JP2021524530A - ガラス繊維強化tpu - Google Patents
ガラス繊維強化tpu Download PDFInfo
- Publication number
- JP2021524530A JP2021524530A JP2021500790A JP2021500790A JP2021524530A JP 2021524530 A JP2021524530 A JP 2021524530A JP 2021500790 A JP2021500790 A JP 2021500790A JP 2021500790 A JP2021500790 A JP 2021500790A JP 2021524530 A JP2021524530 A JP 2021524530A
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- JP
- Japan
- Prior art keywords
- composition
- polyol
- chain extender
- diisocyanate
- filler
- 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.)
- Pending
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- 150000003077 polyols Chemical class 0.000 claims abstract description 88
- 229920005862 polyol Polymers 0.000 claims abstract description 78
- 239000004970 Chain extender Substances 0.000 claims abstract description 66
- 239000000945 filler Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 30
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 46
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- 229920000570 polyether Polymers 0.000 claims description 13
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 16
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 4
- 239000011152 fibreglass Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
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- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 230000000996 additive effect Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical class O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
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- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
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- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
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- NUMHJBONQMZPBW-UHFFFAOYSA-K bis(2-ethylhexanoyloxy)bismuthanyl 2-ethylhexanoate Chemical compound [Bi+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O NUMHJBONQMZPBW-UHFFFAOYSA-K 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
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- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
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- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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Abstract
Description
(a)ポリイソシアネート組成物(IZ)とポリオール組成物(PZ)との反応により得られる又は得ることができる熱可塑性ポリウレタン(TPU−1)であって、ポリオール組成物(PZ)が少なくとも1種のポリオール(P1)、鎖延長剤(KV1)及び鎖延長剤(KV2)を含む、熱可塑性ポリウレタン(TPU−1)、及び
(b)フィラー(F1)
を含む組成物によって達成される。
(i)以下の成分
(a)ポリイソシアネート組成物(IZ)とポリオール組成物(PZ)との反応により得られる又は得ることができる熱可塑性ポリウレタン(TPU−1)であって、ポリオール組成物(PZ)が少なくとも1種のポリオール(P1)、鎖延長剤(KV1)及び鎖延長剤(KV2)を含む、熱可塑性ポリウレタン(TPU−1)、及び
(b)フィラー(F1)
を混合する工程を含む。
(b)フィラー(F1)
を含む、組成物。
(b)フィラー(F1)
を含む組成物であって、
前記鎖延長剤(KV1)が1,4−ブタンジオールであり、前記鎖延長剤(KV2)が1,3−プロパンジオールであり、前記ポリオール(P1)がポリエーテルポリオールである、組成物。
(b)フィラー(F1)
を含む組成物であって、
前記鎖延長剤(KV1)が1,4−ブタンジオールであり、前記鎖延長剤(KV2)が1,3−プロパンジオールであり、前記ポリオール(P1)がポリエーテルポリオールであり、
前記フィラー(F1)が、繊維状のものであり、いずれの場合もASTM D578−98に従って決定された、3mm〜4mmの範囲の長さ及び1μm〜20μmの範囲の直径を有する、組成物。
(b)フィラー(F1)
を含む組成物であって、
前記鎖延長剤(KV1)が1,4−ブタンジオールであり、前記鎖延長剤(KV2)が1,3−プロパンジオールであり、前記ポリオール(P1)がポリエーテルポリオールであり、
前記フィラー(F1)が、前記組成物の全体に基づいて40質量%〜60質量%の範囲の量で含まれる、組成物。
(i)以下の成分
(a)ポリイソシアネート組成物(IZ)とポリオール組成物(PZ)との反応により得られる又は得ることができる熱可塑性ポリウレタン(TPU−1)であって、ポリオール組成物(PZ)が少なくとも1種のポリオール(P1)、鎖延長剤(KV1)及び鎖延長剤(KV2)を含む、熱可塑性ポリウレタン(TPU−1)、及び
(b)フィラー(F1)
を混合する工程を含む、方法。
Chopvantage HP3550 EC10−3,8:PPG Industries Fiber Glass,Energieweg 3,9608 PC Westerbroek,オランダからのガラス繊維、Eガラス、フィラメント径10μm、長さ3.8mm。
2.1 手動キャスティングプロセスによる製造(TPU 1〜3)
基本配合(表1)で特定しているポリオール及び鎖延長剤の量を秤量してブリキ缶に入れ、窒素で簡単に覆った。この缶を蓋で閉じ、オーブンで約90℃に加熱した。
以下の表3は、個々の出発材料が質量部(pbw)で報告されている組成を示している。いずれの場合も、10個のバレルセクションに分割した、35Dのプロセス部分の長さを有するBerstorffからの二軸押出機モデルZE40Aを使用して、混合物を製造した。連続的ペレット化を使用した。
TPU 2の処理は不可能であった。この材料は非常に高い融点範囲を有し、ガラス繊維化合物の製造は不可能であった。
ショア硬度A:DIN ISO 7619−1、ショア硬度試験A(3s)
引張強度:DIN EN ISO 527
破断伸び:DIN EN ISO 527
引裂伝播抵抗:DIN ISO 34−1,B(b。
Kunststoffhandbuch,第VII巻,Vieweg及びHoechtlen編,Carl Hanser Verlag,Munich 1966年(103〜113頁)
EP 0 922 552 A1
DE 101 03 424 A1
WO 2006/072461 A1
Claims (14)
- (a)ポリイソシアネート組成物(IZ)とポリオール組成物(PZ)との反応により得られる又は得ることができる熱可塑性ポリウレタン(TPU−1)であって、前記ポリオール組成物(PZ)が少なくとも1種のポリオール(P1)、鎖延長剤(KV1)及び鎖延長剤(KV2)を含み、鎖延長剤が、20:1〜3:1の範囲のKV1:KV2のモル混合比で使用される、熱可塑性ポリウレタン(TPU−1)、及び
(b)フィラー(F1)
を含む、組成物。 - 前記鎖延長剤(KV1)及び/又は前記鎖延長剤(KV2)が、1,2−エタンジオール、1,3−プロパンジオール、1,4−ブタンジオール及び1,6−ヘキサンジオール、ジエチレングリコール、トリエチレングリコール、ヒドロキノンビス−2−ヒドロキシエチルエーテル及びビス(2−ヒドロキシエチル)テレフタレートからなる群から選択される、請求項1に記載の組成物。
- 前記鎖延長剤(KV1)が1,4−ブタンジオールである、請求項1又は2に記載の組成物。
- 前記ポリオール(P1)がポリエーテルポリオールである、請求項1から3のいずれか一項に記載の組成物。
- 前記ポリイソシアネート組成物(IZ)が、フェニレン1,2−、1,3−及び/又は1,4−ジイソシアネート、トリフェニルメタン4,4’,4’’−トリイソシアネート、ナフチレン1,5−ジイソシアネート(NDI)、トリレン2,4−及び/又は2,6−ジイソシアネート(TDI)、ビフェニル2,4’−、4,4’−及び/又は2,2−ジイソシアネート、ジフェニルメタン2,2’−、2,4’−及び/又は4,4’−ジイソシアネート(MDI)、ポリフェニルポリメチレンポリイソシアネート、キシリレン1,2−、1,3−及び/又は1,4−ジイソシアネート及びm−テトラメチルキシリレンジイソシアネート(TMXDI)からなる群から選択されるポリイソシアネート(PI)を含む、請求項1から4のいずれか一項に記載の組成物。
- 前記フィラー(F1)が繊維状のものである、請求項1から5のいずれか一項に記載の組成物。
- 前記フィラー(F1)が、ガラス繊維、炭素繊維、アラミド繊維、チタン酸カリウム繊維、液晶ポリマーから構成される繊維、金属繊維、ポリエステル繊維、ポリアミド繊維、有機の繊維状フィラー及び無機の繊維状フィラーからなる群から選択される、請求項1から6のいずれか一項に記載の組成物。
- 前記フィラー(F1)が、いずれの場合もASTM D578−98に従って決定された、3mm〜4mmの範囲の長さ及び1μm〜20μmの範囲の直径を有する、請求項1から7のいずれか一項に記載の組成物。
- 前記フィラー(F1)が、前記組成物の全体に基づいて40質量%〜60質量%の範囲の量で含まれる、請求項1から8のいずれか一項に記載の組成物。
- 前記熱可塑性ポリウレタンが、DIN ISO 7619−1に従って決定された、40D〜90D、好ましくは70D〜90Dの範囲のショア硬度を有する、請求項1から9のいずれか一項に記載の組成物。
- 組成物の製造方法であって、
(i)以下の成分
(a)ポリイソシアネート組成物(IZ)とポリオール組成物(PZ)との反応により得られる又は得ることができる熱可塑性ポリウレタン(TPU−1)であって、前記ポリオール組成物(PZ)が少なくとも1種のポリオール(P1)、鎖延長剤(KV1)及び鎖延長剤(KV2)を含み、鎖延長剤が、20:1〜3:1の範囲のKV1:KV2のモル混合比で使用される、熱可塑性ポリウレタン(TPU−1)、及び
(b)フィラー(F1)
を混合する工程を含む、方法。 - 請求項11に記載の方法により得られる又は得ることができる、組成物。
- 請求項1から10のいずれか一項に記載の組成物、又は請求項11に記載の方法により得られる又は得ることができる組成物を、成形体の製造に使用する方法。
- 請求項1から10のいずれか一項に記載の組成物、又は請求項11に記載の方法により得られる又は得ることができる組成物を含む、成形体。
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- 2019-07-11 WO PCT/EP2019/068677 patent/WO2020011919A1/de active Search and Examination
- 2019-07-11 TW TW108124487A patent/TW202006066A/zh unknown
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JPS49113897A (ja) * | 1973-02-14 | 1974-10-30 | ||
JP2017520673A (ja) * | 2014-06-23 | 2017-07-27 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 熱可塑性ポリウレタン粉末の使用 |
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US20210163714A1 (en) | 2021-06-03 |
WO2020011919A1 (de) | 2020-01-16 |
CN112424250A (zh) | 2021-02-26 |
JP2024041987A (ja) | 2024-03-27 |
EP3820925A1 (de) | 2021-05-19 |
KR20210030432A (ko) | 2021-03-17 |
TW202006066A (zh) | 2020-02-01 |
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