JP2011513547A - 1,1,1−トリフルオロ−3−クロロプロペンおよびジメトキシメタンの共沸様組成物 - Google Patents
1,1,1−トリフルオロ−3−クロロプロペンおよびジメトキシメタンの共沸様組成物 Download PDFInfo
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- JP2011513547A JP2011513547A JP2010549629A JP2010549629A JP2011513547A JP 2011513547 A JP2011513547 A JP 2011513547A JP 2010549629 A JP2010549629 A JP 2010549629A JP 2010549629 A JP2010549629 A JP 2010549629A JP 2011513547 A JP2011513547 A JP 2011513547A
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- dimethoxymethane
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- 239000000203 mixture Substances 0.000 title claims abstract description 119
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 title claims abstract description 19
- LDTMPQQAWUMPKS-UHFFFAOYSA-N 1-chloro-3,3,3-trifluoroprop-1-ene Chemical group FC(F)(F)C=CCl LDTMPQQAWUMPKS-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000003507 refrigerant Substances 0.000 claims abstract description 42
- 238000005057 refrigeration Methods 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000003380 propellant Substances 0.000 claims abstract description 6
- 239000000314 lubricant Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 13
- 238000001704 evaporation Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 239000004088 foaming agent Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- -1 polyol ester Chemical class 0.000 claims description 2
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 abstract description 12
- 239000004604 Blowing Agent Substances 0.000 abstract description 8
- 239000006260 foam Substances 0.000 description 7
- 239000012530 fluid Substances 0.000 description 6
- 239000002952 polymeric resin Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004378 air conditioning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AHSZBZTYLKTYJI-UHFFFAOYSA-N (2,2-dimethyl-3-nonanoyloxypropyl) nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)(C)COC(=O)CCCCCCCC AHSZBZTYLKTYJI-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 101100214695 Staphylococcus aureus aacA-aphD gene Proteins 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/5068—Mixtures of halogenated and non-halogenated solvents
- C11D7/5077—Mixtures of only oxygen-containing solvents
- C11D7/5086—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being different from alcohols, e.g. mixtures of water and ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/12—Organic compounds only containing carbon, hydrogen and oxygen atoms, e.g. ketone or alcohol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
- C08J2203/142—Halogenated saturated hydrocarbons, e.g. H3C-CF3
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2207/00—Foams characterised by their intended use
- C08J2207/04—Aerosol, e.g. polyurethane foam spray
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/11—Ethers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/32—The mixture being azeotropic
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- Thermal Sciences (AREA)
- Combustion & Propulsion (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Lubricants (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Description
本明細書において用いられる「共沸様」という用語は、厳密に共沸である組成物と共沸混合物のように挙動する組成物の両方を含めるべく広い意味において意図されている。基本的な原理から、流体の熱力学的状態は、圧力、温度、液体組成および蒸気組成によって規定される。共沸混合物は、液体組成と蒸気組成が指定圧力および指定温度で等しい2種以上の成分の系である。実際には、これは、共沸混合物の成分の沸点が一定であり、相変化中に分離され得ないことを意味する。
本発明の共沸様組成物は、安定剤、金属不活性化剤および腐食抑制剤などを含む任意の多様な添加剤のいずれかを更に含んでもよい。
本組成物は広範な用途において有用性を有する。例えば、本発明の一実施形態は本共沸様組成物を含む冷媒組成物に関する。
認定された圧力ゲージを備えた高圧セルを真空ポンプにより排気して、すべての永久ガスを除去した。その後、ステンレススチール製のシリンジポンプにより10gの蟻酸メチルをセルに装填した。温度が0.1℃の精度で制御されたオービタルシェーカーに金属ボンベを入れた。圧力を16℃、22℃および32℃で測定した。平衡を達成するために最少で1時間後、各温度で圧力を測定した。圧力ゲージの精度は±0.1psiaであった。永久ガスが圧力測定を妨害していなかったことを確認するために、ln Pを1000/Tに対してプロットした。良好なリニアフィットをR2=0.9999となるように達成した。それは永久ガスが含まれていなかったことを示している。
LnP=a+b/T
その後、ステンレススチール製のシリンジポンプにより、10.2gの1233zdを高圧セルに装填した。0.3グラムから3グラムの増分でジメトキシメタンを添加した。一旦ジメトキシメタンの添加が完了すると、圧力セルを注意深く秤量した。永久ガスおよび残留ジメトキシメタンがPTx(圧力)測定に寄与しないように、すべてのラインを注意深く吸引する。蒸気圧を16℃、29℃および42℃で測定し、大気圧が14.7psiaであることを仮定して式1を用いて沸点を計算した。結果を図2および表1において示している。
Claims (13)
- 有効量の1,1,1−トリフルオロ−3−クロロプロペンおよびジメトキシメタンを含む共沸様組成物。
- 約20〜58モル%の1,1,1−トリフルオロ−3−クロロプロペンおよび約42〜80モル%のジメトキシメタンから本質的になる請求項1に記載の共沸様組成物。
- 約14.7psiaの圧力で約29.98℃〜35.81℃の沸点を有する請求項1または2に記載の共沸様組成物。
- 潤滑剤を更に含む請求項1〜3いずれか1項に記載の共沸様組成物。
- 前記潤滑剤が、鉱油、アルキルベンゼン、ポリオールエステル、ポリアルキレングリコールおよびそれらの2種以上の組み合わせからなる群から選択される請求項4に記載の共沸様組成物。
- 請求項1〜5いずれか1項に記載の共沸様組成物を含む冷媒組成物。
- 請求項6に記載の冷媒組成物を含む冷凍システム。
- 物品を冷却する方法であって、請求項6に記載の冷媒組成物を凝縮させる工程と、その後、冷却されるべき物品の近傍で前記冷媒組成物を蒸発させる工程とを含む方法。
- 物品を加熱する方法であって、加熱されるべき物品の近傍で請求項6に記載の冷媒組成物を凝縮させる工程と、その後、前記冷媒組成物を蒸発させる工程とを含む方法。
- 噴霧されるべき材料と、請求項1〜5いずれか1項に記載の共沸様組成物を含む噴射剤とを含む噴霧可能な組成物。
- 前記噴霧可能な組成物がエアゾールである請求項10に記載の噴霧可能な組成物。
- 請求項1〜5いずれか1項に記載の共沸様組成物を含む発泡剤。
- 請求項1〜5いずれか1項に記載の共沸様組成物を含む溶媒。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/044,035 | 2008-03-07 | ||
US12/044,035 US7438825B1 (en) | 2008-03-07 | 2008-03-07 | Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and dimethoxymethane |
PCT/US2008/076785 WO2009110925A1 (en) | 2008-03-07 | 2008-09-18 | Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and dimethoxymethane |
Publications (2)
Publication Number | Publication Date |
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JP2011513547A true JP2011513547A (ja) | 2011-04-28 |
JP4951124B2 JP4951124B2 (ja) | 2012-06-13 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2010549629A Active JP4951124B2 (ja) | 2008-03-07 | 2008-09-18 | 1,1,1−トリフルオロ−3−クロロプロペンおよびジメトキシメタンの共沸様組成物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US7438825B1 (ja) |
EP (1) | EP2252671B1 (ja) |
JP (1) | JP4951124B2 (ja) |
KR (1) | KR101472364B1 (ja) |
CN (1) | CN101959988B (ja) |
ES (1) | ES2673950T3 (ja) |
PL (1) | PL2252671T3 (ja) |
WO (1) | WO2009110925A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012506944A (ja) * | 2008-10-28 | 2012-03-22 | ハネウェル・インターナショナル・インコーポレーテッド | 1−クロロ−3,3,3−トリフルオロプロペンを含む共沸混合物様組成物 |
JP2019513173A (ja) * | 2016-03-24 | 2019-05-23 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | Z−1233zdの共沸及び共沸様組成物 |
Families Citing this family (18)
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US20110037016A1 (en) * | 2003-10-27 | 2011-02-17 | Honeywell International Inc. | Fluoropropene compounds and compositions and methods using same |
ES2727525T3 (es) * | 2008-03-07 | 2019-10-16 | Arkema Inc | Composiciones de transferencia térmica de alqueno halogenado con retorno de aceite mejorado |
CN101808966A (zh) | 2008-03-07 | 2010-08-18 | 阿科玛股份有限公司 | 用氯-3,3,3-三氟丙烯配制的稳定系统 |
US9340758B2 (en) | 2008-05-12 | 2016-05-17 | Arkema Inc. | Compositions of hydrochlorofluoroolefins |
US8820079B2 (en) * | 2008-12-05 | 2014-09-02 | Honeywell International Inc. | Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids |
US9926244B2 (en) | 2008-10-28 | 2018-03-27 | Honeywell International Inc. | Process for drying HCFO-1233zd |
US9150768B2 (en) | 2008-10-28 | 2015-10-06 | Honeywell International Inc. | Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene |
US7935268B2 (en) * | 2008-10-28 | 2011-05-03 | Honeywell International Inc. | Azeotrope-like compositions comprising trans-1-chloro-3,3,3-trifluoropropene |
US8703006B2 (en) | 2008-10-28 | 2014-04-22 | Honeywell International Inc. | Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene |
WO2010085399A1 (en) * | 2009-01-22 | 2010-07-29 | Arkema Inc. | Azeotrope and azeotrope-like compositions of e-1-chloro-3,3,3-trifluoropropene and isopropanol |
US8541478B2 (en) | 2009-05-21 | 2013-09-24 | Huntsman International Llc | Rigid polyurethane foam and system and method for making the same |
JP2013504658A (ja) | 2009-09-09 | 2013-02-07 | ハネウェル・インターナショナル・インコーポレーテッド | モノクロロトリフルオロプロペン化合物及び組成物並びにそれを用いる方法 |
US8846754B2 (en) * | 2009-12-16 | 2014-09-30 | Honeywell International Inc. | Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene |
WO2013016632A2 (en) * | 2011-07-28 | 2013-01-31 | Honeywell International Inc. | Foams and flame resistant articles made from foams containing 1-chloro-3,3,3-trifluoropropene (1233zd) |
FR3003566B1 (fr) * | 2013-03-20 | 2018-07-06 | Arkema France | Composition comprenant hf et e-3,3,3-trifluoro-1-chloropropene |
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JP6361721B2 (ja) * | 2016-11-11 | 2018-07-25 | ダイキン工業株式会社 | 洗浄剤組成物及び洗浄方法、並びに溶剤組成物、油類のための溶剤としてのその使用、及びそれを含む油類組成物 |
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JP4951124B2 (ja) | 2012-06-13 |
ES2673950T3 (es) | 2018-06-26 |
US7438825B1 (en) | 2008-10-21 |
WO2009110925A1 (en) | 2009-09-11 |
KR20100134586A (ko) | 2010-12-23 |
KR101472364B1 (ko) | 2014-12-12 |
EP2252671A1 (en) | 2010-11-24 |
EP2252671B1 (en) | 2018-05-16 |
PL2252671T3 (pl) | 2018-08-31 |
CN101959988B (zh) | 2013-06-05 |
EP2252671A4 (en) | 2015-06-10 |
CN101959988A (zh) | 2011-01-26 |
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