WO2023139898A1 - 樹脂組成物、光ファイバ、光ファイバの製造方法、光ファイバリボン、及び光ファイバケーブル - Google Patents

樹脂組成物、光ファイバ、光ファイバの製造方法、光ファイバリボン、及び光ファイバケーブル Download PDF

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WO2023139898A1
WO2023139898A1 PCT/JP2022/041753 JP2022041753W WO2023139898A1 WO 2023139898 A1 WO2023139898 A1 WO 2023139898A1 JP 2022041753 W JP2022041753 W JP 2022041753W WO 2023139898 A1 WO2023139898 A1 WO 2023139898A1
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optical fiber
resin composition
meth
acrylate
ppm
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English (en)
French (fr)
Japanese (ja)
Inventor
祐也 本間
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Sumitomo Electric Industries Ltd
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Sumitomo Electric Industries Ltd
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Priority to JP2023575081A priority Critical patent/JPWO2023139898A1/ja
Priority to CN202280082727.1A priority patent/CN118401484A/zh
Priority to US18/711,952 priority patent/US20250011615A1/en
Publication of WO2023139898A1 publication Critical patent/WO2023139898A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
    • C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C13/00—Fibre or filament compositions
    • C03C13/04—Fibre optics, e.g. core and clad fibre compositions
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/104—Coating to obtain optical fibres
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/104—Coating to obtain optical fibres
    • C03C25/106—Single coatings
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates

Definitions

  • the present disclosure relates to resin compositions for primary coatings of optical fibers, optical fibers, methods of making optical fibers, optical fiber ribbons, and optical fiber cables.
  • This application claims priority based on Japanese application No. 2022-006855 filed on January 20, 2022, and incorporates all the descriptions described in the Japanese application.
  • an optical fiber is provided with a coating resin layer for protecting the glass fiber, which is an optical transmission body.
  • the coating resin layer is composed of, for example, two layers, a primary resin layer in contact with the glass fiber and a secondary resin layer formed on the outer layer of the primary resin layer.
  • an external force lateral pressure
  • microbend loss tends to increase.
  • Patent Documents 1 to 5 describe a resin composition for primary coating containing urethane (meth)acrylate which is a reaction product of polyol, diisocyanate and hydroxyl group-containing (meth)acrylate.
  • a resin composition for primary coating of an optical fiber is a resin composition containing a photopolymerizable compound, a photopolymerization initiator, and a polymerization inhibitor, wherein the photopolymerization compound includes a photopolymerizable compound having a urethane bond and a photopolymerizable compound having no urethane bond, the polymerization inhibitor includes 4-methoxyphenol, and the total content of the polymerization inhibitor is 200 ppm or more and 800 ppm or less.
  • FIG. 1 is a schematic cross-sectional view showing an example of an optical fiber according to this embodiment.
  • FIG. 2 is a schematic cross-sectional view showing an optical fiber ribbon according to one embodiment.
  • FIG. 3 is a schematic cross-sectional view showing an optical fiber ribbon according to one embodiment.
  • FIG. 4 is a plan view showing the appearance of an optical fiber ribbon according to one embodiment.
  • FIG. 5 is a schematic cross-sectional view showing an optical fiber cable according to one embodiment.
  • FIG. 6 is a schematic cross-sectional view showing an optical fiber cable according to one embodiment.
  • An object of the present disclosure is to provide a resin composition that is excellent in stability and capable of forming a resin layer suitable for the primary coating of an optical fiber, and an optical fiber that is excellent in microbend resistance and low temperature properties.
  • An optical fiber primary coating resin composition is a resin composition containing a photopolymerizable compound, a photopolymerization initiator, and a polymerization inhibitor, wherein the photopolymerization compound includes a photopolymerizable compound having a urethane bond and a photopolymerizable compound having no urethane bond, the polymerization inhibitor includes 4-methoxyphenol, and the total content of the polymerization inhibitor is 200 ppm or more and 800 ppm or less.
  • Such a resin composition has excellent stability, can form a resin layer suitable for the primary coating of an optical fiber, and can improve the microbending resistance and low-temperature characteristics of the optical fiber.
  • the polymerization inhibitor may further contain 2,6-di-tert-butyl-p-cresol.
  • the resin composition according to the present embodiment is UV-cured under the conditions of an integrated light quantity of 10 mJ/ cm and an illuminance of 100 mW/ cm .
  • the total content of polymerization inhibitors in the resin composition may be 700 ppm or less, or 600 ppm or less.
  • the total content of polymerization inhibitors in the resin composition may be 300 ppm or more.
  • the content of 4-methoxyphenol may be 80 ppm or more and 750 ppm or less.
  • the photopolymerizable compound having no urethane bond contains an N-vinyl compound, and the content of the N-vinyl compound may be 1 part by mass or more and 15 parts by mass or less based on the total amount of 100 parts by mass of the resin composition.
  • the N-vinyl compound may be N-vinylcaprolactam.
  • the resin composition according to the present embodiment may further contain ⁇ -caprolactam, and the content of ⁇ -caprolactam in the resin composition may be 2000 ppm or less.
  • An optical fiber includes a glass fiber including a core and a clad, a primary resin layer that coats the glass fiber in contact with the glass fiber, and a secondary resin layer that coats the primary resin layer, and the primary resin layer includes a cured product of the resin composition.
  • Such an optical fiber does not cause defects in the primary resin layer and has excellent microbend resistance and low temperature properties.
  • a method for manufacturing an optical fiber according to an aspect of the present disclosure includes a coating step of coating the resin composition on the outer periphery of a glass fiber including a core and a clad, and a curing step of curing the resin composition by irradiating ultraviolet rays after the coating step.
  • An optical fiber ribbon includes a plurality of the optical fibers arranged in parallel and coated with a ribbon resin.
  • Such optical fiber ribbons are excellent in micro-bending resistance and low-temperature properties, and can be densely packed in optical fiber cables.
  • An optical fiber cable according to one aspect of the present disclosure has the optical fiber ribbon housed therein.
  • the optical fiber cable according to the present disclosure may be arranged such that a plurality of the optical fibers are housed in the cable.
  • An optical fiber cable including the optical fiber or optical fiber ribbon according to this embodiment has excellent microbend resistance and low temperature characteristics.
  • the resin composition according to the present embodiment contains a photopolymerizable compound, a photopolymerization initiator, and a polymerization inhibitor, and the photopolymerizable compound contains a photopolymerizable compound having a urethane bond and a photopolymerizable compound having no urethane bond, the polymerization inhibitor contains 4-methoxyphenol, and the total content of the polymerization inhibitor is 200 ppm or more and 800 ppm or less.
  • Polymerization inhibitors are sometimes used during the production of photopolymerizable compounds to prevent gelation, and are sometimes added during the preparation of resin compositions to improve the storage stability of resin compositions.
  • Polymerization inhibitors include, for example, hydroquinone, 4-methoxyphenol, 2,6-di-tert-butyl-p-cresol, p-benzoquinone, phenothiazine, catechol, and tert-butylcatechol.
  • the polymerization inhibitor according to the present embodiment contains 4-methoxyphenol, and may contain 4-methoxyphenol and 2,6-di-tert-butyl-p-cresol, from the viewpoint of adjusting the balance between storage stability and photocurability of the resin composition.
  • the total content of polymerization inhibitors in the resin composition (the total content of polymerization inhibitors relative to the total mass of the resin composition) is 200 ppm or more and 800 ppm or less. If the total content of polymerization inhibitors is less than 200 ppm, the storage stability of the resin composition is likely to deteriorate. Poor curing of the primary resin layer may degrade the low-temperature properties of the optical fiber.
  • the total content of polymerization inhibitors in the resin composition is preferably 700 ppm or less, more preferably 650 ppm or less, and even more preferably 600 ppm or less, from the viewpoint of further improving the low-temperature characteristics of the optical fiber. From the viewpoint of further improving the storage stability of the resin composition, the total content of polymerization inhibitors in the resin composition is preferably 250 ppm or more, more preferably 280 ppm or more, and even more preferably 300 ppm or more.
  • the content of 4-methoxyphenol may be 80 ppm or more and 750 ppm or less, 90 ppm or more and 700 ppm or less, or 110 ppm or more and 600 ppm or less with respect to the total mass of the resin composition.
  • the Young's modulus of the resin film is preferably 0.10 MPa or more and 0.80 MPa or less at 23° C. when the resin composition is UV-cured under the conditions of an integrated light amount of 10 mJ/cm 2 and an illuminance of 100 mW/cm 2 .
  • the Young's modulus of the resin film is 0.10 MPa or more, the low-temperature properties of the optical fiber are likely to be improved, and when the Young's modulus of the resin film is 0.80 MPa or less, the micro-bending resistance of the optical fiber is likely to be improved.
  • the Young's modulus of the resin film is more preferably 0.10 MPa or more and 0.60 MPa or less, and still more preferably 0.10 MPa or more and 0.50 MPa or less.
  • the photopolymerizable compound according to this embodiment includes a photopolymerizable compound having a urethane bond and a photopolymerizable compound having no urethane bond.
  • a photopolymerizable compound having a urethane bond a urethane (meth)acrylate (hereinafter sometimes referred to as "urethane (meth)acrylate (A)") which is a reaction product of a diol, a diisocyanate, and a hydroxyl group-containing (meth)acrylate can be used.
  • Diols include, for example, polyether diols, polyester diols, polycaprolactone diols, polycarbonate diols, polybutadiene diols, and bisphenol A/ethylene oxide addition diols.
  • polyether diols include polytetramethylene glycol (PTMG), polyethylene glycol (PEG), polypropylene glycol (PPG), block copolymers of PTMG-PPG-PTMG, block copolymers of PEG-PPG-PEG, random copolymers of PTMG-PEG, and random copolymers of PTMG-PPG.
  • Polypropylene glycol is preferably used as the diol because it facilitates adjustment of the Young's modulus of the resin layer.
  • the number average molecular weight (Mn) of the diol may be 1800 or more and 20000 or less, 2000 or more and 19000 or less, or 2500 or more and 18500 or less.
  • Geisocyanate for example, 2,4 -4 -4 -triling isocyanate, 2,6 -trilicene isocyanate, isoforon isocyanate, dischicrohexylmethane dizzyisianate, diphenylmetan dizzy socianate, hexicrange isocyanate, xylicrange isocyanate, water -friendly xylle.
  • hydroxyl group-containing (meth)acrylates examples include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, caprolactone (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-(meth)acryloyloxyethyl-2-hydroxyethyl phthalate, 2-hydroxy-o-phenylphenolpropyl (meth)acrylate, 2-hydroxy-3-methacrylpropyl acrylate, and trimethylolpropane (meth)acrylate.
  • acrylates, and pentaerythritol tri(meth)acrylates From the viewpoint of reactivity, 2-hydroxyethyl acrylate is preferred.
  • Methods for preparing the urethane (meth)acrylate (A) include, for example, a method of reacting a diol with a diisocyanate to synthesize an isocyanate group (NCO)-terminated prepolymer and then reacting with a hydroxyl group-containing (meth)acrylate; a method of reacting a diisocyanate with a hydroxyl group-containing (meth)acrylate, and then reacting the diol; and a method of simultaneously reacting a diol, a diisocyanate, and a hydroxyl group-containing (meth)acrylate.
  • a hydroxyl group-containing (meth)acrylate may be used by mixing with a monohydric alcohol or an active hydrogen-containing silane compound.
  • the proportion of the (meth)acryloyl group, which is a photopolymerizable group, can be reduced, and the Young's modulus of the primary resin layer can be reduced.
  • Examples of monohydric alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-2-propanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 2-methyl-2-butanol, and 3-methyl-2-butanol.
  • the ratio of the (meth)acryloyl group, which is a photopolymerizable group, can be reduced, the Young's modulus of the primary resin layer can be reduced, and the adhesion to the glass fiber can be improved.
  • active hydrogen-containing silane compounds include N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, and 3-mercaptopropyltrimethoxysilane. Silanes are mentioned.
  • the molar ratio of NCO and OH (NCO/OH) when the diol and diisocyanate are reacted is preferably 1.1 or more and 4.0 or less, more preferably 1.2 or more and 3.5 or less, and still more preferably 1.4 or more and 3.0 or less.
  • the molar ratio of hydroxyl group-containing (meth)acrylate to NCO in the NCO-terminated prepolymer is preferably 1.00 or more and 1.15 or less, more preferably 1.03 or more and 1.10 or less.
  • the molar ratio of the total of the hydroxyl group-containing (meth)acrylate, the active hydrogen-containing silane compound, and the monohydric alcohol to the NCO of the NCO-terminated prepolymer is preferably 1.00 or more and 1.15 or less, more preferably 1.03 or more and 1.10 or less, and the total molar ratio of the active hydrogen-containing silane compound and the monohydric alcohol to the NCO of the NCO-terminated prepolymer is 0.01 or more and 0.5.
  • the following are preferred.
  • the resin composition according to the present embodiment may further contain, as a photopolymerizable compound having a urethane bond, a urethane (meth)acrylate (hereinafter sometimes referred to as "urethane (meth)acrylate (B)"), which is a reaction product of a polyoxyalkylene monoalkyl ether, a diisocyanate, and a hydroxyl group-containing (meth)acrylate.
  • urethane (meth)acrylate (B) urethane (meth)acrylate
  • a polyoxyalkylene monoalkyl ether is a compound having an oxyalkylene group, an alkoxy group and a hydroxyl group. ⁇ (C 12 ⁇ C 14 ) ⁇
  • the polyoxyalkylene monoalkyl ether is preferably polyoxypropylene monobutyl ether.
  • the Mn of the polyoxyalkylene monoalkyl ether is preferably 2000 or more and 10000 or less, may be 2100 or more or 2200 or more, and may be 8000 or less or 7000 or less.
  • the Mn of the diol and polyoxyalkylene monoalkyl ether can be calculated from the following formula (1) by measuring the hydroxyl value based on JIS K 0070.
  • the diol has two functional groups, and the polyoxyalkylene monoalkyl ether has one functional group.
  • Mn 56.1 ⁇ number of functional groups ⁇ 1000 / hydroxyl value (1)
  • Mn of the urethane (meth)acrylate (A) may be 6000 or more and 50000 or less, 8000 or more and 45000 or less, or 10000 or more and 40000 or less.
  • Mn of the urethane (meth)acrylate (B) may be 4000 or more and 20000 or less, 5000 or more and 18000 or less, or 6000 or more and 15000 or less.
  • the Mn of urethane (meth)acrylate (A) and urethane (meth)acrylate (B) can be measured by gel permeation chromatography (GPC).
  • the content of the urethane (meth)acrylate (A) is preferably 15 parts by mass or more and 80 parts by mass or less, more preferably 20 parts by mass or more and 75 parts by mass or less, and even more preferably 25 parts by mass or more and 70 parts by mass or less, based on the total amount of 100 parts by mass of the resin composition.
  • the content of urethane (meth)acrylate (B) may be 0 to 70 parts by mass, 10 to 50 parts by mass, or 20 to 45 parts by mass, based on the total amount of 100 parts by mass of the resin composition.
  • the content of the photopolymerizable compound having a urethane bond may be 30 to 90 parts by mass, 40 to 80 parts by mass, or 45 to 70 parts by mass, based on the total amount of the resin composition.
  • Organotin compounds include, for example, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin malate, dibutyltin bis(2-ethylhexyl mercaptoacetate), dibutyltin bis(isooctyl mercaptoacetate), and dibutyltin oxide.
  • the amount of the catalyst added is preferably 100 ppm or more and 1000 ppm or less, more preferably 200 ppm or more and 800 ppm or less, relative to the total mass of the photopolymerizable compound having a urethane bond to be synthesized.
  • Dibutyltin dilaurate or dibutyltin diacetate is preferably used as the catalyst from the standpoint of ready availability or catalytic performance.
  • the amount of the polymerization inhibitor added is preferably 150 ppm to 2000 ppm, more preferably 180 ppm to 1500 ppm, even more preferably 200 ppm to 1200 ppm, relative to the total mass of the photopolymerizable compound having a urethane bond to be synthesized.
  • the photopolymerizable compound according to the present embodiment includes a photopolymerizable compound having no urethane bond (hereinafter referred to as "monomer").
  • monomers include (meth)acrylic acid esters, N-vinyl compounds, and (meth)acrylamide compounds.
  • the monomer may be a monofunctional monomer having one photopolymerizable ethylenically unsaturated group, or a polyfunctional monomer having two or more ethylenically unsaturated groups.
  • Examples of monofunctional (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, isobutyl (meth)acrylate, n-pentyl (meth)acrylate, isopentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, isoamyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate,
  • polyfunctional (meth)acrylic acid esters include ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, cyclohexanedimethanol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, neopentylglycol hydroxypivalate di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate).
  • acrylates 1,4-butanediol di(meth)acrylate, diethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, 1,14-tetradecanediol di(meth)acrylate, 1,16-hexadecanediol di(meth)acrylate, 1,20-eicosandiol di(meth)acrylate, isopentyldiol di(meth)acrylate meth)acrylate, 3-ethyl-1,8-octanediol di(meth)acrylate, tricyclodecanol di(meth)acrylate, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene di(meth)acrylate, bisphenol A epoxy di(meth)acrylate
  • (Meth)acrylamide compounds include, for example, dimethyl (meth)acrylamide, diethyl (meth)acrylamide, (meth)acryloylmorpholine, hydroxymethyl (meth)acrylamide, hydroxyethyl (meth)acrylamide, isopropyl (meth)acrylamide, dimethylaminopropyl (meth)acrylamide, dimethylaminopropylacrylamide/methyl chloride salt, diacetoneacrylamide, (meth)acryloylpiperidine, (meth)acryloylpyrrolidine, (meth)acrylamide, N-hexyl (meth) Acrylamide, N-methyl(meth)acrylamide, N-butyl(meth)acrylamide, N-methylol(meth)acrylamide, and N-methylolpropane(meth)acrylamide.
  • (Meth)acrylate and (meth)acrylamide compounds generally contain 4-methoxyphenol as a polymerization inhibitor.
  • the amount of 4-methoxyphenol contained in the (meth)acrylic acid ester and (meth)acrylamide compound may be 80 ppm or more and 1600 ppm or less, 90 ppm or more and 1400 ppm or less, or 100 ppm or more and 1000 ppm or less.
  • N-vinyl compounds include N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylmethyloxazolidinone, N-vinylimidazole, and N-vinyl-N-methylacetamide.
  • the content of the monomer is preferably 5 parts by mass or more and 70 parts by mass or less, more preferably 10 parts by mass or more and 60 parts by mass or less, and even more preferably 15 parts by mass or more and 50 parts by mass or less, based on the total amount of 100 parts by mass of the resin composition.
  • N-vinyl compound By including the N-vinyl compound in the photopolymerizable compound, the curing speed of the resin composition can be improved.
  • N-vinyl compound N-vinylcaprolactam is particularly preferred.
  • N-vinylcaprolactam may contain ⁇ -caprolactam as an impurity.
  • the amount of ⁇ -caprolactam contained in N-vinylcaprolactam is, for example, about 5000 ppm to 25000 ppm.
  • the content of ⁇ -caprolactam in the resin composition is preferably 2000 ppm or less, and may be 1800 ppm or less, 1600 ppm or less, or 1400 ppm or less. This is probably because ⁇ -caprolactam is basic.
  • the content of the N-vinyl compound may be from 1 part by mass to 15 parts by mass, from 2 parts by mass to 14 parts by mass, or from 3 parts by mass to 13 parts by mass, based on the total amount of the resin composition of 100 parts by mass.
  • the photopolymerization initiator can be appropriately selected from known radical photopolymerization initiators and used.
  • photopolymerization initiators include 1-hydroxycyclohexylphenyl ketone (Omnirad 184, manufactured by IGM Resins), 2,2-dimethoxy-2-phenylacetophenone (Omnirad 651, manufactured by IGM Resins), 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Omnirad TPO, manufactured by IGM Resins), ethyl (2,4,6 -trimethylbenzoyl)-phenylphosphinate (Omnirad TPO-L, IGM Resins), 2-benzyl-2-dimethylamino-4'-morpholinobtyrophenone (Omnirad 369, IGM Resins), 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one
  • the photopolymerization initiator preferably contains 2,4,6-trimethylbenzoyldiphenylphosphine oxide because the resin composition has excellent rapid curing properties.
  • the content of the photopolymerization initiator is preferably 0.1 to 5 parts by mass, more preferably 0.3 to 4 parts by mass, and even more preferably 0.4 to 3 parts by mass, based on the total amount of the resin composition.
  • the resin composition according to this embodiment may further contain sensitizers, photoacid generators, silane coupling agents, leveling agents, antifoaming agents, antioxidants, ultraviolet absorbers, and the like.
  • sensitizers include anthracene compounds such as 9,10-dibutoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, and 9,10-bis(2-ethylhexyloxy)anthracene; thioxanthone compounds such as 2,4-diethylthioxanthone, 2,4-diethylthioxanthen-9-one, 2-isopropylthioxanthone, and 4-isopropylthioxanthone; and triethanol.
  • examples include amine compounds such as amines, methyldiethanolamine and triisopropanolamine, benzoin compounds, anthraquinone compounds, ketal compounds, and benzophenone compounds.
  • An onium salt having a structure of A + B ⁇ may be used as the photoacid generator.
  • photoacid generators include sulfonium salts such as CPI-100P, 101A, 110P, 200K, 210S, 310B, and 410S (manufactured by San-Apro Co., Ltd.), Omnicat 270 and 290 (manufactured by IGM Resins), CPI-IK-1 (manufactured by San-Apro Co., Ltd.), Omnicat 250 (manufactured by IGM Resins), and WPI. -113, 116, 124, 169, 170 (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) and other iodonium salts.
  • Silane coupling agents include, for example, tetramethylsilicate, tetraethylsilicate, mercaptopropyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyltris( ⁇ -methoxy-ethoxy)silane, ⁇ -(3,4-epoxycyclohexyl)-ethyltrimethoxysilane, dimethoxydimethylsilane, diethoxydimethylsilane, 3-(meth)acryloxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldisilane, Ethoxysilane, ⁇ -methacryloxypropyltrimethoxysilane, N-( ⁇ -aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N-( ⁇ -aminoethyl)-
  • the viscosity of the resin composition according to the present embodiment at 25° C. is preferably 0.5 Pa s or more and 20 Pa s or less, more preferably 0.8 Pa s or more and 18 Pa s or less, and even more preferably 1 Pa s or more and 15 Pa s or less.
  • the viscosity of the resin composition at 25° C. can be measured using a rheometer (“MCR-102” manufactured by Anton Paar) under conditions of cone plate CP25-2 and shear rate of 10 s ⁇ 1 .
  • FIG. 1 is a schematic cross-sectional view showing an example of an optical fiber according to this embodiment.
  • the optical fiber 10 includes a glass fiber 13 including a core 11 and a clad 12 , and a coating resin layer 16 including a primary resin layer 14 and a secondary resin layer 15 provided around the glass fiber 13 .
  • the cladding 12 surrounds the core 11.
  • the core 11 and the clad 12 mainly contain glass such as quartz glass.
  • the core 11 may be germanium-doped quartz glass or pure quartz glass
  • the clad 12 may be pure quartz glass or fluorine-doped quartz glass.
  • the outer diameter (D2) of the glass fiber 13 is about 100 ⁇ m to 125 ⁇ m, and the diameter (D1) of the core 11 forming the glass fiber 13 is about 7 ⁇ m to 15 ⁇ m.
  • the thickness of the coating resin layer 16 is usually about 22 ⁇ m to 70 ⁇ m.
  • the thickness of each layer of the primary resin layer 14 and the secondary resin layer 15 may be about 5 ⁇ m to 50 ⁇ m.
  • the thickness of each of the primary resin layer 14 and the secondary resin layer 15 may be about 10 ⁇ m to 50 ⁇ m.
  • the primary resin layer 14 may be 35 ⁇ m thick and the secondary resin layer 15 may be 25 ⁇ m thick.
  • the outer diameter of the optical fiber 10 may be about 245 ⁇ m to 265 ⁇ m.
  • the thickness of each layer of the primary resin layer 14 and the secondary resin layer 15 may be about 8 ⁇ m to 38 ⁇ m.
  • the primary resin layer 14 may be 25 ⁇ m thick and the secondary resin layer 15 may be 10 ⁇ m thick.
  • the outer diameter of the optical fiber 10 may be about 165 ⁇ m to 221 ⁇ m.
  • the thickness of each of the primary resin layer 14 and the secondary resin layer 15 may be about 5 ⁇ m to 32 ⁇ m.
  • the primary resin layer 14 may be 25 ⁇ m thick and the secondary resin layer 15 may be 10 ⁇ m thick.
  • the outer diameter of the optical fiber 10 may be about 144 ⁇ m to 174 ⁇ m.
  • the method for manufacturing an optical fiber according to the present embodiment includes a coating step of coating the resin composition on the outer periphery of the glass fiber including the core and the clad, and a curing step of curing the resin composition by irradiating ultraviolet rays after the coating step.
  • the Young's modulus of the primary resin layer is preferably 0.80 MPa or less, more preferably 0.70 MPa or less, still more preferably 0.60 MPa or less, and even more preferably 0.50 MPa or less at 23°C ⁇ 2°C, from the viewpoint of improving the microbending resistance of the optical fiber.
  • the Young's modulus of the primary resin layer exceeds 0.80 MPa, the external force is likely to be transmitted to the glass fiber, which may increase the transmission loss due to microbending.
  • the Young's modulus of the primary resin layer may be 0.10 MPa or more, 0.15 MPa or more, or 0.20 MPa or more at 23° C. ⁇ 2° C. from the viewpoint of improving the low-temperature characteristics of the optical fiber.
  • the Young's modulus of the primary resin layer can be measured by the Pullout Modulus (POM) method at 23°C. Two locations of the optical fiber are fixed with two chuck devices, the coating resin layer (primary resin layer and secondary resin layer) portion between the two chuck devices is removed, then one chuck device is fixed, and the other chuck device is gently moved in the direction opposite to the fixed chuck device.
  • POM Pullout Modulus
  • the secondary resin layer 15 can be formed, for example, by curing a resin composition containing a photopolymerizable compound containing urethane (meth)acrylate, a photopolymerization initiator, and the like.
  • the resin composition forming the secondary resin layer has a different composition from the resin composition for the primary coating.
  • a resin composition for the secondary coating can be prepared using conventionally known techniques.
  • the Young's modulus of the secondary resin layer is preferably 800 MPa or higher, more preferably 1000 MPa or higher, and still more preferably 1200 MPa or higher at 23°C ⁇ 2°C.
  • the upper limit of the Young's modulus of the secondary resin layer is not particularly limited, it may be 3000 MPa or less, 2500 MPa or less, or 2000 MPa or less at 23° C. ⁇ 2° C. from the viewpoint of imparting appropriate toughness to the secondary resin layer.
  • the Young's modulus of the secondary resin layer can be measured by the following method. First, the optical fiber is immersed in a mixed solvent of acetone and ethanol, and only the coating resin layer is pulled out in a cylindrical shape. At this time, the primary resin layer and the secondary resin layer are integrated, but since the Young's modulus of the primary resin layer is 1/1000 or more and 1/10000 or less of that of the secondary resin layer, the Young's modulus of the primary resin layer can be ignored. Next, after the solvent is removed from the coating resin layer by vacuum drying, a tensile test is performed at 23° C. (at a tensile speed of 1 mm/min), and the Young's modulus can be obtained by the secant formula of 2.5% strain.
  • the method for manufacturing an optical fiber according to the present embodiment can manufacture an optical fiber having excellent microbend resistance and low temperature properties by using the resin composition according to the present embodiment as the resin composition for the primary coating.
  • optical fiber ribbon An optical fiber ribbon can be produced using the optical fiber according to the present embodiment.
  • the optical fiber ribbon is formed by arranging a plurality of the above optical fibers in parallel and coating them with a ribbon resin.
  • FIG. 2 is a schematic cross-sectional view showing an optical fiber ribbon according to one embodiment.
  • the optical fiber ribbon 100 has a plurality of optical fibers 10 and a connecting resin layer 40 in which the optical fibers 10 are (integrally) coated with ribbon resin and connected.
  • FIG. 2 shows four optical fibers 10 as an example, but the number is not particularly limited.
  • the optical fibers 10 may be integrated in a state in which they are in contact with each other, or may be integrated in a state in which some or all of the optical fibers 10 are arranged in parallel at regular intervals.
  • a center-to-center distance F between adjacent optical fibers 10 may be 220 ⁇ m or more and 280 ⁇ m or less. When the center-to-center distance is 220 ⁇ m or more and 280 ⁇ m or less, the optical fibers can be easily mounted on the existing V-grooves, and an optical fiber ribbon having excellent collective fusibility can be obtained.
  • the thickness T of the optical fiber ribbon 100 may be 164 ⁇ m or more and 285 ⁇ m or less, depending on the outer diameter of the optical fiber 10 .
  • FIG. 3 is a schematic cross-sectional view showing an example of an integrated optical fiber ribbon in which optical fibers are arranged side by side at regular intervals.
  • the optical fiber ribbon 100A shown in FIG. 3 has 12 optical fibers 10 connected at regular intervals by ribbon resin.
  • the ribbon resin forms the connecting resin layer 40 .
  • a resin material generally known as a ribbon material can be used as the ribbon resin.
  • the ribbon resin may contain a thermosetting resin such as silicone resin, epoxy resin, or urethane resin, or an ultraviolet curable resin such as epoxy acrylate, urethane acrylate, or polyester acrylate, from the viewpoint of preventing damage to the optical fiber 10 and easiness of cutting.
  • the thickness of the connecting portion at the center between the optical fibers 10 may be 150 ⁇ m or more and 220 ⁇ m or less. Since the optical fiber ribbon is easily deformed when it is housed in the cable, the optical fiber ribbon may have depressions at the connecting portions of the optical fibers. The recess may be formed in a triangular shape with a narrower angle on one surface of the connecting portion.
  • the optical fiber ribbon according to this embodiment may have intermittent connected portions and non-connected portions in the longitudinal direction and width direction.
  • FIG. 4 is a plan view showing the appearance of an optical fiber ribbon according to one embodiment.
  • the optical fiber ribbon 100B has a plurality of optical fibers, a plurality of connecting portions 20 and non-connecting portions (dividing portions) 21 .
  • the non-connecting portions 21 are intermittently formed in the longitudinal direction of the optical fiber ribbon.
  • the optical fiber ribbon 100B is an intermittently connected optical fiber ribbon in which a connecting portion 20 and a non-connecting portion 21 are provided intermittently in the longitudinal direction for every two optical fibers 10A.
  • a “connected portion” is a portion where adjacent optical fibers are integrated via a connecting resin layer
  • a “non-connected portion” is a portion where adjacent optical fibers are not integrated via a connecting resin layer and there is a gap between the optical fibers.
  • the non-connecting portions 21 are intermittently provided in the connecting portions 20 provided every two cores, so the optical fiber ribbon is easily deformed. Therefore, when the optical fiber ribbon is mounted on the optical fiber cable, the optical fiber ribbon can be easily rolled and mounted, so that the optical fiber ribbon can be made suitable for high-density mounting. In addition, since the connecting portion 20 can be easily torn from the non-connecting portion 21 as a starting point, the single core separation of the optical fibers 10 in the optical fiber ribbon is facilitated.
  • the optical fiber ribbon according to the present embodiment is excellent in microbending resistance and low temperature characteristics, and can be densely filled in the optical fiber cable.
  • the optical fiber ribbon is housed inside the cable.
  • An example of the optical fiber cable is a slot-type optical fiber cable having a plurality of slot grooves.
  • the optical fiber ribbons can be mounted in the slot grooves so that the mounting density in each slot groove is about 25% to 65%.
  • Packing density refers to the ratio of the cross-sectional area of the optical fiber ribbon mounted in the slot groove to the cross-sectional area of the slot groove.
  • the optical fiber cable according to this embodiment may be arranged such that the plurality of optical fibers are housed in the cable without being coated with the ribbon resin.
  • optical fiber cable An example of the optical fiber cable according to this embodiment will be described with reference to FIGS. 5 and 6, an intermittently connected optical fiber ribbon is stored, but a plurality of optical fibers that are not coated with ribbon resin may be stored in a bundled state.
  • FIG. 5 is a schematic cross-sectional view of a slotless type optical fiber cable 60 that uses the intermittent connection type optical fiber ribbon 100B described above.
  • the optical fiber cable 60 has a cylindrical tube 61 and a plurality of optical fiber ribbons 100B.
  • a plurality of optical fiber ribbons 100B may be bundled with intervening material 62 such as aramid fibers.
  • the plurality of optical fiber ribbons 100B may have different markings.
  • the optical fiber cable 60 has a structure in which a plurality of bundled optical fiber ribbons 100B are twisted together, a resin that forms a tube 61 is extruded around it, and a jacket 64 is covered together with a tension member 63.
  • a water absorbing yarn may be inserted inside the tube 61 if waterproofness is required.
  • the tube 61 can be formed using resin such as polybutylene terephthalate and high-density polyethylene, for example.
  • a tear string 65 may be provided on the outside of the tube 61 .
  • FIG. 6 is a schematic cross-sectional view of a slot-type optical fiber cable 70 that uses the intermittent connection-type optical fiber ribbon 100B described above.
  • the optical fiber cable 70 has a slot rod 72 with a plurality of slot grooves 71 and a plurality of optical fiber ribbons 100B.
  • the optical fiber cable 70 has a structure in which a slot rod 72 having a tension member 73 in the center is provided with a plurality of radial slot grooves 71 .
  • the plurality of slot grooves 71 may be provided in a shape twisted in a spiral or SZ shape in the longitudinal direction of the optical fiber cable 70 .
  • Each slot groove 71 accommodates a plurality of optical fiber ribbons 100B separated from a parallel state and brought into a dense state.
  • Each optical fiber ribbon 100B may be bundled with a bundle material for identification.
  • a hold-down tape 74 is wound around the slot rod 72 , and a jacket 75 is formed around the hold-down tape 74 .
  • An optical fiber cable comprising an optical fiber or an optical fiber ribbon according to this embodiment is excellent in microbending resistance and low temperature characteristics.
  • a urethane acrylate (A-2) of Mn 11100 was obtained in the same manner as in (A-1), except that the amount of BHT added was changed to 500 ppm.
  • a urethane acrylate (A-3) with an Mn of 11700 was obtained in the same manner as in (A-1) except that the amount of BHT added was changed to 200 ppm.
  • a urethane acrylate (A-4) with an Mn of 11200 was obtained in the same manner as in (A-1) except that the polymerization inhibitor was changed from BHT to MEHQ, and MEHQ was combined with MEHQ derived from HEA and added so as to be 1000 ppm with respect to the final total charged amount.
  • a urethane acrylate (A-5) with an Mn of 11600 was obtained in the same manner as in (A-1), except that the polymerization inhibitor was changed from BHT to MEHQ, and MEHQ was combined with HEA-derived MEHQ and added so as to be 500 ppm with respect to the final total charged amount.
  • A-6 Polypropylene glycol of Mn 18000 (trade name "Preminol S 4318F” manufactured by AGC) and TDI were charged into the reactor so that the NCO/OH ratio was 2.0. Subsequently, 200 ppm of dibutyltin dilaurate was added as a catalyst to the final total charge amount, and 500 ppm of BHT was added as a polymerization inhibitor to the final total charge amount. After that, the mixture was reacted at 60° C. for 1 hour to prepare an NCO-terminated prepolymer. Next, HEA was added so that the OH molar ratio of HEA to NCO of the NCO-terminated prepolymer was 1.05, and the mixture was reacted at 60° C. for 1 hour to obtain urethane acrylate (A-6) with Mn 37,100. The content of MEHQ, which is a polymerization inhibitor derived from HEA, in urethane acrylate (A-6) was 6 ppm.
  • HEA was added so that the OH molar ratio of HEA to NCO of the NCO-terminated prepolymer was 1.05, and the mixture was reacted at 60° C. for 1 hour to obtain urethane acrylate (B-1) with Mn of 6400.
  • the content of HEA-derived MEHQ in the urethane acrylate (B-1) was 18 ppm.
  • Table 1 shows the Mn and polymerization inhibitor content of urethane acrylate (A) and urethane acrylate (B).
  • the Mn of polypropylene glycol and polyoxypropylene monobutyl ether is the value obtained from the hydroxyl value and is the value described in the catalog for each product.
  • Mn of urethane acrylate was determined using Waters' ACQUITY APC RI system, sample concentration: 0.2% by mass THF solution, injection volume: 20 ⁇ L, sample temperature: 15° C., mobile phase: THF, XT column for organic solvents: particle diameter 2.5 ⁇ m, pore size 450 ⁇ , column inner diameter 4.6 ⁇ column length 150 mm + particle diameter 2.5 ⁇ m, pore size 125 ⁇ , column inner diameter 4.6 ⁇ column Measurement was performed under the conditions of length 150 mm + particle diameter 1.7 ⁇ m, pore size 45 ⁇ , column inner diameter 4.6 ⁇ column length 150 mm, column temperature: 40° C., flow rate: 0.8 mL/min.
  • Nonylphenol polyethylene glycol acrylate (EO4NPA), neopentyl glycol diacrylate (NPGDA), acryloylmorpholine (ACMO), and N-vinylcaprolactam (NVCL) shown in Table 2 were prepared as monomers of the resin composition for the primary coating.
  • Omnirad TPO was prepared as a photopolymerization initiator.
  • 3-acryloxypropyltrimethoxysilane (APTMS) was prepared as a silane coupling agent.
  • the content of MEHQ in the urethane acrylate (A), urethane acrylate (B), monomer, and resin composition was determined using gas chromatography (trade name "GC2030" manufactured by Shimadzu Corporation) under the following measurement conditions. First, a calibration curve was created using MEHQ's acetone standard solution (0 to 200 ppm). Next, the urethane acrylate (A), the urethane acrylate (B), the monomer and the resin composition were each diluted with acetone to appropriate concentrations and quantified by gas chromatography. Column: Frontier Lab Co., Ltd.
  • Resin composition for primary coating A photopolymerizable compound, a photopolymerization initiator, and a silane coupling agent were mixed in the blending amounts (parts by mass) shown in Table 3 or Table 4 to prepare a resin composition for primary coating of each test example.
  • Test Examples 1 to 10 correspond to Examples, and Test Examples 11 to 15 correspond to Comparative Examples.
  • the resin film was punched out into a dumbbell shape of JIS K 7127 type 5, and under the conditions of 23 ⁇ 2 ° C. and 50 ⁇ 10% RH, using a tensile tester, it was pulled at a tensile speed of 1 mm / min and a gauge line distance of 25 mm to obtain a stress-strain curve.
  • the Young's modulus of the resin film was determined by dividing the stress determined by the secant formula for 2.5% strain by the cross-sectional area of the resin film.
  • a resin composition for secondary coating was obtained by mixing 25 parts by mass of urethane acrylate (Z-1), 36 parts by mass of tripropylene glycol diacrylate, 37 parts by mass of Viscoat #540 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), 1 part by mass of Omnirad TPO, and 1 part by mass of Omnirad 184.
  • a primary coating resin composition and a secondary coating resin composition were applied to the outer peripheral surface of a glass fiber 13 having a diameter of 125 ⁇ m. Then, each resin composition was cured by irradiating with ultraviolet rays to form a coating resin layer 16 having a primary resin layer 14 and a secondary resin layer 15, and an optical fiber 10 was produced.
  • An optical fiber having an outer diameter of 195 ⁇ m was obtained by setting the thickness of the primary resin layer 14 to 20 ⁇ m and the thickness of the secondary resin layer 15 to 15 ⁇ m. The optical fiber was produced at a production speed of 3000 m/min.
  • the Young's modulus of the primary resin layer of the optical fiber 10 was measured by the Pullout Modulus (POM) method.
  • the transmission loss of light with a wavelength of 1550 nm was measured by an OTDR (Optical Time Domain Reflectometer) method when the optical fiber 10 was wound in a single layer on a bobbin with a diameter of 280 mm covered with sandpaper.
  • OTDR Optical Time Domain Reflectometer
  • the difference in transmission loss of light with a wavelength of 1550 nm was evaluated as "A" when it was less than 0.5 dB/km, "B” when it was 0.5 dB/km or more and 1.0 dB/km or less, and "C" when it exceeded 1.0 dB/km.

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