JP2014515409A - フッ素化オキシランを含むポリマー発泡体、その調製及び使用方法 - Google Patents
フッ素化オキシランを含むポリマー発泡体、その調製及び使用方法 Download PDFInfo
- Publication number
- JP2014515409A JP2014515409A JP2014511367A JP2014511367A JP2014515409A JP 2014515409 A JP2014515409 A JP 2014515409A JP 2014511367 A JP2014511367 A JP 2014511367A JP 2014511367 A JP2014511367 A JP 2014511367A JP 2014515409 A JP2014515409 A JP 2014515409A
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- JP
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- Prior art keywords
- oxirane
- composition
- fluorinated
- carbon atoms
- fluorinated oxirane
- 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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- 238000000034 method Methods 0.000 title claims abstract description 16
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical class CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 111
- 150000002924 oxiranes Chemical class 0.000 claims abstract description 63
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 56
- 239000002667 nucleating agent Substances 0.000 claims abstract description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 239000002243 precursor Substances 0.000 claims abstract description 19
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- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
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- DLXDAPOINQCHSK-UHFFFAOYSA-N 2,3-difluoro-2-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-3-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C1(F)OC1(F)C(F)(F)F DLXDAPOINQCHSK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- LOUICXNAWQPGSU-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxirane Chemical compound FC1(F)OC1(F)F LOUICXNAWQPGSU-UHFFFAOYSA-N 0.000 description 2
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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Abstract
【選択図】図1
Description
本開示は、ポリマー発泡体の製造、特に、ポリウレタン発泡体及びフェノール発泡体の製造における成核剤としてのフッ素化オキシランの使用に関する。
「Cellular Materials」,Encyclopedia of Polymer Science and Engineering,vol.3,pages 1〜59,(2d ed.John Wiley & Sons,1985)によれば、発泡プラスチックは、実質的にその塊を通して配置される多数のセルの存在によって見掛け密度が低下するプラスチックとして定義されている。発泡プラスチックにおける気相は、一般的に、セル中に分布しており、前記セルは、好ましくは、良好な断熱性を提供するために非常に細かい。
したがって、所望の環境的及び毒物学的特性を呈し、且つ許容可能な成核剤として機能し、且つより高性能のポリマー発泡体が得られる成核剤が必要とされている。ポリマー発泡体を調製するための発泡性組成物、ポリマー発泡体を調製するプロセス、ポリマー発泡体を調製するための発泡剤組成物、及びそれを用いて製造される発泡体を提供する。提供された発泡性組成物は、本明細書に記載する通り、少なくとも1つの発泡剤と、少なくとも1つの発泡性ポリマー又はその前駆体組成物と、少なくとも1つの成核剤と、を含む。提供されたプロセスは、本明細書に記載する通り、少なくとも1つの発泡性ポリマー又はその前駆体組成物と少なくとも1つの成核剤との存在下で、少なくとも1つの液体若しくは気体状の発泡剤を蒸発させるか、又は少なくとも1つの気体状発泡剤を発生させる工程を含むポリマー発泡体を調製するプロセスを含む。提供される発泡剤組成物は、本明細書に記載する通り、少なくとも1つの発泡剤と少なくとも1つの成核剤とを含む。
(式中、Rf 1、Rf 2、Rf 3及びRf 4は、それぞれ、水素原子、フッ素原子、又はフルオロアルキル基から選択され、前記Rf基の炭素原子の合計は、2〜10個であり、前記Rf基のうちの任意の2個が結合してペルフルオロシクロアルキル環を形成してもよい)。成核剤及び発泡剤は、1:9未満のモル比であってもよい。発泡剤は、約5〜約7個の炭素原子を有する脂肪族炭化水素、約5〜7個の炭素原子を有する脂環式炭化水素、炭化水素エステル及び水からなる群から選択することができる。
「鎖内ヘテロ原子」とは、炭素−ヘテロ原子−炭素鎖を形成するように、炭素鎖内で炭素原子に結合している炭素以外の原子(例えば、酸素及び窒素)を意味する。
以下の説明において、本明細書の説明の一部を構成し幾つかの特定の実施形態が例として示される添付の一連の図面を参照する。本発明の範囲又は趣旨を逸脱せずに、その他の実施形態が考えられ、実施され得ることを理解すべきである。したがって、以下の詳細な説明は、限定的な意味で解釈されるべきではない。
(式中、Rf 1、Rf 2、Rf 3、及びRf 4は、それぞれ、水素原子、フッ素原子、又はフルオロアルキル基から、好ましくは、フッ素原子又はペルフルオロアルキル基から選択され、前記ペルフルオロオキシランの炭素原子の合計は、2〜10個である)。幾つかの実施形態では、前記Rf基のうちの任意の2つが結合して、フルオロシクロアルキル環、好ましくは、ペルフルオロシクロアルキル環を形成してもよい。C4〜C12フルオロオキシランは、3個以下の水素原子を有し、典型的には、実質的に炭素−水素結合を有しない。
(式中、Rf 1及びRf 4は、それぞれ、水素原子、フッ素原子、又はフルオロアルキル基から選択され、Rf 5は、2〜5個の炭素原子のフルオロアルキレン基であり、炭素原子の合計は4〜12個である)のフルオロシクロアルキル環を形成してもよい。好ましくは、Rf 1及びRf 4は、それぞれ、フッ素原子又はペルフルオロアルキル基から選択される。
ミキサ及び冷却ジャケットを取り付けた1.5リットルガラスリアクター内に、400グラムのアセトニトリル、200グラムの1,1,1,2,3,4,5,5,5−ノナフルオロ−4−トリフルオロメチル−ペンタ−2−エン、及び150グラムの50%水酸化カリウムを添加した。リアクター温度を、リアクター冷却ジャケットを使用して0℃に制御した。次に、100グラムの50%過酸化水素を、リアクター温度を0℃に制御しながら強力混合下でリアクターにゆっくりと添加した。全ての過酸化水素を約2時間以内で添加した後、ミキサを停止し、粗生成物を溶媒及び水性相から位相分離させた。155グラムの粗生成物を、底部の生成物相から収集した。粗生成物を次に、200グラムの水で洗浄して溶媒アセトニトリルを除去し、次に15℃まで冷却された凝縮器を伴う40−トレーOldershaw分留カラム内で精製した。分留カラムは、還流速度(分留カラムへ戻る蒸留流速対生成物収集シリンダーへ向かう蒸留流速)が10:1であるように操作した。最終生成物を、分留カラム内のヘッド温度が52℃〜53℃の間のときに、凝縮物として収集した。
ミキサ及び冷却ジャケットを取り付けた1.5リットルガラスリアクター内に、400グラムのアセトニトリル、200グラムのHFP三量体(C9F18)、及び150グラムの50%水酸化カリウムを添加した。リアクター温度を、リアクター冷却ジャケットを使用して0℃に制御した。次に、100グラムの50%過酸化水素を、リアクター温度を0℃〜20℃の間に制御しながら強力混合下でリアクターにゆっくりと添加した。全ての過酸化水素を約2時間以内で添加した後、ミキサを停止し、粗生成物を溶媒及び水性相から位相分離させた。180グラムの粗生成物を、底部の生成物相から収集した。次に、粗生成物を、200グラムの水で洗浄して溶媒アセトニトリルを除去し、次に15℃まで冷却された凝縮器を伴う40−トレーOldershaw分留カラム内で精製した。分留カラムは、還流速度(分留カラムへ戻る蒸留流速対生成物収集シリンダーへ向かう蒸留流速)が10:1であるように操作した。最終生成物を、分留カラム内のヘッド温度が120℃〜122℃の間のときに、凝縮物として収集した。
実施例1〜6及び比較例1〜3で用いる組成物を表2及び3に示す。フッ素化成核剤(3.5グラム)を、6000rpmの高剪断ミキサを用いてBAYTHERM VP−PU 1751 A/2(118g)及びシリコーン界面活性剤B−8423(3.5g)に乳化させた。次いで、6000rpmで15秒間混合しながらDESMODUR 44V−20(225g)をこのエマルションに添加した。得られた混合物を、50℃に予熱した350cm×350cm×60cmのアルミニウム型に注いだ。型内で約30分間反応を続けた。ポリウレタンサンプルを型から外し、切断した。発泡体の熱伝導率(ラムダ)の値を、発泡体の上昇方向に対して垂直に、200cm×200cm×25cmの試験サンプルにおいて測定した。±0.1ミリワット/メートル*ケルビンの再現性を有するHesto Lambda Control A−50熱伝導率分析機を用いて、初期に23℃の温度で及び50℃で2週間熱老化させた後に熱伝導率を測定した。実施例及び比較例に記載したセルの直径の範囲を以下の通り指定した。
以下の実施例では、ポリオール製剤内に成核剤のエマルションを形成し、経時的に精製するフッ化物イオンの濃度を測定することによって、フッ素化成核剤のアミン触媒との反応性を評価した。水、界面活性剤、及び触媒を含有するポリオールのマスターバッチを調製した。このマスターバッチから、表4に示す通りのそれぞれの濃度で、発泡剤及びフッ素化成核剤の混合物をポリオールに乳化させることによってサンプルを調製した。次いで、サンプルをフッ化物イオンの発生について調べ、初期測定は、サンプル調製直後に、更なる測定は、サンプルの老化と共に経時的に行った。
(式中、Rf 1、Rf 2、Rf 3及びRf 4は、それぞれ、水素原子、フッ素原子又はフルオロアルキル基から選択され、前記Rf基の炭素原子の合計は、2〜10個であり、前記Rf基のうちの任意の2個が結合してペルフルオロシクロアルキル環を形成してもよい)。
(式中、Rf 1、Rf 2、Rf 3及びRf 4は、それぞれ、水素原子、フッ素原子、又はフルオロアルキル基から選択され、前記Rf基の炭素原子の合計は、2〜10個であり、前記Rf基のうちの任意の2個が結合してペルフルオロシクロアルキル環を形成してもよい)。
(式中、Rf 1、Rf 2、Rf 3及びRf 4は、それぞれ、水素原子、フッ素原子又はフルオロアルキル基から選択され、前記Rf基の炭素原子の合計は、2〜10個であり、前記Rf基のうちの任意の2個が結合してペルフルオロシクロアルキル環を形成してもよい)。
Claims (22)
- 少なくとも1つの発泡剤と、少なくとも1つの発泡性ポリマー又はその前駆体組成物と、成核剤と、を含み、前記成核剤が、フッ素化オキシランを含む、発泡性組成物。
- 前記フッ素化オキシランが、最高3個までの水素原子を含む、請求項1に記載の発泡性組成物。
- 前記フッ素化オキシランが、炭素原子に結合している水素原子を実質的に含有しない、請求項2に記載の発泡性組成物。
- 前記フッ素化オキシランが、合計約4〜約12個の炭素原子を有する、請求項1に記載の発泡性組成物。
- 前記成核剤及び発泡剤が、1:9未満のモル比である、請求項1に記載の発泡性組成物。
- 前記発泡剤が、約5〜約7個の炭素原子を有する脂肪族炭化水素、約5〜約7個の炭素原子を有する脂環式炭化水素、炭化水素エステル、及び水からなる群から選択される、請求項1に記載の発泡性組成物。
- 少なくとも1つの発泡性ポリマー又はその前駆体組成物と成核剤との存在下で、少なくとも1つの液体若しくは気体状の発泡剤を蒸発させるか、又は少なくとも1つの気体状発泡剤を発生させる工程を含む、ポリマー発泡体を調製するプロセスであって、前記成核剤がフッ素化オキシランを含む、プロセス。
- 前記フッ素化オキシランが、最高3個までの水素原子を含む、請求項8に記載のポリマー発泡体を調製するプロセス。
- 前記フッ素化オキシランが、炭素原子に結合している水素原子を実質的に含有しない、請求項9に記載のポリマー発泡体を調製するプロセス。
- 前記フッ素化オキシランが、合計約4〜約12個の炭素原子を有する、請求項8に記載のポリマー発泡体を調製するプロセス。
- 前記成核剤及び発泡剤が、1:9未満のモル比である、請求項8に記載のポリマー発泡体を調製するプロセス。
- 発泡剤と成核剤とを含み、前記成核剤が、フッ素化オキシランを含む、組成物。
- 前記フッ素化オキシランが、最高3個までの水素原子を含む、請求項14に記載の組成物。
- 前記フッ素化オキシランが、炭素原子に結合している水素原子を実質的に含有しない、請求項15に記載の組成物。
- 前記フッ素化オキシランが、合計約4〜約12個の炭素原子を有する、請求項14に記載の組成物。
- 前記成核剤及び発泡剤が、1:9未満のモル比である、請求項14に記載の組成物。
- 請求項1に記載の発泡性組成物で製造された、発泡体。
- 請求項8に記載のプロセスに従って製造された、発泡体。
- 請求項14に記載の組成物で製造された、発泡体。
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- 2012-04-10 JP JP2014511367A patent/JP2014515409A/ja active Pending
- 2012-04-10 KR KR1020137032875A patent/KR20140045386A/ko not_active Application Discontinuation
- 2012-04-10 CN CN201280022092.2A patent/CN103502334B/zh not_active Expired - Fee Related
- 2012-04-10 WO PCT/US2012/032827 patent/WO2012158280A1/en active Application Filing
- 2012-04-10 US US14/112,595 patent/US20140058003A1/en not_active Abandoned
- 2012-04-10 EP EP12715268.4A patent/EP2710055A1/en not_active Withdrawn
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2019117292A1 (ja) * | 2017-12-15 | 2019-06-20 | 株式会社イノアックコーポレーション | ポリウレタンフォームの製造方法 |
US11753495B2 (en) | 2017-12-15 | 2023-09-12 | Inoac Corporation | Method for producing polyurethane foam |
Also Published As
Publication number | Publication date |
---|---|
EP2710055A1 (en) | 2014-03-26 |
US20140058003A1 (en) | 2014-02-27 |
WO2012158280A1 (en) | 2012-11-22 |
CN103502334B (zh) | 2015-03-18 |
KR20140045386A (ko) | 2014-04-16 |
CN103502334A (zh) | 2014-01-08 |
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