EP1474465A1 - Siloxanes a fonction aminomethylene - Google Patents
Siloxanes a fonction aminomethyleneInfo
- Publication number
- EP1474465A1 EP1474465A1 EP03739443A EP03739443A EP1474465A1 EP 1474465 A1 EP1474465 A1 EP 1474465A1 EP 03739443 A EP03739443 A EP 03739443A EP 03739443 A EP03739443 A EP 03739443A EP 1474465 A1 EP1474465 A1 EP 1474465A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- groups
- halogen
- replaced
- general formula
- amino
- 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.)
- Withdrawn
Links
- -1 siloxanes Chemical class 0.000 title claims description 38
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004756 silanes Chemical class 0.000 claims description 3
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 229910018540 Si C Inorganic materials 0.000 claims 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 20
- 239000004205 dimethyl polysiloxane Substances 0.000 description 19
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 14
- CBWLQRUXCZLHIA-UHFFFAOYSA-N [methoxy(dimethyl)silyl]methanamine Chemical compound CO[Si](C)(C)CN CBWLQRUXCZLHIA-UHFFFAOYSA-N 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 229910008051 Si-OH Inorganic materials 0.000 description 3
- 229910006358 Si—OH Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JLXAGVQVPKOSMC-UHFFFAOYSA-N (aminomethyl-methyl-trimethylsilyloxysilyl)methanamine Chemical compound C[Si](C)(C)O[Si](C)(CN)CN JLXAGVQVPKOSMC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 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
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XYPHMSJXRRVDQC-UHFFFAOYSA-N [ethoxy(dimethyl)silyl]methanamine Chemical compound CCO[Si](C)(C)CN XYPHMSJXRRVDQC-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- ZCSLOBFDVTWIBL-UHFFFAOYSA-N chloromethyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCl ZCSLOBFDVTWIBL-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 150000001354 dialkyl silanes Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- YWOSGXSBVHJBEJ-UHFFFAOYSA-N silylmethanamine Chemical group NC[SiH3] YWOSGXSBVHJBEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C08G77/22—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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
Definitions
- the invention relates to aminomethylene-functional siloxanes and a process for their production using alkoxysilanes.
- Aminoalkyl polysiloxanes are useful in many fields of application, including the preparation of polyidene and polyetherimides. However, the commercial use of these compounds on a larger scale is prevented by a relatively expensive manufacturing process.
- DE-A-2500020 describes a process for the preparation of aminomethylsiloxanes.
- OH-terminated siloxanes with secondary aminomethylsilanes with elimination of Alcohol implemented.
- the advantage of this process is a reaction of a siloxane with an alkoxysilane without equilibrating the reaction mixture, which would lead to the formation of cycles as a by-product and is therefore not wanted.
- the disadvantage of this process is that, because of the secondary amino function, the silicone oils thus produced cannot be used for the production of, for example, siloxane-polyimide copolymers, since a primary amino function is essential here.
- the object was therefore to provide such amino-functional siloxanes with which, inter alia, Polysiloxane-polyimide copolymers can also be produced.
- the invention relates to amino-functional organosiloxanes of the general formula I,
- R is a hydrogen atom or a monovalent, optionally with -CN, -NCO, -N X 2 -COOH, -COOR x , -halogen, -acrylic,
- NR X - can be replaced and in which one or more non-adjacent methine units by groups
- R ⁇ hydrogen or an optionally substituted with -CN or halogen C] _- C2o hydrocarbon radical
- s is an integer of at least 1, s + t + u the value 2, t, u the values 0 or 1 and p the value 0 or an integer from 1 to 100,000.
- the amino-functional organosiloxanes of the general formula I have a primary amino function which is bonded to a silicon atom of the siloxane chain by a carbon atom.
- Amino functions are very reactive.
- polysiloxane-polyimide copolymers can therefore be easily produced with the amino-functional siloxanes.
- R can be aliphatic saturated or unsaturated, aromatic, straight chain or branched.
- R is preferably an unbranched C ] _-C3 alkyl radical, which can be substituted.
- R is particularly preferably a methyl radical.
- R ⁇ can be aliphatic saturated or unsaturated, aromatic, straight-chain or branched.
- R ⁇ preferably has 1 to 12 atoms, in particular 1 to 6 atoms, preferably only carbon atoms, or an alkoxy oxygen atom and otherwise only carbon atoms.
- R - * - is preferably a straight-chain or branched C ⁇ -Cg-
- Alkyl The radicals methyl, ethyl, phenyl, vinyl and trifluoropropyl are particularly preferred.
- R2 can, independently of one another, also be aliphatically saturated or unsaturated, aromatic, straight-chain or branched.
- R ⁇ is preferably a C] _- C3 ⁇ alkyl radical or hydrogen.
- R ⁇ is particularly preferably hydrogen.
- amino-functional organosiloxanes of the general formula I are preferably aminoalkyl-terminated
- Polydimethylsiloxanes which carry an aminoalkyl group on at least 90% of the chain ends.
- that carries an aminoalkyl group on at least 90% of the chain ends.
- Aminoalky-terminated polydimethylsiloxane has at least 99% of the chain ends an aminoalkyl group.
- T is preferably 0.
- P is preferably from 4 to 500.
- the invention also relates to a process for the preparation of amino-functional organosiloxane of the general formula I, in which the organosiloxane general formula II
- alkoxysilane of the general formula III (R 3 0) R 1 2 SiCR 2 2NH 2 (III),
- R-3 can also be aliphatic saturated or unsaturated, aromatic, straight chain or branched.
- R ⁇ is preferably a C ⁇ -C3 alkyl radical. -3 ethyl or methyl is particularly preferred. R ⁇ is very particularly preferably a methyl radical.
- alkoxysilanes of the general formula III used can be obtained simply and in high yields by amination of the corresponding chloroalkyl (alkoxy) dialkylsilanes e.g. be produced under pressure in an ammonia atmosphere as described in the patent specification SU 395371.
- alkoxysilanes prepared in this way react simply and very quickly with hydroxy-functional siloxanes of the general formula II.
- the use of special catalysts is not necessary.
- the organosiloxane of the general formula II Contain hydroxy groups.
- the reaction proceeds with elimination of the alcohol R- ⁇ OH.
- the amount of alkoxysilanes of the general formula III used depends on the amount of the silanol groups to be functionalized. However, if the OH groups are to be fully functionalized, the alkoxysilane must be added in at least equimolar amounts.
- the hydrolysis product obtained is a disiloxane of the general formula (IV)
- the process is preferably carried out at 0.degree. C. to 100.degree. C., particularly preferably at least 10.degree. C. to at least 40.degree. C.
- the process can be carried out either with the inclusion of solvents or else without the use of solvents in suitable reactors. If necessary, the process is carried out under vacuum or under superatmospheric pressure or at normal pressure (0.1 MPa). The alcohol formed can then be removed from the reaction mixture under reduced pressure at room temperature or at elevated temperature.
- solvents are inert, especially aprotic solvents such as aliphatic hydrocarbons, such as. B. Heptane or decane and aromatic hydrocarbons such as toluene or xylene preferred. Ethers such as THF, diethyl ether or MTBE can also be used.
- the amount of solvent should be sufficient to ensure adequate homogenization of the reaction mixture. Solvents or solvent mixtures with a boiling point or boiling range of up to 120 ° C. at 0.1 MPa are preferred.
- the alkoxysilane of the general formula III is added to the organosiloxane of the general formula II in deficit, residual unreacted Si-OH groups can remain in the amino-functional organosiloxane of the general formula I or with other compounds which react with Si-OH groups, are implemented so that a further reduction in the Si-OH content can be achieved and, for example unreactive end groups can be introduced into the silicone oil mixture, which can be used to limit the molecular weight in later copolymerizations. Isolation of the intermediate product is not absolutely necessary.
- Chlormethyldimethylmethoxysilan (Starfire Systems, Troy, USA) in an autoclave with 300 g of liquid ammonia at a temperature of 100 ° C to react. After 5 hours was allowed to cool to room temperature, the autoclave was depressurized to normal pressure and 500 ml of dry heptane were added. The precipitated ammonium chloride was filtered off, the heptane was removed by distillation and the product was purified by distillation. 56 g of aminomethyldimethylmethoxysilane were obtained.
- Example 3 100 g of bishydroxy-terminated polydimethylsiloxane with an average molecular weight of 13000 g / mol were mixed at 50 ° C. with
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
La présente invention concerne des organosiloxanes à fonction amino de formule générale [(HO)R2SiO1/2]t[R3SiO1/2]U[R2SiO2/2]p[O1/2SiR12CR22NH2]S (I), dans laquelle: s est un nombre entier valant au moins 1; s + t + u vaut 2, t ou u vaut 0 ou 1; et p vaut 0 ou un nombre entier de 1 à 100000; et R, R1 et R2 ont les correspondances indiquées dans la revendication 1. L'invention a également pour objet un procédé pour préparer ces composés.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10206124 | 2002-02-14 | ||
| DE10206124A DE10206124A1 (de) | 2002-02-14 | 2002-02-14 | Aminomethylenfunktionelle Siloxane |
| PCT/EP2003/000701 WO2003068845A1 (fr) | 2002-02-14 | 2003-01-23 | Siloxanes a fonction aminomethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1474465A1 true EP1474465A1 (fr) | 2004-11-10 |
Family
ID=27674631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03739443A Withdrawn EP1474465A1 (fr) | 2002-02-14 | 2003-01-23 | Siloxanes a fonction aminomethylene |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20050085612A1 (fr) |
| EP (1) | EP1474465A1 (fr) |
| JP (1) | JP2005517749A (fr) |
| CN (1) | CN1633458A (fr) |
| DE (1) | DE10206124A1 (fr) |
| WO (1) | WO2003068845A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10303693A1 (de) * | 2003-01-30 | 2004-08-12 | Consortium für elektrochemische Industrie GmbH | Aminomethylenfunktionelle Siloxane |
| DE10358060A1 (de) * | 2003-12-11 | 2005-07-14 | Wacker-Chemie Gmbh | Verfahren zur Herstellung hochviskoser Organopolysiloxane |
| DE102004014217A1 (de) * | 2004-03-23 | 2005-10-13 | Wacker-Chemie Gmbh | Vernetzbare Massen auf der Basis von Organosiliciumverbindungen |
| DE102007037198A1 (de) * | 2007-08-07 | 2009-02-12 | Wacker Chemie Ag | Vernetzbare Massen auf der Basis von Organosiliciumverbindungen |
| US7781554B2 (en) * | 2008-03-05 | 2010-08-24 | Bausch & Lomb Incorporated | Polysiloxanes and polysiloxane prepolymers with vinyl or epoxy functionality |
| DE102010001071A1 (de) * | 2010-01-21 | 2011-07-28 | Robert Bosch GmbH, 70469 | Tetraaminodisiloxane und damit hergestellte Polyamide |
| DE102014222826A1 (de) | 2014-11-07 | 2016-05-12 | Wacker Chemie Ag | Vernetzbare Organopolysiloxanzusammensetzungen |
| DE102015207673A1 (de) * | 2015-04-27 | 2016-10-27 | Wacker Chemie Ag | Verfahren zur Herstellung von Aminogruppen aufweisenden Organosiliciumverbindungen |
| DE102016201633A1 (de) * | 2016-02-03 | 2017-08-03 | Wacker Chemie Ag | Verfahren zur Herstellung von Aminogruppen aufweisenden Organopolysiloxanen |
| JP7310894B2 (ja) | 2019-08-09 | 2023-07-19 | 信越化学工業株式会社 | 第１級アミノシロキサン化合物の製造方法 |
| CN120025547A (zh) * | 2025-04-23 | 2025-05-23 | 山东东岳有机硅材料股份有限公司 | 侧链氨基硅油及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE902190C (de) * | 1950-06-30 | 1954-01-21 | Dow Corning | Verfahren zur Herstellung neuer Aminomethylsiloxane |
| US2942019A (en) * | 1956-10-12 | 1960-06-21 | Union Carbide Corp | Organosilicon methylideneamino compounds and process for producing the same |
| DE1196869B (de) * | 1960-05-14 | 1965-07-15 | Bayer Ag | Verfahren zur Herstellung von Aminomethyl-gruppen tragenden Polymethylsiloxanen |
| US3544498A (en) * | 1968-07-17 | 1970-12-01 | Gen Electric | Detergent resistant silicone polish |
| BE756928A (fr) * | 1969-10-01 | 1971-03-16 | Bayer Ag | Polysiloxanes aminomethyl-substitues comme agents d'enduction hydrofuges et de brillantage |
| DE2500020A1 (de) * | 1975-01-02 | 1976-07-15 | Bayer Ag | Verfahren zur herstellung von organopolysiloxanen mit sich tief 2-nhr- endgruppen |
| US4496705A (en) * | 1984-01-04 | 1985-01-29 | General Electric Company | Synthesis of zwitterionic siloxane polymers |
| US5512650A (en) * | 1986-06-20 | 1996-04-30 | Minnesota Mining And Manufacturing Company | Block copolymer, method of making the same, diamine precursors of the same, method of making such diamines and end products comprising the block copolymer |
| GB9311509D0 (en) * | 1993-06-03 | 1993-07-21 | Dow Corning | Process for the preparation of organopolysiloxanes |
-
2002
- 2002-02-14 DE DE10206124A patent/DE10206124A1/de not_active Withdrawn
-
2003
- 2003-01-23 WO PCT/EP2003/000701 patent/WO2003068845A1/fr not_active Ceased
- 2003-01-23 CN CNA03803848XA patent/CN1633458A/zh active Pending
- 2003-01-23 US US10/504,351 patent/US20050085612A1/en not_active Abandoned
- 2003-01-23 EP EP03739443A patent/EP1474465A1/fr not_active Withdrawn
- 2003-01-23 JP JP2003567967A patent/JP2005517749A/ja not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO03068845A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005517749A (ja) | 2005-06-16 |
| CN1633458A (zh) | 2005-06-29 |
| DE10206124A1 (de) | 2003-09-04 |
| US20050085612A1 (en) | 2005-04-21 |
| WO2003068845A1 (fr) | 2003-08-21 |
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