DE3706521A1 - Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellung - Google Patents
Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellungInfo
- Publication number
- DE3706521A1 DE3706521A1 DE19873706521 DE3706521A DE3706521A1 DE 3706521 A1 DE3706521 A1 DE 3706521A1 DE 19873706521 DE19873706521 DE 19873706521 DE 3706521 A DE3706521 A DE 3706521A DE 3706521 A1 DE3706521 A1 DE 3706521A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- benzoylthiourea
- organosilanes
- isothiocyanate
- 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
- 238000000034 method Methods 0.000 title claims abstract description 13
- 150000001282 organosilanes Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical group NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 6
- -1 benzoylthiourea groups Organosilanes Chemical class 0.000 description 4
- 229920000592 inorganic polymer Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873706521 DE3706521A1 (de) | 1987-02-28 | 1987-02-28 | Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellung |
| US07/154,408 US4855470A (en) | 1987-02-28 | 1988-02-10 | Organosilanes containing benzoyl thiourea groups and method of preparation |
| DE8888102050T DE3876263D1 (de) | 1987-02-28 | 1988-02-12 | Benzoylthioharnstoffgruppenhaltige organosilane, verfahren zu ihrer herstellung. |
| EP88102050A EP0280946B1 (de) | 1987-02-28 | 1988-02-12 | Benzoylthioharnstoffgruppenhaltige Organosilane, Verfahren zu ihrer Herstellung |
| AT88102050T ATE82979T1 (de) | 1987-02-28 | 1988-02-12 | Benzoylthioharnstoffgruppenhaltige organosilane, verfahren zu ihrer herstellung. |
| JP63044674A JPS63238090A (ja) | 1987-02-28 | 1988-02-29 | ベイゾイルチオ尿素基含有オルガノシラン、およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873706521 DE3706521A1 (de) | 1987-02-28 | 1987-02-28 | Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3706521A1 true DE3706521A1 (de) | 1988-09-08 |
| DE3706521C2 DE3706521C2 (enExample) | 1988-12-08 |
Family
ID=6322007
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873706521 Granted DE3706521A1 (de) | 1987-02-28 | 1987-02-28 | Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellung |
| DE8888102050T Expired - Fee Related DE3876263D1 (de) | 1987-02-28 | 1988-02-12 | Benzoylthioharnstoffgruppenhaltige organosilane, verfahren zu ihrer herstellung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8888102050T Expired - Fee Related DE3876263D1 (de) | 1987-02-28 | 1988-02-12 | Benzoylthioharnstoffgruppenhaltige organosilane, verfahren zu ihrer herstellung. |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4855470A (enExample) |
| EP (1) | EP0280946B1 (enExample) |
| JP (1) | JPS63238090A (enExample) |
| AT (1) | ATE82979T1 (enExample) |
| DE (2) | DE3706521A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3800564C1 (enExample) * | 1988-01-12 | 1989-03-16 | Degussa Ag, 6000 Frankfurt, De | |
| DE3821465A1 (de) * | 1988-06-25 | 1989-12-28 | Degussa | Verfahren zur herstellung ein- oder mehrfach substituierter organyloxysilylfunktioneller thioharnstoffe und diese verbindungen |
| DE3821464A1 (de) * | 1988-06-25 | 1989-12-28 | Degussa | Verfahren zur herstellung substituierter organyloxysilylfunktioneller, cyclischer thioharnstoffe und diese verbindungen |
| DE3837418A1 (de) * | 1988-11-04 | 1990-05-10 | Degussa | Organosiloxanamin-copolykondensate, verfahren zu ihrer herstellung und verwendung (i) |
| DE3837415A1 (de) * | 1988-11-04 | 1990-05-10 | Degussa | Organopolysiloxan-harnstoff- und organopolysiloxan-thioharnstoff-derivate, verfahren zu ihrer herstellung und verwendung |
| DE3925356A1 (de) * | 1989-07-31 | 1991-02-07 | Degussa | N,n'-disubstituierte und n,n,n'-/n,n',n'-trisubstituierte thioharnstoffe und verfahren zur herstellung (ii) |
| DE3925358A1 (de) * | 1989-07-31 | 1991-02-07 | Degussa | Aminoalkylsubstituierte organopolysiloxan-thioharnstoff-derivate, verfahren zu ihrer herstellung und verwendung |
| JPH04257593A (ja) * | 1991-02-08 | 1992-09-11 | Shin Etsu Chem Co Ltd | 有機けい素化合物 |
| DE4142129C1 (enExample) * | 1991-12-20 | 1993-07-01 | Degussa Ag, 6000 Frankfurt, De | |
| DE4223539C1 (de) * | 1992-07-17 | 1993-11-25 | Degussa | Geformte Sulfonatgruppen-haltige Organopolysiloxane, Verfahren zu ihrer Herstellung und Verwendung |
| DE4409140A1 (de) * | 1994-03-17 | 1995-09-21 | Degussa | Wäßrige Lösungen von Organopolysiloxan-Ammoniumverbindungen, ihre Herstellung und Verwendung |
| DE19807864C1 (de) * | 1998-02-25 | 1999-05-06 | Seidel Wolfahrt Prof Dr | Verfahren zur permeativen Trennung von Palladium und Platin durch Membranfiltration |
| US6005129A (en) * | 1999-02-09 | 1999-12-21 | Degussa Corporation | Process for producing thiocyanatopropyltriethoxysilane |
| US7074491B2 (en) * | 2003-11-04 | 2006-07-11 | Dionex Corporation | Polar silanes for binding to substrates and use of the bound substrates |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3208971A (en) * | 1962-06-04 | 1965-09-28 | Dow Corning | Bis-silyl ureas and copolymers thereof |
| US3642855A (en) * | 1969-01-03 | 1972-02-15 | Gen Electric | Silyl-containing dithiocarbamates with functional groups on sulfuralkyl ester side chain |
| SU379580A1 (ru) * | 1971-07-12 | 1973-04-20 | Способ получения кремнийорганических производных тиомочевины, содержащих этокси- группы у атома кремния | |
| US4234573A (en) * | 1978-06-15 | 1980-11-18 | Ciba-Geigy Corporation | 1-Trimethylsilylphenyl-3-mono- and -di-halobenzoyl-ureas, insecticidal compositions containing them and their use in controlling insect pests |
| DD212190A1 (de) * | 1982-12-09 | 1984-08-08 | Bitterfeld Chemie | Verfahren zur quecksilbergewinnung aus waessrigen loesungen |
| DE3314435A1 (de) * | 1983-04-21 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,1-disubstituierten thioharnstoffen |
-
1987
- 1987-02-28 DE DE19873706521 patent/DE3706521A1/de active Granted
-
1988
- 1988-02-10 US US07/154,408 patent/US4855470A/en not_active Expired - Fee Related
- 1988-02-12 DE DE8888102050T patent/DE3876263D1/de not_active Expired - Fee Related
- 1988-02-12 EP EP88102050A patent/EP0280946B1/de not_active Expired - Lifetime
- 1988-02-12 AT AT88102050T patent/ATE82979T1/de active
- 1988-02-29 JP JP63044674A patent/JPS63238090A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE82979T1 (de) | 1992-12-15 |
| EP0280946A2 (de) | 1988-09-07 |
| US4855470A (en) | 1989-08-08 |
| DE3876263D1 (de) | 1993-01-14 |
| JPS63238090A (ja) | 1988-10-04 |
| EP0280946B1 (de) | 1992-12-02 |
| EP0280946A3 (en) | 1990-05-09 |
| DE3706521C2 (enExample) | 1988-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |