聚合物(B)54.9~80质量份、聚合引发剂(C)0.1~10质量份及造影剂(X)0.5~70质量份。
7.如权利要求1所述的硬组织修补用组合物,其中,造影剂(X)的体积平均粒径为3.0~25.1μm。
8.如权利要求1所述的硬组织修补用组合物,其中,硬组织修补用组合物中包含的粒子整体的体积平均粒径为32μm以下。
9.如权利要求1所述的硬组织修补用组合物,其中,聚合引发剂(C)为有机硼化合物。
10.硬组织修补用套装,其具有将权利要求1所述的硬组织修补用组合物中包含的单体(A)、聚合物(B)、聚合引发剂(C)、及造影剂(X)的各成分以任意的组合分成3部分以上而进行收纳的构件。
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