JPH11100571A - Ice-melting dehydrating agent and ice-melting dehydrating refrigerant composition - Google Patents
Ice-melting dehydrating agent and ice-melting dehydrating refrigerant compositionInfo
- Publication number
- JPH11100571A JPH11100571A JP9279869A JP27986997A JPH11100571A JP H11100571 A JPH11100571 A JP H11100571A JP 9279869 A JP9279869 A JP 9279869A JP 27986997 A JP27986997 A JP 27986997A JP H11100571 A JPH11100571 A JP H11100571A
- Authority
- JP
- Japan
- Prior art keywords
- ice
- melting
- refrigerant
- dehydrating
- lubricant
- 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
Links
- 239000003507 refrigerant Substances 0.000 title claims abstract description 36
- 239000012024 dehydrating agents Substances 0.000 title claims abstract description 5
- 238000002844 melting Methods 0.000 title abstract description 22
- 239000000314 lubricant Substances 0.000 claims abstract description 14
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 150000003377 silicon compounds Chemical class 0.000 claims description 5
- -1 polyethyleneoxy group Polymers 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000008018 melting Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 238000004378 air conditioning Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- OVHUTIJPHWTHKJ-UHFFFAOYSA-N 2-methylpropane;propane Chemical compound CCC.CC(C)C OVHUTIJPHWTHKJ-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229960000510 ammonia Drugs 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- DFQPLGZDHXLIDJ-UHFFFAOYSA-N dichloro(difluoro)methane;1,1-difluoroethane Chemical compound CC(F)F.FC(F)(Cl)Cl DFQPLGZDHXLIDJ-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
Landscapes
- Extraction Or Liquid Replacement (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は融氷脱水剤及び融氷
脱水冷媒組成物に関し、特に融氷性、脱水性に優れる融
氷脱水剤及び冷媒組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a deicing agent and a defrosting refrigerant composition, and more particularly to a deicing agent and a refrigerant composition having excellent melting and dewatering properties.
【０００２】[0002]
【従来の技術】従来より知られている脱水冷媒組成物と
しては、特公平２−６１２８２で開示されている、冷
媒、潤滑剤及び有機シラン脱水剤からなる組成物であ
る。該組成物で使用される有機シラン化合物は水分によ
り加水分解可能な加水分解性基を持つことが特徴の化合
物であり、加水分解性基としてはアルコキシ基、アミノ
基、メルカプト基、アシロキシ基が示されている。ま
た、けい素原子にアルキレン基が結合したポリオキシア
ルキレン基を有するシラン化合物が例示されている。2. Description of the Related Art A conventionally known dehydrating refrigerant composition is a composition comprising a refrigerant, a lubricant and an organic silane dehydrating agent disclosed in Japanese Patent Publication No. 2-61282. The organosilane compound used in the composition is a compound characterized by having a hydrolyzable group that can be hydrolyzed by water, and examples of the hydrolyzable group include an alkoxy group, an amino group, a mercapto group, and an acyloxy group. Have been. Further, a silane compound having a polyoxyalkylene group in which an alkylene group is bonded to a silicon atom is exemplified.
【０００３】[0003]
【発明が解決しようとする課題】加水分解性基としてメ
トキシ基やエトキシ基といったアルコキシ基を持ったシ
ランでは融氷性能がなく、融氷剤としてメタノールやエ
タノールを添加する必要がある。このようなアルコール
は冷媒の性能を低下させることが問題となっていた。ま
た、アミノ基、メルカプト基、アシロキシ基などを有す
る有機シラン化合物を用いた場合には、加水分解により
生じるアミン、メルカプタン又は酸により冷媒ユニット
が腐食するという問題があった。また、ポリオキシアル
キレン基含有シラン化合物は融氷性能に問題があった。A silane having an alkoxy group such as a methoxy group or an ethoxy group as a hydrolyzable group does not have the ability to melt ice, and it is necessary to add methanol or ethanol as an ice melting agent. Such alcohols have a problem in that the performance of the refrigerant is reduced. Further, when an organic silane compound having an amino group, a mercapto group, an acyloxy group, or the like is used, there is a problem that the refrigerant unit is corroded by amine, mercaptan, or acid generated by hydrolysis. Further, the polyoxyalkylene group-containing silane compound has a problem in ice melting performance.
【０００４】そこで、本発明は、融氷性能及び脱水性能
に優れる有機けい素化合物を含有する融氷脱水剤並びに
融氷性能、脱水性能及び冷媒性能に優れる組成物を提供
することを目的とする。Accordingly, an object of the present invention is to provide an ice-melt dewatering agent containing an organosilicon compound having excellent ice-melting performance and dewatering performance, and a composition excellent in ice-melting performance, dewatering performance and refrigerant performance. .
【０００５】[0005]
【課題を解決するための手段】本発明の融氷脱水剤は、
式(1)で表される有機けい素化合物からなることを特徴
とするものである。Means for Solving the Problems The deicing agent of the present invention comprises:
It comprises an organosilicon compound represented by the formula (1).
【０００６】[0006]
【化２】 Embedded image
【０００７】〔式中、Ｒ1 は炭素原子数２〜６の１価炭
化水素基を表わし、CH3CH2-, CH3(CH2)2-, CH3CH(CH3)
-, CH3(CH2)4-, (CH3)2CHCH2-, (CH3)3C-, CH3(CH2)4-,
CH3(CH2)5- 等が例示され、Ｒ2 は炭素原子数３〜６の
２価炭化水素基を表わし、-CH2CH(CH3)-, -CH(CH3)CH
2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6- 等が例
示され、Ｒ3 は炭素原子数１〜６の１価の炭化水素基を
表わし、CH3-, CH3CH2-, CH3(CH2)2-, CH3CH(CH3)-, CH
3(CH2)3-, CH3(CH2)4-, CH3(CH2)5- 等が例示され、好
ましくは CH3-であり、Ｒ4 は炭素原子数１〜４の１価
炭化水素基を表わし、CH3-, CH3CH2-, CH3(CH2)2-, CH3
CH(CH3)-, CH3(CH2)3- 等を表わし、好ましくはCH3-, C
H3CH2-であり、ａは０又は１であり、ｂは１又は２であ
り、ｍは０〜１０の整数であり、好ましくは０〜３であ
り、ｎは３〜１０の整数であり、好ましくは３〜１０で
あり、より好ましくは３〜５である。〕[Wherein, R 1 represents a monovalent hydrocarbon group having 2 to 6 carbon atoms, and CH 3 CH 2- , CH 3 (CH 2 ) 2- , CH 3 CH (CH 3 )
-, CH 3 (CH 2) 4 -, (CH 3) 2 CHCH 2 -, (CH 3) 3 C-, CH 3 (CH 2) 4 -,
CH 3 (CH 2 ) 5- and the like are exemplified, and R 2 represents a divalent hydrocarbon group having 3 to 6 carbon atoms, and —CH 2 CH (CH 3 ) —, —CH (CH 3 ) CH
2 -,-(CH 2 ) 3 -,-(CH 2 ) 4 -,-(CH 2 ) 5 -,-(CH 2 ) 6- and the like, and R 3 is 1 to 6 carbon atoms. CH 3- , CH 3 CH 2- , CH 3 (CH 2 ) 2- , CH 3 CH (CH 3 )-, CH
3 (CH 2) 3 -, CH 3 (CH 2) 4 -, CH 3 (CH 2) 5 - and the like are exemplified, preferably CH 3 - a and, R 4 is a monovalent 1 to 4 carbon atoms Represents a hydrocarbon group, CH 3- , CH 3 CH 2- , CH 3 (CH 2 ) 2- , CH 3
CH (CH 3 )-, CH 3 (CH 2 ) 3- and the like, preferably CH 3- , C
H 3 CH 2 —, a is 0 or 1, b is 1 or 2, m is an integer of 0 to 10, preferably 0 to 3, and n is an integer of 3 to 10. Yes, preferably 3 to 10, more preferably 3 to 5. ]
【０００８】また、本発明は、式(1)で表される有機け
い素化合物及び冷媒を含有する冷媒組成物を提供する。
さらに、本発明は、式(1)で表される有機けい素化合物
及び潤滑剤を含有する融氷脱水剤組成物を提供するもの
である。[0008] The present invention also provides a refrigerant composition containing an organic silicon compound represented by the formula (1) and a refrigerant.
Further, the present invention provides a melt-ice dewatering agent composition containing the organosilicon compound represented by the formula (1) and a lubricant.
【０００９】[0009]
【発明の実施の形態】有機けい素化合物 式（１）で表される有機けい素化合物としては下記の式
（１−１）〜（１−１９）の化合物が例示される。BEST MODE FOR CARRYING OUT THE INVENTION Organosilicon compounds As the organosilicon compounds represented by the formula (1), compounds of the following formulas (1-1) to (1-19) are exemplified.
【００１０】 (CH3)2-Si-[(OCH2CH2 )3-OCH3]2 (1-1) (CH3)2-Si-[(OCH2CH2)4-OCH3]2 (1-2) (CH3)2-Si-[(OCH2CH2)5-OCH3]2 (1-3) (CH3)2-Si-[(OCH2CH2)3-OCH2CH3]2 (1-4) (CH3)2-Si-[(OCH2 CH2)3-O(CH2)3CH3]2 (1-5)(CH 3 ) 2 -Si-[(OCH 2 CH 2 ) 3 -OCH 3 ] 2 (1-1) (CH 3 ) 2 -Si-[(OCH 2 CH 2 ) 4 -OCH 3 ] 2 (1-2) (CH 3 ) 2 -Si-[(OCH 2 CH 2 ) 5 -OCH 3 ] 2 (1-3) (CH 3 ) 2 -Si-[(OCH 2 CH 2 ) 3 -OCH 2 CH 3 ] 2 (1-4) (CH 3 ) 2 -Si-[(OCH 2 CH 2 ) 3 -O (CH 2 ) 3 CH 3 ] 2 (1-5)
【００１１】[0011]
【化３】 Embedded image
【００１２】[0012]
【化４】 Embedded image
【００１３】[0013]
【化５】 Embedded image
【００１４】この有機けい素化合物は融氷性能及び脱水
性能を有するポリオキシエチレンオキシ基を分子内に少
なくとも一つもち、且つ非加水分解性の有機基を分子内
に２つ有することが特徴である。この化合物の性状は液
体であり、冷媒及び／又は潤滑剤と混合した後も固化し
て流通管やバルブが閉塞されることもなく、さらに脱水
性能を発揮し、該化合物が加水分解縮合した後に生じる
一方の生成物はシリコーンオイルであり、性状は液体で
あるためこのものが固化して流通管やバルブが閉塞され
ることがない。また、該化合物が脱水性能を発揮した後
に生じるもう一つの生成物はアルキル（ポリオキシエチ
レン含有）ハイドロオキサイドであり、この化合物も性
状が液体であり、固化することはなくさらに有機酸やア
ミンといったアルカリ成分は生じないため、ユニットの
金属部分への腐食もない。このような有機けい素化合物
は次のような方法で合成が可能である。This organosilicon compound is characterized in that it has at least one polyoxyethyleneoxy group having melting-ice performance and dehydration performance in the molecule and two non-hydrolyzable organic groups in the molecule. is there. This compound is liquid and solidifies even after being mixed with a refrigerant and / or a lubricant, and does not block the flow pipe or valve. One of the resulting products is a silicone oil, which is a liquid and does not solidify and does not block the flow pipes and valves. Another product generated after the compound exhibits dehydration performance is an alkyl (polyoxyethylene-containing) hydroxide, which is also liquid in nature and does not solidify and further contains organic acids and amines. Since no alkali component is generated, there is no corrosion to the metal part of the unit. Such an organic silicon compound can be synthesized by the following method.
【００１５】製造法１： 式：Production method 1: Formula:
【００１６】[0016]
【化６】 Embedded image
【００１７】〔式中、Ｒ1及びａは前記の通りであ
る。〕で表わされるクロルシランと、式： H(OR2)m (OCH2CH2) n OR3 〔式中、Ｒ2、Ｒ3、ｍ及びｎは前記の通りである。〕で
表わされるアルキル（ポリオキシエチレン含有）ハイド
ロオキサイドとをモル比１：０．５〜３．０、好ましく
は１：０．５〜２．５で脱ＨＣｌ反応し、さらに残存し
たクロル基を式R4OHで表わされるアルコールと脱ＨＣｌ
反応させることで製造することが可能である。また、該
有機けい素化合物は、先にR4OH（ここで、Ｒ4は前記の
通り）で表わされるアルコールと前記クロルシランとを
反応させた後、前記アルキル（ポリオキシエチレン含
有）ハイドロオキサイドと反応させてもよい。Wherein R 1 and a are as defined above. And chlorosilane represented by the formula: H (OR 2 ) m (OCH 2 CH 2 ) n OR 3 wherein R 2 , R 3 , m and n are as defined above. With an alkyl (polyoxyethylene-containing) hydroxide represented by the following formula: at a molar ratio of 1: 0.5 to 3.0, preferably 1: 0.5 to 2.5, to remove the remaining chloro group. Alcohol represented by the formula R 4 OH and HCl removal
It can be produced by reacting. In addition, the organosilicon compound is prepared by reacting the alcohol represented by R 4 OH (where R 4 is as described above) with the chlorosilane, and then reacting with the alkyl (polyoxyethylene-containing) hydroxide. You may make it react.
【００１８】上記製法における反応温度は２０〜１５０
℃でよく、好ましくは５０〜１００℃である。また、こ
の際脱塩酸剤を加えることも任意である。脱塩酸剤とし
ては尿素やトリエチルアミン、ピリジン等のアミン化合
物があげられる。The reaction temperature in the above process is 20 to 150.
° C, preferably 50 to 100 ° C. At this time, it is optional to add a dehydrochlorinating agent. Examples of the dehydrochlorinating agent include amine compounds such as urea, triethylamine and pyridine.
【００１９】製造法２ 式：Production method 2 Formula:
【００２０】[0020]
【化７】 Embedded image
【００２１】〔式中、Ｒ1、Ｒ4及びａは前記の通りであ
る。〕で表わされるアルコキシシランと、式： H-(OR2) m (OCH2CH2) n OR3 〔式中、Ｒ2，Ｒ3、ｍ及びｎは前記の通りである〕で表
わされるアルキル（ポリオキシエチレン含有）ハイドロ
オキサイドとをモル比１：０．１〜３．０で脱アルコー
ル反応させることで製造することができる。この際、脱
アルコール反応促進触媒の使用は任意であり、例えばジ
ブチル錫ジラウレート、ジブチル錫ジオレート、ジブチ
ル錫オキサイド等の錫化合物、テトラブチルチタネー
ト、テトライソプロピルチタネート等のチタン化合物、
トリフェニルフォスフィン等の燐化合物、水酸化ナトリ
ウムや水酸化カリウム等のアルカリ化合物、塩酸や硫酸
等の酸及びフッ化カリウム、フッ化ナトリウム等があげ
られる。Wherein R 1 , R 4 and a are as defined above. And an alkyl represented by the formula: H- (OR 2 ) m (OCH 2 CH 2 ) n OR 3 wherein R 2 , R 3 , m and n are as defined above. It can be produced by subjecting a (polyoxyethylene-containing) hydroxide to a dealcoholation reaction at a molar ratio of 1: 0.1 to 3.0. At this time, the use of a dealcoholation reaction promoting catalyst is optional, for example, tin compounds such as dibutyltin dilaurate, dibutyltindiolate, dibutyltin oxide, tetrabutyl titanate, titanium compounds such as tetraisopropyl titanate,
Examples include phosphorus compounds such as triphenylphosphine, alkali compounds such as sodium hydroxide and potassium hydroxide, acids such as hydrochloric acid and sulfuric acid, and potassium fluoride and sodium fluoride.
【００２２】冷媒 本発明の組成物に用いられる冷媒としては従来公知のも
のを使用することができ、例えばCCl3F 、 CCl2F2 、CClF
3 、 C2Cl3F3 、 C2Cl2F4 、 CHClF2 、冷媒５００、冷媒５
０２、冷媒５０３、冷媒３１／１１４、冷媒１２／３１
等のＣＦＣ類、アンモニア、エチルクロライド、メチル
クロライド、メチレンクロライド、プロパンイソブタン
等の炭化水素類、ジメチルエーテル等が挙げられる。該
有機けい素化合物は融氷性能及び脱水性能に優れるの
で、単独で融氷脱水剤として使用することができ、また
必要により潤滑剤等を添加して組成物状態で使用しても
よい。該有機けい素化合物に冷媒を配合することによ
り、融氷、脱水の性能を有する冷媒組成物として使用す
ることもできる。勿論、該冷媒組成物には潤滑剤と冷媒
をともに配合することもできる。The refrigerant as a refrigerant used in the composition of the present invention can be used those known in the art, for example, CCl 3 F, CCl 2 F 2 , CClF
3, C 2 Cl 3 F 3 , C 2 Cl 2 F 4, CHClF 2, the refrigerant 500, refrigerant 5
02, refrigerant 503, refrigerant 31/114, refrigerant 12/31
And the like, ammonia, ethyl chloride, methyl chloride, methylene chloride, hydrocarbons such as propane isobutane, and dimethyl ether. Since the organosilicon compound is excellent in ice melting performance and dewatering performance, it can be used alone as a deicing agent for deicing, or may be used in the form of a composition to which a lubricant or the like is added if necessary. By blending a refrigerant with the organosilicon compound, it can be used as a refrigerant composition having melting ice and dewatering performance. Of course, a lubricant and a refrigerant may be mixed together in the refrigerant composition.
【００２３】潤滑剤 本発明の組成物に用いられる潤滑剤としては、従来この
種の組成物に使用されているものは特に制限なく使用す
ることができ、例えばパラフィン系、シクロパラフィン
系、芳香族系のミネラルオイル、アルキルベンゼン系、
エステル系、グリコール系の合成オイル等が挙げられ
る。これらの潤滑剤は、例えば、ＳＵＮＩＳＯ ３ＧＳ
（日本サン石油株式会社製）、ＰＯＥ ＶＧ６８（同
左）等の商品名で市販されている。 Lubricants As the lubricant used in the composition of the present invention, those conventionally used in this type of composition can be used without any particular limitation. For example, paraffins, cycloparaffins, aromatics Mineral oil, alkyl benzene,
Examples include ester-based and glycol-based synthetic oils. These lubricants are, for example, SUNISO 3GS
(Manufactured by Nippon Sun Oil Co., Ltd.) and POE VG68 (same as the left).
【００２４】配合 本発明の冷媒組成物中の有機けい素化合物の添加量は任
意であるが、好ましくは冷媒及び潤滑油に対して１００
ｐｐｍから５０％であり、より好ましくは５００ｐｐｍ
から５％である。また、潤滑剤の量は、冷媒１００重量
部当り、通常１〜１００重量部、好ましくは１０〜５０
重量部である。 Blending The amount of the organosilicon compound in the refrigerant composition of the present invention is optional, but is preferably 100 parts by weight with respect to the refrigerant and the lubricating oil.
ppm to 50%, more preferably 500 ppm
From 5%. The amount of the lubricant is usually 1 to 100 parts by weight, preferably 10 to 50 parts by weight, per 100 parts by weight of the refrigerant.
Parts by weight.
【００２５】[0025]
＜実施例１〜８、比較例１〜６＞ ＜融氷試験＞本発明の冷媒組成物に含まれる有機けい素
化合物は融氷性能をもつことが特徴であり、以下この融
氷性能を測定した。各例において、表１又は表２に示す
有機けい素化合物１０ｇ及び潤滑油ＳＵＮＩＳＯ ３Ｇ
Ｓ（日本サン石油（株）社製）４０ｇをそれぞれ混合
し、−２０℃にて氷５ｇと混合し、−２０℃中で融氷性
能を測定した。１日後（２４時間後）及び２日後（４８
時間後）の結果を表１又は表２に示す。<Examples 1 to 8, Comparative Examples 1 to 6><Ice melting test> The organosilicon compound contained in the refrigerant composition of the present invention is characterized by having ice melting performance, and this ice melting performance is measured below. did. In each example, 10 g of the organosilicon compound shown in Table 1 or Table 2 and the lubricating oil SUNISO 3G
S (manufactured by Nippon Sun Oil Co., Ltd.) was mixed with each, 40 g of ice was mixed at −20 ° C., and the melting performance at −20 ° C. was measured. One day (24 hours) and two days (48
Table 1 or Table 2 shows the results after (hours).
【００２６】[0026]
【表１】 [Table 1]
【００２７】[0027]
【表２】 注：[Table 2] note:
【００２８】[0028]
【化８】 CH3-(CH2)3-O-(CH2CH2O)3-CH2CH2CH2-Si(CH3)(OCH3)2 (2-6)Embedded image CH 3- (CH 2 ) 3 -O- (CH 2 CH 2 O) 3 -CH 2 CH 2 CH 2 -Si (CH 3 ) (OCH 3 ) 2 (2-6)
【００２９】＜実施例９〜１１、比較例７、８＞ ＜脱水試験＞本発明の冷媒組成物に含まれる有機けい素
化合物はさらに脱水性能をもつことが特徴であり、以下
この脱水性能を測定した。なお、この試験では本有機け
い素化合物の残存率を測定することで脱水性能を比較し
た。各例において、表３に示す有機けい素化合物１０ｇ
とイオン交換水１０ｇ及び内部標準物質としてｎ−デカ
ン１０ｇを混合し、振とう下、経時でガスクロマトグラ
フ分析を行なった。結果を表３に示した。<Examples 9 to 11 and Comparative Examples 7 and 8><Dehydrationtest> The organic silicon compound contained in the refrigerant composition of the present invention is characterized by further having a dehydration property. It was measured. In this test, the dehydration performance was compared by measuring the residual ratio of the present organosilicon compound. In each case, 10 g of the organic silicon compound shown in Table 3
And 10 g of ion-exchanged water and 10 g of n-decane as an internal standard substance, and subjected to gas chromatographic analysis over time under shaking. The results are shown in Table 3.
【００３０】[0030]
【表３】 注：[Table 3] note:
【００３１】[0031]
【化９】 Embedded image
【００３２】[0032]
【発明の効果】本発明の融氷脱水剤は融氷性能、脱水性
能に優れる。また、本発明の融氷脱水冷媒組成物は、冷
媒性能を低下させるアルコールの添加を必要とせず、か
つまたアルコールを副生しないため良好な融氷性能を発
揮でき、同時に優れた融氷及び脱水の性能を有する。The ice-melt dewatering agent of the present invention is excellent in ice-melting performance and dewatering performance. In addition, the ice-melt dewatering refrigerant composition of the present invention can exhibit good ice-melting performance because it does not require the addition of alcohol that lowers refrigerant performance and does not produce alcohol as a by-product, and at the same time has excellent ice-melting and dewatering. It has the performance of
【００３３】さらに、本発明の融氷脱水剤及び冷媒組成
物は融氷前、脱水後ともに固化することがないため、流
通管やバルブが閉塞することもなく、また、酸性物質や
アルカリ性物質を含まず、かつ脱水反応によってもこれ
らの物質を生じることがないため、冷凍機ユニットや空
調ユニットを腐食する恐れがない。本発明の融氷脱水剤
及び組成物は商業用、家庭用及び自動車用の空調ユニッ
トや商業用、家庭用冷凍機、冷蔵庫等に使用が可能であ
る。Further, since the deicing agent and the refrigerant composition of the present invention do not solidify both before and after defrosting, the flow pipes and valves are not blocked, and acidic and alkaline substances are not removed. Since these substances are not contained and these substances are not generated even by the dehydration reaction, there is no possibility that the refrigerator unit or the air conditioning unit is corroded. The deicing agent and the composition of the present invention can be used in commercial, domestic and automotive air conditioning units, commercial and household refrigerators, refrigerators and the like.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 井上 凱夫 群馬県碓氷郡松井田町大字人見１番地10 信越化学工業株式会社シリコーン電子材料 技術研究所内 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor, Kaio Inoue 1-10, Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Technology Laboratory
Claims (3)
なる融氷脱水剤。 【化１】 （式中、Ｒ1 は炭素原子数２〜６の１価炭化水素基、Ｒ
2 は炭素原子数３〜６の２価炭化水素基、Ｒ3 は炭素原
子数１〜６の１価炭化水素基、Ｒ4 は炭素原子数１〜４
の１価炭化水素基、ａは０又は１、ｂは１又は２、ｍは
０〜１０の整数、そしてｎは３〜１０の整数を示す。）1. An ice-melt dehydrating agent comprising an organosilicon compound represented by the formula (1). Embedded image (Wherein, R 1 is a monovalent hydrocarbon group having 2 to 6 carbon atoms,
2 is a divalent hydrocarbon group having 3 to 6 carbon atoms, R 3 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, R 4 is 1 to 4 carbon atoms.
A represents 0 or 1, b represents 1 or 2, m represents an integer of 0 to 10, and n represents an integer of 3 to 10. )
けい素化合物及び冷媒を含有する冷媒組成物。2. A refrigerant composition comprising the organic silicon compound represented by the formula (1) according to claim 1 and a refrigerant.
けい素化合物及び潤滑剤を含有する融氷脱水剤組成物。3. An ice-melt dehydrating composition comprising the organosilicon compound represented by the formula (1) according to claim 1 and a lubricant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27986997A JP3441937B2 (en) | 1997-09-26 | 1997-09-26 | Melting ice dewatering agent and defrosting refrigerant composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27986997A JP3441937B2 (en) | 1997-09-26 | 1997-09-26 | Melting ice dewatering agent and defrosting refrigerant composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11100571A true JPH11100571A (en) | 1999-04-13 |
| JP3441937B2 JP3441937B2 (en) | 2003-09-02 |
Family
ID=17617087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27986997A Expired - Fee Related JP3441937B2 (en) | 1997-09-26 | 1997-09-26 | Melting ice dewatering agent and defrosting refrigerant composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3441937B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008044934A (en) * | 2006-08-16 | 2008-02-28 | Samsung Sdi Co Ltd | Silane compound, organic electrolyte solution using the same and lithium cell |
| JP2016053021A (en) * | 2014-09-03 | 2016-04-14 | 国立研究開発法人産業技術総合研究所 | Alkoxysilanes, and oligosiloxanes and method for producing the same |
-
1997
- 1997-09-26 JP JP27986997A patent/JP3441937B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008044934A (en) * | 2006-08-16 | 2008-02-28 | Samsung Sdi Co Ltd | Silane compound, organic electrolyte solution using the same and lithium cell |
| JP4625052B2 (en) * | 2006-08-16 | 2011-02-02 | 三星エスディアイ株式会社 | Silane compound, organic electrolyte and lithium battery using the same |
| US8034489B2 (en) | 2006-08-16 | 2011-10-11 | Samsung Sdi Co., Ltd. | Silane compound, organic electrolyte solution using the silane compound, and lithium battery using the organic electrolyte solution |
| JP2016053021A (en) * | 2014-09-03 | 2016-04-14 | 国立研究開発法人産業技術総合研究所 | Alkoxysilanes, and oligosiloxanes and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3441937B2 (en) | 2003-09-02 |
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