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US-12617912-B2 - Laminate and medical device

US12617912B2US 12617912 B2US12617912 B2US 12617912B2US-12617912-B2

Abstract

Provided is a laminate having high sterilization resistance and suitable as a medical device constituent component and a medical device including the laminate. The laminate has a substrate, an interlayer on the substrate, and a polymer coating layer on the interlayer. The interlayer has a porous layer including a siloxane compound, and the siloxane compound has at least one of a constituent component derived from a compound bearing a reactive functional group and a hydrolyzable group or a constituent component derived from a compound bearing a hydrolyzable group having a reactive functional group.

Inventors

  • Yoshihiro Nakai
  • Kazushi Furukawa

Assignees

  • FUJIFILM CORPORATION

Dates

Publication Date
20260505
Application Date
20230530
Priority Date
20201224

Claims (20)

  1. 1 . A laminate comprising a substrate, an interlayer on the substrate, and a polymer coating layer on the interlayer, wherein the interlayer has a porous layer including a siloxane compound and a primer layer on the porous layer, the siloxane compound has at least one of a constituent component derived from a compound bearing a reactive functional group and a hydrolyzable group or a constituent component derived from a compound bearing a hydrolyzable group having a reactive functional group, and the porous layer has an average pore size of 100 nm to 10 μm.
  2. 2 . The laminate according to claim 1 , wherein the reactive functional group includes at least one of an amino group, a (meth)acryloyl group, a mercapto group, a phosphorus-containing group, or an acyl group.
  3. 3 . The laminate according to claim 1 , wherein the interlayer is the porous layer, the siloxane compound included in the porous layer is a dehydrated condensate of at least one of an alkoxysilane compound or a hydroxysilane compound and at least one of a silane coupling agent, a titanium alkoxide compound, a zirconium alkoxide compound, or an aluminum alkoxide compound, and the silane coupling agent, the titanium alkoxide compound, the zirconium alkoxide compound, and the aluminum alkoxide compound have the reactive functional group.
  4. 4 . The laminate according to claim 3 , wherein the siloxane compound included in the porous layer is a dehydrated condensate of at least one of an alkoxysilane compound or a hydroxysilane compound and a silane coupling agent, and the silane coupling agent has the reactive functional group.
  5. 5 . The laminate according to claim 1 , wherein the substrate includes at least one of iron, a nonferrous metal, an inorganic material other than metal, or an organic material.
  6. 6 . The laminate according to claim 5 , wherein the substrate includes the nonferrous metal and the nonferrous metal includes at least one of aluminum, titanium, magnesium, nickel, copper, lead, zinc, tin, chromium, tungsten, cobalt, or an alloy of at least two of these metals.
  7. 7 . The laminate according to claim 5 , wherein the substrate includes the inorganic material other than metal and the inorganic material other than metal includes at least one of glass or ceramic.
  8. 8 . The laminate according to claim 5 , wherein the substrate includes the organic material and the organic material includes at least one of a thermoplastic resin or a thermosetting resin.
  9. 9 . The laminate according to claim 1 , wherein the primer layer has a reactive functional group.
  10. 10 . The laminate according to claim 9 , wherein the reactive functional group of the primer layer includes at least one of an amino group, a (meth)acryloyl group, an epoxy group, a mercapto group, an acid anhydride group, a phosphorus-containing group, a hydroxy group, a carboxy group, a sulfonyl group, or an acyl group.
  11. 11 . The laminate according to claim 1 , wherein the primer layer includes at least one of a silane coupling agent, a titanium alkoxide compound, an aluminum alkoxide compound, or a zirconium alkoxide compound.
  12. 12 . The laminate according to claim 11 , wherein the primer layer includes at least one of a titanium alkoxide compound, an aluminum alkoxide compound, or a zirconium alkoxide compound.
  13. 13 . The laminate according to claim 12 , wherein the primer layer includes a titanium alkoxide compound.
  14. 14 . The laminate according to claim 11 , wherein the primer layer includes the titanium alkoxide compound and the titanium alkoxide compound includes a compound represented by general formula (a) or (b): R 1a m1 —Ti—(OR 2a ) 4-m1 General formula (a): O—[Ti—(OR 2a ) 3 ] 2 General formula (b): where R 1a represents a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, an aryl group, or an unsaturated aliphatic group, R 2a represents a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, an alkenyl group, an aryl group, a phosphonate group, or —SO 2 R S1 , where R S1 represents a substituent, and m1 is an integer of 0 to 3.
  15. 15 . The laminate according to claim 14 , wherein the compound represented by general formula (a) or (b) includes at least one atom selected from the group consisting of N, P, and S.
  16. 16 . The laminate according to claim 11 , wherein the primer layer includes the aluminum alkoxide compound and the aluminum alkoxide compound includes a compound represented by general formula (c) or (d): R 1b m2 —Al—(OR 2b ) 3-m2 General formula (c): O—[Al—(OR 2b ) 2 ] 2 General formula (d): where R 1b represents a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, an aryl group, or an unsaturated aliphatic group, R 2b represents a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, an alkenyl group, an aryl group, a phosphonate group, or —SO 2 R S2 , where R S2 represents a substituent, and m2 is an integer of 0 to 2.
  17. 17 . The laminate according to claim 16 , wherein in general formulae (c) and (d), at least one OR 2b has an acetonato structure or an acetato structure.
  18. 18 . The laminate according to claim 11 , wherein the primer layer includes the zirconium alkoxide compound and the zirconium alkoxide compound includes a compound represented by general formula (e) or (f): R 1c m3 —Zr—(OR 2c ) 4-m3 General formula (e): O—[Zr—(OR 2c ) 3 ] 2 General formula (f): where R 1c represents a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, an aryl group, or an unsaturated aliphatic group, R 2c represents a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, an alkenyl group, an aryl group, a phosphonate group, or —SO 2 R S3 , where R S3 represents a substituent, and m3 is an integer of 0 to 3.
  19. 19 . The laminate according to claim 18 , wherein in general formulae (e) and (f), at least one OR 2c has an acetonato structure, an acetato structure, or a lactato structure.
  20. 20 . The laminate according to claim 1 , wherein the polymer coating layer includes at least one of a thermoplastic polymer or a thermosetting polymer.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application is a Continuation of PCT International Application No. PCT/JP2021/043515 filed on Nov. 29, 2021, which claims priority under 35 U.S.C. § 119 (a) to Japanese Patent Application No. 2020-215765 filed in Japan on Dec. 24, 2020. Each of the above applications is hereby expressly incorporated by reference, in its entirety, into the present application. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a laminate and a medical device. 2. Description of the Related Art Siloxane compounds (polysiloxane compounds) are excellent in heat resistance, flexibility, and the like and are widely used as functional materials in the food field, the medical field, and the like. For example, JP2019-151710A discloses a laminate having a support and a cured film on the support. The cured film is obtained by curing a silicone resin composition including an organopolysiloxane having a specific structure, an organosilicon compound having a specific structure, a mineral filler having a specific refractive index and band gap, and a phosphoric acid-based catalyst. According to the technique described in JP2019-151710A, the laminate can reflect ultraviolet rays at a high rate to produce an enhanced sterilization effect in sterilization treatment using ultraviolet rays and has high resistance to ultraviolet rays. JP2010-149294A, JP2003-291256A, and WO2017/111121A disclose laminates each having a substrate and a siloxane compound-containing layer on the substrate. SUMMARY OF THE INVENTION Medical devices used for examining or treating the human body are required to have high degrees of cleanliness, and needs to be washed and disinfected with chemicals after each use. In particular, medical devices that are inserted into or applied to blood vessels, the trachea, the digestive tract, or other body cavities or tissues are required to have high cleanliness at the level of sterilization exceeding disinfection in order to prevent bacterial infection. As such sterilization treatment, sterilization treatment with ethylene oxide gas (EOG) has been widely performed, and application of hydrogen peroxide plasma treatment has also been desired. The surface of a medical device that is subjected to such sterilization treatment is often constituted by a polymer coating layer having a single-layer or multi-layer structure, and the polymer coating layer is formed so as to be close contact with an underlying substrate. When such a laminate is repeatedly subjected to sterilization treatment as described above, constituent materials of the laminate may be, for example, degraded, resulting in a decrease in adhesiveness between polymer layers constituting the laminate or between a polymer layer and a substrate. This decrease in adhesion causes a decrease in medical device performance. Therefore, constituent members of medical devices are required to have high sterilization resistance. It is an object of the present invention to provide a laminate having high sterilization resistance and suitable as a medical device constituent component and a medical device including the laminate. In view of the above-described problems, the present inventors have conducted studies on the formation of a polymer coating layer in a laminate. The studies have demonstrated that the above problems can be solved by employing a configuration in which an interlayer is disposed between a substrate and a polymer coating layer, the interlayer having a porous layer including a siloxane compound, and further incorporating a constituent component derived from a compound bearing a reactive functional group and a hydrolyzable group independent of each other or a constituent component derived from a compound bearing a hydrolyzable group having a reactive functional group into the siloxane compound constituting the porous layer. The present invention has been completed by further conducting studies based on these findings. The above object of the present invention has been achieved by the following means. <1> A laminate having a substrate, an interlayer on the substrate, and a polymer coating layer on the interlayer, wherein the interlayer has a porous layer including a siloxane compound, and the siloxane compound has at least one of a constituent component derived from a compound bearing a reactive functional group and a hydrolyzable group or a constituent component derived from a compound bearing a hydrolyzable group having a reactive functional group. <2> The laminate according to <1>, wherein the porous layer has an average pore size of 50 nm to 100 μm. <3> The laminate according to <2>, wherein the porous layer has an average pore size of 100 nm to 10 μm. <4> The laminate according to any one of <1> to <3>, wherein the reactive functional group includes at least one of an amino group, a (meth)acryloyl group, a mercapto group, a phosphorus-containing group, or an acyl group. <5> The laminate accordi