WO2021019756A1 - ワイヤーハーネスおよびワイヤーハーネスの製造方法ならびに光硬化性組成物およびその硬化物 - Google Patents

ワイヤーハーネスおよびワイヤーハーネスの製造方法ならびに光硬化性組成物およびその硬化物 Download PDF

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Publication number
WO2021019756A1
WO2021019756A1 PCT/JP2019/030173 JP2019030173W WO2021019756A1 WO 2021019756 A1 WO2021019756 A1 WO 2021019756A1 JP 2019030173 W JP2019030173 W JP 2019030173W WO 2021019756 A1 WO2021019756 A1 WO 2021019756A1
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WIPO (PCT)
Prior art keywords
meth
acrylate
mass
photopolymerization initiator
wire harness
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Ceased
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PCT/JP2019/030173
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English (en)
French (fr)
Japanese (ja)
Inventor
慎太郎 南原
崇志 高田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Wiring Systems Ltd
AutoNetworks Technologies Ltd
Sumitomo Electric Industries Ltd
Original Assignee
Sumitomo Wiring Systems Ltd
AutoNetworks Technologies Ltd
Sumitomo Electric Industries Ltd
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Filing date
Publication date
Application filed by Sumitomo Wiring Systems Ltd, AutoNetworks Technologies Ltd, Sumitomo Electric Industries Ltd filed Critical Sumitomo Wiring Systems Ltd
Priority to CN202410921489.XA priority Critical patent/CN118888195A/zh
Priority to PCT/JP2019/030173 priority patent/WO2021019756A1/ja
Priority to CN202410921485.1A priority patent/CN118888194A/zh
Priority to JP2021536569A priority patent/JP7315003B2/ja
Priority to US17/630,635 priority patent/US20220282009A1/en
Priority to CN201980098796.XA priority patent/CN114175181B/zh
Publication of WO2021019756A1 publication Critical patent/WO2021019756A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
    • C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
    • H01B13/012—Apparatus or processes specially adapted for manufacturing conductors or cables for manufacturing wire harnesses
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
    • H01B13/32—Filling or coating with impervious material
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B7/00—Insulated conductors or cables characterised by their form
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B7/00—Insulated conductors or cables characterised by their form
    • H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
    • H01B7/28—Protection against damage caused by moisture, corrosion, chemical attack or weather
    • H01B7/282—Preventing penetration of fluid, e.g. water or humidity, into conductor or cable
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R13/00—Details of coupling devices of the kinds covered by groups H01R12/70 or H01R24/00 - H01R33/00
    • H01R13/46—Bases; Cases
    • H01R13/52—Dustproof, splashproof, drip-proof, waterproof, or flameproof cases
    • H01R13/5219—Sealing means between coupling parts, e.g. interfacial seal
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R4/00—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation
    • H01R4/70—Insulation of connections
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R43/00—Apparatus or processes specially adapted for manufacturing, assembling, maintaining, or repairing of line connectors or current collectors or for joining electric conductors
    • H01R43/005—Apparatus or processes specially adapted for manufacturing, assembling, maintaining, or repairing of line connectors or current collectors or for joining electric conductors for making dustproof, splashproof, drip-proof, waterproof, or flameproof connection, coupling, or casing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A30/00—Adapting or protecting infrastructure or their operation
    • Y02A30/14—Extreme weather resilient electric power supply systems, e.g. strengthening power lines or underground power cables

Definitions

  • the present disclosure relates to a method for manufacturing a wire harness and a wire harness in which an exposed conductor portion of an insulated wire is covered with a water blocking material, a photocurable composition suitable as the water blocking material, and a cured product thereof.
  • a wire harness composed of a bundle of a plurality of insulated wires has a splice portion in which a part of the covering material is removed at the middle portion or the end portion of the plurality of insulated wires and the exposed conductor portions are joined to each other. May have.
  • This splice portion needs to be properly waterproofed.
  • the waterproof treatment of the splice portion is performed by covering the exposed conductor portion of the plurality of insulated wires including the splice portion with an insulating material.
  • One of the insulating materials used for waterproofing the splice portion is an ultraviolet curable material.
  • Patent Documents 1 and 2 describe that the exposed conductor portion of a plurality of insulated wires including the splice portion is covered with an ultraviolet curable material to waterproof the splice portion.
  • the distance from the center of the conductor bundle to the outer circumference of the water blocking material is on the order of millimeters, considering the conductor diameter, etc.
  • the thickness of the material increases. If this water blocking material is an ultraviolet curable material, there is a problem in the curability of the deep part.
  • An object to be solved in the present disclosure is to provide a wire harness having excellent deep curability of a portion covered with a waterproof material. Another object of the present invention is to provide a method for manufacturing the wire harness. Another object of the present invention is to provide a photocurable composition suitable as a water blocking material and a cured product thereof.
  • the wire harness according to the present disclosure is a wire harness in which the exposed conductor portion of the insulated wire is covered with a water blocking material, and the water blocking material is a photocurable resin and photopolymerization initiation.
  • the photocurable composition according to the present disclosure is used as a water blocking material for stopping the conductor portion of the insulated wire, contains a photocurable resin and a photopolymerization initiator, and contains the photopolymerization initiator. However, it is 0.2 parts by mass or more and 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin.
  • the cured product according to the present disclosure is a cured product of the photocurable composition according to the present disclosure.
  • the method for manufacturing a wire harness according to the present disclosure is a method for manufacturing a wire harness in which the exposed conductor portion of the insulated wire is covered with a waterproof material, and the photocurable composition according to the present disclosure is used for the insulation.
  • the water blocking material is formed by covering the exposed conductor portion of the electric wire and curing the photocurable composition covering the exposed conductor portion of the insulated wire.
  • the deep curability of the portion covered with the waterproof material is excellent.
  • the photocurable composition according to the present disclosure is suitable as a water blocking material thereof, and is excellent in deep curability.
  • FIG. 1 is a schematic view of a wire harness according to an embodiment.
  • FIG. 2 is a cross-sectional view taken along the line AA in FIG.
  • FIG. 3 is a process diagram illustrating a method for manufacturing the wire harness shown in FIG.
  • FIG. 4 is a schematic view of a wire harness according to another embodiment.
  • FIG. 5 is a schematic view of a wire harness according to still another embodiment.
  • FIG. 6 is a schematic view illustrating a method for evaluating deep curability.
  • the wire harness according to the present disclosure is a wire harness in which the exposed conductor portion of the insulated wire is covered with a water blocking material, and the water blocking material contains a photocurable resin and a photopolymerization initiator.
  • This is a cured product of the photocurable composition
  • the content of the photopolymerization initiator in the photocurable composition is 0.2 parts by mass or more and 2.0 parts by mass with respect to 100 parts by mass of the photocurable resin. It is as follows.
  • the content of the photopolymerization initiator in the photocurable composition is 0.2 parts by mass or more and 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin. Therefore, it is excellent in deep curability of the part covered with the waterproof material.
  • excellent surface curability and deep curability means that surface and deep curing can be completed in less than 10 seconds, preferably in less than 5 seconds.
  • the photopolymerization initiator may contain an acylphosphine oxide-based photopolymerization initiator.
  • the acylphosphine oxide-based photopolymerization initiator has an excitation wavelength of 360 nm or more and 410 nm or less.
  • the excitation wavelength means that it rises broadly from around 360 nm and converges broadly around 410 nm. Therefore, an LED lamp having a center wavelength of 365 nm or more and 395 nm or less can be used as a light source for light irradiation.
  • the photopolymerization initiator may further contain an alkylphenone-based photopolymerization initiator. This is because, by combining the acylphosphine oxide-based photopolymerization initiator with the alkylphenone-based photopolymerization initiator, the photocurable composition is excellent in surface curability and deep curability even at a high irradiance of 2000 mW / cm 2 or more. .. In the present specification, the irradiance is the illuminance without attenuation.
  • the photocurable composition contains 0.1 part by mass or more and 1.0 part by mass or less of the acylphosphine oxide-based photopolymerization initiator with respect to 100 parts by mass of the photocurable resin, and the alkylphenone-based photopolymerization.
  • the initiator may be contained in an amount of 0.5 parts by mass or more and 3.0 parts by mass or less. 200 mW / cm 2 or less 2000 mW / cm 2 or more low irradiance, it is excellent in surface curability and depth curability of the photocurable composition at high irradiance.
  • the photocurable resin may contain urethane (meth) acrylate. This is because the waterproof material has excellent waterproof performance in a low temperature environment.
  • the photocurable composition may further contain (meth) acrylate other than urethane (meth) acrylate. This is because the photocurable composition contains urethane (meth) acrylate and (meth) acrylate other than urethane (meth) acrylate, so that the waterproof material has excellent waterproof performance even in a high temperature environment.
  • the urethane (meth) acrylate is preferably a urethane (meth) acrylate having any one of a polyether chain, a polyester chain, and a polycarbonate chain. This is because it is easy to introduce a soft component into the molecular structure and to make the cured product relatively soft.
  • the distance from the radial center to the radial outer side of the portion covered with the water blocking material may be 3 mm or more.
  • the content of the photopolymerization initiator in the photocurable composition is 0.2 parts by mass or more with respect to 100 parts by mass of the photocurable resin even in such a thick portion. When the amount is 2.0 parts by mass or less, the deep curability of the portion covered with the waterproof material is excellent.
  • the exposed conductor portion of the insulated wire may include a splice portion in which the exposed conductor portions of a plurality of insulated wires are joined to each other. This is because even in the exposed conductor portion of the insulated wire including the splice portion, the deep curability of the portion covered with the waterproof material is excellent.
  • the photocurable composition according to the present disclosure is used as a water blocking material for stopping the conductor portion of the insulated wire, contains a photocurable resin and a photopolymerization initiator, and contains the photopolymerization initiator.
  • the amount is 0.2 parts by mass or more and 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin.
  • the photocurable composition according to the present disclosure is deeply cured when the content of the photopolymerization initiator is 0.2 parts by mass or more and 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin. Excellent in sex.
  • the photocurable composition according to the present disclosure can be used not only for water blocking of the splice portion described above, but also for use as an anticorrosive agent. Specifically, it can also be used as an anticorrosive agent for preventing the intrusion of electrolytes at joints between dissimilar metals such as aluminum electric wires and copper terminals.
  • the photopolymerization initiator may contain an acylphosphine oxide-based photopolymerization initiator.
  • the acylphosphine oxide-based photopolymerization initiator has an excitation wavelength of 360 nm or more and 410 nm or less.
  • the excitation wavelength means that it rises broadly from around 360 nm and converges broadly around 410 nm. Therefore, an LED lamp having a center wavelength of 365 nm or more and 395 nm or less can be used as a light source for light irradiation.
  • the photopolymerization initiator may further contain an alkylphenone-based photopolymerization initiator. This is because, by combining the acylphosphine oxide-based photopolymerization initiator with the alkylphenone-based photopolymerization initiator, the photocurable composition is excellent in surface curability and deep curability even at a high irradiance of 2000 mW / cm 2 or more. ..
  • the photocurable composition contains 0.1 part by mass or more and 1.0 part by mass or less of the acylphosphine oxide-based photopolymerization initiator with respect to 100 parts by mass of the photocurable resin, and the alkylphenone-based photopolymerization.
  • the initiator may be contained in an amount of 0.5 parts by mass or more and 3.0 parts by mass or less. 200 mW / cm 2 or less 2000 mW / cm 2 or more low irradiance, it is excellent in surface curability and depth curability of the photocurable composition at high irradiance.
  • the photocurable resin may contain urethane (meth) acrylate. This is because the waterproof material has excellent waterproof performance in a low temperature environment.
  • the photocurable composition may further contain (meth) acrylate other than urethane (meth) acrylate. This is because the photocurable composition contains urethane (meth) acrylate and (meth) acrylate other than urethane (meth) acrylate, so that the waterproof material has excellent waterproof performance even in a high temperature environment.
  • the urethane (meth) acrylate is preferably a urethane (meth) acrylate having any one of a polyether chain, a polyester chain, and a polycarbonate chain. This is because it is easy to introduce a soft component into the molecular structure and to make the cured product relatively soft.
  • the cured product according to the present disclosure is a cured product of the photocurable composition according to the present disclosure.
  • the content of the photopolymerization initiator in the photocurable composition according to the present disclosure is 0.2 parts by mass or more and 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin, deep curability Excellent for.
  • the method for manufacturing a wire harness according to the present disclosure is a method for manufacturing a wire harness in which an exposed conductor portion of an insulated wire is covered with a waterproof material, and the photocurable composition according to the present disclosure is described above.
  • the water blocking material is formed by covering the exposed conductor portion of the insulated wire and curing the photocurable composition covering the exposed conductor portion of the insulated wire.
  • the photocurable composition covering the exposed conductor portion of the insulated wire may be cured by irradiating with light of 365 nm or more and 395 nm or less.
  • an LED lamp having a center wavelength of 365 nm or more and 395 nm or less can be used as a light source for light irradiation.
  • the photocurable composition covering the exposed conductor portion of the insulated wire may be cured with an irradiance of 200 mW / cm 2 or less. This is because the photocurable composition according to the present disclosure is excellent in surface curability and deep curability even at a low irradiance of 200 mW / cm 2 or less.
  • the wire harness 10 is composed of a bundle of electric wires in which a plurality of (three) insulated wires 1 to 3 are bundled.
  • the insulated wire 1 is an insulated wire that serves as the main line
  • the insulated wires 2 and 3 are insulated wires that serve as branch lines connected to the insulated wire 1 that serves as the main line at the splice portion 4.
  • the splice portion 4 is a splice portion (intermediate splice portion) in the intermediate portion of the insulated wire 1 which is the main line.
  • Each of the insulated wires 1 to 3 is composed of a conductor 5 made of a core wire whose outer circumference is covered with a covering material 6 made of an insulator.
  • the covering material 6 is partially removed at the intermediate portion in the length direction, and a part of the conductor 5 inside is exposed.
  • the covering material 6 is partially removed at the end portion in the length direction to expose a part of the conductor 5 inside.
  • the covering material 6 of each of the insulated wires 1 to 3 is partially removed, and a plurality of conductors 5 of the insulated wires 1 to 3 are joined to each other in the exposed conductor portion. It is composed of.
  • the conductors 5 may be joined by welding, crimping using a crimp terminal, or any other known joining method.
  • the wire harness 10 includes a conductor exposed portion 7 which is an exposed conductor portion of a plurality of insulated wires 1 to 3 including the splice portion 4, and an end of each covering material of the insulated wires 1 to 3 adjacent to the conductor exposed portion 7.
  • the outer peripheral surfaces of the portions 1a to 3a and 1b are covered with the waterproof material 8.
  • a resin film 9 is arranged on the outside of the water blocking material 8 so as to cover the outside of the water blocking material 8 in a wider range than the water blocking material 8.
  • the water blocking material 8 is composed of a cured product of a photocurable composition containing a photocurable resin and a photopolymerization initiator.
  • the photocurable resin examples include (meth) acrylates such as (meth) acrylate oligomers and (meth) acrylate monomers.
  • the photocurable resin preferably contains urethane (meth) acrylate. Urethane (meth) acrylate easily introduces a soft component into the molecular structure, and when the photocurable resin contains urethane (meth) acrylate, the waterproof material 8 is excellent in waterproof performance in a low temperature environment.
  • the photocurable resin may be composed of only urethane (meth) acrylate, or may be composed of urethane (meth) acrylate and (meth) acrylate other than urethane (meth) acrylate.
  • (meth) acrylates other than urethane (meth) acrylates generally have a soft component that is difficult to enter into the molecular structure, and the cured product tends to be relatively hard. Therefore, when the photocurable resin contains (meth) acrylate other than urethane (meth) acrylate, the waterproof material 8 is excellent in waterproof performance even in a high temperature environment.
  • the low temperature environment means a temperature environment of -40 ° C or lower.
  • the high temperature environment means a temperature environment of 120 ° C. or higher.
  • Urethane (meth) acrylate preferably has a glass transition point of -20 ° C or less when cured alone. It is more preferably ⁇ 25 ° C. or lower, still more preferably ⁇ 30 ° C. or lower.
  • the lower limit of the glass transition point is not particularly limited, but the glass transition point is preferably ⁇ 100 ° C. or higher.
  • the (meth) acrylate other than the urethane (meth) acrylate preferably has a glass transition point of 35 ° C. or higher when cured alone. It is more preferably 50 ° C. or higher, and even more preferably 100 ° C. or higher.
  • the upper limit of the glass transition point is not particularly limited, but the glass transition point is preferably 150 ° C. or lower.
  • the content of urethane (meth) acrylate in the entire photocurable resin is preferably 30% by mass or more and 80% by mass or less because it makes the cured product of the photocurable resin relatively flexible. More preferably, it is 40% by mass or more and 70% by mass or less.
  • (meth) acrylate other than urethane (meth) acrylate is contained, the content of (meth) acrylate other than urethane (meth) acrylate in the entire photocurable resin makes the cured product of the photocurable resin relatively hard. Since it is easy, it is preferably 20% by mass or more and 70% by mass or less. More preferably, it is 30% by mass or more and 60% by mass or less.
  • Urethane (meth) acrylate is an oligomer having a urethane bond obtained by reacting an isocyanate group and a hydroxy group and a (meth) acryloyl group.
  • urethane (meth) acrylate can be designed from hard to soft.
  • Urethane (meth) acrylate has a (meth) acryloyl group at the end of the molecular chain, so that it can be photocured (ultraviolet curable).
  • Urethane (meth) acrylate is synthesized from polyol, isocyanate and hydroxy group-containing (meth) acrylate.
  • Urethane (meth) acrylate can be classified according to the type of polyol.
  • the urethane (meth) acrylate in which the polyol is a polyester polyol is a polyester-based urethane (meth) acrylate having a polyester chain in the molecular structure.
  • the urethane (meth) acrylate in which the polyol is a polyether polyol is a polyether urethane (meth) acrylate having a polyether chain in the molecular structure.
  • the urethane (meth) acrylate in which the polyol is a polycarbonate polyol is a polycarbonate-based urethane (meth) acrylate having a polycarbonate chain in the molecular structure.
  • urethane (meth) acrylate a polyester-based urethane (meth) acrylate having a polyester chain in the molecular structure, in the molecular structure, because it is easy to introduce a soft component into the molecular structure and make the cured product relatively flexible.
  • Polyester-based urethane (meth) acrylate having a polyether chain is preferable, and polycarbonate-based urethane (meth) acrylate having a polycarbonate chain in the molecular structure is preferable.
  • the polyester polyol used for the synthesis of urethane (meth) acrylate is obtained from a polybasic organic acid and a polyol having a low molecular weight, and those having a hydroxyl group as a terminal group can be mentioned as suitable ones.
  • the polybasic organic acid is not particularly limited, but is a saturated fatty acid such as oxalic acid, succinic acid, glutaric acid, adipic acid, pimelli acid, suberic acid, azelaic acid, sebacic acid, isosebacic acid, maleic acid, Unsaturated fatty acids such as fumaric acid, dicarboxylic acids such as aromatic acids such as phthalic acid, isophthalic acid and terephthalic acid, acid anhydrides such as maleic anhydride and phthalic anhydride, dialkyl esters such as dimethyl terephthalate and unsaturated fatty acids. Examples thereof include dimer acid obtained by dimerization of.
  • the low molecular weight polyol used together with the polybasic organic acid is not particularly limited, and is, for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, 1,6.
  • -Diols such as hexylene glycol, triols such as trimethylolethane, trimethylolpropane, hexanetriols and glycerins, hexaols such as sorbitol and the like can be mentioned. These may be used individually by 1 type, or may be used in combination of 2 or more type.
  • polyether polyol used for the synthesis of urethane (meth) acrylate
  • examples of the polyether polyol used for the synthesis of urethane (meth) acrylate include polypropylene glycol (PPG), polytetramethylene glycol (PTMG), these ethylene oxide-modified type polyols, and polyethylene glycol (PEG). These may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the polycarbonate polyol (polycarbonate diol) used for the synthesis of urethane (meth) acrylate can be obtained by polymerizing with a low molecular weight carbonate compound using an alkylene diol as a monomer.
  • alkylene diol examples include 1,6-hexanediol, 1,5-pentanediol, 1,4-butanediol, cyclohexanedimethanol and the like.
  • the alkylene diol as a monomer may be only one of these, or may be two or more.
  • polycarbonate diol examples include polyhexamethylene carbonate diol, polypentamethylene carbonate diol, and polybutylene carbonate diol. These may be used individually by 1 type, or may be used in combination of 2 or more type.
  • Polyisocyanates used in the synthesis of urethane (meth) acrylate include diphenylmethane diisocyanate (MDI), polymethylene polyphenylene polyisocyanate (polymeric MDI), crude MDI (c-MDI) which is a mixture of MDI and polypeptide MDI, and dicyclohexylmethane diisocyanate.
  • MDI diphenylmethane diisocyanate
  • polymeric MDI polymethylene polyphenylene polyisocyanate
  • c-MDI crude MDI which is a mixture of MDI and polypeptide MDI
  • dicyclohexylmethane diisocyanate dicyclohexylmethane diisocyanate
  • Hydrocyanate MDI tolylene diisocyanate
  • TDI tolylene diisocyanate
  • HDI hexamethylene diisocyanate
  • TMHDI trimethylhexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TODI orthotoluidine diisocyanate
  • NDI naphthylene diisocyanate
  • XDI isocyanate
  • PDI paraphenylenediocyanate
  • LDI lysine diisocyanate methyl ester
  • DDI dimethyl diisocyanate
  • Examples of the hydroxy group-containing (meth) acrylate used for the synthesis of urethane (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. .. These may be used individually by 1 type, or may be used in combination of 2 or more type.
  • Examples of (meth) acrylates other than urethane (meth) acrylate include alkyl (meth) acrylate, cycloalkyl (meth) acrylate, alkenyl (meth) acrylate, hydroxyalkyl (meth) acrylate, benzyl (meth) acrylate, and polyether (meth) acrylate. ) Acrylate, polyester (meth) acrylate and the like can be mentioned.
  • the (meth) acrylates other than urethane (meth) acrylates are mono (meth) acrylates, which are monofunctional (meth) acrylates, di (meth) acrylates, which are bifunctional or higher polyfunctional (meth) acrylates, and tri (meth) acrylates. ) It may be any poly (meth) acrylate such as acrylate.
  • (Meta) acrylates other than urethane (meth) acrylates which are classified as mono (meth) acrylates, more specifically, isobornyl (meth) acrylates, Bornyl (meth) acrylates, and tricyclodeca.
  • (Meta) acrylates other than urethane (meth) acrylates which are classified as poly (meth) acrylates, more specifically, butanediol di (meth) acrylates and hexanediol di (meth) acrylates.
  • the photopolymerization initiator is a compound that absorbs light such as ultraviolet rays to initiate radical polymerization of a photocurable resin.
  • the photopolymerization initiator include an acylphosphine oxide-based photopolymerization initiator, an alkylphenone-based photopolymerization initiator, an intramolecular hydrogen abstraction type photopolymerization initiator, an oxime ester-based photopolymerization agent, and a cationic photopolymerization initiator. Be done. These may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the distance from the outer circumference of the photocurable composition arranged around the exposed conductor 7 to the center of the conductor bundle is not on the order of ⁇ m but on the order of mm.
  • the photocurable composition arranged around the conductor exposed portion 7 is photocured, how deep in the depth direction of the photocurable composition arranged around the conductor exposed portion 7 is such a thickness. It is important to deliver the light. Therefore, the content of the photopolymerization initiator in the photocurable composition is 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin.
  • the content of the photopolymerization initiator is small, the absorption of the irradiation light by the photopolymerization initiator located on the surface side of the photocurable composition arranged around the conductor exposed portion 7 is suppressed, and the conductor exposed portion 7 is suppressed.
  • the irradiation light easily enters the depth direction of the photocurable composition arranged around the above, and the photocurable composition can be sufficiently photocured to the depth direction.
  • the content of the photopolymerization initiator is relatively small, 200 mW / cm 2 or less 2000 mW / cm 2 or more low irradiance, photocured arranged around the conductor exposed portion 7 even at high irradiance
  • the sexual composition has excellent surface curability and deep curability.
  • the content of the photopolymerization initiator in the photocurable composition is more preferably 1.0 part by mass or less, still more preferably 0.5 part by mass, based on 100 parts by mass of the photocurable resin. It is as follows.
  • the content of the photopolymerization initiator in the photocurable composition is determined from the viewpoint of ensuring a sufficient amount for photocuring the photocurable composition arranged around the exposed conductor portion 7. It is 0.2 parts by mass or more with respect to 100 parts by mass of the photocurable resin. It is more preferably 0.25 parts by mass or more, and further preferably 0.3 parts by mass or more.
  • the distance from the radial center to the radial outside of the portion of the exposed conductor 7 covered with the water blocking material 8 is on the order of mm, and is 2 mm or more and 6 mm or less considering the specific size of the conductor diameter. Yes, it is preferably 3 mm or more and 5 mm or less.
  • the photopolymerization initiator preferably contains an acylphosphine oxide-based photopolymerization initiator.
  • the acylphosphine oxide-based photopolymerization initiator has an excitation wavelength of 360 nm or more and 410 nm or less.
  • the excitation wavelength means that it rises broadly from around 360 nm and converges broadly around 410 nm. Therefore, when irradiating light, it is preferable to use a light source having a center wavelength of 365 nm or more and 395 nm or less. Examples of such a light source include an LED lamp and the like. The LED lamp is preferable as a light source in terms of power saving.
  • the photopolymerization initiator may further contain an alkylphenone-based photopolymerization initiator in addition to the acylphosphine oxide-based photopolymerization initiator.
  • the alkylphenone-based photopolymerization initiator has an excitation wavelength in the vicinity of 245 nm and is not in the range of 365 nm or more and 395 nm or less. Therefore, when a light source having a center wavelength of 365 nm or more and 395 nm or less is used, the photocurable composition cannot be cured by the alkylphenone-based photopolymerization initiator alone.
  • alkyl phenone photopolymerization initiator acylphosphine oxide-based photopolymerization initiator are combined, 200 mW / cm 2 or less 2000 mW / cm 2 or more low irradiance, also disposed around the conductor exposed portion 7 with high irradiance
  • the photocurable composition is excellent in surface curability and deep curability.
  • an acylphosphine oxide-based photopolymerization initiator and an alkylphenone-based photopolymerization initiator are included as the photopolymerization initiator, if a light source having a center wavelength of 365 nm or more and 395 nm or less is used, the excitation wavelength is outside the irradiation wavelength range. Many alkylphenone-based photopolymerization initiators remain undecomposed in the cured product after light irradiation. On the other hand, many acylphosphine oxide-based photopolymerization initiators having an excitation wavelength within the irradiation wavelength range are decomposed in the cured product after light irradiation. Therefore, the cured product after light irradiation contains a larger amount of alkylphenone-based photopolymerization initiator than the acylphosphine oxide-based photopolymerization initiator.
  • the photocurable composition initiates acylphosphine oxide-based photopolymerization with respect to 100 parts by mass of the photocurable resin. It is preferable that the agent is contained in an amount of 0.1 part by mass or more and 1.0 part by mass or less, and the alkylphenone-based photopolymerization initiator is contained in an amount of 0.5 part by mass or more and 3.0 parts by mass or less.
  • acylphosphine oxide-based photopolymerization initiator 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2 , 4,4-trimethyl-Pentylphosphine oxide and the like.
  • Commercially available products include IGM Resins B.I. V. Examples thereof include Omnirad TPO and Omnirad 819 manufactured by Japan.
  • alkylphenone-based photopolymerization initiator examples include benzyldimethylketal-based photopolymerization initiators such as 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxycyclohexyl-phenyl-ketone, and 2-hydroxy.
  • benzyl dimethyl ketal-based photopolymerization initiators include IGM Resins B.I. V. Omnirad 651 manufactured by Japan, and the like.
  • ⁇ -hydroxyalkylphenone-based photopolymerization initiators include IGM Resins B.I. V. Examples thereof include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127, and the like.
  • commercially available ⁇ -aminoacetophenone-based photopolymerization initiators include IGM Resins B.I. V. Examples thereof include Omnirad 907, Omnirad 369, and Omnirad 379 manufactured by Japan.
  • Examples of the intramolecular hydrogen abstraction type photopolymerization initiator include IGM Resins B.I. V. Examples include Omnirad MBF and Omnirad 754 manufactured by Japan. Examples of the oxime ester-based photopolymerization initiator include CGI-325 manufactured by BASF Japan, Irgacure OXE01, Irgacure OXE02, and N-1919 manufactured by ADEKA. Examples of the cationic photopolymerization initiator include IGM Resins B.I. V. Examples thereof include Omnirad 250 and Omnirad 270 manufactured by Japan.
  • the photocurable composition constituting the water blocking material 8 may contain an additive.
  • the resin film 9 holds the photocurable composition around the conductor exposed portion 7 so that the photocurable composition before curing does not flow from the periphery of the conductor exposed portion 7.
  • the resin film 9 may or may not be adhered to the outer surface of the water blocking material 8.
  • the resin film 9 has light transmittance so that the photocurable composition arranged around the conductor exposed portion 7 can be photocured. That is, the photocurable composition transmits the irradiation light for photocuring to the extent that it can be photocured. From the viewpoint of excellent light transmittance, the resin film 9 preferably has an ultraviolet transmittance of 50% or more. It is more preferably 70% or more, still more preferably 90% or more. Further, the resin film 9 has the flexibility to be deformable by following the deformation of the photocurable composition.
  • the thickness of the resin film 9 is preferably 200 ⁇ m or less, more preferably 150 ⁇ m or less, further preferably 100 ⁇ m or less, still more preferably 5 ⁇ m or more and 50 ⁇ m or less.
  • the resin film 9 examples include olefin resins such as polyethylene and polypropylene, polyesters such as polyvinyl chloride, polyvinylidene chloride and vinylidene chloride, polyethylene terephthalate, and wrap sheets of resins such as polyamide such as nylon.
  • olefin resins such as polyethylene and polypropylene
  • polyesters such as polyvinyl chloride, polyvinylidene chloride and vinylidene chloride, polyethylene terephthalate
  • wrap sheets of resins such as polyamide such as nylon.
  • polyvinyl chloride resin, polyvinylidene chloride resin, and polyvinylidene fluoride from the viewpoint of good self-adhesion (adhesion) and easy wrapping around the photocurable composition that covers the periphery of the exposed conductor portion 7.
  • a resin wrap sheet is suitable.
  • the resin film 9 may have an adhesive layer on its surface.
  • an adhesive layer it is preferable in that the position can be easily fixed when wound.
  • the upper limit of the thickness of the adhesive layer may be 50 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less.
  • the conductor 5 of the insulated wires 1 to 3 is composed of a stranded wire in which a plurality of strands are twisted together, but it may be a single wire.
  • the conductor 5 may be made of a metal having excellent conductivity such as copper, a copper alloy, aluminum, and an aluminum alloy.
  • the metal surface may be further plated with a metal such as nickel.
  • the covering material 3 may be formed of a resin, a thermoplastic elastomer, rubber, or the like. Examples of the material include polyolefin, PVC and the like.
  • the wire harness 10 can be manufactured as follows.
  • FIG. 3 shows a process for explaining a method for manufacturing a wire harness.
  • the covering material 6 of each of the insulated wires 1 to 3 is partially removed, and the conductors 5 of the plurality of insulated wires 1 to 3 are joined to each other in the exposed conductor portion.
  • the splice portion 4 is formed by.
  • a resin film 9 having a size that covers the conductor exposed portion 7 in a wider range than the conductor exposed portion 7 including the splice portion 4 is prepared.
  • the surface (inner side surface) of the resin film 9 has an adhesive layer containing an adhesive.
  • a photocurable composition 8a constituting the water blocking material 8 is supplied from the nozzle 11 of the discharge device in an amount sufficiently covering the exposed conductor portion 7.
  • the photocurable composition 8a at the time of discharge may be kept at room temperature or heated, and may be in a liquid state.
  • the exposed conductor portion 7 including the splice portion 4 is placed on the photocurable composition 8a on the resin film 9.
  • the resin film 9 is folded back so as to cover the exposed conductor portion 7 including the splice portion 4 and the supplied photocurable composition 8a.
  • the edges of the folded resin film 9 are overlapped with each other.
  • the ends of the laminated resin films 9 are bonded to each other by an adhesive.
  • the overlapped portion of the resin film 9 may be squeezed toward the splice portion 4.
  • the photocurable composition 8a can permeate between the wire coatings and along the coating surface, and the splice diameter can be kept constant.
  • the light (ultraviolet) irradiation device 12 irradiates the photocurable composition 8a covering the exposed conductor portion 7 with light (ultraviolet rays) through the resin film 9.
  • Irradiance of the irradiation light may be a 50 mW / cm 2 or more 10000 mW / cm 2 or less, it is preferable that the 50 mW / cm 2 or more 5000 mW / cm 2 or less.
  • the photocurable composition 8a is photocured and becomes a cured product to form a water blocking material 8. Next, the overlapped ends of the resin film 9 are cut if necessary. As described above, the wire harness 10 is manufactured.
  • the photocurable composition 8a constituting the water blocking material 8 is the above-mentioned photocurable composition.
  • the photocurable composition contains a photocurable resin and a photopolymerization initiator.
  • the content of the photopolymerization initiator in the photocurable composition is 0.2 parts by mass or more and 2.0 parts by mass or less with respect to 100 parts by mass of the photocurable resin.
  • the light irradiation time can be 1 second or more and 120 seconds or less, preferably 1 second or more and less than 10 seconds, and more preferably 1 second or more and less than 5 seconds.
  • the photocurable composition 8a constituting the water blocking material 8 can contain an acylphosphine oxide-based photopolymerization initiator as the photopolymerization initiator. Since the acylphosphine oxide-based photopolymerization initiator has an excitation wavelength of 360 nm or more and 410 nm or less, the photocurable composition 8a constituting the water blocking material 8 is cured by irradiating with light of 365 nm or more and 395 nm or less. be able to. Then, a power-saving LED lamp having a center wavelength of 365 nm or more and 395 nm or less can be used as a light source. The excitation wavelength means that it rises broadly from around 360 nm and converges broadly around 410 nm.
  • the photocurable composition 8a constituting the water blocking material 8 can contain an acylphosphine oxide-based photopolymerization initiator and an alkylphenone-based photopolymerization initiator as the photopolymerization initiator.
  • an acylphosphine oxide-based photopolymerization initiator and an alkylphenone-based photopolymerization initiator as the photopolymerization initiator.
  • the light irradiation time can be 1 second or more and 120 seconds or less, preferably 1 second or more and less than 10 seconds, and more preferably 1 second or more and less than 5 seconds.
  • the deep curable portion of the portion covered with the water blocking material 8 is excellent.
  • the resin film 9 is used because the photocurable composition 8a is easily applied to a predetermined range. However, the photocurable composition 8a is applied to a predetermined range by another method. If possible, the resin film 9 may not be used. Further, if the adhesion of the photocurable composition 8a to the cured product is low, the resin film 9 can be peeled off after curing to obtain a wire harness without the resin film 9.
  • FIG. 4 shows a wire harness 20 without the resin film 9.
  • the wire harness 20 has the same configuration as the wire harness 10 except that the resin film 9 is not provided, and other description thereof will be omitted.
  • FIG. 5 shows a wire harness according to still another embodiment.
  • the wire harness 30 is composed of a bundle of electric wires in which a plurality of (4) insulated wires 31 to 34 are bundled.
  • Each of the insulated wires 31 to 34 is composed of a conductor 5 made of a core wire whose outer circumference is covered with a covering material 6 made of an insulator. In each of the insulated wires 31 to 34, the covering material 6 is partially removed at the end portion in the length direction, and a part of the conductor 5 inside is exposed.
  • the splice portion 35 of the wire harness 30 is formed by joining the conductors 5 of a plurality of insulated wires 31 to 34 to each other in the exposed conductor portion.
  • the conductors 5 may be joined by welding, crimping using a crimp terminal, or any other known joining method.
  • the splice portion 35 is a splice portion (end splice portion) at the end portions of all the insulated wires of the plurality of insulated wires 31 to 34.
  • the wire harness 30 includes a conductor exposed portion 36 composed of a bundle of exposed conductors of a plurality of insulated wires 31 to 34 including the splice portion 35, and each covering material of the insulated wires 31 to 34 adjacent to the conductor exposed portion 36. It has a water blocking material 37 that continuously covers the outer peripheral surfaces of the ends 31a to 34a to stop water. Since the conductor exposed portion 36 is covered with the waterproof material 37, water can be prevented from entering the conductor exposed portion 36 from the outside, and a waterproof effect can be obtained. Like the water blocking material 8, the water blocking material 37 is composed of a cured product of the photocurable composition.
  • the wire harness 30 is, for example, filled with the photocurable composition in a cap-shaped transparent container 38 having a light transmittance that transmits irradiation light for photocuring the photocurable composition to a extent that it can be photocured.
  • the photocurable composition can be produced by immersing it in a light-curing composition and irradiating it with light in this state.
  • the water blocking material 37 may be taken out from the cap-shaped transparent container 38.
  • a photocurable composition was prepared by blending a urethane acrylate oligomer, an acrylate monomer, and a photopolymerization initiator with the compositions shown in Table 1.
  • the photocurable composition 42 is arranged on the quartz plate 41 so that the height of the liquid level is 5 mm, and the parallel disk type rheometer is placed on the arranged photocurable composition 42.
  • the photocurable composition 42 had a columnar shape having the same circular area as the ⁇ 12 mm plate 43.
  • Ultraviolet light 100 mW / cm 2
  • LED-UV lamp LED-UV lamp
  • the content of the photopolymerization initiator is 0.2 parts by mass or more with respect to 100 parts by mass of the photocurable resin. It can be seen that when the amount is 2.0 parts by mass or less, the deep curing is started even with a thickness of 5 mm, and the deep curing property is excellent. If the content of the photopolymerization initiator is less than 0.2 parts by mass with respect to 100 parts by mass of the photocurable resin, the amount of the photopolymerization initiator sufficient for photocuring is insufficient, and the thickness is 5 mm even if the irradiation time is 30 seconds. Deep curing did not start.
  • the content of the photopolymerization initiator is more than 2.0 parts by mass with respect to 100 parts by mass of the photocurable resin, the amount of light sufficient for photocuring does not sufficiently reach the deep part having a thickness of 5 mm, and the irradiation time is 30. Deep curing with a thickness of 5 mm did not start even in seconds.

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PCT/JP2019/030173 2019-08-01 2019-08-01 ワイヤーハーネスおよびワイヤーハーネスの製造方法ならびに光硬化性組成物およびその硬化物 Ceased WO2021019756A1 (ja)

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CN202410921489.XA CN118888195A (zh) 2019-08-01 2019-08-01 线束及线束的制造方法和光固化性组合物及其固化物
PCT/JP2019/030173 WO2021019756A1 (ja) 2019-08-01 2019-08-01 ワイヤーハーネスおよびワイヤーハーネスの製造方法ならびに光硬化性組成物およびその硬化物
CN202410921485.1A CN118888194A (zh) 2019-08-01 2019-08-01 线束及线束的制造方法和光固化性组合物及其固化物
JP2021536569A JP7315003B2 (ja) 2019-08-01 2019-08-01 ワイヤーハーネスおよびワイヤーハーネスの製造方法ならびに光硬化性組成物およびその硬化物
US17/630,635 US20220282009A1 (en) 2019-08-01 2019-08-01 Wiring harness, wiring harness manufacturing method, photocurable composition and cured product of same
CN201980098796.XA CN114175181B (zh) 2019-08-01 2019-08-01 线束及线束的制造方法和光固化性组合物及其固化物

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