JP2019500450A - フィラメントワインディングのためのポリウレタン系樹脂 - Google Patents
フィラメントワインディングのためのポリウレタン系樹脂 Download PDFInfo
- Publication number
- JP2019500450A JP2019500450A JP2018528589A JP2018528589A JP2019500450A JP 2019500450 A JP2019500450 A JP 2019500450A JP 2018528589 A JP2018528589 A JP 2018528589A JP 2018528589 A JP2018528589 A JP 2018528589A JP 2019500450 A JP2019500450 A JP 2019500450A
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate
- filament winding
- reaction mixture
- polyurethane
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000009730 filament winding Methods 0.000 title claims abstract description 57
- 229920005749 polyurethane resin Polymers 0.000 title description 6
- 229920005989 resin Polymers 0.000 claims abstract description 71
- 239000011347 resin Substances 0.000 claims abstract description 71
- 150000003077 polyols Chemical class 0.000 claims abstract description 62
- 229920005862 polyol Polymers 0.000 claims abstract description 60
- 239000012948 isocyanate Substances 0.000 claims abstract description 43
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 43
- 239000011541 reaction mixture Substances 0.000 claims abstract description 40
- 239000004814 polyurethane Substances 0.000 claims abstract description 37
- 229920002635 polyurethane Polymers 0.000 claims abstract description 37
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000001294 propane Substances 0.000 claims abstract description 16
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 12
- 150000004072 triols Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- -1 phosphate triesters Chemical class 0.000 claims description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 239000004359 castor oil Substances 0.000 claims description 12
- 235000019438 castor oil Nutrition 0.000 claims description 12
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
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- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 2
- LBUSGXDHOHEPQQ-UHFFFAOYSA-N propane-1,1,1-triol Chemical class CCC(O)(O)O LBUSGXDHOHEPQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 14
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- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 4
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- 239000002518 antifoaming agent Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 4
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- KVVSCMOUFCNCGX-UHFFFAOYSA-N cardol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1 KVVSCMOUFCNCGX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- LOOCNDFTHKSTFY-UHFFFAOYSA-N 1,1,2-trichloropropyl dihydrogen phosphate Chemical compound CC(Cl)C(Cl)(Cl)OP(O)(O)=O LOOCNDFTHKSTFY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- UFMJCOLGRWKUKO-UHFFFAOYSA-N cardol diene Natural products CCCC=CCC=CCCCCCCCC1=CC(O)=CC(O)=C1 UFMJCOLGRWKUKO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 229920000620 organic polymer Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 150000003003 phosphines Chemical group 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
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- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
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- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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Abstract
Description
イソシアネート構成成分は、少なくとも1つのポリイソシアネート、及び/または少なくとも1つのポリイソシアネート由来の少なくとも1つのイソシアネート末端プレポリマーなどの、少なくとも1つのイソシアネートを含む。例示的な実施形態において、イソシアネート構成成分は、追加の添加剤を含んでもよい。
イソシアネート反応性構成成分は、イソシアネート反応性構成成分の総重量に基づき、5重量%〜95重量%の1つ以上のポリオールを含む。各ポリオールは、50g/mol〜8,000g/molの数平均分子量を有する。ポリオールは、活性ヒドロキシル基を含有し、その活性ヒドロキシル基のイソシアネート部分との反応は、ウレタン結合の形成をもたらす。1つ以上のポリオールは、1つ以上のポリエーテルポリオール、1つ以上のポリエステルポリオール、及び/または1つ以上の天然油由来ポリオールを含んでもよい。各ポリエーテルポリオールは、プロピレンオキシド、エチレンオキシド、及び/またはブチレンオキシド由来であってもよい。
イソシアネート反応性構成成分は、2重量%〜30重量%(例えば、2重量%〜25重量%、5重量%〜20重量%、5重量%〜15重量%など)の1つ以上のプロパン系トリオールを含む。プロパン系トリオールとは、トリオールであり、トリオール官能性を可能にするための置換プロパン基本構造として、従来の命名プロトコルによって識別され得る化合物を意味する。例示的なプロパン系トリオールとしては、トリメチロールプロパンが挙げられる。例示的な実施形態において、2重量%〜30重量%(例えば、2重量%〜25重量%、5重量%〜20重量%、5重量%〜15重量%など)のトリメチロールプロパンが、イソシアネート反応性構成成分の総重量に基づき含まれてもよい(例えば、1つ以上のプロパン系トリオールは、トリメチロールプロパンのみを含んでもよい)。
イソシアネート反応性構成成分は、1重量%〜15重量%(例えば、1重量%〜10重量%、2重量%〜9重量%、2重量%〜7重量%、3.0重量%〜7重量%など)の1つ以上のリン酸トリエステルを含む。例示的なリン酸トリエステルとしては、リン酸トリエチル、リン酸トリメチル、及びリン酸トリプロピルが挙げられる。例示的な実施形態において、1重量%〜15重量%(例えば、1重量%〜10重量%、2重量%〜9重量%、2重量%〜7重量%、3.0重量%〜7重量%など)のリン酸トリエチルが、イソシアネート反応性構成成分の総重量に基づき含まれてもよい(1つ以上のリン酸トリメステル(trimester−phosphate)は、リン酸トリエチルのみを含んでもよい)。
様々な添加剤が、ポリウレタン系フィラメントワインディング樹脂反応混合物に添加されて、得られる樹脂の特徴を調節してもよく、例えば、当業者に既知の添加剤が使用されてもよい。添加剤は、イソシアネート構成成分及び/またはイソシアネート反応性構成成分の一部として添加されてもよい。例示的な添加剤としては、水分捕捉剤、泡止め剤、触媒、連鎖延長剤(ポリオール以外の)、接着促進剤、リン酸、硬化剤、pH中和剤、可塑剤、相溶剤、充填剤(機能充填剤、シリカ系充填剤、及び鉱物系充填剤など)、色素/染料、ならびに/または架橋剤(ポリオール以外の)が挙げられる。除外され得る例示的な添加剤としては、炭酸プロピレン及び/またはリン酸トリクロロプロピルなどの、粘度低下剤として作用する既知の低粘度溶媒が挙げられる。あるいは、炭酸プロピレン及び/またはリン酸トリクロロプロピルなどの、粘度低下剤として作用する既知の低粘度溶媒は、少量で(例えば、イソシアネート反応性構成成分の総重量に基づき、20重量%未満、10重量%未満、5重量%未満、及び/または1重量%未満の量で)含まれてもよい。
イソシアネート反応性構成成分などのポリウレタン系フィラメントワインディング樹脂反応混合物の個々の構成成分は、樹脂浴に添加される前に混合されてもよい。さらに、ポリウレタン系フィラメントワインディング樹脂反応混合物は、樹脂浴内で、かつ/または樹脂浴に添加される前に混合されてもよい。混合は、特定の用途及び利用可能な設備に応じて、任意の便利な方法で行われ得る。構成成分の混合は、バッチ式で行われるか、手で、または様々な種類のバッチ混合デバイスを使用することによって混合されてもよい。
フィラメントワインディングは、例えば、フィラメントとポリウレタン系樹脂との架橋マトリクスに基づく、複合体の製作のために使用される。実施形態に従ったポリウレタン樹脂を使用したフィラメントワインディング動作において、フィラメントは、樹脂浴に通されてもよく、かつ/または樹脂浴は、コーティングされたフィラメントを形成するためにフィラメントに適用される注入ダイに通されてもよい。次いで、コーティングされたフィラメントは、基材に巻き取られてもよい。ポリウレタン樹脂は、1成分系(例えば、イソシアネート構成成分及びイソシアネート反応性構成成分が混合されて、樹脂浴を形成し、次いで、フィラメントに適用される)、または2成分系(例えば、イソシアネート構成成分及びイソシアネート反応性構成成分が別々にフィラメントに適用される)であってもよい。得られる生成物は、硬化されて(例えば、熱及び/または放射線の印加によって)、最終複合物品を形成してもよい。
Claims (10)
- ポリウレタン系フィラメントワインディング樹脂反応混合物であって、前記反応混合物は、
1つ以上のイソシアネートを含むイソシアネート構成成分と、
イソシアネート反応性構成成分の総重量に基づき、50g/mol〜8,000g/molの数平均分子量を有する、5重量%〜95重量%の1つ以上のポリオール、2重量%〜30重量%の1つ以上のプロパン系トリオール、及び1重量%〜15重量%の1つ以上のリン酸トリエステルを含む前記イソシアネート反応性構成成分と、を含み、前記1つ以上のリン酸トリエステルの総重量に対する前記1つ以上のプロパン系トリオールの総重量の比率は、1.1〜5.0である、ポリウレタン系フィラメントワインディング樹脂反応混合物。 - 前記混合物は、前記イソシアネート構成成分と前記イソシアネート反応性構成成分との混合の20分後、25℃において5,000cps未満の粘度を有する、請求項1に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- 前記1つ以上のリン酸トリエステルは、リン酸トリエチルを含む、請求項1または請求項2に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- 前記1つ以上のプロパン系トリオールは、トリメチロールプロパンを含む、請求項1〜3のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- 前記1つ以上のポリオールは、(i)175g/mol超及び1000g/mol未満の数平均分子量、ならびに2〜3の公称ヒドロキシル官能価を有する、ポリエーテルポリオールと、(ii)天然油ポリオールと、を含む、請求項1〜4のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- 前記1つ以上のポリオールは、(i)50g/mol〜175g/molの数平均分子量及び2〜3の公称ヒドロキシル官能価を有する、1重量%〜15重量%の単純ポリオールと、(ii)175g/mol超及び1000g/mol未満の数平均分子量及び2〜3の公称ヒドロキシル官能価を有する、10重量%〜40重量%のポリエーテルポリオールと、(iii)ヒマシ油を含む、20重量%〜60重量%の天然油ポリオールと、を含む、請求項1〜4のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- イソシアネート指数は、85〜150である、請求項1〜6のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- 前記イソシアネート反応性構成成分は、リン酸をさらに含む、請求項1〜7のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物。
- フィラメントワインディングプロセスのための樹脂浴であって、請求項1〜8のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物を含む、樹脂浴。
- フィラメントワインディング装置であって、
ガラス繊維フィラメントと、
請求項1〜8のいずれか1項に記載のポリウレタン系フィラメントワインディング樹脂反応混合物を含む樹脂浴であって、前記ガラス繊維フィラメントに適用されて、コーティングされたガラス繊維フィラメントを形成する、樹脂浴と、
前記コーティングされたガラス繊維フィラメントを使用して、複合物品を形成するための基材と、を備える、フィラメントワインディング装置。
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