JP2011021188A - ポリウレタン系の製造におけるカルボン酸の金属塩の使用 - Google Patents
ポリウレタン系の製造におけるカルボン酸の金属塩の使用 Download PDFInfo
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- JP2011021188A JP2011021188A JP2010161685A JP2010161685A JP2011021188A JP 2011021188 A JP2011021188 A JP 2011021188A JP 2010161685 A JP2010161685 A JP 2010161685A JP 2010161685 A JP2010161685 A JP 2010161685A JP 2011021188 A JP2011021188 A JP 2011021188A
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- JP
- Japan
- Prior art keywords
- polyurethane
- foam
- carboxylic acid
- catalyst system
- acid
- 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
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 37
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 34
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 27
- 239000002184 metal Substances 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 65
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- 239000006260 foam Substances 0.000 claims description 74
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 28
- 239000011496 polyurethane foam Substances 0.000 claims description 27
- 150000001735 carboxylic acids Chemical class 0.000 claims description 19
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 7
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- 239000011358 absorbing material Substances 0.000 claims description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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- 239000011493 spray foam Substances 0.000 claims 1
- 229920005862 polyol Polymers 0.000 description 22
- 150000003077 polyols Chemical class 0.000 description 17
- 239000012948 isocyanate Substances 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 16
- -1 ether polyols Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 229910052718 tin Inorganic materials 0.000 description 11
- 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 11
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 238000012360 testing method Methods 0.000 description 6
- 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 5
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 5
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- 150000007513 acids Chemical class 0.000 description 4
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- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
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- 238000012545 processing Methods 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 239000012974 tin catalyst Substances 0.000 description 4
- 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 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- RXGPYPPCEXISOV-UHFFFAOYSA-N 2-propylheptanoic acid Chemical compound CCCCCC(C(O)=O)CCC RXGPYPPCEXISOV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004114 Ammonium polyphosphate Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
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- 150000001721 carbon Chemical group 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
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- 238000001879 gelation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- COPLXRFZXQINJM-UHFFFAOYSA-N isocyanic acid;hydrate Chemical compound O.N=C=O COPLXRFZXQINJM-UHFFFAOYSA-N 0.000 description 2
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- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 2
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- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
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- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】本発明は、ポリウレタン系の製造を触媒するのに適した触媒系であって、カルボン酸が2位に単一のエチルまたはn−プロピル分枝のみを有しないとの条件で、水素原子または炭化水素基がカルボン酸のカルボニル炭素に結合している、カルボン酸の金属塩を含有することを特徴とする、触媒系に関する。
【選択図】図1
Description
ポリウレタンフォームを製造するために、以下の配合物を使用した:ポリエテロール100重量部(ヒドロキシル価=47mg KOH/g、EO 11〜12%)、水4重量部、TEGOSTAB(登録商標)BF 2370(Evonik Goldschmidt GmbHから市販のシリコーン安定剤)1重量部、第3級アミン0.1重量部、トルエンジイソシアネートT80(指数110)50.6重量部、および可変量のKOSMOS(登録商標)29(オクタン酸スズ、Evonik Goldschmidt GmbH)または考察されるカルボン酸スズ。比較のために、2−エチルヘキサン酸、2−エチル酪酸および2−プロピルヘプタン酸、すなわち、イソノナン酸スズに対して近い構造的関係を有する分子が、本発明に従わない化合物として選択された。
製造したフォームを以下の物理的性質に関して評価した:
a)上昇段階(rise phase)後のフォームの沈降(=沈降):
沈降または上昇後(after-rise)は、フォームを直接解放した後およびフォームを解放して3分後のフォームの高さの差によって得られる。フォームの高さは、フォームドーム中央において最大でセンチメートル尺度に固定された針を用いて測定される。
b)フォームの高さ:
フォームの最終的な高さは、解放後のフォーム高さから沈降または上昇後を引く、または解放後のフォーム高さに沈降または上昇後を加えることによって決定される。
c)フォーム密度(FD):
この測定は、コア密度を測定することによって、試験A下にてASTM D 3574−08に記載のように行われる。
d)空気透過性/多孔性
e)圧縮荷重たわみ CLD、40%
f)70℃で22時間90%圧縮した後の圧縮永久ひずみ
g)反撥レジリエンス(ボール反撥試験)
方法:
フォーム上でのバンキングアップ圧力(banking-up pressure)測定によって、フォームの空気透過性/多孔性を決定した。測定されたバンキングアップ圧力はアルコール(mm)で報告され、バンキングアップ圧力値が低いと、よりオープン(open)なフォームとなる特徴を有する。この値は、0〜300mmの範囲で測定された。
測定装置は、工場内窒素ラインによって供給され、したがって工場内窒素ラインに連結され、かつ互いに連結された以下の部品を含む:
圧力計を備えた減圧弁、
流量調整スクリュー、
洗浄瓶、
流量測定装置、
T継手、
敷設ノズル、
アルコールで満たされたガラス目盛管
減圧弁を使用して、窒素吸入圧力を1バールに設定した。流量調整スクリューを用いて、好適な480リットル/時に流量を調節した。アルコールを用いて、ガラス目盛管中の液体の量を、圧力差が増加せず、読み取ることができるレベルにした。試験片の実際の測定については、個々の5つの測定、すなわち、試験片の4つの角上で4つの測定、試験片の中央で1つの測定を行った。この目的のために、エッジを有するコーナーフラッシュ(corners flush)に敷設ノズルを設置した;試験片の中央が推定される。一定のバンキングアップ圧力が確立された時に読み取りを行う。
方法の測定上限は、液体の300mm(CL)である。記録に関しては、3つの異なる場合を区別しなければならない:
1.5つすべての値がCL300mm未満である。この場合には、相加平均が形成され、記録される。
2.5つすべての値がCL300mm以上である。この場合には、300以上の値は記録すべきである。
3.5つの測定値の中で、a)値を明確に決定することができ、b)値が300以上であり:5つの値の相加平均が形成され、300はb)測定値に関してそれぞれ使用される。300以上の数値は同様に記録され、斜線によって平均から分けられる。
例:
4つの測定値がCL180、210、118および200mmに相当し;1つの測定値はCL>300mm(180+210+118+200+300)/5である。記録入力:202/1。
酸放出は、Mercedes-Benz試験法PB VWT 709に基づく方法によって決定された。
Hewlett Packard HP6890/HP5973 GC/MSDシステムと併せて、Gerstel,Muelheimから市販の試料交換器と共に、熱脱着装置「TDS2」を使用して熱脱着を行う。
b)測定条件:
較正のために、Tenax TA(メッシュ35/60)で充填された清潔な吸着管に、ペンタン中のトルエンとヘキサデカン(それぞれ0.6mg/ml)の混合物1μlを導入し、測定する(脱着:5分;280℃)。
d)試料の調製
3つの試験片のフォーム10mgを熱脱着管に押し込む。フォームが圧縮されないように注意を払う。
e)評価
酸放出を定量化するために、例えば、質量スペクトルによって2−エチルヘキサン酸と同定されるピークが、較正からのトルエンの応答因子(response factor)を用いて、そのピーク領域によりトルエン等価物のppmとして決定される。
実施例1〜35に示すようにフォームを製造した。触媒系の濃度は様々である。2−エチルヘキサン酸、3,3−ジメチル酪酸、2−プロピルヘプタン酸、シクロヘキサンカルボン酸およびn−オクタン酸の塩を使用して、フォームを製造した。得られたフォームを調べて、その多孔度を決定した。これらの試験の結果を図1に示す
Claims (13)
- ポリウレタン系の製造を触媒するのに適した触媒系であって、カルボン酸が2位に単一のエチルまたはn−プロピル分枝のみを有しないとの条件で、水素原子または炭化水素基がカルボン酸のカルボニル炭素に結合している、カルボン酸の金属塩を含有することを特徴とする、触媒系。
- 前記炭化水素基が、前記酸が少なくとも4つの炭素原子を有するように選択されることを特徴とする、請求項1に記載の触媒系。
- 前記触媒系における前記金属塩が、非分枝状アルキル基またはメチル基分枝のみを有するアルキル基にカルボン酸のカルボキシ基が結合している、カルボン酸の塩のみであることを特徴とする、請求項1または2に記載の触媒系。
- 金属塩が、3,5,5−トリメチルヘキサン酸およびn−オクタン酸の1つまたは複数の塩から選択されることを特徴とする、請求項1〜3のいずれか一項に記載の触媒系。
- 1つまたは複数の有機溶媒を含有することを特徴とする、請求項1〜4のいずれか一項に記載の触媒系。
- 前記カルボン酸が、2位に単一のエチルまたはn−プロピル分枝を有しないことを特徴とする、請求項1〜5のいずれか一項に記載の触媒系。
- ポリウレタンコーティング、ポリウレタン接着剤、ポリウレタンシーラント、ポリウレタンエラストマーまたはポリウレタンフォームの製造における、請求項1〜6のいずれか一項に記載の触媒系の使用。
- 前記触媒系が、反応前または反応中に反応混合物に添加されることを特徴とする、請求項7に記載の使用。
- カルボン酸が2位に単一のエチルまたはn−プロピル分枝のみを有しないとの条件で、炭化水素基がカルボン酸のカルボニル炭素に結合している、カルボン酸またはカルボン酸の塩を含有することを特徴とする、ポリウレタン系。
- 非分枝状であるか、またはメチル基分枝のみを有する、カルボン酸またはその塩のみを含むことを特徴とする、請求項9に記載のポリウレタン系。
- カルボン酸が2位に単一のエチルまたはn−プロピル分枝を有しないという条件で、炭化水素基がカルボン酸カルボニル炭素に結合しているカルボン酸またはその金属塩の質量による割合が、0.001〜2質量%であることを特徴とする、請求項9または10に記載のポリウレタン系。
- ポリウレタンコーティング、ポリウレタン接着剤、ポリウレタンシーラント、ポリウレタンエラストマー、硬質ポリウレタンフォーム、可撓性ポリウレタンフォーム、粘弾性フォーム、HRフォーム、半硬質ポリウレタンフォーム、熱成形可能なポリウレタンフォームまたはインテグラルフォームであることを特徴とする、請求項9〜11のいずれか一項に記載のポリウレタン系。
- 冷蔵庫の断熱材、断熱板、サンドイッチ構成要素、パイプ断熱材、スプレーフォーム、1−および1.5−成分缶フォーム、模造木材、模型フォーム、包装フォーム、マットレス、室内装飾材料、自動車シート材料、ヘッドレスト、ダッシュボード、自動車内装品、自動車の屋根外装材、吸音材料、ハンドル、靴底、カーペット裏当てフォーム、フィルターフォーム、封止用フォーム、シーラントおよび接着剤としての、または相当する製品を製造するための、請求項9〜12のいずれか一項に記載のポリウレタン系の使用。
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WO2013102208A1 (en) | 2011-12-29 | 2013-07-04 | Firestone Building Products Co., LLC | Roofing membranes with expandable graphite as flame retardant |
US9441140B2 (en) | 2012-07-12 | 2016-09-13 | Firestone Building Products Co., LLC | Asphaltic sheet materials including expandable graphite |
US8968853B2 (en) | 2012-11-07 | 2015-03-03 | Firestone Building Products Company, Llc | Pressure-sensitive adhesives including expandable graphite |
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DE102013204991A1 (de) | 2013-03-21 | 2014-09-25 | Evonik Industries Ag | Herstellung von Polyurethanschäumen, die Polyole auf Polyolefinbasis enthalten |
US10415249B2 (en) | 2014-07-03 | 2019-09-17 | Firestone Building Products Co., LLC | EPDM roofing membranes with expandable graphite as flame retardant |
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- 2010-07-14 US US12/836,155 patent/US8841403B2/en active Active
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EP2770001B1 (de) | 2021-01-06 |
JP5530283B2 (ja) | 2014-06-25 |
EP2500369B2 (de) | 2018-01-03 |
EP2770001A1 (de) | 2014-08-27 |
CN101955573B (zh) | 2013-04-24 |
BRPI1002427A2 (pt) | 2012-05-15 |
PT2770001T (pt) | 2021-02-25 |
DE102009033710A1 (de) | 2011-01-20 |
BRPI1002427B1 (pt) | 2019-10-29 |
ES2392330T3 (es) | 2012-12-07 |
US20140058004A1 (en) | 2014-02-27 |
CN103214644B (zh) | 2016-02-24 |
US8841403B2 (en) | 2014-09-23 |
CN101955573A (zh) | 2011-01-26 |
EP2289960A1 (de) | 2011-03-02 |
EP2500369A1 (de) | 2012-09-19 |
US20110015290A1 (en) | 2011-01-20 |
PL2500369T5 (pl) | 2018-05-30 |
DK2770001T3 (da) | 2021-03-29 |
ES2854294T3 (es) | 2021-09-21 |
PL2500369T3 (pl) | 2014-12-31 |
PL2289960T3 (pl) | 2013-01-31 |
HUE053662T2 (hu) | 2021-07-28 |
PL2770001T3 (pl) | 2021-06-14 |
CN103214644A (zh) | 2013-07-24 |
EP2289960B1 (de) | 2012-08-22 |
EP2500369B1 (de) | 2014-08-06 |
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