JP6659048B2 - 光ファイバー用の単色化学線硬化性被覆 - Google Patents
光ファイバー用の単色化学線硬化性被覆 Download PDFInfo
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- JP6659048B2 JP6659048B2 JP2017503129A JP2017503129A JP6659048B2 JP 6659048 B2 JP6659048 B2 JP 6659048B2 JP 2017503129 A JP2017503129 A JP 2017503129A JP 2017503129 A JP2017503129 A JP 2017503129A JP 6659048 B2 JP6659048 B2 JP 6659048B2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- BFYJDHRWCNNYJQ-UHFFFAOYSA-N oxo-(3-oxo-3-phenylpropoxy)-(2,4,6-trimethylphenyl)phosphanium Chemical compound CC1=CC(C)=CC(C)=C1[P+](=O)OCCC(=O)C1=CC=CC=C1 BFYJDHRWCNNYJQ-UHFFFAOYSA-N 0.000 description 1
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- 230000035882 stress Effects 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
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- 238000009864 tensile test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XOTMHFNWERTCLG-UHFFFAOYSA-N tris(4-ethenoxybutyl) benzene-1,2,4-tricarboxylate Chemical compound C=COCCCCOC(=O)C1=CC=C(C(=O)OCCCCOC=C)C(C(=O)OCCCCOC=C)=C1 XOTMHFNWERTCLG-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/104—Coating to obtain optical fibres
- C03C25/1065—Multiple coatings
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- 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
- C03C25/26—Macromolecular compounds or prepolymers
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- 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
- C03C25/26—Macromolecular compounds or prepolymers
- C03C25/28—Macromolecular compounds or prepolymers obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C03C25/285—Acrylic resins
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- 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
- C03C25/26—Macromolecular compounds or prepolymers
- C03C25/32—Macromolecular compounds or prepolymers obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C03C25/326—Polyureas; Polyurethanes
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- 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
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- 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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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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
- C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/125—Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
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Description
本発明は、一般に、光ファイバーの被覆方法、および光ファイバー上への使用に適しており単色ランプを用いて製造される放射線硬化性二次被覆に関する。
[001]本出願は、2014年8月17日に出願された米国仮特許出願第62/038357号明細書、2015年4月2日に出願された米国仮特許出願第62\142217号明細書、2014年9月28日に出願された米国仮特許出願第62/056592号明細書、および2014年9月28日に出願された米国仮特許出願第62/056594号明細書の出願日の利益を主張し、これらの開示全体が参照により本明細書に援用される。
[002]光ファイバーは、線引きによって製造された直後に、2つ以上重ねられた放射線硬化性被覆で被覆されることが多い。光ファイバーに直接接触する被覆は「内部一次被覆」と呼ばれ、上に重ねられる被覆は「外部一次被覆」と呼ばれる。一部の参考文献では、内部一次被覆は単に「一次被覆」とも呼ばれ、外部一次被覆は「二次被覆」と呼ばれる。内部一次被覆は、二次被覆よりも弾性率がはるかに小さい。
[022]本発明の第1の態様は、光ファイバーの被覆方法であって:(a)線引き塔からガラス光ファイバーを線引きするステップと;(b)ガラス光ファイバーの表面上に一次被覆組成物を塗布するステップと;(c)場合により、一次被覆組成物を、紫外線を放出可能な第1の発光ダイオード(LED)に曝露して、前記一次被覆組成物を硬化させるステップと;(d)一次被覆組成物に二次被覆組成物を塗布するステップと;(e)一次被覆組成物および二次被覆組成物を、第1の発光ダイオード(LED)、および紫外線を放出可能な第2の発光ダイオード(LED)からなる群の少なくとも1つに曝露して、前記一次被覆組成物および前記二次被覆組成物を硬化させて、光ファイバーの表面上の硬化一次被覆、および硬化一次被覆の表面上の硬化二次被覆を形成するステップとを含み;二次被覆組成物が、(i)二次被覆組成物の全重量に対して5重量%〜20重量%のビニルエーテルモノマーであって、エチレンオキシド、プロピレンオキシド、またはブチレンオキシドからなる群から選択される主鎖を含むビニルエーテルモノマーと;(ii)ウレタン(メタ)アクリレートオリゴマーと;(iii)1種類以上のフリーラジカル光開始剤とを含む、被覆方法である。
[028]特許請求される発明の第1の実施形態は、光ファイバーの被覆方法であって:
(a)線引き塔からガラス光ファイバーを線引きするステップと;
(b)ガラス光ファイバーの表面上に一次被覆組成物を塗布するステップと;
(c)場合により、一次被覆組成物を、紫外線を放出可能な第1の発光ダイオード(LED)に曝露して、前記一次被覆組成物を硬化させるステップと;
(d)一次被覆組成物に二次被覆組成物を塗布するステップと;
(e)一次被覆組成物および二次被覆組成物を、第1の発光ダイオード(LED)、および紫外線を放出可能な第2の発光ダイオード(LED)からなる群の少なくとも1つに曝露して、前記一次被覆組成物および前記二次被覆組成物を硬化させて、光ファイバーの表面上の硬化一次被覆、および硬化一次被覆の表面上の硬化二次被覆を形成するステップとを含み;
二次被覆組成物が:
i.二次被覆組成物の全重量に対して5重量%〜20重量%のビニルエーテルモノマーであって、エチレンオキシド、プロピレンオキシド、またはブチレンオキシドからなる群から選択される主鎖を含むビニルエーテルモノマーと;
ii.ウレタン(メタ)アクリレートオリゴマーと;
iii.1種類以上のフリーラジカル光開始剤と
を含む、方法である。
(a)液体放射線硬化性組成物の全重量に対して0.5重量%〜20重量%の量で存在する、ビニル基に結合した電子供与置換基を有する成分と;
(b)(メタ)アクリレートオリゴマーと;
(c)(メタ)アクリレート希釈剤モノマーと;
(d)フリーラジカル光開始剤成分とを含み;
前記組成物が約355nm〜約420nmのピークスペクトル出力を有する単色化学線源によって硬化される場合に、LED DSC法に準拠して少なくとも約71%、より好ましくは少なくとも約75%、好ましくは少なくとも約80%の上面パーセント反応アクリレート不飽和(%RAU)が得られるように組成物が構成される、組成物である。
1)UV LEDランプシステムの数は1〜12、より好ましくは2〜10、最も好ましくは4〜8で変化させることができる。
2)LEDランプシステムは、選択された波長において0.5W/cm2〜40W/cm2の間、より好ましくは10W/cm2〜18W/cm2の間のピーク放射度のいずれかで中心軸ターゲットを有することができる。
3)光ファイバーをUV LED光に曝露する間に、酸素を抑制するために窒素を使用する場合も、使用しない場合もある。
4)処理速度は、1m/分〜4000m/分、より好ましくは1000m/分〜3000m/分の間の範囲となりうる。
5)基材がアプリケーターダイに入る前に、空気を置換するために二酸化炭素が使用される場合も、使用されない場合もある。
[051]驚くべきことに、ビニル基に結合した電子供与置換基を有する成分の混入によって、特に単色化学線源によって硬化される組成物中に混入した場合に、このような被覆層の表面硬化を改善することができ、同時に、透過硬化、および本発明の別の目的の実現を妨害しないことが分かった。
[059]エチレン性不飽和重合性化合物は、1つまたは2つ以上のオレフィン性二重結合を含有することができる。これらは低分子量(モノマー)または高分子量(オリゴマー)の化合物であってよい。
[060]1つの二重結合を含有するより低分子量のモノマーの典型的な例は、アクリル酸またはメタクリル酸アルキルまたはヒドロキシアルキル、たとえばアクリル酸メチル、エチル、ブチル、2−エチルヘキシル、および2−ヒドロキシエチル、アクリル酸イソボルニル,ならびにメタクリル酸メチルおよびエチルである。これらのモノマーのさらなる例は、アクリロニトリル、アクリルアミド、メタクリルアミド、N−置換(メタ)アクリルアミド、酢酸ビニルなどのビニルエステル、スチレン、アルキルスチレン、ハロスチレン、N−ビニルピロリドン、N−ビニルカプロラクタム、塩化ビニル、および塩化ビニリデンである。2つ以上の二重結合を含有するモノマーの例は、エチレングリコールジアクリレート、プロピレングリコールジアクリレート、ネオペンチルグリコールジアクリレート、ヘキサメチレングリコールジアクリレート、ビスフェノールAジアクリレート、4,4’−ビス(2−アクリロイルオキシエトキシ)ジフェニルプロパン、トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレートおよびテトラアクリレート、アクリル酸ビニル、ジビニルベンゼン、コハク酸ジビニル、フタル酸ジアリル、リン酸トリアリル、イソシアヌル酸トリアリル、またはイソシアヌル酸トリス(2−アクリロイルエチル)である。
[062]一般に、光ファイバー被覆材料は、オリゴマーとして、アクリレート基、ウレタン基、および主鎖を含むウレタンアクリレートオリゴマーを含む。この主鎖は、ジイソシアネートおよびヒドロキシアルキルアクリレートと反応させたポリオールから誘導される。
[086]好ましい実施形態では、本発明の光ファイバーを被覆するための液体放射線硬化性樹脂はフリーラジカル光開始剤成分を含む。光開始剤は、光の作用、または光の作用と増感色素の電子励起との間の相乗作用によって化学的に変化して、ラジカル、酸、および塩基の少なくとも1つを生成する化合物である。
(式中、R50は、C1〜C12アルキル、シクロヘキシル、または非置換、もしくは1〜4個のハロゲンもしくはC1〜C8アルキルで置換されたフェニルであり;
R51およびR52は、それぞれ独立して、別のC1〜C8アルキルまたはC1〜C8アルコキシであり;
R53は、水素またはC1〜C8アルキルであり;
R54は水素またはメチルである)
で表される。
(式中、
R1およびR2は、互いに独立して、C1〜C12アルキル、ベンジル、非置換、またはハロゲン、C1〜C8アルキル、および/またはC1〜C8アルコキシで1〜4回置換されたフェニルである、またはシクロヘキシルもしくは基−COR3である、または
R1は−OR4であり;
R3は、非置換、またはC1〜C8アルキル、C1〜C8アルコキシ、C1〜C8アルキルチオ、および/またはハロゲンで1〜4回置換されたフェニルであり;
R4はC1〜C8アルキル、フェニル、またはベンジルである)
で表される。たとえば、R1は−OR4である。たとえばR2は、非置換、ハロゲン、C1〜C8アルキル、および/またはC1〜C8アルコキシで1〜4回置換されたフェニルである。たとえばR3は、非置換、またはC1〜C8アルキルで1〜4回置換されたフェニルである。たとえば、本発明のモノアシルホスフィンオキシドは、2,4,6−トリメチルベンゾイルエトキシフェニルホスフィンオキシド(CAS#84434−11−7)または2,4,6−トリメチルベンゾイルジフェニルホスフィンオキシド(CAS#127090−72−6)である。
(式中、
R11およびR12は、互いに独立して、水素、C1〜C6アルキル、フェニル、C1〜C6アルコキシ、OSiR16(R17)2、または−O(CH2CH2O)q−C1〜C6アルキルであるか、
R11およびR12とそれらが結合する炭素原子とを合わせたものがシクロヘキシル環を形成するかであり;
qは1〜20の数であり;
R13は、OH、C1〜C16アルコキシ、または−O(CH2CH2O)q−C1〜C6アルキルであり;
R14は、水素、C1〜C18アルキル、C1〜C12ヒドロキシアルキル、C1〜C18アルコキシ、−OCH2CH2−OR15、−CH=CH2、−C(CH3)=CH2、または
であり、
nは2〜10の数であり;
R15は、水素、−COCH=CH2、または−COC(CH3)=CH2であり;
R16およびR17は、互いに独立して、C1〜C8アルキルまたはフェニルであり;
G3およびG4互いに独立して、ポリマー構造末端基、好ましくは水素またはメチルである)
で表されるα−ヒドロキシケトン光開始剤を使用することもできる。
である光開始剤である。
である化合物も興味深い。
α−ヒドロキシシクロヘキシルフェニルケトン、
2−ヒドロキシ−2−メチル−1−フェニルプロパノン、
2−ヒドロキシ−2−メチル−1−(4−イソプロピルフェニル)プロパノン、
2−ヒドロキシ−2−メチル−1−(4−ドデシルフェニル)プロパノン、
2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]−フェニル}−2−メチル−プロパン−1−オン、および
2−ヒドロキシ−2−メチル−1−[(2−ヒドロキシエトキシ)フェニル]プロパノンである。
である。
(式中、Yは、C1〜C12アルキレン、シクロヘキスリエン(cyclohexlyene)、1回以上シクロへキシレン、O、S、またはNR30によって中断されたC2〜C40アルキレンであり、R30は、水素、C1〜C12アルキル、またはフェニルであり、好ましくはYはCH2CH2−O−CH2CH2である)
のグリオキサル酸フェニル。
[0104]改善された貯蔵寿命、改善された被覆の酸化安定性および加水分解安定性などの特定の所望の特性を実現するために、典型的には光ファイバー被覆に添加剤も加えられる。多くの異なる種類の望ましい添加剤が存在し、本明細書で議論される本発明は、想定される実施形態に含まれるにもかかわらずこれらによって限定されることは意図されないが、その理由はそれらが望ましい効果を有するからである。
[0111]光重合を促進するために、たとえば、欧州特許出願公開第A−438 123号明細書、および英国特許出願公開第A−2 180 358号明細書に記載されるように、促進剤、共開始剤、および自動酸化剤、たとえばチオール類、チオエーテル類、ジスルフィド類、およびホスフィン類を加えることができる。
[0118]これらの実施例は、本発明の実施形態を示している。表1は、本発明の実施例に使用される組成物の種々の成分を示している。
[ポリウレタンジアクリレートオリゴマーAの製造方法]
[0119]オリゴマーAを製造するために、上記の表2中に指定される比率ですべての成分が使用される。500mLの乾燥させた四口フラスコに、63.75gのトルエンジイソシアネート80/20を投入し、0.30gの安定剤(BHT)を反応器に加え、乾燥空気下で撹拌しながら周囲温度で維持した。次に、42.51gの2−ヒドロキシエトキシルアクリレート(HEA)を加えた。次に、反応温度が60℃未満に制限されるような速度で反応性エンドキャップ剤(HEA)を量り入れ、1時間撹拌した。次に、193.29gのPluracol P1010を加え、最後に、触媒の0.15gのジブチルスズジラウレートを加えた。対応する発熱反応による初期の温度上昇を確認した後、溶液を80℃にして、その温度を約2時間維持した。次に、未反応イソシアネート基の量が0.10%未満になるまで、未反応イソシアネート基(NCO)の存在を1時間に1回測定した。
[0120]使用可能な成分を混合して組成物を形成し、次に約60℃に加熱し、混合して均一混合物を形成した。
[0121]硬化度測定用の被覆試料を硬化させるためのLEDランプを取り付けた光DSCを使用するLED−DSC法を以下に説明する。単色光源(LEDなど)を使用する被覆方法は酸素阻害がより生じやすいので、表面硬化度は、硬化中のN2パージした空気条件中のO2含有量に特に敏感である。通常のフィルム試料を作製するために一般に使用されるコンベアベルトでは、関連する開放環境中のO2含有量を正確に制御することが困難であるため、表面硬化の大きなばらつきが問題となる。この点において、光DSC装置を利用する後述のLED−DSC法は、試料室中の大気条件に関してより良好な制御が行われるという点で優れている。これによって、弱いレベルの精度、反復性、および再現性の被覆表面の硬化度データが得られる。
%RAU=[(RL−RF)×100]/RL
から計算され、式中、RLは液体試料の面積比であり、RFは硬化フィルムの面積比である。
[0128]弾性率を含む引張特性は、試料の応力−ひずみ曲線を求めるために適切な任意の計器を使用することによって求めることができる。この分析に適切な計器としては、インストロン・インコーポレーテッド(Instron,Inc.)の製造する計器が挙げられ、インストロン(Instron)5564が挙げられる。本発明による硬化被覆組成物の弾性率測定では、円筒形テンプレートを用いて放射線硬化性組成物の試料からロッドを形成した。これらのロッドは、最初にエラストマー性透明シリコーンゴム管材料に液体被覆を満たすことによって作製した。次に、満たされたロッドを、アルミニウム箔で覆ったガラス板上に置き、次にフュージョン(Fusion)UVプロセッサーによって硬化させた。線量および放射照度は、UVA/UVB波長範囲の強度および線量を測定するInternational Light TechnologiesのILT490 Profiling Belt Radiometerを用いて測定した。次に以下の試験条件を使用した:放射照度約8.2W/cm2の600W/インチDランプから約1.0J/cm2、および約8ft3/分のN2流量。
[0131]YI−E313測定用のフィルム試料の作製:各試料を4インチ×5インチのガラス板(厚さ1/8インチ以下)(Herb’s Glass and Mirrorより入手可能)上にドローダウンし、窒素ガスをパージしながら、液体ドローダウンフィルムを硬化させた。380〜420nmの範囲の単色出力スペクトル、約395nmにおけるピーク放射照度、および125mm×20mmの発光ウィンドウを有するPhoseon RX Fireline(商標)395 LED 8W/cm2水冷(AGT 1.7kW冷却器による)ランプを使用することによって硬化を行った。適切な線量を得るためにコンベアユニット(ランプの下)のベルト速度を調節することができ、ランプの高さを変更することによって試料表面における光の放射照度を調節することもできた。380〜420nmの波長範囲で強度、線量、および温度を測定するように設計されているUV−T SD.Int.Phoseon Technology Radiometerを用いて線量および放射照度を測定した。各パスで720mJ/cm2の適切な線量が得られるようにコンベアユニット(ランプの下)のベルト速度を制御しながら、光の強度を約3.3W/cm2で維持した。N2流量は約8ft3/分であった。3パス後、カミソリの刃を用いて、硬化したフィルムをガラスから取り外した。測色の領域中の3つの異なる位置で較正したマイクロメーターを用いて各試料のフィルム厚さを測定した。フィルム試料の厚さは20±2ミルの範囲内であった。
広域視野(Large Area View)(LAV)
正反射成分を含む(Specular Component Included)(SCI)
D65光源
UVフィルターを含む
10°の観測者角度
[0134]驚くべきことに、アクリレートモノマー成分の一部をビニル基に結合した電子供与置換基を有する成分で置換することによって、光開始剤の選択の制約を少なくすることができ、それによって望ましくない黄色化を誘発せずに十分な表面硬化および透明硬化が可能となった。上記の表3からこのことが容易に分かる。本発明の実施例S1〜S4は、この場合はトリエチレングリコールジビニルエーテルであるアルコキシル化ビニル基に結合した電子供与置換基を有する成分の量を増加させた場合、表3に示されるような制御された全C=C二重結合濃度で、対照試料の比較例Ex S2と同じであることを示している。比較例Ex S2に見られるような対照と比較すると、ビニル基に結合した電子供与置換基を有する成分の量を増加させると、同時に表面硬化も増加することが容易に分かり、この場合約71%から約80%である。しかし、これらの例ではすべて同量のBAPO光開始剤を使用しており、黄色度指数に示されるように黄色度が着実に減少していることに留意されたい。さらに、黄色度指数を硬化後の一定時間間隔で測定し、図3(a)および3(b)に示されるように図に示すと、このビニルエーテルは、初期黄色化の減少に対してだけ非常に驚くべき効果を有するのではなく、通常BAPO光開始剤と関連する光退色効果の実質的改善にも相乗効果が得られることが分かる。本発明者の知る限り、官能化モノマーを用いたこのような効果はこれまで確認されていない。しかし、この驚くべき効果の結果として、BAPO光開始剤は、その使用に関連する通常の高レベルの黄色化の形態での制約のために他の場合に予想できた量よりも多い量で使用することができる。
Claims (27)
- 光ファイバーの被覆方法であって:
(a)線引き塔からガラス光ファイバーを線引きするステップと;
(b)前記ガラス光ファイバーの表面上に一次被覆組成物を塗布するステップと;
(c)場合により、前記一次被覆組成物を、紫外線を放出可能な第1の発光ダイオード(LED)に曝露して、前記一次被覆組成物を硬化させるステップと;
(d)前記一次被覆組成物に二次被覆組成物を塗布するステップと;
(e)前記一次被覆組成物および前記二次被覆組成物を、前記第1の発光ダイオード(LED)、および紫外線を放出可能な第2の発光ダイオード(LED)からなる群の少なくとも1つに曝露して、前記一次被覆組成物および前記二次被覆組成物を硬化させて、前記光ファイバーの表面上の硬化一次被覆、および前記硬化一次被覆の表面上の硬化二次被覆を形成するステップとを含み;
前記二次被覆組成物が、
i 前記二次被覆組成物の全質量に対して5質量%〜20質量%のビニルエーテルモノマーであって、エチレンオキシド、プロピレンオキシド、またはブチレンオキシドからなる群から選択される主鎖を含み、トリエチレングリコールジビニルエーテルまたはジエチレングリコールジビニルエーテルを含む、ビニルエーテルモノマーと;
ii ウレタン(メタ)アクリレートオリゴマーと;
iii 1種類以上のフリーラジカル光開始剤と
を含む、被覆方法。 - 前記1種類以上のフリーラジカル光開始剤が、モノアシルホスフィンオキシドおよびビスアシルホスフィンオキシドからなる群から選択される、請求項1に記載の光ファイバーの被覆方法。
- 前記被覆が、二次被覆組成物またはインク組成物であり:
前記二次被覆組成物の全質量に対して乾燥質量で約0%〜約10%の量の、顔料または顔料の組合せまたは別の着色材料をさらに含む、請求項1または2に記載の光ファイバーの被覆方法。 - 前記第1のLEDまたは第2のLEDの少なくとも1つが、約395nmの波長でピーク強度を有する放射線を放出する、請求項1〜3のいずれか一項に記載の光ファイバーの被覆方法。
- 前記第1のLEDおよび第2のLEDの両方が、約395nmの波長でピーク強度を有する放射線を放出する、請求項1〜4のいずれか一項に記載の光ファイバーの被覆方法。
- 成分(ii)がビニルエーテルおよびビニルエーテル変性基を含まない、請求項1〜5のいずれか一項に記載の光ファイバーの被覆方法。
- 前記二次被覆組成物が、前記二次被覆組成物の全質量に対して約0質量%〜約3質量%の量のペンタエリスリトールテトラ−3−メルカプトプロピオネートをさらに含む、請求項1〜6のいずれか一項に記載の光ファイバーの被覆方法。
- 前記硬化二次被覆の上面が、約71%以上のパーセント反応アクリレート不飽和(%RAU)を有する、請求項1〜7のいずれか一項に記載の光ファイバーの被覆方法。
- 前記硬化二次被覆の上面が、約75%以上のパーセント反応アクリレート不飽和(%RAU)を有する、請求項1〜8のいずれか一項に記載の光ファイバーの被覆方法。
- 前記硬化二次被覆の上面が、約80%以上のパーセント反応アクリレート不飽和(%RAU)を有する、請求項1〜9のいずれか一項に記載の光ファイバーの被覆方法。
- 前記ガラス光ファイバーが少なくとも1800m/分のライン速度で線引きされる、請求項1〜10のいずれか一項に記載の光ファイバーの被覆方法。
- 前記ガラス光ファイバーが2300m/分未満のライン速度で線引きされる、請求項1〜11のいずれか一項に記載の光ファイバーの被覆方法。
- 前記ビニルエーテルモノマーが、前記二次被覆組成物の全質量に対して約5質量%〜約10質量%の量で存在する、請求項1〜12のいずれか一項に記載の光ファイバーの被覆方法。
- 成分(iii)が、前記二次被覆組成物の全質量に対して約0.1質量%〜約5質量%の量で存在するTPO/BAPO光開始剤のブレンドである、請求項1〜13のいずれか一項に記載の光ファイバーの被覆方法。
- 光ファイバーを被覆するための液体放射線硬化性組成物であって:
(a)前記液体放射線硬化性組成物の全質量に対して0.5質量%〜20質量%の量で存在する、ビニル基に結合した電子供与置換基を有する成分と;
(b)(メタ)アクリレートオリゴマーと;
(c)(メタ)アクリレート希釈剤モノマーと;
(d)フリーラジカル光開始剤成分とを含み;
前記ビニル基に結合した電子供与置換基を有する成分が、多官能性のビニルエーテルモノマーであり、
前記組成物が約355nm〜約420nmのピークスペクトル出力を有する単色化学線源によって硬化される場合に、LED DSC法に準拠して少なくとも約71%、より好ましくは少なくとも約75%、好ましくは少なくとも約80%の上面パーセント反応アクリレート不飽和(%RAU)が得られるように組成物が構成される、組成物。 - 前記ビニルエーテルモノマーがアルコキシル化される、請求項15に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 前記ビニルエーテルモノマーが、前記組成物の全質量に対して、0.5質量%〜15質量%の量で存在し、エチレンオキシド、プロピレンオキシド、またはブチレンオキシドからなる群から選択される主鎖を含む、請求項15または16に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 前記単色化学線源が1つ以上の発光ダイオード(LED)である、請求項15〜17のいずれか一項に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 0質量%〜2質量%のイソプロピルチオキサントンと;
0質量%〜3質量%のペンタエリスリトールテトラ−3−メルカプトプロピオネートと
を含む添加剤パッケージをさらに含む、請求項15〜18のいずれか一項に記載の光ファイバーを被覆するための液体放射線硬化性組成物。 - 前記フリーラジカル光開始剤成分(d)が、任意の1分子中に平均12個以下の共役二重結合を有する、請求項15〜19のいずれか一項に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 前記添加剤パッケージが染料、着色剤、または顔料をさらに含む、請求項15〜20のいずれか一項に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 前記組成物が、硬化後45分以内に30未満、より好ましくは硬化後45分以内に20未満、最も好ましくは硬化後45分以内に12未満の黄色度指数が達成されるように構成される、請求項15〜21に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 前記組成物の全質量に対して、
前記ウレタン(メタ)アクリレートオリゴマーが10質量%〜90質量%の量で存在し;
前記(メタ)アクリレート希釈剤モノマーが10質量%〜90質量%の量で存在し;
前記フリーラジカル光開始剤成分が0.1質量%〜10質量%の量で存在し;
前記染料、着色剤、または顔料が、乾燥質量で0質量%〜10質量%の量で存在する、請求項15〜22のいずれか一項に記載の光ファイバーを被覆するための液体放射線硬化性組成物。 - 前記1つのフリーラジカル光開始剤成分(d)が、モノアシルホスフィンオキシドからなる、請求項15〜23のいずれか一項に記載の光ファイバーを被覆するための液体放射線硬化性組成物。
- 請求項1〜14のいずれか一項に記載の方法によって製造された、または請求項15〜24のいずれか一項に記載の組成物から製造された、被覆光ファイバー。
- 前記被覆光ファイバーが:
ガラスコアと;
前記ガラスコアを取り囲んでこれに接触する外部環状クラッド領域と;
前記外部クラッド領域を取り囲んでこれに接触する一次被覆と、
前記一次被覆を取り囲んでこれに接触する二次被覆と、
を含む、請求項25に記載の被覆光ファイバー。 - 前記一次被覆が20〜約50マイクロメートルの範囲内の厚さを有し、前記二次被覆が20〜約40マイクロメートルの範囲内の厚さを有する、請求項26に記載の被覆光ファイバー。
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US62/142,217 | 2015-04-02 | ||
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AU2015417227A1 (en) * | 2015-12-16 | 2018-07-19 | Politecnico Di Milano | Optical fibre with enhanced high temperature resistance |
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US20180215661A1 (en) * | 2017-01-27 | 2018-08-02 | Corning Incorporated | Led curing of high modulus fiber coating |
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WO2019090218A1 (en) * | 2017-11-03 | 2019-05-09 | Dsm Ip Assets, B.V. | Water-blocking systems including fibers coated with liquid radiation curable sap compositions |
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US20210208333A1 (en) * | 2018-06-01 | 2021-07-08 | Dsm Ip Assets B.V. | Radiation curable compositions for coating optical fiber via alternative oligomers and the coatings produced therefrom |
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WO2020239564A1 (en) * | 2019-05-24 | 2020-12-03 | Dsm Ip Assets B.V. | Radiaton curable compositions for coating optical fiber with enhanced high-speed processability |
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