JP2022511791A - 抗菌剤含有シリコーン潤滑性コーティング - Google Patents
抗菌剤含有シリコーン潤滑性コーティング Download PDFInfo
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- JP2022511791A JP2022511791A JP2021530893A JP2021530893A JP2022511791A JP 2022511791 A JP2022511791 A JP 2022511791A JP 2021530893 A JP2021530893 A JP 2021530893A JP 2021530893 A JP2021530893 A JP 2021530893A JP 2022511791 A JP2022511791 A JP 2022511791A
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- coating
- medical device
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Images
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Abstract
Description
本出願は、2018年11月29日出願の米国仮出願第62/773,102号の利益を主張し、全ての目的のためにその内容全体が参照により本明細書に援用される。
本発明の属する技術分野は、抗菌剤含有シリコーン系潤滑性コーティング、具体的には、抗菌剤を含む医療用具において使用するためのシリコーン系潤滑性コーティングである。
本発明の一態様は、外科用縫合針及び縫合糸及び他のポリマー医療用具などの医療用具の表面をコーティングするのに特に有用な新規潤滑性シリコーンコーティング組成物を目的とする。
log μcSt=1.00+0.0123M0.5
(Journal of Applied Physics 17,1020(1946)にA.J.Barryによって公開)。
本明細書で使用するとき、本発明との使用について記載されるシリカ含有組成物は、別個の成分(表面処理シリカなど)としての、又は架橋性シリコーンポリマー混合物中にシリカを含有する市販の組成物からのシリカ材料を含む。
好適な抗菌剤は、コーティング組成物のポリマーマトリクス全体にわたって均一に分布することができるものであり得る。例えば、抗菌剤は、クロルヘキシジン、ポリヘキサメチレンビグアニド(PHMB)、オクテニジン、銀粒子、トリクロサン等を含む、抗生物質又は抗菌機能を有する任意の薬剤であってよい。一形態では、抗菌剤に対して高い親和性を有する材料の粒子は、ポリマーマトリクス全体に分布することができる。例えば、ポリカプロラクトン、及びポリカプロラクトンに基づくコポリマーは、トリクロサンに対して高い親和性を有することが知られている。したがって、トリクロサンが抗菌剤として選択される場合、ポリカプロラクトンの(コ)ポリマーの粒子を磨耗性コーティング中に含めることができる。本発明の使用において好ましい抗菌剤はトリクロサンである。好ましくは、コーティング組成物中のトリクロサンの重量%は、約1~40重量%(全固形分に対して)、より好ましくは約3~約30重量%、最も好ましくは約5~20重量%である。
GE SiliconeのBruce Karstedtは、1970年始めに高活性白金触媒(「カールシュテット触媒」)を発明した(米国特許第3,775,452号)。ビニル末端ポリジメチルシロキサンは、わずか10ppmのKarstedt触媒を用いて、周囲温度において1分未満でポリメチルヒドロシロキサン架橋剤と反応し得る。典型的には、触媒活性が高いことから従来の針及び縫合糸の製造プロセスにおいてこの触媒を使用することは困難であるか又は不可能であるが、その理由は、従来の生産プロセスの経済的側面から、理想的に、そして、典型的には、全触媒シリコーンコーティング溶液の場合は最長8時間の可使時間が必要とされるためである。この問題に対処するために本発明の新規速硬性白金触媒が開発され、本発明の架橋性シリコーンポリマー、例えばビニル末端ポリジメチルシロキサン及びポリメチルヒドロシロキサン、シリカ充填剤とこの新規触媒とから得られる混合物は、約8時間超にわたって周囲温度で安定であり得る。本発明の新規触媒の存在下における、架橋性シリコーンポリマーと架橋剤、例えば、ビニル末端ポリジメチルシロキサン及びポリメチルヒドロシロキサンとの架橋反応は、高温で10秒未満に作動し得る。本発明の新規触媒は、以下に示すスキーム1に従ってカールシュテット触媒とビニルシクロヘキサノールとを反応させることによって調製される。本発明の新規触媒は、シリコーンコーティング溶液の硬化中にわたってより優れた制御を提供する。これは、通常、「コマンド硬化」と呼ばれる。
Pt[(CH2=CH)(CH3)2Si]2O・C6H10(OH)(C=CH)。
上記シリコーンポリマー及び新規白金触媒は、低沸点有機溶媒中に分散して、潤滑性コーティング溶液を形成する。シリコーン分散液には、低温脂肪族溶媒が使用される。芳香族溶媒及びテトラメチルジシロキサンが、シリコーン分散液に一般に使用される。典型例としては、ペンタン、ヘプタン、ヘキサン、及びこれらの混合物が挙げられるが、これらに限定されない。シリコーンポリマー成分を均質なコーティング溶液に有効にブレンドするのに十分な濃度で有機溶媒を添加する。総溶媒濃度は、コーティング厚さ要件、この場合、医療用具の種類に応じて約20重量%~99重量%である。当業者は、コーティング溶液の固形分含量を変化させることによってコーティング厚さを操作できることを理解するであろう。
本発明の新規シリコーン潤滑性コーティング溶液は、従来のコーティング技術及びプロセス、並びに従来のコーティング設備を用いて、ポリエステル縫合糸などの医療用具の表面に塗布される。コーティング設備の例は、単純なディップコーティングタンク及びコーティングを硬化させるためのインライン対流式オーブンであり得る。コーティングはまた、刷毛塗り、ロール塗り、又は噴霧プロセスによって塗布され得る。ビニルシリル化付加架橋反応は、乾燥オーブンを通過させることによってインラインで完了させることができる。硬化時間は、100℃の温度で20秒、95℃で120秒、又は70℃で60分もの短時間であり得る。本潤滑性シリコーンコーティングによって、フラッシュ硬化(Flash cure)を達成することができる。
上述の通り、新規潤滑性コーティングでコーティングされ得る医療用具としては、外科用縫合針及び縫合糸、皮下針、カテーテル、外科用プローブ、内視鏡、注射器、メス、切刃、整形外科用インプラント、トロカール、カニューレ、ドレインなどの従来の医療用具が挙げられる。医療用具は、外科用ステンレス鋼、チタン、PTFE、ガラス、合金鋼、高融点金属合金、記憶合金、シリコーン、ポリマー、金属及び非金属部材成分を含む複合材、これらの組み合わせなどを含む従来の生体適合性材料から構築される。生体適合性材料としては、非吸収性材料及び生体吸収性材料を挙げることができる。
阻止帯(ZOI)試験:
トリクロサン含有シリコーンコーティングされた試験物品を、試験生物を接種した寒天培地に入れる。抗菌剤トリクロサンがシリコーン担体を通じて寒天培地に拡散する場合、抗菌剤の濃度が最小阻止濃度(MIC)を上回る限り、感受性微生物は、ある距離にわたってディスクの上又は周囲では増殖しない。この距離を阻止帯と呼ぶ。抗菌剤が培地中で拡散速度を有すると仮定すると、試験物品の周囲に阻止帯が存在することは、抗菌剤が存在しなければ順調に増殖する培地に抗菌剤が存在することによって生物が阻害されることを示す。阻止帯の直径はMICに反比例する。
4gのGelest SIP 6831(キシレン中2.2%白金ジビニルテトラメチルジシロキサン錯体、カールシュテット触媒)を、周囲温度で5時間、4gのビニルシクロヘキサノールキシレン溶液と混合したところ、混合物は暗褐色に変化する。混合物を、その使用前に792gのテトラメチルジシロキサンで希釈した。
この実施例は、表2aにまとめた成分の混合物を含むトリクロサン含有シリコーンコーティング溶液を提供する。
以下の試験物品のリストを実施例2aの溶液に5秒間浸漬し、100℃で5分間硬化させた。
2b-1:ステンレス鋼製縫合糸:Ethicon外科用鋼製縫合糸M650G
2b-2:シリコーンドレイン:Blake(登録商標)シリコーンドレイン2233
2b-3:チタン製ピン:Synthes 2.0mm Ti Kirschnerワイヤ492.20(大腸菌でのみ試験)
2b-2EO:シリコーンドレイン:Blake(登録商標)シリコーンドレイン2233
2b-3EO:チタン製ピン:Synthes 2.0mm Ti Kirschnerワイヤ492.20(大腸菌でのみ試験)
上記試験物品を、個々の無菌ペトリ皿に無菌的に置き、10コロニー形成単位(CFU)の黄色ブドウ球菌又は大腸菌を含有する100マイクロリットルの接種材料に曝露した。トリプチケースソイ寒天培地(TSA)を各皿に注ぎ、固化させた。プレートを37℃の温度で24時間インキュベートした。インキュベーション後、プレートを暗視野コロニー計数器で検査し、阻止帯(ZOI)を測定した。結果を表2cにまとめる。
この実施例は、表3aにまとめた成分の混合物を含むトリクロサン含有シリコーンコーティング溶液を提供する。
試験物品を実施例2aの溶液に5秒間浸漬し、100℃の温度で5分間硬化させた。
3b-1:ステンレス鋼製縫合糸:Ethicon外科用鋼製縫合糸M650G
3b-2:シリコーンドレイン:Blake(登録商標)シリコーンドレイン2233
3b-2EO:シリコーンドレイン:Blake(登録商標)シリコーンドレイン2233。
実施例3bの試験物品を、個々の無菌ペトリ皿に無菌的に置き、10コロニー形成単位(CFU)の黄色ブドウ球菌又は大腸菌を含有する100マイクロリットルの接種材料に曝露した。トリプチケースソイ寒天培地(TSA)を各皿に注ぎ、固化させた。プレートを37℃の温度で24時間インキュベートした。インキュベーション後、プレートを暗視野コロニー計数器で検査し、阻止帯を測定した。結果を表3cにまとめる。
この実施例は、表4aにまとめた成分の混合物を含むトリクロサン含有シリコーンコーティング溶液を提供する。
以下の試験物品を実施例2aの溶液に5秒間浸漬し、100℃の温度で5分間硬化させた。
4b-1:ステンレス鋼製縫合糸:Ethicon外科用鋼製縫合糸M650G
4b-2:シリコーンドレイン:Blake(登録商標)シリコーンドレイン2233
4b-2EO:シリコーンドレイン:Blake(登録商標)シリコーンドレイン2233。
実施例4bの試験物品を、個々の無菌ペトリ皿に無菌的に置き、10コロニー形成単位(CFU)の黄色ブドウ球菌又は大腸菌を含有する100マイクロリットルの接種材料に曝露した。トリプチケースソイ寒天培地(TSA)を各皿に注ぎ、固化させた。プレートを37℃の温度で24時間インキュベートした。インキュベーション後、プレートを暗視野コロニー計数器で検査し、阻止帯(ZOI)を測定した。結果を表4cにまとめる。
この実施例は、表5aにまとめた成分の混合物を含むトリクロサン含有シリコーンコーティング溶液を提供する。
1メートルのシルク製縫合糸(Ethicon 2-0Mersilene)を実施例5aのコーティング製剤に5秒間浸漬し、100℃の温度で5分間硬化させた。
5b-1:2-0シルク製縫合糸
5b-2:1PET(Mersilene(登録商標)縫合糸)
実施例5bの縫合糸試験物品を、個々の無菌ペトリ皿に無菌的に置き、10コロニー形成単位(CFU)の黄色ブドウ球菌を含有する100マイクロリットルの接種材料に曝露した。トリプチケースソイ寒天培地(TSA)を各皿に注ぎ、固化させた。プレートを37℃の温度で24時間インキュベートした。インキュベーション後、プレートを暗視野コロニー計数器で検査し、阻止帯(ZOI)を測定した。試験物品をペトリ皿から抽出し、別の無菌ペトリ皿に無菌的に置き、10コロニー形成単位(CFU)の黄色ブドウ球菌を含有する100マイクロリットルの接種材料に曝露した。トリプチケースソイ寒天培地(TSA)を各皿に注ぎ、固化させた。プレートを37℃の温度で更に24時間インキュベートした。インキュベーション後、プレートを暗視野コロニー計数器で検査し、阻止帯(ZOI)を測定した。各サンプルの3つの複製物を各試験物品に使用し、結果を表5cにまとめる。
この実施例は、トリクロサンリザーバを作製するために、限定された空間におけるより高負荷のトリクロサンのためのより厚いコーティングを調製するためのものである。
実施例6aのコーティングされた積層体を、試験物品としての1/2”の研磨された316ステンレス鋼製クーポンを抗菌処理するためのトリクロサンリザーバとして使用した。実際には、実施例6aのトリクロサンコーティングされた積層体と、約-20インチの水銀の中程度の真空下で図3に示す加熱プロファイルに従って加熱した容器の内容物と共に、試験クーポンを密閉容器に入れた。実施例6aの積層体からのトリクロサンを、加熱サイクルの終了までに、ステンレス鋼製試験クーポンの表面上に移した。次いで、処理したステンレス鋼製クーポンを、溶液1立方センチメートル当たり105個の細菌の初期黄色ブドウ球菌接種材料を含有する寒天プレートにおいて38℃の温度で24時間インキュベートした。図4は、処理された試験クーポンの周囲に約20mmの保護阻止帯が形成されたことを示し、これは、実施例6aのコーティングされた積層体のトリクロサンが加熱サイクル中に316ステンレス鋼製試験クーポンに首尾よく移動したことを示す。
(1) 潤滑性シリコーンコーティングでコーティングされた医療用具であって、
表面を有する医療用具と、
前記表面の少なくとも一部上の潤滑性シリコーンコーティングであって、
反応性官能基を有する架橋性シリコーンポリマー、
任意選択で、シリカ含有組成物、
シリコーン架橋剤、
抗菌剤、及び
触媒、を含むコーティング組成物から形成されている、潤滑性シリコーンコーティングと、を含み、前記触媒が、以下の式:
Pt[(CH2=CH)(CH3)2Si]2O・C6H10(OH)(C=CH)
を有する白金ジビニルテトラメチルジシロキサンビニルシクロヘキサノール錯体から本質的になる、医療用具。
(2) 前記架橋性シリコーンポリマーが、ビニル末端ポリジアルキルシロキサン、ビニル末端ポリジメチルシロキサン、ビニル末端ポリジフェニルシラン-ジメチルシロキサンコポリマー、ビニル末端ポリフェニルメチルシロキサン、ビニル末端ポリフルオロプロピルメチル-ジメチルシロキサンコポリマー、及びビニル末端ポリジエチルシロキサンからなる群から選択される、実施態様1に記載の医療用具。
(3) 前記架橋性シリコーンポリマーが、ビニル末端ポリジメチルシロキサンを含む、実施態様1に記載の医療用具。
(4) 前記抗菌剤が、トリクロサン、クロルヘキシジン、ポリヘキサメチレンビグアニド(PHMB)、オクテニジン、及び銀からなる群から選択される、実施態様1に記載の医療用具。
(5) 前記抗菌剤が、トリクロサンである、実施態様1に記載の医療用具。
(7) 前記シリコーン架橋剤が、ポリメチルヒドロシロキサンを含む、実施態様1に記載の医療用具。
(8) 前記シリカ含有組成物が、トリメチルシリル表面処理シリカ充填剤を含む、実施態様1に記載の医療用具。
(9) 前記シリカ含有組成物が、HCR(高一貫性ゴム)ベース及びLSR(液体シリコーンゴム)ベースを含む、市販の反応性シリカ含有シリコーンベースから選択される、実施態様1に記載の医療用具。
(10) 前記シリカ含有組成物が、液体シリコーンゴムベースである、実施態様9に記載の医療用具。
(12) 前記コーティング溶液が、約1~40重量%(全固形分)のトリクロサン抗菌剤を含む、実施態様1に記載の医療用具。
(13) 前記コーティング組成物が、全固形分に基づいて、約0.2重量%~約1.8重量%の前記シリコーン架橋剤を含み、前記コーティング組成物が、前記コーティング組成物の重量に基づいて、約75重量%~約99.5重量%の有機溶媒を更に含む、実施態様1に記載の医療用具。
(14) 前記コーティング組成物が、全固形分に基づいて、約0.0004重量%~約0.0036重量%の白金触媒を含み、前記コーティング組成物が、前記コーティング組成物の重量に基づいて、約75重量%~約99.5重量%の有機溶媒を更に含む、実施態様1に記載の医療用具。
(15) 前記コーティング組成物が、キシレン、トルエン、ペンタン、ヘキサン、ヘプタン、オクタン、高分子量オレフィンの混合物、及びこれらの組み合わせからなる群から選択される溶媒を更に含む、実施態様1に記載の医療用具。
(17) 前記医療用具が、外科用縫合針、縫合糸、皮下針、外科用メス、カテーテル、切刃、外科用プローブ、内視鏡、ハサミ、及び切刃からなる群から選択される、実施態様1に記載の医療用具。
(18) 前記医療用具が、外科用縫合糸を含む、実施態様17に記載の医療用具。
(19) 前記コーティングが、非架橋性シロキサンを更に含む、実施態様1に記載の医療用具。
(20) 前記非架橋性シロキサンが、トリメチルシリル末端ポリジメチルシロキサンである、実施態様19に記載の医療用具。
反応性官能基を有する架橋性シリコーンポリマー、
任意選択で、シリカ含有組成物、
任意選択で、非架橋性シロキサン、
シリコーン架橋剤、
抗菌剤、及び
触媒、を含み、前記触媒が、以下の式:
Pt[(CH2=CH)(CH3)2Si]2O・C6H10(OH)(C=CH)
を有する白金ジビニルテトラメチルジシロキサンビニルシクロヘキサノール錯体から本質的になる、コーティング組成物。
(22) 前記組成物が、約70℃を超える温度で硬化可能である、実施態様21に記載のコーティング組成物。
(23) 前記組成物が、約95℃の温度において約2分で硬化可能である、実施態様22に記載のコーティング組成物。
Claims (23)
- 潤滑性シリコーンコーティングでコーティングされた医療用具であって、
表面を有する医療用具と、
前記表面の少なくとも一部上の潤滑性シリコーンコーティングであって、
反応性官能基を有する架橋性シリコーンポリマー、
任意選択で、シリカ含有組成物、
シリコーン架橋剤、
抗菌剤、及び
触媒、を含むコーティング組成物から形成されている、潤滑性シリコーンコーティングと、を含み、前記触媒が、以下の式:
Pt[(CH2=CH)(CH3)2Si]2O・C6H10(OH)(C=CH)
を有する白金ジビニルテトラメチルジシロキサンビニルシクロヘキサノール錯体から本質的になる、医療用具。 - 前記架橋性シリコーンポリマーが、ビニル末端ポリジアルキルシロキサン、ビニル末端ポリジメチルシロキサン、ビニル末端ポリジフェニルシラン-ジメチルシロキサンコポリマー、ビニル末端ポリフェニルメチルシロキサン、ビニル末端ポリフルオロプロピルメチル-ジメチルシロキサンコポリマー、及びビニル末端ポリジエチルシロキサンからなる群から選択される、請求項1に記載の医療用具。
- 前記架橋性シリコーンポリマーが、ビニル末端ポリジメチルシロキサンを含む、請求項1に記載の医療用具。
- 前記抗菌剤が、トリクロサン、クロルヘキシジン、ポリヘキサメチレンビグアニド(PHMB)、オクテニジン、及び銀からなる群から選択される、請求項1に記載の医療用具。
- 前記抗菌剤が、トリクロサンである、請求項1に記載の医療用具。
- 前記シリコーン架橋剤が、ポリメチルヒドロシロキサン、ポリメチルヒドロ-コ-ポリジメチルシロキサン、ポリエチヒドロシロキサン、ポリメチルヒドロシロキサン-コ-オクチルメチルシロキサン、及びポリメチルヒドロシロキサン-コ-メチルフェニルシロキサンからなる群から選択される、請求項1に記載の医療用具。
- 前記シリコーン架橋剤が、ポリメチルヒドロシロキサンを含む、請求項1に記載の医療用具。
- 前記シリカ含有組成物が、トリメチルシリル表面処理シリカ充填剤を含む、請求項1に記載の医療用具。
- 前記シリカ含有組成物が、HCR(高一貫性ゴム)ベース及びLSR(液体シリコーンゴム)ベースを含む、市販の反応性シリカ含有シリコーンベースから選択される、請求項1に記載の医療用具。
- 前記シリカ含有組成物が、液体シリコーンゴムベースである、請求項9に記載の医療用具。
- 前記コーティング組成物が、前記コーティング組成物の重量に基づいて、約20重量%~約99.5重量%の有機溶媒を更に含む、請求項1に記載の医療用具。
- 前記コーティング溶液が、約1~40重量%(全固形分)のトリクロサン抗菌剤を含む、請求項1に記載の医療用具。
- 前記コーティング組成物が、全固形分に基づいて、約0.2重量%~約1.8重量%の前記シリコーン架橋剤を含み、前記コーティング組成物が、前記コーティング組成物の重量に基づいて、約75重量%~約99.5重量%の有機溶媒を更に含む、請求項1に記載の医療用具。
- 前記コーティング組成物が、全固形分に基づいて、約0.0004重量%~約0.0036重量%の白金触媒を含み、前記コーティング組成物が、前記コーティング組成物の重量に基づいて、約75重量%~約99.5重量%の有機溶媒を更に含む、請求項1に記載の医療用具。
- 前記コーティング組成物が、キシレン、トルエン、ペンタン、ヘキサン、ヘプタン、オクタン、高分子量オレフィンの混合物、及びこれらの組み合わせからなる群から選択される溶媒を更に含む、請求項1に記載の医療用具。
- 前記医療用具が、ステンレス鋼、PTFE、ガラス、セラミクス、ポリマー、高融点金属合金、記憶合金、並びに金属及び非金属の複合材からなる群から選択される生体適合性材料を含む、請求項1に記載の医療用具。
- 前記医療用具が、外科用縫合針、縫合糸、皮下針、外科用メス、カテーテル、切刃、外科用プローブ、内視鏡、ハサミ、及び切刃からなる群から選択される、請求項1に記載の医療用具。
- 前記医療用具が、外科用縫合糸を含む、請求項17に記載の医療用具。
- 前記コーティングが、非架橋性シロキサンを更に含む、請求項1に記載の医療用具。
- 前記非架橋性シロキサンが、トリメチルシリル末端ポリジメチルシロキサンである、請求項19に記載の医療用具。
- コーティング組成物であって、
反応性官能基を有する架橋性シリコーンポリマー、
任意選択で、シリカ含有組成物、
任意選択で、非架橋性シロキサン、
シリコーン架橋剤、
抗菌剤、及び
触媒、を含み、前記触媒が、以下の式:
Pt[(CH2=CH)(CH3)2Si]2O・C6H10(OH)(C=CH)
を有する白金ジビニルテトラメチルジシロキサンビニルシクロヘキサノール錯体から本質的になる、コーティング組成物。 - 前記組成物が、約70℃を超える温度で硬化可能である、請求項21に記載のコーティング組成物。
- 前記組成物が、約95℃の温度において約2分で硬化可能である、請求項22に記載のコーティング組成物。
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