CA2341783A1 - Poly(aminoorganofunctionalsiloxanes) - Google Patents
Poly(aminoorganofunctionalsiloxanes) Download PDFInfo
- Publication number
- CA2341783A1 CA2341783A1 CA002341783A CA2341783A CA2341783A1 CA 2341783 A1 CA2341783 A1 CA 2341783A1 CA 002341783 A CA002341783 A CA 002341783A CA 2341783 A CA2341783 A CA 2341783A CA 2341783 A1 CA2341783 A1 CA 2341783A1
- Authority
- CA
- Canada
- Prior art keywords
- homopolymer
- hexamethyldisiloxane
- poly
- mixture
- ranges
- 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.)
- Abandoned
Links
- -1 poly(3-aminopropylmethylsiloxanes) Polymers 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 21
- KWQQHTNSJIJFBO-UHFFFAOYSA-N 3-[methyl-bis(trimethylsilyloxy)silyl]propan-1-amine Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CCCN KWQQHTNSJIJFBO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 229920001519 homopolymer Polymers 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 229940073561 hexamethyldisiloxane Drugs 0.000 claims description 20
- 239000012530 fluid Substances 0.000 claims description 9
- 150000004679 hydroxides Chemical class 0.000 claims description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 8
- 229920005565 cyclic polymer Polymers 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 150000002484 inorganic compounds Chemical class 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical class C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 8
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- BOBMDNIYRSTZLQ-UHFFFAOYSA-N 1-[diethoxy(methyl)silyl]propan-2-amine Chemical compound CCO[Si](C)(CC(C)N)OCC BOBMDNIYRSTZLQ-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- URRAYBPMSCNCBY-UHFFFAOYSA-N 4-[4,6-bis(4-aminobutyl)-1,3,5,2,4,6-trioxatrisilinan-2-yl]butan-1-amine Chemical compound NCCCC[SiH]1O[SiH](O[SiH](O1)CCCCN)CCCCN URRAYBPMSCNCBY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- CVNCFZIIZGNVFD-UHFFFAOYSA-N n,n-bis(trimethylsilyl)prop-2-en-1-amine Chemical compound C[Si](C)(C)N([Si](C)(C)C)CC=C CVNCFZIIZGNVFD-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- 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
- C08G77/32—Post-polymerisation treatment
- C08G77/34—Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/532,714 | 2000-03-22 | ||
| US09/532,714 US6339137B1 (en) | 2000-03-22 | 2000-03-22 | Poly (aminoorganofunctionalsiloxanes) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2341783A1 true CA2341783A1 (en) | 2001-09-22 |
Family
ID=24122855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002341783A Abandoned CA2341783A1 (en) | 2000-03-22 | 2001-03-20 | Poly(aminoorganofunctionalsiloxanes) |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6339137B1 (enExample) |
| EP (1) | EP1136514B1 (enExample) |
| JP (1) | JP2001335585A (enExample) |
| AT (1) | ATE272668T1 (enExample) |
| CA (1) | CA2341783A1 (enExample) |
| DE (1) | DE60104586T2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6353073B1 (en) * | 2000-03-22 | 2002-03-05 | Archimica (Florida), Inc. | Poly (aminoorganofunctionaldisiloxanes) |
| US6670413B1 (en) * | 2002-06-05 | 2003-12-30 | Mcdermott Phillip J. | Thixotropic catalyst for condensation cure siloxane materials |
| US7847023B2 (en) * | 2007-03-12 | 2010-12-07 | Sabic Innovative Plastics Ip B.V. | Polysiloxane/polyimide copolymer blends |
| US20080236864A1 (en) * | 2007-03-28 | 2008-10-02 | General Electric Company | Cross linked polysiloxane/polyimide copolymers, methods of making, blends thereof, and articles derived therefrom |
| US7732516B2 (en) | 2008-01-31 | 2010-06-08 | Sabic Innovative Plastics Ip B.V. | Flame retardant polyimide/polyester-polycarbonate compositions, methods of manufacture, and articles formed therefrom |
| US20120285721A1 (en) | 2011-05-11 | 2012-11-15 | Gallucci Robert R | Silicone polyetherimide copolymers |
| EP3118277B1 (en) * | 2014-03-10 | 2019-10-23 | Kyoto University | Method for producing surface-modified substrate, method for producing conjugate, novel hydrosilane compound, surface treatment agent, surface treatment agent kit, and surface-modified substrate |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947771A (en) * | 1956-10-12 | 1960-08-02 | Union Carbide Corp | Aminoalkylpolysiloxanes and process for their production |
| US3045036A (en) * | 1957-11-18 | 1962-07-17 | Union Carbide Corp | End-blocked aminoalkylpolysiloxanes and process for cyclic aminoalkyl-siloxanes |
| US3814730A (en) | 1970-08-06 | 1974-06-04 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| US3775452A (en) | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| DE2408480A1 (de) | 1974-02-22 | 1975-09-04 | Bayer Ag | Verfahren zur herstellung von gammaaminopropylalkoxysilanen |
| JPS61296184A (ja) * | 1985-06-20 | 1986-12-26 | 信越化学工業株式会社 | 繊維処理剤 |
| GB8602226D0 (en) | 1986-01-30 | 1986-03-05 | Dow Corning Ltd | Preparation of primary aminosiloxanes |
| JPH0633288B2 (ja) | 1986-10-06 | 1994-05-02 | 東レ・ダウコ−ニング・シリコ−ン株式会社 | 付加反応方法 |
| JP2535028B2 (ja) * | 1987-07-31 | 1996-09-18 | 東燃株式会社 | アミノプロピルアルコキシシラン類の製造方法 |
| JPH0796555B2 (ja) | 1987-12-14 | 1995-10-18 | 東燃株式会社 | アミノプロピルシリル化合物の製造方法 |
| US5026890A (en) | 1988-05-20 | 1991-06-25 | General Electric Company | Method and intermediates for preparation of bis(aminoalkyl)polydiorganosiloxanes |
| JP2606924B2 (ja) * | 1989-05-31 | 1997-05-07 | 東燃株式会社 | アミノプロピルシラン化合物の製造方法 |
| JP2684130B2 (ja) * | 1991-08-15 | 1997-12-03 | 信越化学工業株式会社 | アミノ基含有ポリシロキサンの製造方法 |
| GB9311509D0 (en) | 1993-06-03 | 1993-07-21 | Dow Corning | Process for the preparation of organopolysiloxanes |
| DE4344082C1 (de) | 1993-12-23 | 1994-12-22 | Goldschmidt Ag Th | Verfahren zur Herstellung von Organopolysiloxanen mit über Kohlenstoff an Silicium gebundenen sekundären Aminoalkylgruppen |
| JPH0925343A (ja) * | 1995-07-12 | 1997-01-28 | Toshiba Silicone Co Ltd | アミノ基含有オルガノポリシロキサンの製造方法 |
| DE19738192C1 (de) * | 1997-09-02 | 1998-12-24 | Goldschmidt Ag Th | Trennmittel für Formen zur Herstellung von Formkörpern aus Kunststoffen |
| JP4144926B2 (ja) | 1998-01-16 | 2008-09-03 | ダウ・コ−ニング・コ−ポレ−ション | 特定のγ−アミノプロピルシリル基を有する有機ケイ素化合物の製造方法 |
| US5892084A (en) | 1998-02-03 | 1999-04-06 | Pcr, Inc. | Aminoorganofunctionalsiloxanes |
| DE19849308A1 (de) * | 1998-10-27 | 2000-05-04 | Degussa | Aminopropyl-funktionelle Siloxan-Oligomere |
| US6353073B1 (en) * | 2000-03-22 | 2002-03-05 | Archimica (Florida), Inc. | Poly (aminoorganofunctionaldisiloxanes) |
-
2000
- 2000-03-22 US US09/532,714 patent/US6339137B1/en not_active Expired - Lifetime
-
2001
- 2001-03-20 DE DE60104586T patent/DE60104586T2/de not_active Expired - Lifetime
- 2001-03-20 AT AT01810280T patent/ATE272668T1/de not_active IP Right Cessation
- 2001-03-20 EP EP01810280A patent/EP1136514B1/en not_active Expired - Lifetime
- 2001-03-20 CA CA002341783A patent/CA2341783A1/en not_active Abandoned
- 2001-03-21 JP JP2001080655A patent/JP2001335585A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1136514B1 (en) | 2004-08-04 |
| DE60104586T2 (de) | 2005-08-11 |
| DE60104586D1 (de) | 2004-09-09 |
| EP1136514A2 (en) | 2001-09-26 |
| ATE272668T1 (de) | 2004-08-15 |
| JP2001335585A (ja) | 2001-12-04 |
| EP1136514A3 (en) | 2002-03-20 |
| US6339137B1 (en) | 2002-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |