CA2274040C - Silicones chelateurs - Google Patents

Silicones chelateurs Download PDF

Info

Publication number: CA2274040C
Authority: CA; Canada
Prior art keywords: group; polymer according; metal; formula; hydrophobic
Prior art date: 1999-05-27
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

CA 2274040

Other languages

English (en)

Other versions

CA2274040A1 (fr

Inventor

Michael A. Brook

Rodica S. Stan

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.)

McMaster University

Original Assignee

McMaster University

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.)

1999-05-27

Filing date

1999-05-27

Publication date

2010-11-30

1999-05-27 Application filed by McMaster University filed Critical McMaster University

1999-05-27 Priority to CA 2274040 priority Critical patent/CA2274040C/fr

2000-05-26 Priority to CA 2309486 priority patent/CA2309486C/fr

2000-11-27 Publication of CA2274040A1 publication Critical patent/CA2274040A1/fr

2010-11-30 Application granted granted Critical

2010-11-30 Publication of CA2274040C publication Critical patent/CA2274040C/fr

2019-05-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920001296 polysiloxane Polymers 0.000 title description 30
229910052751 metal Inorganic materials 0.000 claims abstract description 34
239000002184 metal Substances 0.000 claims abstract description 34
229920000642 polymer Polymers 0.000 claims description 29
150000001735 carboxylic acids Chemical class 0.000 claims description 14
125000001165 hydrophobic group Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
229920002554 vinyl polymer Polymers 0.000 claims description 9
125000002009 alkene group Chemical group 0.000 claims description 8
125000002355 alkine group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
230000007935 neutral effect Effects 0.000 claims description 8
150000007942 carboxylates Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical group 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000001408 amides Chemical group 0.000 claims description 3
150000002148 esters Chemical group 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
229910020485 SiO4/2 Inorganic materials 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
125000005647 linker group Chemical group 0.000 claims 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
230000009920 chelation Effects 0.000 claims 1
150000002739 metals Chemical class 0.000 abstract description 15
230000002209 hydrophobic effect Effects 0.000 abstract description 9
239000003446 ligand Substances 0.000 abstract description 7
229920005573 silicon-containing polymer Polymers 0.000 abstract description 4
229920001795 coordination polymer Polymers 0.000 abstract description 2
229910052710 silicon Inorganic materials 0.000 abstract description 2
239000010703 silicon Substances 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
230000008859 change Effects 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
239000011149 active material Substances 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000007480 spreading Effects 0.000 description 2
238000003892 spreading Methods 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
230000004913 activation Effects 0.000 description 1
238000001042 affinity chromatography Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000003010 ionic group Chemical group 0.000 description 1
239000002563 ionic surfactant Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
238000000034 method Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004530 micro-emulsion Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
-1 polydimethylsiloxane Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
230000008961 swelling Effects 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon

Landscapes

Chemical & Material Sciences (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Silicon Polymers (AREA)
Paints Or Removers (AREA)

CA 2274040 1999-05-27 1999-05-27 Silicones chelateurs Expired - Fee Related CA2274040C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA 2274040 CA2274040C (fr)	1999-05-27	1999-05-27	Silicones chelateurs
CA 2309486 CA2309486C (fr)	1999-05-27	2000-05-26	Polymeres de silicones chelateurs

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2274040 CA2274040C (fr)	1999-05-27	1999-05-27	Silicones chelateurs

Publications (2)

Publication Number	Publication Date
CA2274040A1 CA2274040A1 (fr)	2000-11-27
CA2274040C true CA2274040C (fr)	2010-11-30

Family

ID=30774293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2274040 Expired - Fee Related CA2274040C (fr)	1999-05-27	1999-05-27	Silicones chelateurs

Country Status (1)

Country	Link
CA (1)	CA2274040C (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8168741B2 (en)	2005-08-02	2012-05-01	Joint Intellectual Property Policy Of Mcmaster University	Chelating silicon-based polymers
DE102005057460A1 (de)	2005-12-01	2007-06-06	Wacker Chemie Ag	Zu hochfesten Elastomeren vernetzbare ionisch und/oder organometallisch funktionalisierte Siliconpolymere
JP6340437B2 (ja)	2014-05-21	2018-06-06	ダウシリコーンズコーポレーション	架橋アミノシロキサンポリマー及び生成方法

1999
- 1999-05-27 CA CA 2274040 patent/CA2274040C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2274040A1 (fr)	2000-11-27

Legal Events

Date	Code	Title	Description
2004-05-20	EEER	Examination request
2015-07-08	MKLA	Lapsed	Effective date: 20150527

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US5248783A (en)	1993-09-28	Silicone alkoxylated esters carboxylate salts
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US5391227A (en)	1995-02-21	Siloxane fluid from methylchlorosilane residue waste
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