WO2010137366A1 - 有機圧電材料、超音波振動子、超音波探触子及び超音波医用画像診断装置 - Google Patents
有機圧電材料、超音波振動子、超音波探触子及び超音波医用画像診断装置 Download PDFInfo
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- WO2010137366A1 WO2010137366A1 PCT/JP2010/052720 JP2010052720W WO2010137366A1 WO 2010137366 A1 WO2010137366 A1 WO 2010137366A1 JP 2010052720 W JP2010052720 W JP 2010052720W WO 2010137366 A1 WO2010137366 A1 WO 2010137366A1
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- 238000007598 dipping method Methods 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 238000002592 echocardiography Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
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- 239000007772 electrode material Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical group CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
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- 239000005033 polyvinylidene chloride Substances 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- LNKHTYQPVMAJSF-UHFFFAOYSA-N pyranthrene Chemical group C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 LNKHTYQPVMAJSF-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007751 thermal spraying Methods 0.000 description 1
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- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N30/00—Piezoelectric or electrostrictive devices
- H10N30/80—Constructional details
- H10N30/85—Piezoelectric or electrostrictive active materials
- H10N30/857—Macromolecular compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B8/00—Diagnosis using ultrasonic, sonic or infrasonic waves
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S7/00—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00
- G01S7/52—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00 of systems according to group G01S15/00
- G01S7/52017—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00 of systems according to group G01S15/00 particularly adapted to short-range imaging
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S7/00—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00
- G01S7/52—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00 of systems according to group G01S15/00
- G01S7/52017—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00 of systems according to group G01S15/00 particularly adapted to short-range imaging
- G01S7/52019—Details of transmitters
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N30/00—Piezoelectric or electrostrictive devices
- H10N30/01—Manufacture or treatment
- H10N30/09—Forming piezoelectric or electrostrictive materials
- H10N30/098—Forming organic materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
Definitions
- organic piezoelectric materials such as polyvinylidene fluoride (hereinafter abbreviated as “PVDF”) and polycyanovinylidene (hereinafter abbreviated as “PVDCN”) have also been developed (see, for example, Patent Document 1).
- PVDF polyvinylidene fluoride
- PVDCN polycyanovinylidene
- This organic piezoelectric material is excellent in processability such as thin film and large area, can be made in any shape and form, and has features such as low elastic modulus and low dielectric constant. It has a feature that enables highly sensitive detection when considering use.
- the present invention has been made in view of the above-described problems and situations, and a solution to that problem is to provide an organic piezoelectric material having excellent piezoelectric characteristics and handleability. Furthermore, it is to provide an ultrasonic transducer, an ultrasonic probe, and an ultrasonic medical image diagnostic apparatus using them.
- the organic polymer material constituting the base material is preferably a thermoplastic resin, a thermosetting resin, or a photocurable resin.
- alkyl group that is a substituent of the aromatic group and the cycloalkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, and an octadecyl group. And a cyclohexyl group.
- the alkyl group as a substituent is preferably an alkyl group having 5 to 20 carbon atoms, and more preferably an alkyl group having 6 to 15 carbon atoms.
- alkoxy group examples include methoxy group, ethoxy group, propyloxy group, pentyloxy group, cyclopentyloxy group, hexyloxy group, octyloxy group, decyloxy group, octadecyloxy group, cyclohexyloxy group and the like.
- alkoxy group an alkoxy group having 5 to 20 carbon atoms is preferable, and an alkoxy group having 6 to 15 carbon atoms is more preferable.
- the solvent used for the polymerization is preferably a solvent in which the reaction substrate and the target substance are well dissolved, aliphatic hydrocarbons such as cyclohexane, pentane and hexane, aromatic hydrocarbons such as benzene, toluene and chlorobenzene, THF (tetrahydrofuran) And solvents such as ethers such as diethyl ether and ethylene glycol diethyl ether, ketones such as acetone, methyl ethyl ketone and 4-methyl-2-pentanone, and esters such as methyl propionate, ethyl acetate and butyl acetate. These may be used in combination.
- aliphatic hydrocarbons such as cyclohexane, pentane and hexane
- aromatic hydrocarbons such as benzene, toluene and chlorobenzene
- THF tetrahydrofuran
- solvents such as ethers
- the measurement conditions are as follows.
- thermoplastic resin a thermosetting resin or a photocurable resin having a number average molecular weight of 1500 or more is used.
- thermoplastic resin any resin having a number average molecular weight of 1500 or more, preferably 1500 to 100,000 can be used without particular limitation. If the number average molecular weight of the thermoplastic resin is less than 1500, the glass transition temperature is too low, and the mechanical stability of the organic piezoelectric film may be lowered.
- thermosetting resin it is possible to use various resins including those commercially available such as epoxy adhesives and acrylic adhesives.
- photocurable resin various resins including those that are commercially available such as an adhesive that is cured by visible light, UV light, electron beam, or the like can be used. These non-liquid crystalline polymer substances may be appropriately selected in view of the method for producing the organic piezoelectric film and the required durability.
- a bisphenol A type is preferable as the main agent.
- a main agent in which the bisphenol A portion is a bisphenol compound as shown below can also be used.
- the compound (1) may be used by mixing with another ferroelectric polymer.
- amide polymer such
- Organic piezoelectric material of the present invention can be obtained by forming a film containing the specific compound (1) and a base material made of a resin, or by subjecting the film to further polarization treatment. Can be formed.
- the organic piezoelectric film When stress is applied to the piezoelectric film, the organic piezoelectric film causes a charge of opposite sign to appear on both end faces of the piezoelectric film, that is, a phenomenon called electric polarization. It has the property (piezoelectric performance) that a distortion proportional to that occurs when it is put into (applying an electric field).
- piezoelectric performance a phenomenon proportional to that occurs when it is put into (applying an electric field).
- a large piezoelectric effect is generated by polarization due to orientation freezing of the dipole moment of the polymer main chain or side chain.
- the organic piezoelectric film is preferably formed by coating.
- the coating method include spin coating, solvent casting, melt casting, melt press, roll coating, flow coating, printing, dip coating, and bar coating.
- the corona discharge treatment can be performed by using a commercially available device comprising a high voltage power source and electrodes.
- the voltage of the high voltage power supply is ⁇ 1 to ⁇ 20 kV
- the current is 1 to 80 mA
- the distance between the electrodes is 1 to 10 cm.
- the applied voltage is preferably 0.5 to 2.0 MV / m.
- electrodes needle-like electrodes, linear electrodes (wire electrodes), and mesh electrodes conventionally used are preferable, but the invention is not limited thereto.
- the selection of the substrate differs depending on the use and usage of the organic piezoelectric film according to the present invention.
- It may be a plastic plate or film such as polyimide, polyamide, polyimide amide, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polymethyl methacrylate (PMMA), polycarbonate resin, cycloolefin polymer.
- the surface may be covered with aluminum, gold, copper, magnesium, silicon or the like.
- a single crystal plate or film of aluminum, gold, copper, magnesium, silicon simple substance, or rare earth halide may be used.
- a multilayer piezoelectric element As a method of using a multilayer in which piezoelectric elements are stacked, there is a method of superposing an organic piezoelectric film according to the present invention on a ceramic piezoelectric element via an electrode. PZT is used as the ceramic piezoelectric element, but in recent years, one containing no lead has been recommended.
- PZT is preferably within the range of the formula of Pb (Zr 1-X Ti X ) O 3 (0.47 ⁇ X ⁇ 1).
- Pb Zr 1-X Ti X
- K potassium niobium tantalate
- BaTiO 3 barium titanate
- LiTaO 3 lithium tantalate
- strontium titanate SrTiO 3
- the composition of various ceramic materials can be appropriately selected in terms of use performance.
- the ultrasonic transducer according to the present invention is characterized by using an organic piezoelectric film formed using the organic piezoelectric material of the present invention.
- the ultrasonic transducer is preferably an ultrasonic receiving transducer used in an ultrasonic medical diagnostic imaging device probe including an ultrasonic transmitting transducer and an ultrasonic transmitting transducer. .
- an ultrasonic vibrator has a pair of electrodes sandwiched between layers (or films) made of a film-like piezoelectric material (also referred to as “piezoelectric film”, “piezoelectric film”, or “piezoelectric layer”).
- An ultrasonic probe is configured by arranging a plurality of transducers, for example, one-dimensionally.
- a predetermined number of transducers in the major axis direction in which a plurality of transducers are arranged is set as the aperture, and the plurality of transducers belonging to the aperture are driven to converge the ultrasonic beam on the measurement site in the subject. And has a function of receiving reflected echoes of ultrasonic waves emitted from the subject by a plurality of transducers belonging to the aperture and converting them into electrical signals.
- FIG. 1 shows an example of the basic configuration of the ultrasonic transducer.
- electrodes 2 are arranged on both sides of the piezoelectric material 1.
- the electrode 2 may be disposed over the entire surface of the piezoelectric material 1 as necessary, or may be disposed on a part of the organic piezoelectric material 1.
- An ultrasonic receiving vibrator is a vibrator having an ultrasonic receiving piezoelectric material used for a probe for an ultrasonic medical diagnostic imaging apparatus, and the piezoelectric material constituting the ultrasonic receiving vibrator is an element of the present invention.
- An embodiment using an organic piezoelectric film formed using an organic piezoelectric material is preferable.
- the organic piezoelectric material or the organic piezoelectric film used for the ultrasonic receiving vibrator preferably has a relative dielectric constant of 10 to 50 at the thickness resonance frequency.
- the relative dielectric constant is adjusted by adjusting the number, composition, degree of polymerization, etc. of the polar functional groups such as the substituent R, CF 2 group, and CN group of the compound constituting the organic piezoelectric material, and the polarization treatment described above. Can be done by.
- the organic piezoelectric film constituting the receiving vibrator of the present invention may be configured by laminating a plurality of polymer materials.
- the polymer material to be laminated the following polymer material having a relatively low relative dielectric constant can be used in addition to the above polymer material.
- the numerical value in parentheses indicates the relative dielectric constant of the polymer material (resin).
- the polymer material having a low relative dielectric constant is preferably selected in accordance with various purposes such as adjusting the piezoelectric characteristics or imparting the physical strength of the organic piezoelectric film. .
- the ultrasonic transmission vibrator according to the present invention is preferably made of a piezoelectric material having an appropriate relative dielectric constant in relation to the vibrator having the receiving piezoelectric material. Moreover, it is preferable to use a piezoelectric material excellent in heat resistance and voltage resistance.
- ultrasonic transmission vibrator constituting material
- various known organic piezoelectric materials and inorganic piezoelectric materials can be used.
- organic piezoelectric material a polymer material similar to the above-described organic piezoelectric material for constituting an ultrasonic receiving vibrator can be used.
- Inorganic materials include quartz, lithium niobate (LiNbO 3 ), potassium tantalate niobate [K (Ta, Nb) O 3 ], barium titanate (BaTiO 3 ), lithium tantalate (LiTaO 3 ), or titanate Lead zirconate (PZT), strontium titanate (SrTiO 3 ), barium strontium titanate (BST), or the like can be used.
- PZT is preferably Pb (Zr 1-n Ti n ) O 3 (0.47 ⁇ n ⁇ 1).
- the piezoelectric (body) vibrator according to the present invention is manufactured by forming electrodes on both surfaces or one surface of a piezoelectric film (layer) and polarizing the piezoelectric film.
- the electrode on the first surface used for the polarization treatment may be used as it is.
- the electrode is formed using an electrode material mainly composed of gold (Au), platinum (Pt), silver (Ag), palladium (Pd), copper (Cu), nickel (Ni), tin (Sn), or the like. .
- a base metal such as titanium (Ti) or chromium (Cr) is formed to a thickness of 0.02 to 1.0 ⁇ m by sputtering, and then the metal mainly composed of the above metal element and the above A metal material made of the above alloy and, if necessary, a part of insulating material is formed to a thickness of 1 to 10 ⁇ m by sputtering, vapor deposition or other suitable methods.
- these electrodes can be formed by screen printing, dipping, or thermal spraying using a conductive paste in which fine metal powder and low-melting glass are mixed.
- a piezoelectric element can be obtained by supplying a predetermined voltage between the electrodes formed on both surfaces of the piezoelectric film to polarize the piezoelectric film.
- the ultrasonic probe according to the present invention is a main component of an ultrasonic diagnostic imaging apparatus and has a function of generating ultrasonic waves and transmitting / receiving ultrasonic beams.
- the internal configuration of the ultrasonic probe may take various forms, but as a general configuration, from the tip (surface contacting the living body that is the subject), the “acoustic lens”, “acoustic matching layer”, A configuration of an aspect in which “ultrasonic transducer (element)” and “backing” are juxtaposed in this order may be employed.
- An ultrasonic probe according to the present invention is a probe for an ultrasonic medical image diagnostic apparatus including an ultrasonic transmission transducer and an ultrasonic reception transducer.
- the ultrasonic receiving transducer according to the invention is used.
- both the transmission and reception of ultrasonic waves may be performed by a single transducer, but more preferably, the transducer is configured separately for transmission and reception in the probe.
- the piezoelectric material constituting the transmitting vibrator may be a conventionally known ceramic inorganic piezoelectric material or an organic piezoelectric material.
- the ultrasonic receiving transducer of the present invention can be arranged on or in parallel with the transmitting transducer.
- the structure for laminating the ultrasonic receiving transducer of the present invention on the ultrasonic transmitting transducer is good, and in this case, the ultrasonic receiving transducer of the present invention is another high-frequency transducer.
- the film thickness of the receiving vibrator and the other polymer material be matched to a preferable receiving frequency band in terms of probe design. In view of a practical ultrasonic medical image diagnostic apparatus and biological information collection from a practical frequency band, the film thickness is preferably 40 to 150 ⁇ m.
- the probe may be provided with a backing layer, an acoustic matching layer, an acoustic lens, and the like. Also, a probe in which vibrators having a large number of piezoelectric materials are two-dimensionally arranged can be used. A plurality of two-dimensionally arranged probes can be sequentially scanned to form a scanner.
- FIG. 2 shows an example of the basic configuration of the ultrasonic probe.
- the ultrasonic probe 20 has a transmission ultrasonic transducer 12 in which an electrode 2 is attached to a transmission piezoelectric material 5 on a backing layer 6, and has a substrate 7 on the transmission ultrasonic transducer 12. Then, the receiving ultrasonic transducer 13 having the electrode 2 attached to the receiving organic piezoelectric material 11 is provided on the substrate 7, and the acoustic matching layer 8 and the acoustic lens 9 are further provided thereon.
- Materials used for the acoustic matching layer include aluminum, aluminum alloy (eg, AL-Mg alloy), magnesium alloy, macor glass, glass, fused quartz, carbon graphite, copper graphite, polyethylene (PE), polypropylene (PP), and polycarbonate.
- PC polycarbonate
- ABC resin polyphenylene ether (PPE), ABS resin, AAS resin, AES resin, nylon (PA6, PA6-6), PPO (polyphenylene oxide), PPS (polyphenylene sulfide: glass fiber can be included
- PPE Polyphenylene ether
- PEEK polyetheretherketone
- PAI polyamideimide
- PETP polyethylene terephthalate
- PC polycarbonate
- epoxy resin urethane resin, etc.
- thermosetting resin such as an epoxy resin which is molded by adding zinc white, titanium oxide, silica, alumina, bengara, ferrite, tungsten oxide, yttrium oxide, barium sulfate, tungsten, molybdenum, etc. as a filler. Can do.
- the acoustic matching layer may be a single layer or a plurality of layers, but preferably has two or more layers.
- the layer thickness of the acoustic matching layer needs to be determined to be ⁇ / 4 where ⁇ is the wavelength of the ultrasonic wave. If this is not satisfied, a plurality of unnecessary spurious noises appear at frequency points different from the original resonance frequency, and the basic acoustic characteristics greatly vary. As a result, reverberation time increases and sensitivity and S / N decrease due to waveform distortion of the reflected echo are undesirable.
- the total thickness of such an acoustic matching layer is generally in the range of 30 to 500 ⁇ m.
- a backing layer is provided on the back surface of the ultrasonic transducer for the purpose of suppressing propagation of ultrasonic waves to the rear. Thereby, the pulse width can be shortened.
- the backing layer is an ultrasonic absorber that supports the piezoelectric element and can absorb unnecessary ultrasonic waves.
- the backing material used for the backing layer is natural rubber, ferrite rubber, a material obtained by press molding powders of tungsten oxide, titanium oxide, ferrite, etc.
- epoxy resin vinyl chloride, polyvinyl butyral (PVB), ABS resin, polyurethane (PUR), polyvinyl alcohol (PVAL), polyethylene (PE), polypropylene (PP), polyacetal (POM), polyethylene terephthalate (PET), fluororesin (PTFE) polyethylene glycol, polyethylene terephthalate-polyethylene glycol copolymer, etc.
- a plastic resin or the like can be used.
- a preferable backing material is made of a rubber-based composite material and / or an epoxy resin composite material, and the shape thereof can be appropriately selected according to the shape of the piezoelectric body or the probe head including the piezoelectric body.
- a material containing a rubber component and a filler is preferable, and hardness from A70 with a type A durometer to D70 with a type D durometer in a spring hardness tester (durometer hardness) according to JIS K6253.
- various other compounding agents can be added as necessary.
- rubber components include ethylene propylene rubber (EPDM or EPM), hydrogenated nitrile rubber (HNBR), chloroprene rubber (CR), silicone rubber, EPDM and HNBR blend rubber, and EPDM and nitrile rubber (NBR) blend rubber.
- EPDM and / or HNBR and high styrene rubber (HSR) blend rubber, EPDM and HSR blend rubber, and the like are preferable.
- ethylene propylene rubber EPDM or EPM
- hydrogenated nitrile rubber HNBR
- EPDM and HNBR blend rubber EPDM and nitrile rubber blend rubber
- NBR and / or HNBR and high styrene rubber HSR
- Blend rubber EPDM and HSR blend rubber, and the like.
- one of rubber components such as vulcanized rubber and thermoplastic elastomer may be used alone, but a blend rubber obtained by blending two or more rubber components such as a blend rubber is used. Also good.
- the filler to be added to the rubber component can be selected in various forms together with the blending amount from those usually used to those having a large specific gravity.
- glass Examples include powders, various fine metal powders such as tungsten and molybdenum, and various balloons such as glass balloons and polymer balloons.
- These fillers can be added in various ratios, preferably 50 to 3000 parts by weight, more preferably about 100 to 2000 parts by weight, or about 300 to 1500 parts by weight with respect to 100 parts by weight of the rubber component. preferable. These fillers may be added alone or in combination of two or more.
- compounding agents can be added to the rubber-based composite material as necessary.
- examples of such compounding agents include vulcanizing agents, cross-linking agents, curing agents, auxiliaries, and deterioration inhibitors. , Antioxidants, colorants and the like.
- carbon black, silicon dioxide, process oil, sulfur (vulcanizing agent), dicumyl peroxide (Dicup, crosslinking agent), stearic acid and the like can be blended.
- These compounding agents are used as necessary, and the amount used is generally about 1 to 100 parts by mass with respect to 100 parts by mass of the rubber component, but may be appropriately changed depending on the overall balance and characteristics. You can also.
- the epoxy resin composite agent preferably contains an epoxy resin component and a filler, and various compounding agents can be added as necessary.
- the epoxy resin component include bisphenol A type, bisphenol F type, resol novolak type, novolac type epoxy resin such as phenol-modified novolak type, naphthalene structure-containing type, anthracene structure-containing type, fluorene structure-containing type, etc.
- Type epoxy resin hydrogenated alicyclic epoxy resin, liquid crystalline epoxy resin and the like.
- the epoxy resin component of this invention may be used independently, you may mix and use two or more types of epoxy resin components like a blend resin.
- any of the same fillers mixed with the rubber component to composite particles prepared by pulverizing the rubber-based composite can be preferably used.
- the composite particles include particles in which silicone rubber is filled with ferrite and pulverized with a pulverizer to a particle size of about 200 ⁇ m.
- chain aliphatic polyamines such as diethylenetriamine, triethylenetetramine, dipropylenediamine, and diethylaminopropylamine, N-aminoethylpiperazine, men Cyclic aliphatic polyamines such as sendiamine and isophoronediamine, aromatic amines such as m-xylenediamine, metaphenylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone, polyamide resin, piperidine, NN-dimethylpiperazine, triethylenediamine, 2,4 Secondary and tertiary amines such as 2,6-tris (dimethylaminomethyl) phenol, benzyldimethylamine, 2- (dimethylaminomethyl) phenol, 2-methylimidazole, 2-ethyl Midazole, imidazoles such as 1-cyanoethy
- the thickness of the backing material is preferably approximately 1 to 10 mm, and particularly preferably 1 to 5 mm.
- the acoustic lens according to the present invention is arranged to focus an ultrasonic beam using refraction and improve resolution.
- the present invention is characterized in that a substance that emits light when irradiated with excitation light, that is, a luminescent substance is added to a region near the subject surface of the acoustic lens.
- the acoustic lens converges the ultrasonic wave and is in close contact with the living body so as to be matched with the acoustic impedance of the living body (density ⁇ sound speed; 1.4 ⁇ 10 6 to 1.6 ⁇ 10 6 kg / m 2 ⁇ sec). It is necessary that the reflection of the ultrasonic wave can be reduced and that the ultrasonic attenuation amount of the lens itself is small.
- an acoustic lens conventionally made on the basis of a polymer material such as rubber is provided at a portion in contact with the human body to focus the ultrasonic beam.
- the lens material used here it is desirable that the sound velocity is sufficiently smaller than that of the human body, the attenuation is small, and the acoustic impedance is close to the value of the human skin. If the lens material has a sound velocity sufficiently smaller than that of the human body, the lens shape can be made convex, and slipping can be performed safely when making a diagnosis, and if the attenuation is reduced, sensitivity is improved. If the ultrasonic impedance can be transmitted and received and the acoustic impedance is close to the value of the skin of the human body, the reflection will be small, in other words, the transmittance will be large. Because.
- examples of the material constituting the acoustic lens include conventionally known homopolymers such as silicone rubber, fluorosilicone rubber, polyurethane rubber, epichlorohydrin rubber, and ethylene-propylene copolymer rubber obtained by copolymerizing ethylene and propylene. Copolymer rubber etc. can be used. Of these, it is preferable to use silicon rubber.
- silicone rubber examples include silicone rubber and fluorine silicone rubber.
- silicone rubber is an organopolysiloxane having a molecular skeleton composed of Si—O bonds, and having a plurality of organic groups mainly bonded to the Si atoms.
- the main component is methylpolysiloxane, and the entire organic 90% or more of the groups are methyl groups.
- a material in which a hydrogen atom, a phenyl group, a vinyl group, an allyl group or the like is introduced instead of the methyl group can also be used.
- the silicone rubber can be obtained, for example, by kneading a curing agent (vulcanizing agent) such as benzoyl peroxide with organopolysiloxane having a high degree of polymerization, followed by heat vulcanization and curing.
- a curing agent vulcanizing agent
- organic or inorganic fillers such as silica and nylon powder, and vulcanization aids such as sulfur and zinc oxide may be added.
- butadiene rubber used in the present invention examples include butadiene alone or a copolymer rubber mainly composed of butadiene and copolymerized with a small amount of styrene or acrylonitrile.
- butadiene rubber refers to a synthetic rubber obtained by polymerization of butadiene having a conjugated double bond.
- Butadiene rubber can be obtained by 1,4 or 1.2 polymerization of butadiene alone having a conjugated double bond.
- a butadiene rubber vulcanized with sulfur or the like can be used.
- the acoustic lens according to the present invention can be obtained by mixing and curing and curing silicon rubber and butadiene rubber.
- it can be obtained by mixing silicone rubber and butadiene rubber in an appropriate ratio by a kneading roll, adding a vulcanizing agent such as benzoyl peroxide, and heat vulcanizing and crosslinking (curing).
- a vulcanizing agent such as benzoyl peroxide
- heat vulcanizing and crosslinking curing
- zinc oxide as a vulcanization aid.
- Zinc oxide can accelerate vulcanization and shorten the vulcanization time without deteriorating lens characteristics.
- other additives may be added as long as the characteristics of the colorant and the acoustic lens are not impaired.
- the mixing ratio of the silicone rubber and the butadiene rubber is preferably 1: 1 in order to obtain a material whose acoustic impedance is close to that of the human body and whose sound speed is smaller than that of the human body and less attenuated.
- the mixing ratio can be changed as appropriate.
- Silicone rubber can be obtained as a commercial product.
- an inorganic filler such as silica, alumina, titanium oxide, nylon, etc., depending on the purpose of adjusting the speed of sound, adjusting the density, etc., based on the rubber material such as silicon rubber (main component).
- An organic resin or the like can also be blended.
- FIG. 3 shows a conceptual diagram of the configuration of the main part of the ultrasonic medical image diagnostic apparatus according to the embodiment of the present invention.
- This ultrasonic medical diagnostic imaging apparatus transmits an ultrasonic wave to a subject such as a patient, and an ultrasonic probe in which piezoelectric vibrators that receive ultrasonic waves reflected by the subject as echo signals are arranged. (Probe).
- an electric signal is supplied to the ultrasonic probe to generate an ultrasonic wave, and a transmission / reception circuit that receives an echo signal received by each piezoelectric vibrator of the ultrasonic probe, and transmission / reception control of the transmission / reception circuit
- a transmission / reception control circuit is provided.
- an image data conversion circuit for converting the echo signal received by the transmission / reception circuit into ultrasonic image data of the subject is provided. Further, a display control circuit for controlling and displaying the monitor with the ultrasonic image data converted by the image data conversion circuit and a control circuit for controlling the entire ultrasonic medical image diagnostic apparatus are provided.
- the transmission / reception control circuit, the image data conversion circuit, and the display control circuit are connected to the control circuit, and the control circuit controls the operations of these units. Then, an electrical signal is applied to each piezoelectric vibrator of the ultrasonic probe to transmit an ultrasonic wave to the subject, and the reflected wave caused by acoustic impedance mismatch inside the subject is detected by the ultrasonic probe. Receive at.
- the ultrasonic diagnostic apparatus by utilizing the characteristics of the ultrasonic wave receiving vibrator excellent in piezoelectric characteristics and heat resistance of the present invention and suitable for high frequency and wide band, the image quality and its An ultrasonic image with improved reproduction and stability can be obtained.
- the specific compound (1) is a compound having a partial structure represented by the general formula (1A), and (II) the specific compound (1) is the general compound It will be described separately in the case of a polymer having a side chain residue of a compound represented by a compound represented by following general formula in the formula (1B) (1B) via the following Q 1 or Q 2 .
- Synthesis Example 4 Synthesis of Compound 32 12.0 g of 3,5-dinitroaniline was dissolved in 50 ml of methanol and purged with nitrogen. 10% palladium on carbon, 1.0 g was added and hydrogen was introduced. The reaction was performed for 2 hours under a hydrogen atmosphere. After purging the inside of the reaction vessel with nitrogen, palladium carbon was filtered off and methanol was distilled off under reduced pressure. Tetrahydrofuran (THF) 100 ml was added, and the reaction solution was purged with nitrogen. To this, 29 ml of cyclohexyl isocyanate was added dropwise over 1 hour. After stirring at room temperature for 3 hours, water was added to the reaction solvent, and the organic layer was extracted with THF.
- THF Tetrahydrofuran
- Synthesis Example 5 Synthesis of Compound 34 3,5-Dinitroaniline 12.0 g was dissolved in 50 ml of methanol and purged with nitrogen. 1.0 g of 10% palladium carbon was added and hydrogen was introduced. The reaction was performed for 2 hours under a hydrogen atmosphere. After purging the inside of the reaction vessel with nitrogen, palladium carbon was filtered off and methanol was distilled off under reduced pressure. 100 ml of THF was added and dissolved therein, and 30.0 g of 6-ethoxyhexylamine was added. 37 g of 1,1'-thiocarbonyldiimidazole was added separately in 15 minutes and stirred for 4 hours. Water was added to the reaction solvent, and the organic layer was extracted with THF.
- Example 2 Fabrication and evaluation of ultrasonic probe ⁇ Manufacture of piezoelectric material for transmission> Component raw materials CaCO 3 , La 2 O 3 , Bi 2 O 3 and TiO 2 , and subcomponent raw materials MnO are prepared, and for the component raw materials, the final composition of the components is (Ca 0.97 La 0.03 ) Weighed to be Bi 4.01 Ti 4 O 15 . Next, pure water was added, mixed in a ball mill containing zirconia media in pure water for 8 hours, and sufficiently dried to obtain a mixed powder. The obtained mixed powder was temporarily molded and calcined in air at 800 ° C. for 2 hours to prepare a calcined product.
- the dielectric breakdown strength was measured by multiplying the load power P by 5 times, testing for 10 hours, and then returning the load power to the standard to evaluate the relative reception sensitivity.
- the sensitivity was evaluated as good when the decrease in sensitivity was within 1% before the load test, more than 1% and less than 10%, and 10% or more as bad.
- the specific compound (1) is a side chain of the compound represented by the general formula (1B) or the compound represented by the following general formula (1B) via Q 1 or Q 2 below.
- Example 1 Synthesis of Exemplified Compound 1 63 g of silica gel was dispersed in 21 g of nitric acid, and 150 ml of dichloromethane was added. To this dispersion was added a solution of 10 g of 1,2,3-trihexyloxybenzene dissolved in 30 ml of dichloromethane, and the mixture was stirred for 15 minutes, and then the silica gel was removed by filtration. The filtrate was concentrated under reduced pressure, 300 ml of methanol was added and stirred, and the precipitate was collected by filtration to obtain 7.3 g (yield 65%) of 3,4,5-trihexyloxynitrobenzene.
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Abstract
Description
関係式(1):|CLogP(1A)-CLogP(母材)|≦3.0
〔式中、CLogPはHansch,Leoのフラグメントアプローチにより算出される“計算LogP”を表す。〕
2.前記一般式(1A)におけるArが、ベンゼン、ベンゾキノン、アントラセン、トリフェニレン、トルクセン、トリシクロキナゾリン、及びジベンゾピレンから選ばれる芳香族炭化水素環又は芳香族複素環であることを特徴とする前記第1項に記載の有機圧電材料。
(式中、A1は-NR1C(=O)NR2-、-NR1C(=S)NR2-、-OC(=O)O-、-OC(=S)O-、-NHC(=O)O-、-NHC(=S)O-、-NHC(=O)-、-NHC(=S)-、-SO2NH-又は-NHSO2NH-を表す。Q1及びQ2は、各々独立に、無置換の芳香族基、アルキル基若しくはアルコキシ基で置換された芳香族基、又はアルキル基若しくはアルコキシ基で置換されたシクロアルキル基を表す。L1は2価の連結基を表し、nは0~100の整数を表す。A1中にあるR1及びR2は、各々独立して、水素原子又は置換基を表す。)
関係式(2):|CLogP(1B)-CLogP(母材)|≦3.0
〔式中、CLogPはHansch,Leoのフラグメントアプローチにより算出される“計算LogP”を表す。〕
5.前記一般式(1B)におけるQ1及びQ2が、アルコキシ基を有する芳香族基であることを特徴とする前記第4項に記載の有機圧電材料。
関係式:|CLogP(1)-CLogP(母材)|≦3.0
〔式中、CLogPはHansch,Leoのフラグメントアプローチにより算出される“計算LogP”を表す。〕
なお、ここで、特定化合物(1)とは、前記一般式(1A)で表される部分構造を有する化合物、又は前記一般式(1B)で表される化合物又は前記一般式(1B)で表される化合物の残基を下記Q1若しくはQ2を介して側鎖に有する重合体をいう。
本発明の有機圧電材料は、下記一般式(1A)で表される部分構造を有する化合物と、樹脂からなる母材とを含有する有機圧電材料であることを特徴とする。
本発明の有機圧電材料は、下記一般式(1B)で表される化合物又は下記一般式(1B)で表される化合物の残基を下記Q1若しくはQ2を介して側鎖に有する重合体と、樹脂からなる母材とを含有することを特徴とする。
一般式(1B)中、Q1及びQ2は、各々独立に無置換の芳香族基、アルキル基若しくはアルコキシ基で置換された芳香族基、又はアルキル基若しくはアルコキシ基で置換されたシクロアルキル基を表す。Q1又はQ2における、芳香族基としては、例えば、フェニル基、ナフチル基、アントラニル基等を挙げることができ、シクロアルキル基としては、例えば、シクロヘキシル基、シクロペンチル基等を挙げることができる。芳香族基、シクロアルキル基の置換基であるアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、tert-ブチル基、ペンチル基、ヘキシル基、オクチル基、デシル基、オクタデシル基、シクロヘキシル基等が挙げられる。置換基であるアルキル基としては、炭素数5~20のアルキル基が好ましく、さらに炭素数6~15のアルキル基が好ましい。アルコキシ基としては、例えば、メトキシ基、エトキシ基、プロピルオキシ基、ペンチルオキシ基、シクロペンチルオキシ基、ヘキシルオキシ基、オクチルオキシ基、デシルオキシ基、オクタデシルオキシ基、シクロヘキシルオキシ基等が挙げられる。アルコキシ基としては、炭素数が5~20のアルコキシ基が好ましく、さらに炭素数6~15のアルコキシ基が好ましい。
一般式(2)において、Arはアリーレン基を表し、アリーレン基としては、例えば、フェニレン基、ナフチレン基、ビフェニレン基等を挙げることができる。L2は、2価の連結基又は単なる結合手を表し、2価の連結基としては、一般式(1B)のL1で挙げた2価の連結基を挙げることができる。
本発明に係る、上記一般式(1B)で表される化合物の残基を、Q1又はQ2を介して側鎖に有する重合体は、重合性基を有し、Q1又はQ2を介して上記一般式(1B)で表される化合物の残基を有する化合物を重合させることで得られる。
装置 :HLC-8220GPC(東ソー(株)製)
カラム :TSKgel SuperAWM-H×2本(東ソー(株)製)
カラム温度:40℃
試料濃度 :1.0g/L
注入量 :40μl
流量 :0.5ml/min
校正曲線 :標準ポリスチレン:PS-1(Polymer Laboratories社製)Mw=580~2,560,000までの9サンプルによる校正曲線を使用する。
本発明の有機圧電材料は、前記特定化合物(1)と、樹脂からなる母材とを含有する有機圧電材料であって、当該特定化合物(1)と当該母材のCLogPの値をそれぞれCLogP(1)とCLogP(母材)としたとき、下記関係式(1)を満たすことを特徴とする。
当該特定化合物(1)を有機圧電膜に成膜する際には、さらに任意の樹脂(高分子化合物)を、母材として、混合して成膜性を向上させることを要する。
本発明の有機圧電材料は、前記特定化合物(1)と、樹脂からなる母材とを含有する膜を形成することにより、あるいは当該膜に対してさらに分極処理を施すことにより、有機圧電体膜を形成することができる。
有機圧電体膜の形成は、塗布によって膜を形成する方法が好ましい。塗布方法として、例えば、スピンコート法、ソルベントキャスト法、メルトキャスト法、メルトプレス法、ロールコート法、フローコート法、プリント法、ディップコート法、バーコート法等が挙げられる。
本発明に係る分極処理における分極処理方法としては、従来公知の種々の方法が適用され得る。例えば、コロナ放電処理法による場合には、コロナ放電処理は、市販の高電圧電源と電極からなる装置を使用して処理することができる。
基板としては、本発明に係る有機圧電体膜の用途、使用方法等により基板の選択は異なる。ポリイミド、ポリアミド、ポリイミドアミド、ポリエチレンテレフタラート(PET)、ポリエチレンナフタレート(PEN)、ポリメタクリル酸メチル(PMMA)、ポリカーボネート樹脂、シクロオレフィンポリマーのようなプラスチック板又はフィルムでもよいし、これらの素材の表面をアルミニウム、金、銅、マグネシウム、珪素等で覆ったものでもよい。また、アルミニウム、金、銅、マグネシウム、珪素単体、希土類のハロゲン化物の単結晶の板又はフィルムでも構わない。
本発明に係る超音波振動子は、本発明の有機圧電材料を用いて形成した有機圧電膜を用いたことを特徴とする。当該超音波振動子は、超音波送信用振動子と超音波送信用振動子を具備する超音波医用画像診断装置用探触子(プローブ)に用いられる超音波受信用振動子とすることが好ましい。
本発明に係る超音波受信用振動子は、超音波医用画像診断装置用探触子に用いられる超音波受信用圧電材料を有する振動子であって、それを構成する圧電材料が、本発明の有機圧電材料を用いて形成した有機圧電膜を用いた態様であることが好ましい。
本発明に係る超音波送信用振動子は、上記受信用圧電材料を有する振動子との関係で適切な比誘電率を有する圧電体材料により構成されることが好ましい。また、耐熱性・耐電圧性に優れた圧電材料を用いることが好ましい。
本発明に係る圧電(体)振動子は、圧電体膜(層)の両面上又は片面上に電極を形成し、その圧電体膜を分極処理することによって作製されるものである。有機圧電材料を使用した超音波受信用振動子を作製する際には、分極処理を行う際に使用した前記第1面の電極をそのまま使用してもよい。当該電極は、金(Au)、白金(Pt)、銀(Ag)、パラジウム(Pd)、銅(Cu)、ニッケル(Ni)、スズ(Sn)などを主体とした電極材料を用いて形成する。
本発明に係る超音波探触子は、超音波画像診断装置の主要構成部品であって、超音波を発生するとともに、超音波ビームを送受信する機能を有するものである。当該超音波探触子の内部の構成は、種々の態様を採り得るが、一般的構成としては、先端(被検体である生体に接する面)部分から「音響レンズ」、「音響整合層」、「超音波振動子(素子)」、「バッキング」という順に並置された態様の構成を採り得る。
超音波振動子と生体組織の音響インピーダンスの差が大きいために境界面での反射が大きくなり、自由振動が長く続いてしまう。これを補正するために振動子と生体組織との間に両者の中間的な音響インピーダンスを持つ整合層を入れることにより、反射が軽減され自由振動がすみやかに集束し、探触子で送受信される超音波パルス幅が短くなり、生体内に超音波が効果的に伝搬される。
本発明においては、超音波振動子の背面に配置し、後方への超音波の伝搬を抑制することを目的としてバッキング層を備えることも好ましい。これにより、パルス幅を短くすることができる。バッキング層は、圧電素子を支持し、不要な超音波を吸収し得る超音波吸収体である。バッキング層に用いられるバッキング材としては、天然ゴム、フェライトゴム、エポキシ樹脂に酸化タングステンや酸化チタン、フェライト等の粉末を入れてプレス成形した材料、塩化ビニル、ポリビニルブチラール(PVB)、ABS樹脂、ポリウレタン(PUR)、ポリビニルアルコール(PVAL)、ポリエチレン(PE)、ポリプロピレン(PP)、ポリアセタール(POM)、ポリエチレンテレフタレート(PETP)、フッ素樹脂(PTFE)ポリエチレングリコール、ポリエチレンテレフタレート-ポリエチレングリコール共重合体などの熱可塑性樹脂などを用いることができる。
本発明に係る音響レンズは、屈折を利用して超音波ビームを集束し分解能を向上するために配置されている。本発明においては、当該音響レンズの被検体表面に近い領域に、励起光を照射することにより発光する物質すなわち発光物質が添加されていることを特徴とする。
本発明に係る上記超音波探触子は、種々の態様の超音波診断装置に用いることができる。図3に、本発明の実施形態の超音波医用画像診断装置の主要部の構成の概念図を示す。
合成例1:化合物18の合成
窒素置換した反応容器に、2,5-ジヒドロキシ-1-ニトロベンゼン1.5g、3,4,5-トリス[3,4,5-トリ(1-ヘキシルオキシ)ベンジロキシ]ベンジルアルコール26.5g、トリフェニルホスフィン7.9gを脱水テトラヒドロフラン(THF)200mlに溶解し、アゾジカルボン酸ジエチル(diethyl azodicarboxylate、DEAD)2.2Mトルエン溶液15mlを30分かけて滴下した。室温で5時間かき混ぜた後、溶媒を減圧留去し、メチルエチルケトン50mlを加えた。ここに、メタノール100mlを加え、析出した固体をろ別した。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=8:1)により精製を行い、中間体Aが14.7g得られた(収率53%)。
中間体A、14.7gをエタノール200mlに加え、窒素置換した。パラジウム炭素1.0gを添加した後に水素置換を行い、室温で6時間かき混ぜた。パラジウム炭素をろ別後、エタノールを減圧留去し、得られた固体をメチルエチルケトンから再結晶を行い、中間体Bを13.9g(収率96%)得た。
1リットルの三口フラスコに氷冷攪拌下、200mlのアセトンと1.5g(11mmol)の塩化スルフリルと2.5g(25mmol)のトリエチルアミンを入れて、均一な溶液とした。氷冷下、13.9g(5mmol)の中間体B、0.5g(2.5mmol)の2,6-ジアミノアントラセンの混合物を2時間かけて滴下した。その後室温にて24時間撹拌し、次いで400gの氷水を加えた後、1晩撹拌を行った。塩化メチレンにより抽出を行い、有機層を希塩酸で洗い、得られた有機層は硫酸ナトリウムで乾燥した。得られた固体はシリカゲルカラムクロマトグラフィー(トルエン:塩化メチレン=5:1)により精製を行い、化合物18が11.9g得られた(収率41%)。生成物は1H-NMRスペクトルにより同定した。
合成例2:化合物26の合成
窒素置換した反応容器に、2,5-ジヒドロキシ-1-ニトロベンゼン1.5g、3,4,5-トリス[p-(1-ドデシロキシ)ベンジロキシ]ベンジルアルコール20.0g、トリフェニルホスフィン7.9gを脱水テトラヒドロフラン(THF)200mlに溶解し、アゾジカルボン酸ジエチル2.2Mトルエン溶液15mlを30分かけて滴下した。室温で5時間かき混ぜた後、溶媒を減圧留去し、メチルエチルケトン50mlを加えた。ここに、メタノール100mlを加え、析出した固体をろ別した。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=8:1)により精製を行い、中間体Aが11.0g得られた(収率53%)。
中間体A、11.0gをエタノール200mlに加え、窒素置換した。パラジウム炭素1.0gを添加した後に水素置換を行い、室温で6時間かき混ぜた。パラジウム炭素をろ別後、エタノールを減圧留去し、得られた固体をメチルエチルケトンから再結晶を行い、中間体Bを10.4g(収率96%)得た。
中間体B、10.4gを脱水テトラヒドロフラン100mlに溶解し、氷水浴により冷却した。5℃になったことを確認後、p-ヨードベンゼンイソシアナート1.4gを添加した。5℃で30分間かき混ぜた後に、室温で3時間かき混ぜた。溶液に水を加え、テトラヒドロフランにより抽出を行った。得られた有機層は硫酸ナトリウムで乾燥し、溶媒を減圧留去した。得られた固体をシリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=10:1)により精製し、中間体Cが10.3g(89%)得られた。
トルエン100ml中に中間体C、10.3gと1.6-ジエチニルピレン0.5gとジエチルアミン110mlをかき混ぜたところに、ヨウ化銅0.03gと塩化ビス(トリフェニルホスフィンパラジウム)0.13gを加えた。50℃に加熱し、24時間かき混ぜた後に、減圧下でジエチルアミンを留去した。塩化メチレンにより抽出を行い、有機層を希塩酸で洗い、得られた有機層は硫酸ナトリウムで乾燥した。得られた固体はシリカゲルカラムクロマトグラフィー(トルエン:塩化メチレン=5:1)により精製を行い、化合物26が8.3g得られた(収率41%)。生成物は1H-NMRスペクトル、IRスペクトル及びマススペクトル測定により同定した。
IRスペクトル(ATR法、cm-1):3350,3180,1640,1590,1425,1247,1040,784,754,700
マススペクトル(API法、m/e(相対強度)):4581((30)MH+)。
窒素置換した反応容器に、2,5-ジヒドロキシ-1-ニトロベンゼン1.5g、3,4,5-トリス[p-(1-オクチロキシ)ベンジロキシ]ベンジルアルコール16.6g、トリフェニルホスフィン8.0gを脱水テトラヒドロフラン(THF)150mlに溶解し、DEAD(2.2Mトルエン溶液)15mlを30分かけて滴下した。室温で3時間かき混ぜた後、溶媒を減圧留去し、メチルエチルケトン50mlを加えた。ここに、メタノール150mlを加え、析出した固体をろ別した。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=10:1)により精製を行い、中間体Dが8.2g得られた(収率47%)。
中間体D、8.2gをエタノール200mlに加え、窒素置換した。パラジウム炭素0.8gを添加した後に水素置換を行い、室温で4時間かき混ぜた。パラジウム炭素をろ別後、エタノールを減圧留去し、得られた固体をメチルエチルケトンから再結晶を行い、中間体Eを7.9g(収率98%)得た。
中間体E、7.9gを脱水テトラヒドロフラン80mlに溶解し、氷水浴により冷却した。5℃になったことを確認後、p-ヨードベンゼンチオイソシアナート1.5gを添加した。5℃で20分間かき混ぜた後に、室温で6時間かき混ぜた。溶液に水を加え、テトラヒドロフランにより抽出を行った。得られた有機層は硫酸ナトリウムで乾燥し、溶媒を減圧留去した。得られた固体をシリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=10:1)により精製し、中間体Fが7.1g(78%)得られた。
トルエン150ml中に中間体F、7.1gと1.6-ジエチニルピレン0.5gとジエチルアミン100mlをかき混ぜたところに、ヨウ化銅0.03gと塩化ビス(トリフェニルホスフィンパラジウム)0.13gを加えた。50℃に加熱し、30時間かき混ぜた後に、減圧下でジエチルアミンを留去した。塩化メチレンにより抽出を行い、有機層を希塩酸で洗い、得られた有機層は硫酸ナトリウムで乾燥した。得られた固体はシリカゲルカラムクロマトグラフィー(トルエン:塩化メチレン=5:1)により精製を行い、化合物28が7.5g得られた(収率53%)。生成物は1H-NMRスペクトル、IRスペクトル及びマススペクトル測定により同定した。
IRスペクトル(ATR法、cm-1):3350,1642,1588,1425,1410,1247,1042,780,756
マススペクトル(API法、m/e(相対強度)):3940((24)MH+)。
3,5-ジニトロアニリン12.0gをメタノール50mlに溶解し、窒素置換した。10%パラジウム炭素、1.0gを添加し、水素を導入した。水素雰囲気下で2時間反応させた。反応容器内を窒素置換した後、パラジウム炭素をろ別し、メタノールを減圧留去した。テトラヒドロフラン(THF)100mlを加え、反応溶液を窒素置換した。ここにシクロヘキシルイソシアネート29mlを1時間かけて滴下した。室温で3時間かき混ぜた後に、反応溶媒に水を加え、有機層をTHFにより抽出した。硫酸ナトリウムで乾燥後、溶媒を減圧留去し、組成物28gを得た。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=10:1)により精製を行い、目的の化合物2が23.4g(収率78%)得られた。生成物は1H-NMRスペクトル、IRスペクトル及びマススペクトル測定により同定した。
IRスペクトル(ATR法、cm-1):3350,3180,1640,1590,1423,1410,756,700
マススペクトル(API法、m/e(相対強度)):460((82)MH+),415(22)。
3,5-ジニトロアニリン12.0gをメタノール50mlに溶解し、窒素置換した。10%パラジウム炭素1.0gを添加し、水素を導入した。水素雰囲気下で2時間反応させた。反応容器内を窒素置換した後、パラジウム炭素をろ別し、メタノールを減圧留去した。ここにTHF100mlを入れて溶解させ、6-エトキシヘキシルアミン30.0gを加えた。1,1′-チオカルボニルジイミダゾール37gを15分間に分別添加し、4時間かき混ぜた。反応溶媒に水を加え、有機層をTHFにより抽出した。硫酸ナトリウムで乾燥後、溶媒を減圧留去し、組成物46gを得た。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=10:1)により精製を行い、目的の化合物4が37g(収率83%)得られた。生成物は1H-NMRスペクトル、IRスペクトル及びマススペクトル測定により同定した。
IRスペクトル(ATR法、cm-1):3351,3182,1639,1595,1420,1250,759,702
マススペクトル(API法、m/e(相対強度)):685((90)MH+),553(25)。
2,3,4,6,7,8-ヘキサアミノアントラキノン5.0gにTHF50mlを加え、窒素置換後、溶解させた。ヘキシルチオイソシアネート14.3gを1時間かけて滴下し、さらに室温で4時間かき混ぜた。反応溶液に水を加え、有機層をTHFにより抽出した。硫酸ナトリウムで乾燥後、溶媒を減圧留去し、組成物を得た。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=8:1)により精製を行い、目的の化合物18を12.8g得た(収率66%)。生成物の同定は1H-NMRスペクトル、IRスペクトル及びマススペクトル測定により行った。
IRスペクトル(ATR法、cm-1):3348,3180,1641,1589,1420,759,698
マススペクトル(API法、m/e(相対強度)):1061((47)MH+)。
1,2,5,6,8,9,12,13-オクタアミノジベンゾピレン4.2gにTHF50mlを加え、窒素置換後、溶解させた。その後THF100mlにシクロヘキシルスルホニルクロライド14.6gを溶解した溶液を1時間かけて滴下し、さらに室温で4時間かき混ぜた。反応溶液に水を加え、有機層を酢酸エチルにより抽出した。硫酸ナトリウムで乾燥後、溶媒を減圧留去し、組成物を得た。シリカゲルカラムクロマトグラフィー(ヘプタン:酢酸エチル=8:1)により精製を行い、目的の化合物66を7.5g得た(収率51%)。生成物の同定は1H-NMRスペクトルにより行った。
実施例1
有機圧電体膜の作製
あらかじめ表面にアルミ蒸着を行った25μmのポリイミドフィルムに、表5に示す、一般式(1A)で表される化合物と樹脂化合物から、乾燥膜圧が7μmになるように塗布し、乾燥し、有機圧電体膜-1~10を作製した。
得られた有機圧電体膜について、共振法により室温及び100℃まで加熱した状態で圧電特性の評価を行った。その結果を表8に示す。なお圧電特性は、比較有機圧電体膜-Aについて室温で測定した値を100%とした相対値として示す。
超音波探触子の作製と評価
〈送信用圧電材料の作製〉
成分原料であるCaCO3、La2O3、Bi2O3とTiO2、及び副成分原料であるMnOを準備し、成分原料については、成分の最終組成が(Ca0.97La0.03)Bi4.01Ti4O15となるように秤量した。次に、純水を添加し、純水中でジルコニア製メディアを入れたボールミルにて8時間混合し、十分に乾燥を行い、混合粉体を得た。得られた混合粉体を、仮成形し、空気中、800℃で2時間仮焼を行い、仮焼物を作製した。次に、得られた仮焼物に純水を添加し、純水中でジルコニア製メディアを入れたボールミルにて微粉砕を行い、乾燥することにより圧電セラミックス原料粉末を作製した。微粉砕においては、微粉砕を行う時間及び粉砕条件を変えることにより、それぞれ粒子径100nmの圧電セラミックス原料粉末を得た。それぞれ粒子径の異なる各圧電セラミックス原料粉末にバインダーとして純水を6質量%添加し、プレス成形して、厚み100μmの板状仮成形体とし、この板状仮成形体を真空パックした後、235MPaの圧力でプレスにより成形した。次に、上記の成形体を焼成した。最終焼結体の厚さは20μmの焼結体を得た。なお、焼成温度は、それぞれ1100℃であった。1.5×Ec(MV/m)以上の電界を1分間印加して分極処理を施した。
前記実施例1において作製した有機圧電体膜-1の基板の表面にアルミ電極を蒸着で取り付けた後、高圧電源装置HARB-20R60(松定プレシジョン(株)製)を用いて、100MV/mの電場を印加しながら200℃まで5℃/minの速度で昇温させ、200℃で15分間保持した後に、電圧を印加したまま室温まで徐冷してポーリング処理を施した。分極処理を施した有機圧電体膜-1と厚さ50μmのポリエステルフィルムをエポキシ系接着剤にて貼り合わせた積層振動子を作製した。
実施例1
(例示化合物1の合成)
シリカゲル63gを硝酸21gに分散させ、ジクロロメタン150mlを加えた。この分散物に、1,2,3-トリヘキシロキシベンゼン10gをジクロロメタン30mlに溶解した溶液を加え、15分間攪拌した後、シリカゲルをろ過で除いた。ろ液を減圧濃縮した後、メタノール300mlを加えて攪拌し、析出物をろ取することにより3,4,5-トリヘキシロキシニトロベンゼン7.3g(収率65%)を得た。
シリカゲル63gを硝酸21gに分散させ、ジクロロメタン150mlを加えた。この分散物に、1,2,3-トリドデシロキシベンゼン10gをジクロロメタン30mlに溶解した溶液を加え、15分間攪拌した後、シリカゲルをろ過で除いた。ろ液を減圧濃縮した後、メタノール300mlを加えて攪拌し、析出物をろ取することにより3,4,5-トリドデシロキシニトロベンゼン7.9g(収率74%)を得た。
0℃に調温したジクロロメタン150ml中に塩化スルフリル0.95gとトリエチルアミン1.4gを添加し、その後1,3-ビス(アミノメチル)シクロヘキサン0.50gを添加した。その後、例示化合物1または2と同様の合成経路にて合成した、3,4,5-トリオクタデシロキシアニリン6.3gを30分かけて添加し、室温にて1時間攪拌させることにより例示化合物3を2.8g(収率39%)得た。
0℃に調温したピリジン150ml中に、(例示化合物3の合成)で合成した、3,4,5-トリオクタデシロキシアニリン5.0gを添加し、そこに塩化ベンゼンスルホニル0.98gを添加し、室温にて1時間攪拌させることにより例示化合物4を5.2g(収率90%)得た。
シリカゲル63gを硝酸21gに分散させ、ジクロロメタン150mlを加えた。この分散物に、1-(1′-ヒドロキシオクタデシロキシ)-2,3-ジオクタデシロキシベンゼン5.0gをジクロロメタン30mlに溶解した溶液を加え、15分間攪拌した後、シリカゲルをろ過で除いた。ろ液を減圧濃縮した後、メタノール300mlを加えて攪拌し、析出物をろ取することにより3-(1′-ヒドロキシオクタデシロキシ)-4,5-ジオクタデシロキシニトロベンゼン4.0g(収率76%)を得た。
脱気したトルエン100mlに例示化合物13を10g添加し、その後溶液を80℃に加熱し、脱気したトルエン10mlにAIBNを7.9mg溶解した溶液を30分かけて添加し、添加終了後2時間反応させた。その後反応液を濃縮し、ヘキサンとメタノールを用いた再沈殿により精製し、例示化合物17を9.3g得た。GPCより分子量20,000、分子量分布1.5であった。
有機圧電体膜の作製
あらかじめ表面にアルミ蒸着を行った25μmのポリイミドフィルムに、表5に示す一般式(1B)で表される化合物と樹脂化合物から、乾燥膜圧が7μmになるように塗布し、乾燥し、有機圧電体膜-1~10を作製した。
得られた有機圧電体膜について、共振法により室温及び100℃まで加熱した状態で圧電特性の評価を行った。その結果を表9に示す。なお圧電特性は、比較有機圧電体膜-1について室温で測定した値を100とした相対値として示す。
超音波探触子の作製と評価
〈送信用圧電材料の作製〉
成分原料であるCaCO3、La2O3、Bi2O3とTiO2、及び副成分原料であるMnOを準備し、成分原料については、成分の最終組成が(Ca0.97La0.03)Bi4.01Ti4O15となるように秤量した。次に、純水を添加し、純水中でジルコニア製メディアを入れたボールミルにて8時間混合し、十分に乾燥を行い、混合粉体を得た。得られた混合粉体を、仮成形し、空気中、800℃で2時間仮焼を行い、仮焼物を作製した。次に、得られた仮焼物に純水を添加し、純水中でジルコニア製メディアを入れたボールミルにて微粉砕を行い、乾燥することにより圧電セラミックス原料粉末を作製した。微粉砕においては、微粉砕を行う時間及び粉砕条件を変えることにより、それぞれ粒子径100nmの圧電セラミックス原料粉末を得た。それぞれ粒子径の異なる各圧電セラミックス原料粉末にバインダーとして純水を6質量%添加し、プレス成形して、厚み100μmの板状仮成形体とし、この板状仮成形体を真空パックした後、235MPaの圧力でプレスにより成形した。次に、上記の成形体を焼成した。最終焼結体の厚さは20μmの焼結体を得た。なお、焼成温度は、それぞれ1100℃であった。1.5×Ec(MV/m)以上の電界を1分間印加して分極処理を施した。
前記実施例1において作製した有機圧電体膜-1の基板の表面にアルミ電極を蒸着で取り付けた後、高圧電源装置HARB-20R60(松定プレシジョン(株)製)を用いて、100MV/mの電場を印加しながら200℃まで5℃/minの速度で昇温させ、200℃で15分間保持した後に、電圧を印加したまま室温まで徐冷してポーリング処理を施した。分極処理を施した有機圧電体膜-1と厚さ50μmのポリエステルフィルムをエポキシ系接着剤にて貼り合わせた積層振動子を作製した。
2 電極
5 送信用圧電材料
6 バッキング層
7 基板
8 音響整合層
9 音響レンズ
10 超音波振動子
11 受信用有機圧電材料
12 送信用超音波振動子
13 受信用超音波振動子
20 超音波探触子
100 超音波医用画像診断装置
101 生体
102 超音波探触子
103 送信用超音波振動子
104 受信用超音波振動子
105 送受信回路
106 画像データ変換回路
107 表示制御回路
108 画像表示
109 送受信制御回路
110 制御回路
Claims (10)
- 下記一般式(1A)で表される部分構造を有する化合物と、樹脂からなる母材とを含有する有機圧電材料であって、当該部分構造を有する化合物と当該母材のCLogPの値をそれぞれCLogP(1A)とCLogP(母材)としたとき、下記関係式(1)を満たすことを特徴とする有機圧電材料。
関係式(1):|CLogP(1A)-CLogP(母材)|≦3.0
〔式中、CLogPはHansch,Leoのフラグメントアプローチにより算出される“計算LogP”を表す。〕 - 前記一般式(1A)におけるArが、ベンゼン、ベンゾキノン、アントラセン、トリフェニレン、トルクセン、トリシクロキナゾリン、及びジベンゾピレンから選ばれる芳香族炭化水素環又は芳香族複素環であることを特徴とする請求項1に記載の有機圧電材料。
- 前記一般式(1A)におけるLが、単結合であることを特徴とする請求項1又は請求項2に記載の有機圧電材料。
- 下記一般式(1B)で表される化合物又は下記一般式(1B)で表される化合物の残基を下記Q1若しくはQ2を介して側鎖に有する重合体と、樹脂からなる母材とを含有する有機圧電材料であって、当該化合物又は重合体と当該母材のCLogPの値をそれぞれCLogP(1B)とCLogP(母材)としたとき、下記関係式(2)を満たすことを特徴とする有機圧電材料。
一般式(1B):Q1-A1-(L1-A1)n-Q2
(式中、A1は-NR1C(=O)NR2-、-NR1C(=S)NR2-、-OC(=O)O-、-OC(=S)O-、-NHC(=O)O-、-NHC(=S)O-、-NHC(=O)-、-NHC(=S)-、-SO2NH-又は-NHSO2NH-を表す。Q1及びQ2は、各々独立に、無置換の芳香族基、アルキル基若しくはアルコキシ基で置換された芳香族基、又はアルキル基若しくはアルコキシ基で置換されたシクロアルキル基を表す。L1は2価の連結基を表し、nは0~100の整数を表す。A1中にあるR1及びR2は、各々独立して、水素原子又は置換基を表す。)
関係式(2):|CLogP(1B)-CLogP(母材)|≦3.0
〔式中、CLogPはHansch,Leoのフラグメントアプローチにより算出される“計算LogP”を表す。〕 - 前記一般式(1B)におけるQ1及びQ2が、アルコキシ基を有する芳香族基であることを特徴とする請求項4に記載の有機圧電材料。
- 前記母材を構成する樹脂が、熱可塑性樹脂、熱硬化性樹脂、又は光硬化性樹脂であることを特徴とする請求項1から請求項5までのいずれか一項に記載の有機圧電材料。
- 請求項1から請求項6までのいずれか一項に記載の有機圧電材料を用いたことを特徴とする超音波振動子。
- 請求項1から請求項6までのいずれか一項に記載の有機圧電材料を用いた超音波振動子を具備していることを特徴とする超音波探触子。
- 前記超音波振動子が、受信用超音波振動子であることを特徴とする請求項8に記載の超音波探触子。
- 請求項1から請求項6までのいずれか一項に記載の有機圧電材料を用いた超音波探触子を具備していることを特徴とする超音波医用画像診断装置。
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