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Catechol-containing adhesive hydrogel, composition for preparing adhesive hydrogel, and compositions each including said adhesive hydrogel NEW

外国特許コード F200010265
整理番号 K10506US2
掲載日 2020年11月9日
出願国 アメリカ合衆国
出願番号 202016801309
公報番号 20200190362
出願日 令和2年2月26日(2020.2.26)
公報発行日 令和2年6月18日(2020.6.18)
優先権データ
  • 特願2015-106809 (2015.5.26) JP
  • 2016JP65634 (2016.5.26) WO
  • 201715575869 (2017.11.21) US
発明の名称 (英語) Catechol-containing adhesive hydrogel, composition for preparing adhesive hydrogel, and compositions each including said adhesive hydrogel NEW
発明の概要(英語) A hydrogel that adheres to the surface of materials is provided by using as constituent elements a water-soluble main chain monomer, crosslinking agent, polymerization initiator, and adhesive monomer having at least a catechol group in a side chain.
従来技術、競合技術の概要(英語) BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an adhesive hydrogel containing a catechol group, a composition for an adhesive hydrogel, an adhesive including a hydrogel, a bioadhesive, a medical adhesive, a ship bottom antifouling paint, a water-based lubricant, and a coating material for antifouling.
2. Description of the Related Art
A hydrogel is a three-dimensional network structure formed by crosslinking a polymer. Hydrogels are hydrous, endowed with flexibility, rich in absorbency, and present volume phase transition and are therefore utilized in various fields such as medical materials and industrial products. For example, various applications such as wound healing materials to adhere tissues, adhesives of implants, and matrices for drug delivery systems (DDS) are being studied as medical materials.
In recent years, imparting various functions to hydrogels in accordance with their purpose and applying them for the desired purpose have been studied. “Smart gels” in which the gel functions autonomously by sensing an outside stimulus such as heat, electricity, light, or pH are also being actively developed. Although hydrogels that have been imparted various functions in this way are being developed, their application is limited because hydrogels are endowed with virtually no adhesiveness to the surface of other materials such as metals.
The main reasons why hydrogels are not endowed with adhesiveness to the surface of other materials are that water is contained in the three-dimensional network of the crosslinked polymer of the hydrogel and the water content is high and that hydrogels are easily structurally deformed. Various attempts have therefore been made to impart adhesiveness to hydrogels. Methods of introducing photoinitiating groups such as phenylazide groups into a substrate and immobilizing a hydrogel, or affixing after having decomposed part of the gel by an excimer laser have been disclosed to date (Non-patent Documents 1 and 2).
A method of chemically modifying the polymer main chain and introducing an adhesive group has also been disclosed. Patent Document 1 discloses a bioinjectable tissue-adhesive hydrogel having tissue adhesive force through bonding with DOPA (3,4-dihydroxyphenylalanine) or a DOPA derivative. DOPA derivatives are adhesive materials discovered to adhere to the surface of various materials such as rocks, trees, metals, and concrete structures even in environments where mussels typified by common blue mussels are exposed to moist environments and severe tides. The catechol groups included in DOPA secreted from the byssus gland of mussels can adhere firmly to a variety of materials, even in water. Patent Document 1 prepares a hydrogel endowed with adhesiveness by linking a compound having a DOPA derivative to the main chain of a hydrogel.
Patent Document 2 discloses a method for producing a polymer gel endowed with adhesiveness by impregnating a base material porous film with a polymer having a polyacrylate structure or the like in the main chain and a chain-like oligoalkylene oxide structure in a side chain.
特許請求の範囲(英語) [claim1]
1. A composition for preparing adhesive hydrogel including
a water-soluble main chain monomer,
a crosslinking agent,
a polymerization initiator,
an adhesive monomer having a catechol group in a side chain, and
water,
wherein the adhesive monomer is added in a proportion of 5% or more to the total number of mol of the main chain monomer and the adhesive monomer,
and wherein all of the catechol groups of the adhesive monomer can participate in adhesion to a substrate and the hydrogel has a structure in which the catechol groups are present in the polymer in a free state.

[claim2]
2. The composition for preparing adhesive hydrogel according to claim 1, wherein the adhesive monomer is added in a proportion of 8% or more to the total number of mol of the main chain monomer and the adhesive monomer.

[claim3]
3. The composition for preparing adhesive hydrogel according to claim 1, wherein the catechol group is derived from DOPA or a derivative thereof.

[claim4]
4. The composition for preparing adhesive hydrogel according to claim 1, wherein the water-soluble main chain monomer is a vinyl group-containing monomer.

[claim5]
5. The composition for preparing adhesive hydrogel according to claim 1, further comprising an electrolyte and/or a polar solvent.

[claim6]
6. The composition for preparing adhesive hydrogel according to claim 1, wherein the crosslinking agent is a crosslinking agent capable of introducing a three-dimensional crosslinked structure by polymerizable double bonds.

[claim7]
7. An adhesive comprising the composition for preparing adhesive hydrogel according to claim 1.

[claim8]
8. The adhesive according to claim 7, which is used as:
a one-component adhesive wherein the water-soluble main chain monomer, crosslinking agent, polymerization initiator, and adhesive monomer are included in one component, or
a two-component adhesive wherein the water-soluble main chain monomer, crosslinking agent, and adhesive monomer are included in a first component and the polymerization initiator is included in a second component.

[claim9]
9. A method of (i) adhering bone, teeth, or soft tissues, or (ii) of adhering bone, teeth, or soft tissue and a medical member,
with the adhesive of claim 7 in a medical field.

[claim10]
10. The method of adhering according to claim 9, wherein the medical member is a sensor electrode, a stimulation electrode, or an implant.

[claim11]
11. A method of applying an amount of the composition of claim 1 onto a ship bottom effective to antifoul paint.

[claim12]
12. A method of coating a base material with an amount of the composition of claim 1 effective to lubricate the top of the base material.

[claim13]
13. A method of applying an amount of the composition of claim 1 onto a base material effective to antifoul the base material.

[claim14]
14. An adhesive hydrogel including
water,
a water-soluble main chain monomer, and
a crosslinking agent and an adhesive monomer having a catechol group in a side chain,
wherein the adhesive monomer is added in a proportion of 5% or more to the total number of mol of the main chain monomer and the adhesive monomer, and
wherein all of the catechol groups of the adhesive monomer can participate in adhesion to a substrate and the hydrogel has a structure in which the catechol groups are present in the polymer in a free state.

[claim15]
15. The adhesive hydrogel according to claim 14, wherein the adhesive monomer is added in a proportion of 8% or more to the total number of mol of the main chain monomer and the adhesive monomer.

[claim16]
16. The adhesive hydrogel according to claim 14, wherein the catechol group is derived from DOPA or a derivative thereof.

[claim17]
17. The adhesive hydrogel according to claim 14, wherein the water-soluble main chain monomer is a vinyl group-containing monomer.

[claim18]
18. The adhesive hydrogel according to claim 14, further comprising an electrolyte and/or polar solvent.

[claim19]
19. The adhesive hydrogel according to claim 14, wherein the crosslinking agent is a crosslinking agent capable of introducing a three-dimensional crosslinked structure by polymerizable double bonds.

[claim20]
20. A method of adhering biological materials, or of adhering biological materials and a biological member, with the adhesive hydrogel of claim 14.

[claim21]
21. A method for synthesizing an adhesive hydrogel including (i) a step of preparing a prepolymer aqueous solution containing a composition of claim 1, and (ii) a polymerization initiation step for conducting a polymerization initiation reaction in the prepolymer aqueous solution.

[claim22]
22. An adhesive containing an adhesive hydrogel of claim 14, said adhesive used as:
a one-component adhesive where the water-soluble main monomer, crosslinking agent, polymerization initiator, and adhesive monomer are included in one component or
a two-component adhesive where the water-soluble main monomer, crosslinking agent, and adhesive monomer are included in a first component and the polymerization initiator is included in a second component.

[claim23]
23. A method of (i) adhering bone, teeth, or soft tissues, or (ii) of adhering bone, teeth, or soft tissue and a medical member,
with the adhesive hydrogel of claim 14 in a medical field.

[claim24]
24. The method of adhering according to claim 23, wherein the medical member is a sensor electrode, a stimulation electrode, or an implant.

[claim25]
25. A method of applying an amount of the adhesive hydrogel of claim 14 onto a ship bottom effective to antifoul paint.

[claim26]
26. A method of coating a base material with an amount of the adhesive hydrogel of claim 14 effective to lubricate the top of the base material.

[claim27]
27. A method of applying an amount of the adhesive hydrogel of claim 14 onto a base material effective to antifoul the base material.

[claim28]
28. A composition for preparing adhesive hydrogel including a water-soluble main chain monomer, a crosslinking agent, a polymerization initiator, an adhesive monomer having a catechol group in a side chain, and water, provided that any inorganic nano-silicate in not included.

[claim29]
29. An adhesive hydrogel including water, a water-soluble main chain monomer, a crosslinking agent and an adhesive monomer having a catechol group in a side chain, provided that any inorganic nano-silicate in not included.

[claim30]
30. The composition for preparing adhesive hydrogel according to claim 28, substantially composed of a water-soluble main chain monomer, a crosslinking agent, a polymerization initiator, an adhesive monomer having a catechol group in a side chain, agents which is used to make buffer action in the adhesive hydrogel and water, and wherein the adhesive monomer is added in a proportion of 5% or more to the total number of mol of the main chain monomer and the adhesive monomer.

[claim31]
31. The adhesive hydrogel according to claim 29, substantially composed of water, a water-soluble main chain monomer, a crosslinking agent and an adhesive monomer having a catechol group in a side chain, and agents which is used to make buffer action in the adhesive hydrogel, and wherein the adhesive monomer is added in a proportion of 5% or more to the total number of mol of the main chain monomer and the adhesive monomer.
  • 発明者/出願人(英語)
  • YABU HIROSHI
  • NISHIZAWA MATSUHIKO
  • NAGAMINE KUNIAKI
  • SAITO YUTA
  • KAMEI JUN
  • SHIMAZAKI TATSUAKI
  • CHIHARA SHUN
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
参考情報 (研究プロジェクト等) PRESTO Molecular technology and creation of new function AREA
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