JP2016507632A - 脂肪族イソシアネートを取り込むことによるポリマーポリオールを主原料とする熱可塑性ポリウレタンの変色抑制 - Google Patents
脂肪族イソシアネートを取り込むことによるポリマーポリオールを主原料とする熱可塑性ポリウレタンの変色抑制 Download PDFInfo
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- JP2016507632A JP2016507632A JP2015558480A JP2015558480A JP2016507632A JP 2016507632 A JP2016507632 A JP 2016507632A JP 2015558480 A JP2015558480 A JP 2015558480A JP 2015558480 A JP2015558480 A JP 2015558480A JP 2016507632 A JP2016507632 A JP 2016507632A
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- Prior art keywords
- polyisocyanate
- polyurethane
- prepolymer
- cable
- polymer polyol
- Prior art date
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- -1 aliphatic isocyanate Chemical class 0.000 title description 16
- 239000012948 isocyanate Substances 0.000 title description 15
- 239000004433 Thermoplastic polyurethane Substances 0.000 title description 7
- 229920002803 thermoplastic polyurethane Polymers 0.000 title description 7
- 238000002845 discoloration Methods 0.000 title description 4
- 230000001629 suppression Effects 0.000 title 1
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 66
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 63
- 239000004814 polyurethane Substances 0.000 claims abstract description 46
- 229920002635 polyurethane Polymers 0.000 claims abstract description 46
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- 238000004519 manufacturing process Methods 0.000 claims description 11
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- 239000003381 stabilizer Substances 0.000 description 20
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
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- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
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- 239000003063 flame retardant Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
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- 125000004957 naphthylene group Chemical group 0.000 description 2
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- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
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- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
(A)少なくとも一種のポリマーポリオールを、ポリイソシアネートの全量に対して0.1〜20mol%の量の少なくとも一種の第1のポリイソシアネートと接触させて、本質的に末端ヒドロキシ基を有するプレポリマーを生成する工程と、
(B)工程(A)からのプレポリマーを、少なくとも一種の第2のポリイソシアネートと接触させ、及び任意に他の添加剤と接触させてポリウレタンを生成する工程と、
を有することを特徴とするポリウレタンを製造する本発明の方法によって実現される。
本発明の方法の工程(A)は、少なくとも一種のポリマーポリオールを、ポリイソシアネートの全量に対して0.1〜20mol%の量の少なくとも一種の第1のポリイソシアネートと接触させて、本質的に末端ヒドロキシ基を有するプレポリマーを生成することを有する。
本発明による方法の工程(B)が、工程(A)からのプレポリマーを、少なくとも一種の第2のポリイソシアネート及び任意に他の添加剤と接触させてポリウレタンを生成することを含む。
他の好ましい実施形態においては、本発明は、以下の工程(C):
(C)工程(B)で製造されたポリウレタンを30〜120℃の温度でコンディショニング(調整、conditioning)する工程
が工程(B)の後に行われる本発明による方法を提供する。
ポリマーポリオール1:
セバシン酸、アジピン酸及び1,3−プロパンジオールからなるポリエステルジオールを、ポリマーポリオール1、モル質量=1400g/mol、OH数=79.3として使用した。
方法1(比較例)
ポリマーポリオール1は、鎖延長剤1及びイソシアネート1と共に反応させた。同様に、加水分解安定剤を反応混合物に加えた。生成した反応混合物を加熱プレート上に注ぎ出し、120℃で10分間完了まで反応させた。その後、製造されたポリマーシートを80℃で24時間調整した。その後、ポリマーシートを顆粒化し、その顆粒を射出成形方法によって成形し、テストシートを製造した。
第1の工程において、ポリマーポリオール1を5mol%のイソシアネート2と反応させた。これにより末端カルボキシ基を有するニ官能性プレポリマーを生成した。上述のプレポリマー1を貯蔵することができ、すぐに他の処理をする必要がない。
ポリマーポリオール1を最初に1mol%のイソシアネートを反応させる。イソシアネート2を加えた後すぐに、イソシアネート1、鎖延長剤1及び加水分解安定剤1を加え、同様に反応させた。
ポリマーポリオール1が55.90質量%、CE1が7.80質量%、イソシアネート1が35.4質量%及び、加水分解安定剤1が0.90質量%を方法1によって反応させた。表1に結果を示す。
プレポリマー1が56.70質量%、鎖延長剤1が7.65質量%、イソシアネート1が35.20質量%及び、加水分解安定剤1が0.45質量%を方法2によって反応させた。表1に結果を示す。
ポリマーポリオール1が55.90質量%、鎖延長剤1が7.60質量%、イソシアネート1が35.20質量%及び、加水分解安定剤1が1.30質量%を方法1によって反応させた。表1に結果を示す。
ポリマーポリオール1が56.60質量%、鎖延長剤1が7.66質量%、イソシアネート1が35.07質量%、イソシアネート2が0.25質量%、及び加水分解安定剤1が0.45質量%を方法3によって反応させた。表1に結果を示す。
黄色度:ASTM E313
硬度:DIN53505
引っ張り長さ:DIN53504
破壊時の伸び率:DIN53504
引き裂き強度:DIN ISO 34−1、B(b)
摩耗量:DIN ISO 4649
Claims (11)
- 少なくとも以下の工程:
(A)少なくとも一種のポリマーポリオールを、ポリイソシアネートの全量に対して0.1〜20mol%の量の少なくとも一種の第1のポリイソシアネートと接触させて、本質的に末端ヒドロキシ基を有するプレポリマーを生成する工程と、
(B)工程(A)からのプレポリマーを、少なくとも一種の第2のポリイソシアネートと接触させ、及び任意に他の添加剤と接触させてポリウレタンを生成する工程と、
を有することを特徴とするポリウレタンの製造方法。 - 前記少なくとも一種の第1のポリイソシアネートが、少なくとも一種の脂肪族ポリイソシアネートであることを特徴とする請求項1に記載の製造方法。
- 前記少なくとも一種の第1のポリイソシアネートと前記少なくとも一種の第2のポリイソシアネートが異なることを特徴とする請求項1又は2に記載の製造方法。
- 前記少なくとも一種の第1のポリイソシアネートと前記少なくとも一種の第2のポリイソシアネートが同一であることを特徴とする請求項1又は2に記載の製造方法。
- 前記本質的に末端ヒドロキシ基を有するプレポリマーが、工程(A)後に分離されず、工程(B)で直接使用されることを特徴とする請求項1〜4の何れか一項に記載の製造方法。
- 前記本質的に末端ヒドロキシ基を有するプレポリマーが、工程(A)後に分離されることを特徴とする請求項1〜4の何れか一項に記載の製造方法。
- 工程(B)が、20〜250℃の温度で行われることを特徴とする請求項1〜6の何れか一項に記載の製造方法。
- 以下の工程(C)
(C)工程(B)で製造された前記ポリウレタンを30〜120℃の温度でコンデショニングする工程
が、工程(B)の後に行われることを特徴とする請求項1〜7の何れか一項に記載の製造方法。 - 請求項1〜8の何れか一項に記載の製造方法によって製造されるポリウレタン。
- 黄色度が1〜60であることを特徴とする請求項9に記載のポリウレタン。
- 自動車、コーティング、ケーブル、プラグコネクタ、太陽電池モジュール、箔、成形体、靴底及び靴構成部材、ボール及びボール構成部材、ローラー、繊維、プロファイル、積層体及びワイパーブレード、ホース、ケーブルプラグ、蛇腹構造体、牽引用ケーブル、ケーブル外装、ガスケット、不織布、駆動ベルト又は減衰要素におけるクラッディングとしての請求項9又は10に記載のポリウレタンの使用。
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- 2014-02-24 WO PCT/EP2014/053504 patent/WO2014128290A1/de active Application Filing
- 2014-02-24 KR KR1020157026171A patent/KR20150122201A/ko not_active Application Discontinuation
- 2014-02-24 EP EP14706556.9A patent/EP2958952B1/de active Active
- 2014-02-24 CN CN201480023256.2A patent/CN105143296B/zh active Active
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RU2664326C2 (ru) | 2018-08-16 |
BR112015020373A2 (pt) | 2017-07-18 |
US9957347B2 (en) | 2018-05-01 |
KR20150122201A (ko) | 2015-10-30 |
CN105143296A (zh) | 2015-12-09 |
CN105143296B (zh) | 2018-06-12 |
RU2015140721A (ru) | 2017-03-30 |
EP2958952A1 (de) | 2015-12-30 |
MX2015011044A (es) | 2016-04-06 |
WO2014128290A1 (de) | 2014-08-28 |
EP2958952B1 (de) | 2019-10-30 |
JP6486838B2 (ja) | 2019-03-20 |
US20160009851A1 (en) | 2016-01-14 |
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