WO2006090819A1 - Material having polyrotaxane and polymer, and ionic liquid, and method for production thereof - Google Patents

Abstract

Provided are a material which contains a liquid or is swelled by the liquid and which can be swelled by a liquid and exhibits flexibility, stretchability and/or viscoelasticity; and a method for production thereof. The above material which has a first polyrotaxane and a polymer, and an ionic liquid, wherein the first polyrotaxane has a first cyclic molecule, a first linear molecule clathrating the first cyclic molecule in a skewering form and a first sealing group being arranged at both ends of the first linear molecule so as for the first cyclic molecule not to be separated from the first linear molecule, and wherein the first polyrotaxane and at least a part of the polymer are bound via the first cyclic molecule.

Description

 Specification

 Polymouth taxane and polymer, material having ionic liquid, and method for producing the same

 Technical field

 TECHNICAL FIELD [0001] The present invention relates to a polymouth taxane and a polymer, a material having an ionic liquid, and a production method thereof.

 Background art

 [0002] In recent years, attention has been focused on organic substances that are liquid at room temperature and are ionic. This substance is generally called an ionic liquid and is expected to be applied in various fields. For example, an ionic liquid is electrically conductive because it is dissociated into ions at room temperature, and is less likely to evaporate than water. . In addition, it is expected to be applied as an electrolytic solution for a battery having flexibility and using a conductive polymer.

 [0003] However, the development of a flexible conductive polymer battery is still insufficient. For example, in order to provide flexibility, an attempt has been made to include various rubbers in the battery, but the rubber swells with an electrolytic solution, such as water or an ionic liquid, but the content of the electrolytic solution No product has been developed that meets the need for insufficient swelling.

 In addition to flexible conductive polymer batteries, there is a need for the development of materials that have polymer properties together with properties such as stretchability, viscoelasticity, and liquid swelling.

 Disclosure of the invention

 Problems to be solved by the invention

[0004] Therefore, an object of the present invention is to meet the above needs.

Specifically, the object of the present invention is to have a swellability by liquid, represented by a material for a conductive polymer battery having flexibility, and has flexibility, stretchability and Z or viscoelasticity. , A liquid-containing material or a material swollen by a liquid, and a method for producing the same It is in.

 Means for solving the problem

 [0005] As a result of intensive studies aimed at achieving the above object, the present inventors have found that the above-mentioned needs can be met by a material having a polymouth taxane and a polymer and having an ionic liquid. Specifically, the present inventors have found the following invention.

 [0006] <1> A material having a first polymouth taxane and a polymer, and an ionic liquid, wherein the first polymouth taxane is a first cyclic molecule, and the first cyclic molecule is skewered. And a first blockade disposed at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. The above material, which has a group, and in which the first poly (taxane taxane) and at least a part of the polymer are bonded via the first cyclic molecule. Note that the first blocking groups respectively disposed at both ends of the first linear molecule may be the same or different.

 [0007] <2> In the above item <1>, at least a part of the polymer is physically and Z or chemically crosslinked.

 <3> In the above <1> or <2>, the ionic liquid is non-volatile and has a melting point of −100 ° C. or higher, preferably −100 to 150 ° C., more preferably −100 to 100 ° C. It is good to be.

 <4> In any one of the above items 1) to <3>, the ionic liquid is 1,3-dialkylimidazolium salt, N-pyridinium salt, tetraalkylammonium salt, and tetraalkylphosphonium salt. Powerful group power The compound should be chosen.

[0008] <5> In any one of the above items <1> to <4>, the material has a maximum swelling ratio to a state in which a dry state force that does not include an ionic liquid also includes a state in which the ionic liquid is saturated. When the weight in dry state is 1, the weight is 1. 1.1 or more, preferably 2 to: LOO, more preferably 5 to 50.

 <6> In any one of the above items <1> to <5>, the material has a maximum elongation ratio of 5% or more, preferably 5 to 5000%, more preferably 5 to 5% in a state of saturating the ionic liquid. : It should be LOOO%.

<7> In any one of the above items <1> to <6>, the material saturates the ionic liquid. Young's modulus power in the state of containing in the range of 00, OOOPa or less, preferably 1,000 to 50, OOOPa, more preferably ί to 5,000 to 20, with power of OOOPa.

[0009] <8> In any one of the above items 1> to <7>, the weight ratio of the first poly (oral taxane) to the polymer ((first poly (oral) taxane) / (polymer)) is 1Z1000 or more. No, no.

 <9> In any one of the above items <1> to <8>, the polymer has an OH group, an NH group, a COOH group, an epoxy group, a bur group, a thiol group, and a photocrosslink in the main chain or side chain.

 2

 It should have at least one selected group power. Examples of the photocrosslinking group include, but are not limited to, cinnamate, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridium salt, and styrylquinolium salt.

 <10> In any one of the above items <1> to <9>, the polymer is a second polymouth taxane, and the second polymouth taxane is a second cyclic molecule, the second cyclic mouth A second linear molecule that includes the molecules in a skewered manner, and a second linear molecule that is disposed at both ends of the second linear molecule so that the second cyclic molecule is not detached from the second linear molecule. Preferably, the first polyrotaxane has at least two blocking groups, and at least a part of the first polyrotaxane and the second polymouth taxane are bonded via the first cyclic molecule and the Z or second cyclic molecule. Note that the second polymouth taxane may be the same as or different from the first polyrotaxane. The second cyclic molecule may be the same as or different from the first cyclic molecule. The second linear molecule may be the same as or different from the first linear molecule. The second blocking group may be the same as or different from the first blocking group. The first and second poly (oral) taxanes are force only through the first cyclic molecule, only through the second cyclic molecule, or through the first and second cyclic molecules. , Good to join.

[0011] <11> According to any one of the above items <1> to <10>, the first and the seventh or second linear molecule is a linear molecule is polybulal alcohol or polybulurpyrrolidone. , Poly (meth) acrylate, cellulose-based resin (carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, etc.), polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, polybulacetal resin, polyvinyl Polyolefin resins such as nyl methyl ether, polyamine, polyethyleneimine, casein, gelatin, starch, etc. and Z or copolymers thereof, polyethylene, polypropylene, and other resin monomers. Polyester resin, poly salt Polybutyl resin such as polystyrene resin, polystyrene and acrylonitrile styrene copolymer resin, polymethyl methacrylate and (meth) acrylate copolymer, Atari mouth-trimethyl ester copolymer resin Acrylic resin, polycarbonate resin, polyurethane resin, salt resin resin copolymer resin resin, polybutyl petroleum resin, etc .; and derivatives or modified products thereof, polyisobutylene, polytetrahydrofuran, polyary , Acrylonitrile-butadiene-styrene copolymers (ABS resin), polyamides such as nylon, polyimides, polyisoprene, polybutadienes such as polybutadiene, polysiloxanes such as polydimethylsiloxane, polysulfones, polyimines, Polyacetic anhydrides, polyureas, police For example, polyethylene glycol, polyisoprene, polyisobutylene, polybutadiene, polypropylene, selected from the group consisting of fluids, polyphosphazenes, polyketones, polyphenylenes, polyhaloolefins, and derivatives thereof. Pyrenelicol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and a group strength consisting of polypropylene are also selected, preferably a group force consisting of polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and polypropylene is also selected. Particularly preferred is polyethylene glycol.

 <12> In any one of the above items 1 to <11>, the first and Z or second linear molecules have a molecular weight of 10,000 or more, preferably 20,000 or more, more preferably 350,000. That's it.

<13> In any one of the above items <1> to <12>, the first and Z or second blocking groups are dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, Pyrenes, substituted benzenes (substituents include, but are not limited to, alkyl, alkyloxy, hydroxy, halogen, sheared sulfol, carboxyl, amided phenyl, etc. Or a polynuclear aromatic that may be substituted (the substituents include, but are not limited to, the same as above. One or more substituents may be present) It is good to be selected.) The group consisting of dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, and pyrenes is preferably selected, more preferably adamantane groups or trityl groups. It is good.

 [0013] <14> In any one of the above items 1> to 13>, the first and Z or the second cyclic molecule may be an —OH group, an —NH group, a —COOH group, an epoxy group, a vinyl group, A thiol group, and

 2

 It is preferable to have at least one selected from the group power of photocrosslinking group power. Examples of the photocrosslinking group include, but are not limited to, cinnamate, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridium salt, and styrylquinolium salt.

 <15> In any one of the above <1> to <14>, the first and Z or the second cyclic molecules may be substituted, and may be cyclodextrin molecules! /.

 <16> In any one of the above <1> to <15>, the first and Z or second cyclic molecules may be substituted cyclodextrin molecules, and the cyclodextrin molecules are a-cyclodextrin, β-cyclodextrin and γ-cyclodextrin, and their derivative power, group power should be selected.

[0014] <17> According to any one of <1> to <16> above, α-cyclodextrin, wherein the first and seventh or second cyclic molecules may be substituted, And Ζ or the second linear molecule may be polyethylene glycol.

<18> In any one of the above items <1> to <17>, when the first and second ridges or the second cyclic molecule are clasped by the first and second or second linear molecules. Assuming that the amount by which the first and second or second cyclic molecules are maximally included is 1, the first and second or second cyclic molecular forces ^s O.001 to 0.6, preferably ί or 0.01 to It is preferable to be included in a skewered manner in the first and second or second linear molecules in an amount of 0.5, more preferably 0.05 to 0.4.

 <19> In any one of the above items 1> to <18>, the polymer and the cyclic molecule of the first polyrotaxane are chemically bonded by a cross-linking agent.

<20> In the above item 19>, the crosslinking agent may have a molecular weight of less than 2000, preferably less than 1,000, more preferably less than 600, and most preferably less than 400.

 <21> In the above <19> or <20>, the crosslinking agent is cyanuric chloride, trimesyl chloride, terephthalic mouthlid lid, epichlorohydrin, dibromobenzene, glutaraldehyde, phthalenediocyanate, diisocyanic acid. Trilein, divinyl sulfone, 1,1,

-Group power consisting of carbodiimidazole and alkoxysilanes. Yes.

 [0016] <22> In any one of the above items 1> to <21>, the material is a lithium ion battery, a fuel cell, a solar cell, an actuator, an electric double layer capacitor, a light emitting element, an electochromic element, a sensor, Water circuit, polymer electrolyte, electrochemical material, catalyst, separation membrane, and coating power

<23> In any one of the above items <1> to <22>, the material may be a comparative material using dimethyl sulfoxide instead of an ionic liquid, and the storage modulus may be 1 and 1. In this case, the swelling ratio of the material is 0.1 to 10, preferably 0.3 to 3, more preferably 0.8 to 1.5, and the storage elastic modulus is 0.1 to 15, preferably 0. 2 to 5, more preferably 0.3 to 1.3.

[0017] <24> A method for producing a material having a first polymouth taxane and a polymer, and an ionic liquid,

 a) mixing the first cyclic molecule and the first linear molecule in a liquid and including the first cyclic molecule in a skewered manner in the first linear molecule;

 b) A step of preparing a first poly (taxane) taxane by arranging first blocking groups at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. ;

 c) mixing the first polymouth taxane with the polymer; and

 d) binding at least a part of the polymer and the polyortaxane via the first cyclic molecule to obtain a conjugate;

 e) 1) Force to use ionic liquid as a) process liquid 2) b) Process to be performed in ionic liquid, 3) c) Process to be performed in ionic liquid, 4) Process d) Or 5) d) dipping the conjugate obtained in step d into the ionic liquid to obtain the material, or any one of the above 1) to 5) 2 Using the combination of species to 5 species.

 [0018] <25> In the above item 24>, it is preferable to obtain a material by the step e) -5).

<26> In the above 24 or 25, d) using dimethyl sulfoxide as a solvent in step d); e) In step 5), the dimethyl sulfoxide-containing conjugate is immersed in water to replace the dimethyl sulfoxide with water;

 Next, the conjugate containing water is immersed in a mixed solvent of a volatile solvent and an ionic liquid to replace the water with the mixed solvent;

 Furthermore, it is better to obtain a material by immersing a conjugate containing a mixed solvent in an ionic liquid.

<27> In the above 24>, it is preferable to use an ionic liquid as the liquid in step e) -1). In addition, it is preferable to use an ionic liquid as a liquid used in the steps after the a) step.

[0019] In <28> above 24>, it is preferable to obtain a material by the step e) -2). That is, b) It is preferable to use an ionic liquid in the first polymouth taxane preparation step. In addition, b) Use an ionic liquid as the liquid to be used in the processes after step! /.

 <29> In the above 24>, it is preferable to obtain the material by the step e) -3). That is, it is preferable to use an ionic liquid in the c) mixing step. In addition, it is preferable to use an ionic liquid as a working liquid in the steps after the c) step.

 <30> In the above 24>, it is preferable to obtain a material by the step e) -4). That is, d) It is preferable to use an ionic liquid in the step of obtaining the conjugate. In addition, it is preferable to use an ionic liquid as a liquid to be used in the processes after the d) process.

[0020] <31> A method for producing a material having a first poly-ortaxane and a polymer, and an ionic liquid,

 a ′) mixing the first cyclic molecule and the first linear molecule in a liquid and including the first cyclic molecule in a skewered manner in the first linear molecule;

 b ′) A first poly (taxane) taxane is formed by disposing first blocking groups at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. C ′) mixing the first poly (taxane) taxane with the monomer constituting the polymer; d ′) polymerizing the monomer to form the polymer; and

 e ′) binding at least a part of the polymer and the poly (taxane) taxane via the first cyclic molecule to obtain a conjugate;

f) 1) a liquid using an ionic liquid as the liquid in step a ′), 2) performing the step b ′) in the ionic liquid, or 3) performing the step c ′) in the ionic liquid. 4) Step d ') 5) The e ′) step is performed in an ionic liquid, or 6) The conjugate obtained in the e ′) step is immersed in the ionic liquid to obtain the material. Or a combination of 2 or 6 kinds of displacement force of 1) to 6) above.

[0021] <32> In the above 31>, it is preferable to obtain a material by the steps f,) 1).

 33> Above 31> or 32>! /, E, e))! Use dimethyl sulfoxide as a solvent in the step;

 f ′) In step 6), the conjugate containing dimethyl sulfoxide is immersed in water to replace the dimethyl sulfoxide with water;

 Next, the conjugate containing water is immersed in a mixed solvent of a volatile solvent and an ionic liquid to replace the water with the mixed solvent;

 Further, it is preferable to obtain the material by immersing a conjugate containing a mixed solvent in an ionic liquid.

 In the above 34> Above 31>, f,) 1) The ionic liquid should be used as the liquid in the process. In addition, an ionic liquid is preferably used as a liquid used in the steps after the step a ′).

 <35> In the above 31>, the material is preferably obtained by the f ')-2) step. That is, b ') It is preferable to use an ionic liquid in the first step of preparing the poly-ortaxane. Also, b,) Use ionic liquid as the liquid to be used in the processes after the process! /.

<36> In the above item 31>, it is preferable to obtain a material by the step f ′)-3). That is, it is preferable to use an ionic liquid in the c ′) mixing step. Further, it is preferable to use an ionic liquid as a working liquid in the processes after the c,) process.

 <37> Above 31>! /, F ') -4) You can get the material by the process! / ,. That is, d ') In the polymer formation step, an ionic liquid is preferably used. In addition, it is preferable to use an ionic liquid as a liquid to be used in the processes after step d).

 <38> In the above 31>, the material is preferably obtained by the f ')-5) step. That is, an ionic liquid is preferably used in the step of obtaining e ′) conjugate. In addition, it is preferable to use an ionic liquid as the liquid to be used in the processes after e ').

<39> In any one of the above items 24> to <38>, at least a part of the polymer may be physically and Z or chemically crosslinked. <40> In any one of the above items 24> to <39>, the ionic liquid is non-volatile and has a melting point of −100 ° C. or higher, preferably −100 to 150 ° C., more preferably −100 to 100 It should be ° C.

 <41> In any one of the above items 24> to <40>, the ionic liquid includes 1,3-dialkylimidazolium salt, N-pyridinium salt, tetraalkylammonium salt, and tetraalkylphosphonate. -Um salt power Group power It should be the compound chosen.

[0024] <42> In any of the above <24> to <41>, the material has a maximum swelling rate from a dry state containing no ion liquid to a state containing a ionic liquid in saturation. However, when the weight of the material in terms of dry weight is 1, it is 1. 1 or more, preferably 2 to: LOO, more preferably 5 to 50.

 <43> In any one of the above items 24> to <42>, the material has a maximum elongation ratio of 5% or more, preferably 5 to 5000%, more preferably, in a state containing a ionic liquid in a saturated manner. 5 ~: LOOO%! / ヽ.

 <44> In any one of the above items 24> to <43>, the material has a Young's modulus of 100, OOOPa or less, preferably 1,000-50, 0 OOPa, in a state containing a ionic liquid in a saturated manner. Preferably ί until 5,000-20, the power of having OOOPa ^ yo!

[0025] <45> In any one of the above items 24> to <44>, the weight ratio of the first poly (taxane taxane) to the polymer ((the first poly (taxane taxane)) / (polymer)) is 1/1000. That's it ヽ

<46> In any one of the above items <24> to <45>, the polymer may have —OH group, —NH group, —COOH group, epoxy group, vinyl group, thiol group, and light in the main chain or side chain.

 2

 It is preferable to have at least one selected from the group consisting of crosslinking groups. Examples of the photocrosslinking group include, but are not limited to, cinnamate, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridium salt, and styrylquinolium salt.

[0026] <47> In any one of the above items 24> to <46>, the polymer is a second polyoral taxane, and the second polyoral taxane includes a second cyclic molecule, the second The second linear molecule that includes the cyclic molecule in a skewered manner, and the second linear molecule is arranged at both ends of the second linear molecule so that the second cyclic molecule is not detached from the second linear molecule. Having a second blocking group and the first poly The oral taxane and at least a part of the second poly-taxane are preferably bonded via the first cyclic molecule and Z or the second cyclic molecule. Note that the second poly (oral) taxane may be the same as or different from the first poly (oral) taxane. The second cyclic molecule may be the same as or different from the first cyclic molecule. The second linear molecule may be the same as or different from the first linear molecule. The second blocking group may be the same as or different from the first blocking group. The first and second polymouth taxanes are: force only via the first cyclic molecule, only via the second cyclic molecule, or via the first and second cyclic molecules, Good to join

<48> In any one of the above items <24> to <47>, the first and Z or second linear molecules are selected from the group consisting of polybulal alcohol, polybutylpyrrolidone, and poly (meth) acrylic. Acid, cellulose-based resin (carboxymethylcellulose, hydroxyethyl cellulose, hydroxypropylcellulose, etc.), polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, polybulacetal resin, polyvinyl methyl ether, polyamine, Polyolefin resin such as polyethyleneimine, casein, gelatin, starch, etc. and Z or copolymers thereof, polyethylene, polypropylene, and other resin monomers, polyolefin resin, polyester resin, polysalt Vulcanized resin, polystyrene and acryloni Polystyrene-based resins such as silyl styrene copolymer resin, acrylic resin such as polymethyl methacrylate and (meth) acrylic acid ester copolymer, Atari mouth-trimethyl methacrylate copolymer resin, polycarbonate Resin, Polyurethane resin, Salt-Buyl Acetic acid copolymer copolymer resin, Polybutyral resin, etc .; and derivatives or modified products thereof, Polyisobutylene, Polytetrahydrofuran, Polyarylene, Acrylonitrile-Butadiene-Styrene Copolymers (ABS resin), polyamides such as nylon, polyimides, polygens such as polyisoprene and polybutadiene, polysiloxanes such as polydimethylsiloxane, polysulfones, polyimines, polyacetic anhydrides, polyurea , Polysulfides, polyphosphazenes, polyke For example, polyethylene glycol, polyisoprene, polyisobutylene, polybutadiene, polypropylene glycol, polytetrahydrofuran, polytetrafluoroethylene, polyhaloolefins, and derivatives thereof are preferably selected from the group consisting of Dimethylsiloxane, polyethylene, and It is preferable to select a group force which is also a polypropylene force. Preferably, a group force consisting of polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and polypropylene is also preferably selected, and polyethylene glycol is particularly preferable.

 [0028] <49> In any one of the above <24> to <48>, the first and Z or second linear molecules have a molecular weight of 10,000 or more, preferably 20,000 or more, more preferably 3 It should be more than 50,000.

 <50> In any one of the above items <24> to <49>, the first and second blocking capacities, dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, pyrenes , Substituted benzenes (substituents include, but are not limited to, alkyl, alkyloxy, hydroxy, halogen, sheared sulfol, carboxyl, amided phenyl, etc. One or more substituents ), Optionally substituted polynuclear aromatics (substituents include, but are not limited to, the same as above. One or more substituents may be present) ), And the power of steroids is a good group power. In addition, it is preferable to select a group consisting of dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, and pyrenes, more preferably adamantane groups or trityl groups. Is good.

 <0029> <51> According to any one of the above <24> to <50>, the first and seventh or second cyclic molecules may be an —OH group, an —NH group, a —COOH group, an epoxy group, Vinyl group, thiol group, and

 2

 It is preferable to have at least one kind selected from the group power of photocrosslinking group power. Examples of the photocrosslinking group include, but are not limited to, cinnamate, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridinium salt, and styrylquinolium salt.

 <52> According to any of the above <24> to <51>, the first and Z or the second cyclic molecule may be substituted, and it may be a cyclodextrin molecule! /, .

<53> According to any one of the above <24> to <52>, the first and Z or the second cyclic molecule may be substituted, and the cyclodextrin molecule is α- Cyclodextrin, β-cyclodextrin and γ-cyclodextrin, and their group powers, which are their derivatives, are also selected. <54> In any of the above <24> to <53>, the first and seventh or second cyclic molecules may be substituted α-cyclodextrin, and the first and The cage or the second linear molecule should be polyethylene glycol.

<55> According to any of the above <24> to <54>, the first and second or second cyclic molecules are clasped by the first and second or second linear molecules. 1 and 場合 or second cyclic molecular force ^s O. 001 to 0.6, preferably ί, where 1 is the maximum amount of inclusion of the first and Ζ or second cyclic molecule. It is preferably included in a skewered manner in the first and second or second linear molecules in an amount of from 0.01 to 0.5, more preferably from 0.05 to 0.4.

 <56> In any one of the above items 24> to <55>, the polymer and the cyclic molecule of the first poly-polytaxane are chemically bonded by a crosslinking agent!

[0031] <57> In the above 56, the crosslinking agent may have a molecular weight of less than 2000, preferably less than 1,000, more preferably less than 600, and most preferably less than 400.

 <58> In the above 56> or 57>, the cross-linking agent is cyanuric chloride, trimesyl chloride, terephthalic mouthlid lid, epichlorohydrin, dibromobenzene, glutaraldehyde, phthalenediocyanate, diisocyanic acid. The group power consisting of trilein, divinylsulfone, 1,1, -carbodiimidazole, and alkoxysilanes should be selected.

 [0032] <59> In any one of the above items 24> to <58>, the material is a lithium ion battery, a fuel cell, a solar cell, an actuator, an electric double layer capacitor, a light emitting element, an electoric chromism element, a sensor, an It is preferably used for at least one selected from the group consisting of a status circuit, a polymer electrolyte, an electrochemical material, a catalyst, a separation membrane, and a coating agent.

 <60> In any one of the above items 24> to <59>, the material has a swelling ratio of 1 and a storage elastic modulus of 1 of a comparative material using dimethyl sulfoxide instead of ionizable liquid. In this case, the swelling ratio of the material is 0.1 to 10, preferably 0.3 to 3, more preferably 0.8 to 1.5, and the storage elastic modulus is 0.1 to 15, preferably Is preferably 0.2 to 5, more preferably 0.3 to 1.3.

The invention's effect [0033] According to the present invention, there are provided a liquid-containing material or a material swollen by a liquid, which has swelling properties due to liquid and has flexibility, stretchability and Z or viscoelasticity, and a method for producing the same. Can do.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0034] Hereinafter, the present invention will be described in detail.

 The present invention provides a material having a first polymouth taxane and a polymer and an ionic liquid. In the material, the first polytaxane is a first cyclic molecule, a first linear molecule that includes the first cyclic molecule in a skewered manner, and a first linear molecule from the first linear molecule. The first blocking group is arranged at both ends of the first linear molecule so that the cyclic molecule is not eliminated. In addition, the material of the present invention is characterized in that the first polymouth taxane and at least a part of the polymer are bonded through the first cyclic molecule. Furthermore, the material of the present invention has an ionic liquid.

 The polymer may be a second polymouth taxane that may be the same as or different from the first polymouth taxane. Further, the first blocking groups respectively disposed at both ends of the first linear molecule may be the same or different.

[0035] The material of the present invention has the following functions by having the above-described configuration. That is, the cyclic molecule can move on the linear molecule. Therefore, when force (tension and Z or stress) is applied to the material, the material can be expanded and contracted by the movement of the cyclic molecule. In addition, the material of the present invention swells with an ionic liquid to form the material, or the first polymouth taxane bonded through the first cyclic molecule and at least a part of the polymer form the ionic liquid. It can be expressed as including. Thus, it is possible to provide a material having both the characteristics of the ionic liquid and the substance composed of the first polyrotaxane and the polymer by containing the ionic liquid, or swelling by the ionic liquid. it can

[0036] Of the materials of the present invention, the case where no ionic liquid is contained will be described with reference to FIG. FIG. 1 shows a conceptual diagram of a substance 1 consisting of a polymer 3 and a first poly-ortaxane 5 in the case of not containing an ionic liquid among the materials of the present invention. The first poly-ortaxane 5 has a first linear molecule 6, a first cyclic molecule 7, and a first blocking group 8. Polymer 3 and The polymer 3 ′ and the poly (taxane taxane) 5 are bonded via a cyclic molecule 7. When a deformation stress in the direction of the arrow is applied to the substance 1 as shown in Fig. 1 (a), the substance 1 can take the form as shown in Fig. 1 (b). That is, since the first cyclic molecule 7 can move along the first linear molecule 6 (in other words, the linear molecule can move in the cyclic molecule), the deformation stress is applied to the material. Can be absorbed within.

 [0037] The material of the present invention has an ionic liquid. Since the substance 1 shown in FIG. 1 is swollen by or contains an ionic liquid, the material has flexibility, swellability, and Z or extensibility.

 [0038] Specifically, the material has a maximum swelling ratio of 1.1 or more, preferably 2 to: LOO, more preferably 5 to 50. Here, the maximum swelling ratio R means that the material does not contain a cationic liquid s, max

 The dry state force is the change in weight when changing to a state that saturates the ionic liquid.

The dry weight of the material Wd is 1, and the saturated state Ws of the ionic liquid is converted into a weight and standardized. Maximum swelling rate R

 s and max can be expressed as the following equation.

R = Ws / Wd ₀

 s, max

 [0039] The material may have a maximum elongation ratio of 5% or more, preferably 5 to 5000%, more preferably 5 to 1 000%. Here, the maximum elongation ratio means a change in length when the material is uniaxially stretched until it breaks in a state of saturating the ionic liquid. That is, when the material is uniaxially stretched with the length L in the state in which the ionic liquid is saturated being set to 1, the material s

Length of material when ruptures L force Extension distance excluding length L of material before extension L — L ext s ext s is converted to the length L of material before extension and standardized. The maximum expansion rate can be expressed by the following formula.

[0040] Furthermore, the material has flexibility. Specifically, the material has a Young's modulus power of 100, OOOPa or less, preferably 1,000 to 50,000 Pa, more preferably 5,000-20, OOOPa in a state containing ionic liquid in a saturated manner. Good. Here, the Young's modulus is a value representing the hardness of a substance from the relationship between strain and force generated in the material when force is applied to the material, and also means flexibility in a certain aspect. That is, when a force F is applied to a material with a cross-sectional area S and the material is stretched uniaxially, the stress applied to the material σ = FZS is expressed as the material elongation ratio ε = (L −L) ext s Ζ It is a value standardized by the ratio to L. The Young's modulus can be expressed by the following formula.

Ε = σ Ζ ε.

 [0041] Further, the material of the present invention has the following characteristics when the swelling ratio of the comparative material using dimethyl sulfoxide instead of the ionic liquid is 1 and the storage elastic modulus is 1. It is good. That is, the material of the present invention has a swelling ratio of 0.1 to 10, preferably 0.3 to 3, more preferably 0.8 to 1.5, and a storage elastic modulus of 0.1 to 15, It is preferably 0.2 to 5, more preferably 0.3 to 1.3.

 The storage elastic modulus E 'and the loss elastic modulus Ε "are defined as the real and imaginary parts of the response obtained when dynamic strain is applied to the material, respectively.

 [0042] In the material of the present invention, the ionic liquid means a compound that is nonvolatile and has a melting point of -100 ° C or higher, preferably -100 to 150 ° C, more preferably -100 to 100 ° C. Say . In the present invention, examples of the ionic liquid include 1,3-dialkylimidazolium salts, N-pyridinium salts, tetraalkylammonium salts, and tetraalkylphosphonium salts, but are not limited thereto. Not. In particular, the ionic liquid is preferably 1,3-dialkylimidazolium salt or N-pyridium salt, more preferably 1-butyl-3-methylimidazolium chloride, 1- Hexyl-3-methylimidazolium chloride is preferred.

 [0043] The polymer in the material of the present invention may be at least partially physically and Z-crosslinked chemically.

 Due to the presence of the first poly-oral taxane in the material of the present invention, the material can be expanded and contracted as described above. In the material of the present invention, the amount of the first polyortaxane depends on the properties required of the material. For example, the weight ratio of the first polyortaxane to the polymer ((first polyrotaxane) / (polymer )) Is over 1/1000.

The polymer of the material of the present invention depends on the properties required for the material, and is not particularly limited. OH group, —NH group, —COOH group, epoxy group, vinyl group,

 2

It is preferable to have at least one selected from the group consisting of all groups and photocrosslinking groups. Examples of the photocrosslinking group include, but are not limited to, cinnamate, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridinum salt, and styrylquinolium salt. I can't.

 [0045] The polymer in the present invention may be a homopolymer or a copolymer. It is possible to have two or more types of polymers. When two or more types of polymers are used, at least one type of polymer is bonded to the poly (taxane) taxane via a cyclic molecule. When the polymer of the material of the present invention is a copolymer, it may be composed of two, three or more monomers. When it is a copolymer, it may be one of a block copolymer, an alternating copolymer, a random copolymer, a graft copolymer, and the like.

 [0046] Examples of the polymer include poly (bull alcohol), poly (b) pyrrolidone, poly (meth) acrylic acid, cellulose-based resin (carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, etc.), polyacrylamide, polyethylene oxide, Polyethylene glycol, polypropylene glycol, poly (bucacetal) resin, poly (butyl methyl ether), polyamine, polyethyleneimine, casein, gelatin, starch, etc. and their copolymers, polyethylene, polypropylene, and other olefin monomers Polyolefin resins such as copolymer resins, polyester resins, polysalt resin resins, polystyrene resins such as polystyrene and acrylonitrile styrene copolymer resins, and polymethyl resins Acrylic resin such as metatalylate, (meth) acrylic acid ester copolymer, acrylonitrile-methyl acrylate copolymer resin, polycarbonate resin, polyuretan resin, salt butyl acetate copolymer resin, poly Bulputilal resin, etc .; and derivatives or modified products thereof, polyisobutylene, polytetrahydrofuran, polyarine, acrylo-tolyl-butadiene-styrene copolymer (ABS resin), polyamides such as nylon, Polyenes such as polyimides, polyisoprene and polybutadiene, polysiloxanes such as polydimethylsiloxane, polysulfones, polyimines, polyacetic anhydrides, polyureas, polysulfides, polyphosphazenes, polyketones, polyphenols -Len, Polynorolephine, and this Force can be given al derivatives have such limitation. Derivatives include the above-mentioned groups, that is, OH groups, NH groups, COOH groups, epoxy groups.

 2

 It is preferable to have at least one selected from the group consisting of a silyl group, a bur group, a thiol group, and a photocrosslinking group.

[0047] Polyvinyl alcohol as the first linear molecule of the first poly-ortaxane of the material of the present invention. , Polybutylpyrrolidone, poly (meth) acrylic acid, cellulosic resin (carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, etc.), polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, polybulu Acetal-based resin, polymethyl ether, polyamine, polyethyleneimine, casein, gelatin, starch, etc., and copolymers of Z or copolymers thereof, polyethylene, polypropylene, and other olefinic monomers, etc. Polyolefin resins, polyester resins, polyvinyl chloride resins, polystyrene resins such as polystyrene and atta-tolyl-styrene copolymer resins, polymethylmetatalylate and (meth) acrylic acid esters Copolymers, acrylic resins such as acrylonitrile-methyl acrylate copolymer resin, polycarbonate resins, polyurethane resins, salt resins, vinyl acetate copolymer resins, polyvinyl butyral resins, etc .; and their derivatives Or modified product, polyisobutylene, polytetrahydrofuran, polyaniline, acrylonitrile-butadiene-styrene copolymer (ABS resin), polyamides such as nylon, polyimides, polygens such as polyisoprene and polybutadiene, polydimethylol Polysiloxanes such as siloxane, polysulfones, polyimines, polyacetic anhydrides, polyureas, polysulfides, polyphosphazenes, polyketones, polyphenylenes, polyhaloolefins, and derivatives thereof For example, Polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and may be between good tool especially polyethylene glycol that group forces also selected of polypropylene.

 The first linear molecule in the present invention has a molecular weight of 10,000 or more, preferably 20,000 or more, more preferably 350,000 or more.

The first blocking group of the first poly (taxane) taxane of the material of the present invention is not particularly limited as long as the first cyclic molecule has a function that does not desorb the first linear molecular force. Nitrophenyl groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, pyrenes, substituted benzenes (substituents include alkyl, alkyloxy, hydroxy, halogen, cyanurized sulfol, carboxyl, amino However, the present invention is not limited thereto, and one or more substituents may be present), or may be substituted, but may be a polynuclear aromatic (the above-mentioned substituents may be Can mention the same Power s is not limited to these. One or more substituents may be present. ), And the power of steroids. In addition, it is preferably selected from the group consisting of dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, and pyrenes, more preferably adamantane groups or trityl groups. There should be.

 [0049] The first cyclic molecule of the first poly-ortaxane of the material of the present invention is an -OH group, -NH group,

 2 It should have at least one selected from the group consisting of COOH group, epoxy group, bur group, thiol group, and photocrosslinking group. Examples of the photocrosslinking group include, but are not limited to, cinnamate, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridium salt, and styrylquinolium salt.

[0050] The first cyclic molecule is an optionally substituted cyclodextrin molecule. The cyclodextrin molecule is _α -cyclodextrin, / 3-cyclodextrin and γ-cyclodextrin, and derivatives thereof. It is good to choose the group power that is also power.

 At least a portion of the first cyclic molecule in the first polymouth taxane binds to at least a portion of the polymer as described above. At this time, a group that the cyclic molecule has, for example, a ΟΗ group, a ΝΗ group, a COOH group, an epoxy group, a bur group, a thiol group, and a photocrosslinking group,

2

 Groups the polymer has in the main chain and Ζ or side chain, e.g. ΟΗ group, -ΝΗ group, -COO

 2

 It is preferable to bond with a cocoon group, an epoxy group, a bur group, a thiol group, a photocrosslinking group, etc. through a chemical reaction.

 [0051] In the case where the second poly-ortaxane is used as the polymer, a) the first cyclic molecule of the first poly-ortaxane, the second poly-ortaxane, and the force. Or b) the second cyclic molecule of the second polyditaxane and the first polyditaxane are in the first or second cyclic molecule. A force that physically or chemically bonds one of the poly (taxane taxanes) and the second cyclic molecule, and c) has both a) and b) bonds. It is good to be. It is preferable that the first and second polymouth taxanes are chemically bonded via the first and second ring molecules.

[0052] In the material of the present invention, an α-cyclodextrin in which a cyclic molecule may be substituted It is preferred that the linear molecule is polyethylene glycol.

 In the material of the present invention, when the amount of cyclic molecules to be maximally included when the cyclic molecules are included in a skewered manner by linear molecules, the cyclic molecule is 0.001 to 0.00. 6, Preferably it is included in a skewered manner in a linear molecule in an amount of 0.01-0.5, more preferably 0.05-0.4.

 [0053] When the inclusion amount of the cyclic molecule is close to the maximum value, the moving distance of the cyclic molecule on the linear molecule tends to be limited. If the moving distance is limited, the degree of expansion and contraction of the material tends to be limited, which is not preferable.

 The maximum inclusion amount of the cyclic molecule can be determined by the length of the linear molecule and the thickness of the cyclic molecule. For example, if the linear molecule is polyethylene glycol and the cyclic molecule is an a-cyclodextrin molecule, the maximum inclusion amount is experimentally determined (see Macromolecules 1993, 26, 5698-5703). All the contents of this document are incorporated in this specification).

 [0054] In the material of the present invention, the polymer and the cyclic molecule of polypolytaxane are preferably chemically bonded by a crosslinking agent.

 The cross-linking agent should have a molecular weight of less than 2000, preferably less than 1000, more preferably less than 600, and most preferably less than 400.

 Cross-linking agents are: cyanuric chloride, trimesoyl chloride, terephthalyl chloride, epoxy hydrin, dibromobenzene, glutaraldehyde, phenolic diisocyanate, trilein diisocyanate, dibisulfone, 1,1, -carbo- Rudiimidazole and alkoxy silanes are the group power of choice.

[0055] Note that when the material of the present invention has the second polymouth taxane, the second polymouth taxane may be the same as or different from the first polymouth taxane. In addition, the second poly mouth taxane

The two linear molecules, the second cyclic molecule, the second blocking group and the like preferably have the same configuration as described above.

[0056] As described above, the material of the present invention can provide flexibility, swelling, and Z or stretchability due to the presence of the first poly-oral taxane. Note that these characteristics depend on the amount of the first polyrotaxane, the amount of inclusion described above, and the like, depending on the characteristics required for the material. Prefer to control the amount.

 The material of the present invention can be applied to a polymer material that requires the above properties. As this polymer material, optical materials, contact lenses, biomaterials, medical materials, tire materials, coating agents, adhesives, etc .; and environment-related materials, daily necessities, civil engineering and building materials, battery-related materials, food, health Examples include, but are not limited to, goods, sports equipment and materials, clothing 'fashion materials, textiles, toys' entertainment materials, art materials, and automotive materials.

 In particular, the material of the present invention includes a lithium ion battery, a fuel cell, a solar cell, an actuator, an electric double layer capacitor, a light emitting element, an electochromism element, a sensor, an iotas circuit, a polymer electrolyte, an electrochemical material, Forces that can be suitably used for catalysts, separation membranes, coating agents, and the like.

 In addition, the application of these materials is not limited to the following forces.

That is, the application range of the material of the present invention includes, for example, rubber bands, packing materials, agar culture media, fabrics, shoe soles such as sports shoes, cushion materials such as helmets and protectors, or shock absorbers, and cushioning materials for automobiles and various devices. (Bumpers), toys, coating materials for friction parts of equipment (for example, coating materials for pump housings or sliding parts), adhesives, sealing materials for sealing, dehumidifying agents or dew condensation removing materials, water beds Similar bed mat fillers, special effects materials or model materials, soft contact lens materials (especially soft contact lens materials with high, moisture content and Z or excellent strength), tire materials , Electrophoretic gels, new ingredients similar to gum, etc., gum for innu, artificial cornea, artificial lens, artificial vitreous, artificial skin Biomaterials including biocompatible materials such as skin, artificial muscle, artificial joints or artificial cartilage, breast augmentation materials, medical materials used outside the body such as poultices or wound dressings, drug delivery systems, earplugs , Wet suits, protective mats on the outfield wall of the baseball field, disposable computer rests, children's ommu, sanitary napkins or adult incontinence products, photographic materials, fragrances, Various paints and coating agents such as coating materials including the above-mentioned coating materials, separation functional membranes, water-swelling rubber, waterproof tape, sandbags Material for pile pulling material, moisture removal material in oil, moisture conditioning material, moisture absorption gelling agent, dehumidifying agent, indoor snow material for ski resorts, fireproof coating for buildings, debris flow prevention material, concrete laying material Concrete products such as waste mud gelling agent, anti-mudging agent, soil water retention agent or seedling culture medium, greening materials such as seedling culture media, chromatographic carrier materials, bioreactor carrier materials, or various elements of fuel cells, such as Examples include various battery materials such as electrolytes.

 [0058] The above-described materials can be manufactured, for example, by the following method.

 That is, one aspect of the method for producing the material of the present invention is:

 a) mixing the first cyclic molecule and the first linear molecule in a liquid and including the first cyclic molecule in a skewered manner in the first linear molecule;

 b) preparing a first poly (taxane) taxane by arranging first blocking groups at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. C) mixing the first polymouth taxane with the polymer; and

 d) binding at least a part of the polymer and the polymouth taxane via the first cyclic molecule to obtain a conjugate;

 e) 1) a) using an ionic liquid as the liquid in step a) 2) whether b) is performed in ionic liquid, 3) whether c) is performed in ionic liquid, 4) ) The step d) is carried out in an ionic liquid, or 5) the conjugate obtained in the step d) is immersed in an ionic liquid to obtain the material, or one of the above 1) to 5) Using any combination of 2 to 5 types.

 [0059] The polymer may be polymerized at least partially before c) step, c) after step d) before step d) after step e) before step, e) during step, or after e) step. It may have physical and Z or chemical cross-linking steps between them.

This crosslinking step is preferably performed under conventionally known polymer crosslinking conditions. For example, the force that can include the following conditions is not limited to these. For example, if a) the polymer has an active substituent such as an epoxy group, a crosslinking reaction can be caused by heating or the presence of active hydrogen such as an amine anhydride. The crosslinking reaction can also be caused by light irradiation in the presence of a photoacid generator or a photobase generator. I) When the polymer has an unsaturated double bond such as a vinyl group, the crosslinking reaction can be caused by heating or light irradiation in the presence of a heat or photo radical generator. C) When the polymer has the above-mentioned photocrosslinking group, a crosslinking reaction can be caused by heating or light irradiation. D) When the polymer has a hydroxyl group, an amino group, a carboxyl group, etc., a bridge reaction can be caused by the presence of multi-position sulfonates, carpositimides, triazines, and silanes. E) If the polymer has various groups, a crosslinking reaction can also be caused by electron beam irradiation.

 [0060] The ionic liquid is preferably used as the liquid in e) 1) step, that is, the liquid in the a) step in which the first linear molecule and the first cyclic molecule are included. In addition, anionic liquid may be used in the steps after the a) step.

 In the case where the ionic liquid is not used in the step a), the ionic liquid may be used in the case of b) the first polymouth taxane preparation step. In this case, it is preferable to replace the previously used solvent by a conventionally known method. Note that ionic liquid should be used in the subsequent steps of b).

 Even if the ionic liquid is not used in the steps a) and b)! /, the ionic liquid may be used in the mixing step. Note that an ionic liquid may be used in the steps after step c).

 a) to c)! /, or any of the steps! Do not use an ionic liquid! /, even if d) use an ionic liquid in the step of obtaining a conjugate Good. Further, an ionic liquid may be used in the steps after step d).

 Furthermore, a) to d) of steps! /, Or any of the steps! In the case where no ionic liquid is used, even if d), the conjugate obtained in step d) is immersed in the ionic liquid. Thus, the material of the present invention can be obtained.

[0061] In the case of obtaining the material of the present invention by immersing the conjugate obtained in step d) in an ionic liquid, the following operation can be performed. That is, the conjugate containing the solvent used in step d) is immersed in water so that the solvent used in step d), for example, dimethyl sulfoxide, is exchanged with water. Next, i) the combined body containing water is immersed in a mixed solvent of a volatile solvent and an ionic liquid to replace the water with the mixed solvent. And iii) including a mixed solvent The conjugate can be immersed in an ionic liquid to obtain a material.

 By performing such an operation, the volatile solvent can be volatilized and taken out of the material. On the other hand, the non-volatile ionic liquid remains in the material, and the material of the present invention can be efficiently prepared. it can.

 [0062] Here, the volatile solvent refers to a solvent that can be distilled off at room temperature and atmospheric pressure or by using a treatment such as reduced pressure or increased temperature. Specifically, it is a solvent having a boiling point of 20 to 150 ° C, preferably 20 to 100 ° C under atmospheric pressure, such as methanol, ethanol, n-propanol, iso-propanol, 1-butanol, 2- Examples include butanol, t-butanol, acetone, dimethyl ether, and jetyl ether.

 The mixed solvent may have a volatile solvent: ionic liquid weight ratio of 9: 1 to 1: 9, preferably 8: 2 to 2: 8.

 [0063] Steps a) and b) can be performed by a conventionally known method. For example, it can be obtained by the method described in Japanese Patent No. 3475252. In this method, when an ionic liquid is used as a solvent, the following points must be noted. In other words, choose an ionic liquid that dissolves both cyclic and linear molecules! / ヽ. In particular, it is preferable to select an ionic liquid capable of dissolving the cyclic molecule at a high concentration so that the cyclic molecule is efficiently included in the skewered form with the linear molecule. In addition, taking advantage of the non-volatile characteristics of ionic liquids, the cyclic molecules and the linear molecules are dissolved at high temperature and then cooled to a low temperature, so that the cyclic molecules are included in a skewered manner in the linear molecules. It can be realized more efficiently.

 [0064] The mixing step of c) depends on the polymer used, but may be performed without a solvent or in a solvent. As described above, an ionic liquid may be used as a solvent. In the case of using a solvent, as the solvent, ionic liquid, water, toluene, xylene, benzene, azole, cyclohexanone, N-methylpyrrolidone, dimethylformamide, dimethylacetamide, methyl ethyl ketone, black mouth form, dichloromethane , Carbon tetrachloride, hexafluoroisopropyl alcohol, tetrahydrofuran, dioxane, acetone, ethyl acetate, dimethyl sulfoxide, acetonitrile, and the like.

[0065] The coupling step d) includes a group that the polymer has in the main chain and Z or side chain, such as an OH group, NH group, COOH group, epoxy group, bur group, thiol group, photocrosslinking group, etc.

2

 A group that a cyclic molecule has, such as OH group, NH group, COOH group, epoxy group,

 2

 It is preferable to carry out by chemically reacting the thiol group, thiol group, photocrosslinking group and the like. The conditions for the bonding step d) depend on the groups possessed by the polymer, the groups possessed by the cyclic molecule, and the like. As the conditions for the bonding step, for example, the above-mentioned crosslinking conditions can be used in the same manner, but are not limited thereto.

 [0066] The material of the present invention can also be produced by the following production method.

 That is, another aspect of the method for producing the material of the present invention is:

 a ′) mixing the first cyclic molecule and the first linear molecule in a liquid and including the first cyclic molecule in a skewered manner in the first linear molecule;

 b ′) A first poly (taxane) taxane is formed by disposing first blocking groups at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. C ′) mixing the first poly (taxane) taxane with the monomer constituting the polymer; d ′) polymerizing the monomer to form the polymer; and

 e ′) binding at least a part of the polymer and the poly (taxane) taxane via the first cyclic molecule to obtain a conjugate;

 f) 1) A liquid that uses an ionic liquid as the liquid in step a ′), 2) The step b ′) is performed in the ionic liquid, or 3) The step c ′) is performed in the ionic liquid. 4) The step d ′) is performed in an ionic liquid, 5) The step e ′) is performed in an ionic liquid, or 6) The conjugate obtained in the step e ′) is ionized. Or a step of using a combination of! / Of the above 1) to 6) and 2 to 6 displacements.

 [0067] In the same manner as in the above-described production method, the polymer is obtained after (1 '), before), e') after step f.

 It may have a step of physically and Z or chemically cross-linking at least a part of the polymer between the polymers before the ') step, during the f') step, or after the f ') step.

[0068] Further, similarly to the above-described production method, the ionic liquid may be used as a liquid in each step a ′) to e ′) or may be used in the subsequent steps. In addition, in any of the steps a,) to e,), even if an ionic liquid is not used, the conjugate obtained in the step e ′) is immersed in an ionic liquid. Thus, the material of the present invention can be obtained. [0069] In the case of obtaining the material of the present invention by immersing the conjugate obtained in step e ') in an ionic liquid, the following operation can be performed. That is, the conjugate containing the solvent used in step e ′) is immersed in water so that the solvent used in step 0e ′), for example, dimethyl sulfoxide, is exchanged with water. Next, ii) the conjugate containing water is immersed in a mixed solvent of a volatile solvent and an ionic liquid to replace the water with the mixed solvent. Further, iii) a material containing a mixed solution containing a mixed solvent is immersed in an ionic liquid;

 By performing such an operation, the volatile solvent can be volatilized and taken out of the material. On the other hand, the non-volatile ionic liquid remains in the material, and the material of the present invention can be efficiently prepared. it can.

 Here, the volatile solvent has the same definition as described above. The mixed solvent is the same as described above.

 [0070] As described above, the steps a ') and b') can be performed by a conventionally known method.

 The mixing step c ′) may be performed without a solvent or a solvent depending on the monomer used. An ionic liquid may be used as a solvent. When a solvent is used, the solvent includes ionic liquid, water, toluene, xylene, benzene, azole, cyclohexanone, N-methylpyrrolidone, dimethylformamide, dimethylacetamide, methylethylketone, black mouth Examples include, but are not limited to, form, dichloromethane, carbon tetrachloride, hexafluoroisopropyl alcohol, tetrahydrofuran, dioxane, acetone, ethyl acetate, dimethyl sulfoxide, and acetonitrile.

 [0071] The conditions of the step of polymerizing monomers to form a polymer (step d, above) depend on the monomer used. Conventionally known conditions can be used for these conditions. The bonding step e ′) can be performed in the same manner as the above-described step d).

[0072] The first and Z or second poly-ortaxane, polymer, first and / or second cyclic molecule, first and Z or second linear molecule, first and second used in the production method of the present invention As Z or the second blocking group, the same as described above can be used. The monomer constituting the polymer depends on the polymer, but is not particularly limited as long as the polymer can be formed. [0073] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to the examples.

 Example 1

 [0074] A crosslinked polymouthtaxane was prepared by the method for producing a crosslinked polymouthtaxane described in Japanese Patent No. 3475252. That is, PEG (molecular weight 35, 000, 6 g), a-cyclodextrin (hereinafter simply abbreviated as “α-CD”, 24 g), inclusion amount 25%, block group: adamantaneamine 0.32 g, And crosslinker: Crosslinked polyrotaxane A-1 was prepared in dimethyl sulfoxide (DMSO) using 1,1, -carbodiimidazole.

 After the solvent in the crosslinked poly (ortaxane A-1) was replaced with water, it was naturally dried for several days using silica gel and the dry weight was measured (dry weight 22.3 mg).

 The dried cross-linked poly-ortaxane A-1 was immersed in an ionic liquid (1-buty But3-methylimidazolium chloride; hereinafter abbreviated as BMIM-CI) at 80 ° C for 2 days or more. BMIM-C1 is an ionic liquid that has a melting point of about 70 ° C and is compatible with water. The swelling rate and elongation characteristics of the crosslinked poly (taxane taxane A-1) swollen with an ionic liquid were measured.

 Cross-linked poly-ortaxane A-1 swollen with an ionic liquid swollen from a dry weight of 22.3 mg to 381 mg, and the swelling ratio was 17 times the dry weight.

 Figure 2 shows the stress-stretching characteristics of the crosslinked poly-ortaxane A-1 in the swollen state (room temperature). From FIG. 2, it is evident that the maximum elongation of the crosslinked poly (ortaxane A-1) in the swollen state (room temperature) is 55% and the Young's modulus is 11,500 Pa.

 Example 2

[0075] Preparation of polypolytaxane C-1>

 <<Preparation of PEG-powered rubonic acid by TEMPO oxidation of PEG>>

10 g of PEG (molecular weight 350,000), 100 mg of TEMPO (2,2,6,6-tetramethyl-1-piberidi-loxy radical), and lg of sodium bromide were dissolved in 100 ml of water. 5 ml of a commercially available sodium hypochlorite aqueous solution (effective chlorine concentration of about 5%) was added to the resulting solution, and the mixture was allowed to react at room temperature with stirring. As the reaction progressed, the pH of the system rapidly decreased immediately after the addition, but was prepared by adding IN NaOH so as to keep the pH: 10 ~: L 1 as much as possible. The pH drop generally disappeared within 3 minutes, but was stirred for another 10 minutes. Ethanol up to 5m The reaction was terminated within the range of Extraction with 50 ml of methylene chloride was repeated 3 times to extract components other than inorganic salts, and then methylene chloride was distilled off with an evaporator. After dissolving in 250 ml of hot ethanol, it was placed in a freezer at -4 ° C to precipitate PEG-strong rubonic acid, that is, one in which both ends of PEG were substituted with carboxylic acid (one COOH). . The precipitated PEG carboxylic acid was recovered by centrifugation. This cycle of hot ethanol dissolution, precipitation, and centrifugal separation was repeated several times, and finally dried by vacuum drying to obtain PEG-powered rubonic acid. Yield over 95%. Carboxy cocoon rate is 95% or more.

 [0076] <<Preparation of inclusion complex using PEG strong rubonic acid and α-CD>>

 After dissolving 3 g of PEG-powered rubonic acid prepared above and 5 g of α-CD7.5 in 50 ml of warm water of 70 ° C prepared separately, both were mixed and then in a refrigerator (4 ° C). I stood still. The inclusion complex precipitated in the form of cream was lyophilized and recovered.

 [0077] <<Sealing of inclusion complex using adamantanamin and BOP reagent reaction system>

 0.13 g of adamantaneamine in the above inclusion complex, 0.38 g of BOP reagent (benzotriazole-1-yl-oxy-tris (dimethylamino) phospho-hexafluorophosphate), diisopropylethylamine A solution obtained by dissolving 0.14 ml in 50 ml of dehydrated dimethylformamide (DMF) was added, shaken well, and then allowed to stand in a refrigerator. Thereafter, 50 ml of methanol was added, and stirring, centrifugation, and removal of the supernatant were performed. Next, 100 ml of DMFZ methanol = 1: 1 mixed solution was added, and the same operation was performed twice. Further, the same operation was performed twice using 100 ml of methanol, and the resulting precipitate was vacuum-dried and then dissolved in 50 ml of dimethyl sulfoxide (DMSO). This solution was added dropwise to 700 ml of pure water to precipitate a polymouth taxane. Precipitated polymouth taxane was collected by centrifugation and dried in vacuum. Further, the same reprecipitation operation was carried out to obtain 19 g of a polymouth taxane C. As a result of NMR measurement of the obtained poly (oral taxane) C 1, the ratio of CD to PEG monomer (molar ratio) was CD: PEG monomer = 11: 100 (inclusion rate: 22%)

 [0078] <<Oxymethylation of α-CD>>

Dissolve 5 g of the polyoral taxane obtained above in dehydrated DMSOlOOml and add 3.8 g of a 28% methanol solution of sodium methoxide (5.4, etc. to 18 equivalents of the hydroxyl group of the α-CD molecule in the polyortaxane). After that, methanol was distilled off under reduced pressure. Methyl iodide 2.8 After adding 24 g and stirring for 24 hours, the reaction solution was diluted to 150 ml with purified water, and the diluted solution was dialyzed in a dialysis tube (fraction molecular weight: 12,000) for 48 hours under running tap water. . Furthermore, dialysis was performed 4 times for 12 hours in 100 ml of purified water and lyophilized to obtain a methyl-polypolytaxane in which a part of the OH group of a-CD was replaced with OCH group. : 30%). Yield

Three

 4. 6g.

 — NMR, (CDC1 — d, 300 MHz) δ (ppm) 3. 0—4.2 (m, 18.4H), 4.8

 3 6

 -5.2 (m, 3.8H), 5.3—6.0 (m, 1H).

[0079] <Preparation of Material of Crosslinked Poly Mouth Taxane and PVA>

 Polybulal alcohol (abbreviated as “PVA”, degree of polymerization: 2000) was dissolved in 0.03N NaOH aqueous solution to prepare 1.0 ml of 5 wt% solution. To this solution was added 10 mg of methyl-polypolytaxane (Mw: 350,000, methylation rate: 30%, inclusion rate: 22%) and dissolved. This blend

PEG

 Add 10 μL of divinylsulfone (hereinafter abbreviated as “DVS”) to the mixture, leave it at 25 ° C for 20 hours, and form a gelled product B— 1 was obtained (PVA: Methyl 匕 poly oral taxane (weight ratio) = 5: 1).

[0080] <Material of gelled product B-1 and ionic liquid>

 The gel weight B-1 was 137 mg when swollen with water. The dry weight after natural drying for several days using silica gel was 5. Omg. BMI M-C1 was immersed in this gely product B-1 for 2 days or more at 80 ° C., and the swelling ratio and elongation property of gely product B-1 swollen with an ionic liquid were measured.

 Gelatin B-1 swollen with ionic liquid swelled from 5. Omg to 312 mg in dry weight, and the swelling ratio was 62 times the dry weight.

 Fig. 3 shows the stress elongation characteristics of Gely B-1 in the swollen state (room temperature). From Fig. 3, it can be seen that the maximum elongation of Gely B-1 in the swollen state (room temperature) is 80% and the Young's modulus is 60 OOPa.

 Example 3

[0081] A dried crosslinked poly (oral taxane) A-1 obtained by the same method as in Example 1 was immersed in an ionic liquid shown in Table 1 below at 80 ° C for 2 days or more. Table 1 shows the swelling ratio, elongation characteristics, and Young's modulus of the crosslinked poly (ortaxane) A-1 swollen with an ionic liquid. [0082] [Table 1] Table 1. Material properties of Examples 1, 3 to 10

[0083] (Example 11)

 The following was used as the ionic liquid.

 1- ethyl- 3-methylimidazolium

 chloride (hereinafter abbreviated as [C MIM] [C1], purchased from Aldrich (Milwaukee, WI)); 1- buty

 2

 1— 3— methylimiaazolium

 chloride (hereinafter abbreviated as [C MIM] [C1], purchased from Fluka); 1- buty 卜 3-methylimidazo

 Four

 lium

 bromide (hereinafter abbreviated as [C MIM] [Br], purchased from Fluka); 1- hexy 卜 3-methylimidazo

 Four

 lium

 chloride (hereinafter abbreviated as [C MIM] [C1], manufactured by Kanto Chemical Co., Inc.); 1-octyto 3-methylimidazoli

 6

 um chloride (hereinafter [C MIM] [C1]

 8

 1-decy 、 3-methylimidazolium chloride (hereinafter referred to as [C MIM]

 Ten

[CI], manufactured by Kanto Chemical Co., Ltd.); and 1-hexylpyridinium

 chloride (hereinafter abbreviated as [C P] [C1], manufactured by Kanto Chemical Co., Inc.).

 6

These ionic liquids were washed with ethyl acetate and evaporated, then kept at 90 ° C for 1 week to equilibrate the water supply. [0084] <Preparation of cross-linked poly (oral taxane) D-1 using 1,6-hexamethylene diisocyanate> As in Example 2, PEG-powered rubonic acid (molecular weight of PEG: 350,000) , A-CD (manufactured by Nippon Shokuhin Co., Ltd.) and polyadataxane C-1 (inclusion rate: 22-25%) prepared using adamantanamine were used.

Polyditaxane acid C-1 (1. Og) was dissolved in dehydrated DMSO (5.6 g) at room temperature. To this was added 1,6-hexamethylene diisocyanate (0.20 g, 1.19 X 10 ^_3 mol) dissolved in dehydrated DMSO (3.2 g). After stirring for several minutes, it was sealed in a silicone mold (14 × 14 × 4 mm) in a dry glove box and gelled at 60 ° C. for 18 hours to obtain a crosslinked polyditaxane D-1. The obtained cross-linked poly (taxane) taxane D-1 was divided into 4 equal parts to give a size of 7 x 7 x 4 mm (each made to be cross-linked polylotaxane D-la-d), and washed with DMSO for 2 days. . In observing the swelling process of this crosslinked poly (oral taxane) D-1, the steps including and not including the drying step were used as follows.

[0085] <Process including drying process>

 The dry gel (abbreviated as “dried SR gel” in FIG. 4 described later) was prepared by subjecting the above-mentioned DMSO-swollen crosslinked poly (oral taxane D-1) to solvent substitution with methanol and then air-drying. Thereafter, the obtained dried gel was immersed in one of the ionic liquids described above to obtain a crosslinked poly (oral taxane D-1) swollen with the ionic liquid.

 Among the swelling of the gel by the ionic liquid, when the drying process was performed, the ionic liquid containing the halogenone swelled the gel. That is, the dried gel is [C MIM] [C1], [

 2

 [C MIM] [C1], [C MIM] [C1], [C MIM] [C1], [C MIM] [C1], [C MIM] [Br], or [C P] [C1]

The gel obtained after immersion in 4 6 8 10 4 6 swelled with these ionic liquids. It should be noted that the cross-linked poly oral taxane D-1 ′ swollen with an ionic liquid has a slightly increased force including a solvent (that is, an ionic liquid). It was.

[0086] <Process without drying process>

In a process that does not include a drying process, that is, a non-drying process, first, the cross-linked poly (taxane taxane) D-1 is solvent-exchanged with water, and then a mixed solvent of one of the above ionic liquids and methanol (weight ratio 8: It was immersed in 2) at room temperature for 2 weeks. After that, the obtained gel is transferred into a new ionic liquid of about 10 times the weight of the gel and immersed in an ionic liquid at 90 ° C. As a result, the methanol was removed by volatilization to obtain a crosslinked poly (oral taxane) D-1 "swollen with an ionic liquid. No shape destruction such as corner cracking of the substantially rectangular parallelepiped was observed, and the substantially rectangular parallelepiped shape similar to that of the cross-linked polymouth taxane D-1 was maintained. FIG. 4 shows a cross-linked poly (oral taxane) D-1 ”swollen with an ionic liquid. In FIG. 4, (a) shows the result obtained by drying the above-mentioned cross-linked poly (oral) taxane D-1. b) to (j) are each swollen with each solvent, among which (d) to (j) are swollen with an ionic liquid, that is, (b) is swollen with water. (C) is swollen with DMS O (cross-linked polymouth taxane D-1), (d) is swollen with [C MIM] [C1], (e

 2

 ) Is swollen with MIM] [C1], (f) is swollen with MIM] [C1], (g) is MIM] [C1]

4 6 8

C1] swollen, (h) swollen with [C MIM] [C1], (i) swollen with [C MIM] [Br]

 10 4

 And G)

 6 Shows swollen p] [ci].

 <Expansion coefficient and storage elastic modulus>

 The dynamic viscoelasticity was measured using TA Instruments RSAIII, in the compression mode, in the atmosphere, with a strain fixed at 3% and a frequency range of 0.01-lOOradZs. The measurement temperature was 90 ° C (above the melting point of the ionic liquid) for ion liquid gel and room temperature for DMSO gel.

 Table 2 shows the swell ratio and storage modulus of cross-linked polymouth taxane swollen with ionic liquid, DMSO and water.

 Even when the alkyl chain length in the ionic liquid molecule was changed, the swelling rate did not change significantly. In addition, the elastic modulus of the cross-linked polymouth taxane swollen with ionic liquid was almost the same as that of the swollen DMSO, which is a good solvent for polyrotaxane. This means that ionic liquids, like DMSO, are good solvents for polyoral taxanes and penetrate well into the network of crosslinked polyoral taxanes to ideally swell the crosslinked polyoral taxanes. Show me.

[0088] [Table 2] Swollen with ionic liquid, DMS O, and water

 Swelling rate and storage modulus of cross-linked polymouth taxanes

 Ionic liquid Swelling rate (W /, w) Storage modulus (kPa)

[C ₂ MIM] [CI] 17.5 19.1 20. 4 62 71

[C ₄ MI] [CI] 14.6 15.6 16. 9 59 56

[C ₈ IM] [CI] 12.9 13.8 15. 1 56 53

[C ₈ MI] [CI] 11.9 12.8 14. 5 49 43

[C ₁₀ MIM] [CI] 14.9 16.7 19. 4 30 23

[C ₄ I] [Br] 13.1 14.3 16. 2 68 74

[C ₆ P] [CI] 11.5 12.4 13. 3 80 75

DMSO-14.0--64

 Water-2.0-650

 S) Shellfish at IB] 2 days 4 days 6 days 2 days 4 days

[0089] Figure 5 shows the frequency dependence of the storage elastic modulus and loss elastic modulus of the cross-linked poly-ortaxane swollen with ionic liquid and DMSO (black mark indicates storage elastic modulus E ', white mark indicates loss elastic modulus. In the low-frequency region, the storage elastic modulus shows a plateau (flat part), and all the cross-linked polymouth taxanes used in this experiment are close to ideal rubber elasticity !, viscoelasticity In addition, it was suggested that there were no significant heterogeneous structures such as aggregates in the cross-linked polymouth taxane.

 Brief Description of Drawings

[0090] FIG. 1 is a conceptual diagram of a substance that does not contain an ionic liquid in the material of the present invention.

 FIG. 2 is a graph showing the stress extension characteristics of Example 1 (crosslinked poly-ortaxane A-1 swollen with an ionic liquid).

 FIG. 3 is a graph showing the stress extension characteristics of Example 2 (Gerui B-1 swollen with an ionic liquid).

 FIG. 4 is a view showing a crosslinked poly (oral taxane) D-1 ”swollen with an ionic liquid.

 FIG. 5 is a graph showing the frequency dependence of storage elastic modulus and loss elastic modulus of a crosslinked poly (oral taxane) swollen with an ionic liquid and DMSO. The black mark shows the storage elastic modulus E ', and the white mark shows the loss elasticity E ".

Claims

The scope of the claims

 [1] A material having a first polymouth taxane and a polymer and an ionic liquid, wherein the first polymouth taxane includes a first cyclic molecule and the first cyclic molecule in a skewered manner. A first linear molecule, and a first blocking group disposed at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. The above material, wherein the first polyrotaxane and at least a part of the polymer are bonded via the first cyclic molecule.

 [2] The material according to claim 1, wherein at least a part of the polymer is physically and Z-crosslinked chemically.

[3] The material according to claim 1 or 2, wherein the ionic liquid is non-volatile and has a melting point of 100 ° C or higher.

 [4] The ionic liquid is selected from the group consisting of 1,3-dialkylimidazolium salts, N-pyridium salts, tetraalkylammonium salts, and tetraalkylphosphonium salts. The material according to any one of claims 1 to 3, which is a compound.

[5] The above-mentioned material has a dry state force that does not contain an ionic liquid. When the maximum swelling ratio to a state that saturately contains an ionic liquid is converted to a weight with the dry state weight of the material being 1, 1.1 or more The material according to any one of claims 1 to 4, wherein:

6. The material according to any one of claims 1 to 5, wherein the material has a maximum elongation ratio of 5% or more in a state in which the ionic liquid is saturated.

7. The material according to any one of claims 1 to 6, wherein the material has a Young's modulus of 100, OOOPa or less in a state containing an ionic liquid in a saturated manner.

[8] The material according to any one of claims 1 to 7, wherein the weight ratio of the first poly (oral taxane) and the polymer ((first poly (or) taxane) / (polymer)) force is S1Z1000 or more. .

[9] The polymer has —OH group, —NH group, —COOH group, epoxy group in the main chain or side chain.

 2

 9. The material according to claim 1 having at least one selected from the group consisting of: a vinyl group, a thiol group, and a photocrosslinking group.

[10] The polymer is a second polymouth taxane, the second polymouth taxane includes a second cyclic molecule, a second linear molecule that includes the second cyclic molecule in a skewered manner, And the second straight A second blocking molecule disposed at both ends of the second linear molecule so that the second cyclic molecule is not detached from the chain molecule; The material according to any one of claims 1 to 9, wherein at least a part of the two polymouth taxanes is bound via the first cyclic molecule and Z or the second cyclic molecule.

 [11] The first and Z or second linear molecules are selected from polyethylene glycol, polyisoprene, polyisobutylene, polybutadiene, polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and a group force that also has polypropylene power. The material according to any one of claims 1 to 10!

 12. The material according to claim 1, wherein the first and Z or second linear molecules have a molecular weight of 10,000 or more.

 [13] The first and Z or second blocking groups may be replaced with dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, pyrenes, substituted benzenes. The material according to any one of claims 1 to 12, which is selected from the group consisting of polynuclear aromatics and steroids.

 [14] The first and Z or second cyclic molecules are OH group, NH group, COOH group, epoxy

 2

 The material according to any one of claims 1 to 13, which has at least one selected from the group consisting of a xyl group, a vinyl group, a thiol group, and a photocrosslinking group.

[15] The material according to any one of [1] to [14], wherein the first and Z or the second cyclic molecule is a cyclodextrin molecule which may be substituted.

[16] A cyclodextrin molecule in which the first and Z or the second cyclic molecule may be substituted, wherein the cyclodextrin molecule is a-cyclodextrin, j8-cyclodextrin, γ-cyclodextrin, and Derivative power Group power Claimed claims 1-1

5 !, slip or 1 item.

[17] The first and second or second cyclic molecules may be substituted α-cyclodextrins, and the first and second or second linear molecules may be polyethylene glycol. Item 1-16 !, slip or material of item 1.

[18] The first and second or second cyclic molecules are the largest when the first and second or second cyclic molecules are skewered by the first and second or second linear molecules. The amount included in the limit 1, the first and Z or second cyclic molecules are skewered by the first and Z or second linear molecules in an amount of 0.001 to 0.6. Material of any one of ~ 17.

 [19] The material according to any one of [1] to [18], wherein the polymer and the cyclic molecule of the first poly (taxane taxane) are chemically bonded by a crosslinking agent.

 20. The material according to claim 19, wherein the cross-linking agent has a molecular weight of less than 2000.

 [21] The cross-linking agent includes cyanuric chloride, trimesoyl chloride, terephthalic chloride, eprine, hydrin, dibromobenzene, glutaraldehyde, phenol-diisocyanate, trilein diisocyanate, divinylsulfone, 1,1 21. The material according to claim 19 or 20, wherein a group force including the power of, -carbodidiimidazole and alkoxysilane is also selected.

 [22] The material is a lithium ion battery, a fuel cell, a solar cell, an activator, an electric double layer capacitor, a light emitting element, an electochromism element, a sensor, a current circuit, a polymer electrolyte, an electrochemical material, a catalyst. The material according to claim 1, wherein the material is used for at least one selected from the group consisting of: a separation membrane; and a coating agent.

 [23] When the swelling ratio of the comparative material using dimethyl sulfoxide instead of the ionic liquid is 1 and the storage elastic modulus is 1 among the materials, the swelling ratio of the material is 0.1 to The material according to any one of claims 1 to 22, wherein the material has a storage elastic modulus of 0.1 to 15.

 [24] A method for producing a material having a first poly (oral taxane) and a polymer, and an ionic liquid,

 a) mixing the first cyclic molecule and the first linear molecule in a liquid and including the first cyclic molecule in a skewered manner in the first linear molecule;

 b) preparing a first poly (taxane) taxane by arranging first blocking groups at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. C) mixing the first polymouth taxane with the polymer; and

 d) binding at least a part of the polymer and the polymouth taxane via the first cyclic molecule to obtain a conjugate;

e) 1) Koji using an ionic liquid as the liquid in step a), 2) B) 3) The step c) is carried out in an ionic liquid, 4) the step d) is carried out in an ionic liquid, or 5) the conjugate obtained in the step d) The above-mentioned method comprising the steps of: obtaining the material by immersing in an ionic liquid; or using a combination of any two to five of any one of 1) to 5) above.

25. The method according to claim 24, wherein the material is obtained by the step e) -5).

[26] In the step d), dimethyl sulfoxide is used as a solvent.

 In the step e) -5), a dimethyl sulfoxide-containing conjugate is immersed in water to replace the dimethyl sulfoxide with water;

 Next, the conjugate containing water is immersed in a mixed solvent of a volatile solvent and an ionic liquid to replace the water with the mixed solvent;

 26. The method according to claim 24 or 25, further comprising immersing a conjugate containing a mixed solvent in an ionic liquid to obtain the material.

[27] A method for producing a material having a first poly (oral taxane) and a polymer, and an ionic liquid,

 a ′) mixing the first cyclic molecule and the first linear molecule in a liquid and including the first cyclic molecule in a skewered manner in the first linear molecule;

 b ′) A first poly (taxane) taxane is formed by disposing first blocking groups at both ends of the first linear molecule so that the first cyclic molecule is not detached from the first linear molecule. C ′) mixing the first poly (taxane) taxane with the monomer constituting the polymer; d ′) polymerizing the monomer to form the polymer; and

 e ′) binding at least a part of the polymer and the poly (taxane) taxane via the first cyclic molecule to obtain a conjugate;

 f) 1) a liquid that uses an ionic liquid as the liquid in step a ′), 2) the b ′) process is performed in the ionic liquid, or 3) the c ′ process is performed in the ionic liquid. 4) The step d ′) is carried out in an ionic liquid, 5) The step e ′) is carried out in an ionic liquid, or 6) The conjugate obtained in the step e ′) is ionized. A method for obtaining the above-mentioned material by immersing it in an ionic liquid, or using a combination of! / Of the above 1) to 6) and 2 to 6 kinds of displacement forces.

28. The method according to claim 27, wherein the material is obtained by the step 6) of the above. In the step e ′), dimethyl sulfoxide is used as a solvent;

 In the step f ′)-6), a dimethyl sulfoxide-containing conjugate is immersed in water to replace the dimethyl sulfoxide with water;

 Next, the conjugate containing water is immersed in a mixed solvent of a volatile solvent and an ionic liquid to replace the water with the mixed solvent;

 29. The method according to claim 27 or 28, further comprising immersing a conjugate containing a mixed solvent in an ionic liquid to obtain the material.