CA2007821C - Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique - Google Patents

Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique

Info

Publication number: CA2007821C
Authority: CA; Canada
Prior art keywords: organosilane; porous support; porous; zone; group
Prior art date: 1988-02-11
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.): Expired - Fee Related

Application number

CA002007821A

Other languages

English (en)

Other versions

CA2007821A1 (fr

Inventor

Dwight E. Williams

Thomas J. Tangney

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Silicones Corp

Original Assignee

Dow Corning Corp

Priority date (The priority date 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 date listed.)

1988-02-11

Filing date

1990-01-16

Publication date

1999-11-02

1990-01-16 Application filed by Dow Corning Corp filed Critical Dow Corning Corp

1990-01-16 Priority to CA002007821A priority Critical patent/CA2007821C/fr

1991-07-16 Publication of CA2007821A1 publication Critical patent/CA2007821A1/fr

1999-11-02 Application granted granted Critical

1999-11-02 Publication of CA2007821C publication Critical patent/CA2007821C/fr

2010-01-16 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001282 organosilanes Chemical class 0.000 title claims abstract description 102
239000000203 mixture Substances 0.000 title claims abstract description 67
230000009977 dual effect Effects 0.000 title claims abstract description 37
239000000463 material Substances 0.000 title description 30
238000004519 manufacturing process Methods 0.000 title description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 55
239000011148 porous material Substances 0.000 claims abstract description 51
239000000377 silicon dioxide Substances 0.000 claims abstract description 23
239000000725 suspension Substances 0.000 claims abstract description 23
239000000010 aprotic solvent Substances 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
238000000034 method Methods 0.000 claims description 30
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 25
239000002904 solvent Substances 0.000 claims description 24
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
-1 aryl sulfide Chemical compound 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
238000002156 mixing Methods 0.000 claims description 12
230000015572 biosynthetic process Effects 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
238000004458 analytical method Methods 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 7
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 7
229910044991 metal oxide Inorganic materials 0.000 claims description 6
229910052752 metalloid Inorganic materials 0.000 claims description 6
150000002738 metalloids Chemical class 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
239000012454 non-polar solvent Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
238000005259 measurement Methods 0.000 claims description 3
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 3
150000003568 thioethers Chemical class 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Chemical group 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
238000001941 electron spectroscopy Methods 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 10
238000007792 addition Methods 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 7
229910000077 silane Inorganic materials 0.000 description 7
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
238000006884 silylation reaction Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000005051 trimethylchlorosilane Substances 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004364 calculation method Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000009792 diffusion process Methods 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
230000008569 process Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
150000004756 silanes Chemical class 0.000 description 3
238000005211 surface analysis Methods 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000005046 Chlorosilane Substances 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000012856 packing Methods 0.000 description 2
239000011236 particulate material Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
150000004819 silanols Chemical class 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000000758 substrate Substances 0.000 description 2
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
150000001343 alkyl silanes Chemical class 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000006664 bond formation reaction Methods 0.000 description 1
CAURZYXCQQWBJO-UHFFFAOYSA-N bromomethyl-chloro-dimethylsilane Chemical compound C[Si](C)(Cl)CBr CAURZYXCQQWBJO-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
BJLJNLUARMMMLW-UHFFFAOYSA-N chloro-(3-chloropropyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCl BJLJNLUARMMMLW-UHFFFAOYSA-N 0.000 description 1
ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000005373 porous glass Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000006557 surface reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Landscapes

Silicon Compounds (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Oxygen, Ozone, And Oxides In General (AREA)
Catalysts (AREA)

CA002007821A 1988-02-11 1990-01-16 Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique Expired - Fee Related CA2007821C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002007821A CA2007821C (fr)	1988-02-11	1990-01-16	Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US15475488A	1988-02-11	1988-02-11
CA002007821A CA2007821C (fr)	1988-02-11	1990-01-16	Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique

Publications (2)

Publication Number	Publication Date
CA2007821A1 CA2007821A1 (fr)	1991-07-16
CA2007821C true CA2007821C (fr)	1999-11-02

Family

ID=22552642

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002007821A Expired - Fee Related CA2007821C (fr)	1988-02-11	1990-01-16	Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique

Country Status (2)

Country	Link
JP (1)	JP2999498B2 (fr)
CA (1)	CA2007821C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1291080A3 (fr) *	2001-09-10	2004-05-19	Tosoh Corporation	Procédé pour la production d'adsorbants partiellement hydrophilisés
JP6681795B2 (ja) *	2015-09-24	2020-04-15	東京応化工業株式会社	表面処理剤及び表面処理方法

1990
- 1990-01-16 CA CA002007821A patent/CA2007821C/fr not_active Expired - Fee Related
- 1990-02-07 JP JP2621790A patent/JP2999498B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH03242306A (ja)	1991-10-29
CA2007821A1 (fr)	1991-07-16
JP2999498B2 (ja)	2000-01-17

Legal Events

Date	Code	Title	Description
1996-02-07	EEER	Examination request
2006-01-16	MKLA	Lapsed

Publication	Publication Date	Title
EP0437912B1 (fr)	1993-11-18	Méthode de préparation de matériaux à zone duale par utilisation d'un mélange d'organosilanes
US4950634A (en)	1990-08-21	Method for producing dual zone materials by use of an organosilane mixture
US5110784A (en)	1992-05-05	Dual surface porous material
US4705725A (en)	1987-11-10	Substrates with sterically-protected, stable, covalently-bonded organo-silane films
EP0269447B1 (fr)	1992-03-25	Structures à surface modifiée par des silanes bidentates
EP0443860B1 (fr)	1994-02-09	Méthode de préparation d'un garnissage pour chromatographie en phase liquide et matériau ainsi produit
EP0172730B1 (fr)	1988-12-07	Garnis de chromatographie stabilisés par oxyde de métal
CA1252002A (fr)	1989-04-04	Materiaux poreux a deux surfaces a reaction differente
EP1991203A2 (fr)	2008-11-19	Noyaux solides de microparticules poreuses
US5093451A (en)	1992-03-03	Formed organosiloxane amine copolycondensates method of their preparation and use
AU725928B2 (en)	2000-10-26	Improved liquid chromatographic media for polynucleotide separation
JP2611545B2 (ja)	1997-05-21	液体クロマトグラフィー用充填剤の製造方法
EP0161058B1 (fr)	1989-05-24	Matériaux à deux surfaces différentes
CA2007821C (fr)	1999-11-02	Methode de preparation de materiaux a zone mixte grace a l'utilisation d'un melange de silanes organique
Hunnicutt et al.	1986	Reactivity of organosilane reagents on microparticulate silica
JP3691619B2 (ja)	2005-09-07	液体クロマトグラフィー用充填剤及びその処理方法
JP2999499B2 (ja)	2000-01-17	オルガノシラン混合物の使用により二区域多孔性物質を調製する方法
CA2007819C (fr)	1999-11-02	Methode de preparation de materiaux a zone mixte par halogenosilylation catalytique
AU648025B2 (en)	1994-04-14	Method for producing dual zone materials by catalyzed halosilylation
Şener et al.	2005	The effect of silane modification on the adsorptive properties of natural pyrophyllite and synthetic titanium-based powders prepared by the sol-gel process
JP3790303B2 (ja)	2006-06-28	クロマトグラフィー用充填剤の製造法
DE69004678T2 (de)	1994-05-26	Methode zur Herstellung von Dual-Zone-Materialien durch katalysierte Halosilylation.