DE3521201A1 - Organosilicon compounds - Google Patents
Organosilicon compoundsInfo
- Publication number
- DE3521201A1 DE3521201A1 DE19853521201 DE3521201A DE3521201A1 DE 3521201 A1 DE3521201 A1 DE 3521201A1 DE 19853521201 DE19853521201 DE 19853521201 DE 3521201 A DE3521201 A DE 3521201A DE 3521201 A1 DE3521201 A1 DE 3521201A1
- Authority
- DE
- Germany
- Prior art keywords
- propane
- trans
- oxy
- biphenylyl
- formula
- 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- Withdrawn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
- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000003989 dielectric material Substances 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- FDAYLTPAFBGXAB-UHFFFAOYSA-N 2-chloro-n,n-bis(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)CCCl FDAYLTPAFBGXAB-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003377 silicon compounds Chemical class 0.000 claims description 3
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001321 HNCO Methods 0.000 claims description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000001294 propane Substances 0.000 description 208
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 165
- -1 aliphatic amines Chemical class 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004381 surface treatment Methods 0.000 description 6
- 239000001273 butane Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical class Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000005052 trichlorosilane Substances 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IDIOJRGTRFRIJL-UHFFFAOYSA-N iodosilane Chemical compound I[SiH3] IDIOJRGTRFRIJL-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- QQFSIGWYINAJOB-UHFFFAOYSA-N 1,4-dicyclohexylbenzene Chemical class C1CCCCC1C1=CC=C(C2CCCCC2)C=C1 QQFSIGWYINAJOB-UHFFFAOYSA-N 0.000 description 1
- RAYZALBEMJMGEA-UHFFFAOYSA-N 1-cyclohexylnaphthalene Chemical class C1CCCCC1C1=CC=CC2=CC=CC=C12 RAYZALBEMJMGEA-UHFFFAOYSA-N 0.000 description 1
- FSLXCIJOWQAYPN-UHFFFAOYSA-N 1-phenyl-4-prop-2-enoxybenzene Chemical compound C1=CC(OCC=C)=CC=C1C1=CC=CC=C1 FSLXCIJOWQAYPN-UHFFFAOYSA-N 0.000 description 1
- SMHSPYVJAUGNOI-UHFFFAOYSA-N 2-cyclohexyl-1,4-dioxane Chemical class C1CCCCC1C1OCCOC1 SMHSPYVJAUGNOI-UHFFFAOYSA-N 0.000 description 1
- IBLVSWYGUFGDMF-UHFFFAOYSA-N 2-cyclohexylethylcyclohexane Chemical compound C1CCCCC1CCC1CCCCC1 IBLVSWYGUFGDMF-UHFFFAOYSA-N 0.000 description 1
- YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical class C1CCCCC1C1=NC=CC=N1 YJDDXMSIMBMMGY-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- OWMOJMPOZVDZCU-UHFFFAOYSA-N 3-cyclohexyldithiane Chemical compound C1CCCCC1C1SSCCC1 OWMOJMPOZVDZCU-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OOTGNTGVBBCNQK-UBBSCCEASA-N Br[Si](CCCO[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCCCC)(Br)Br Chemical compound Br[Si](CCCO[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCCCC)(Br)Br OOTGNTGVBBCNQK-UBBSCCEASA-N 0.000 description 1
- ZUVNHBBXJGCLMP-UBBSCCEASA-N Cl[SiH](CCCO[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCCCC)Cl Chemical compound Cl[SiH](CCCO[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCCCC)Cl ZUVNHBBXJGCLMP-UBBSCCEASA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BPXMVRKHDAMJJS-UAPYVXQJSA-N N(=C=S)[Si](CCCO[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)OC)(N=C=S)N=C=S Chemical compound N(=C=S)[Si](CCCO[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)OC)(N=C=S)N=C=S BPXMVRKHDAMJJS-UAPYVXQJSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001482 benzyl phenyl ethers Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical group N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GIMWPNOMOXCTFS-UHFFFAOYSA-N dichloro-(5-cyclohexyl-1-propoxycyclohexa-2,4-dien-1-yl)silane Chemical compound Cl[SiH](C1(OCCC)CC(=CC=C1)C1CCCCC1)Cl GIMWPNOMOXCTFS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RBBNOVKRLWDEGC-UHFFFAOYSA-M dodecyl-ethyl-dimethylazanium;4-hexoxybenzoate Chemical compound CCCCCCOC1=CC=C(C([O-])=O)C=C1.CCCCCCCCCCCC[N+](C)(C)CC RBBNOVKRLWDEGC-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- UXKUODQYLDZXDL-UHFFFAOYSA-N fulminic acid Chemical compound [O-][N+]#C UXKUODQYLDZXDL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- QPWCRCMCFOJWQH-UHFFFAOYSA-N tribromo-(5-cyclohexyl-1-propoxycyclohexa-2,4-dien-1-yl)silane Chemical compound C1=CC(OCCC)([Si](Br)(Br)Br)CC(C2CCCCC2)=C1 QPWCRCMCFOJWQH-UHFFFAOYSA-N 0.000 description 1
- YTAFEGCCVSBESG-UHFFFAOYSA-N trichloro-[3-(4-phenylphenoxy)propyl]silane Chemical compound C1=CC(OCCC[Si](Cl)(Cl)Cl)=CC=C1C1=CC=CC=C1 YTAFEGCCVSBESG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- 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
- C07F7/12—Organo silicon halides
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133719—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films with coupling agent molecules, e.g. silane
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Abstract
Description
OrganosiliciumverbindungenOrganosilicon compounds
Organosiliciumverbindungen Die Erfindung betrifft neue Organosiliciumverbindungen der Formel I, R1-A1-A2 -O-C H 2nSX Y Z n a b c worin R1 H, eine Alkylgruppe mit 1 - 10 C-Atomen, worin auch eine oder zwei nicht benachbarte CH2-Gruppen durch O-Atome ersetzt sein können, F, Cl, Br oder CN, A1 und A2 jeweils 1,4-Phenylen- oder 1,4-Cyclohexylengruppen, eine der Gruppen A1 und A auch eine Einfachbindung, X, Y jeweils H, F, Cl, Br, I, CN, NC, OCN, NCO, SCN, und Z oder N3, a, b 0, 1, 2 oder 3 und und c n 2, 3, 4, 5 oder 6 bedeuten, mit der Maßgabe, daß a + b + c = 3 und mindestens einer der Substituenten von H verschieden ist. Organosilicon Compounds The invention relates to novel organosilicon compounds of the formula I, R1-A1-A2 -O-C H 2nSX Y Z n a b c wherein R1 is H, an alkyl group with 1 - 10 C atoms, in which one or two non-adjacent CH2 groups are replaced by O atoms can be replaced, F, Cl, Br or CN, A1 and A2 each 1,4-phenylene or 1,4-cyclohexylene groups, one of the groups A1 and A also has a single bond, X, Y each H, F, Cl, Br, I, CN, NC, OCN, NCO, SCN, and Z or N3, a, b 0, 1, 2 or 3 and and c n 2, 3, 4, 5 or 6, with the proviso that a + b + c = 3 and at least one of the substituents is different from H.
Die Verbindungen der Formel I eignen sich in ausgezeichneter Weise zur homöotropen Ausrichtung flüssigkristalliner Phasen auf Oberflächen, z.B. Glasplatten, die auch beschichtet sein können, wie sie bei der Herstellung elektrooptischer Anzeigeelemente verwendet werden. Derart orientierte flüssigkristalline Phasen können aufgrund ihrer negativen dielektrischen Anisotropie von einem äußeren elektrischen Feld in ihrer Ausrichtung beeinflußt werden. Sie eignen sich zu einer Verwendung in Anzeigen, die nach dem Prinzip der Deformation aufgerichteter Phasen (Appl.Phys.Lett. 19, 391 (1971)), dem Prinzip der dynamischen Streuung (Proc.IEEE 56, 1162 (1968)) oder nach dem Guest-Host-Prinzip (Mol.Cryst.Liq.Cryst.The compounds of the formula I are extremely suitable for homeotropic alignment of liquid crystalline phases on surfaces, e.g. glass plates, which can also be coated, as is the case in the manufacture of electro-optical display elements be used. Such oriented liquid-crystalline phases can due to their negative dielectric anisotropy from an external electric field in their Alignment can be affected. They are suitable for use in advertisements, which according to the principle of deformation of erect phases (Appl.Phys.Lett. 19, 391 (1971)), the principle of dynamic scattering (Proc.IEEE 56, 1162 (1968)) or according to the guest-host principle (Mol.Cryst.Liq.Cryst.
63, 19 (1981)) betrieben werden.63, 19 (1981)).
Die Erzeugung einer gleichförmigen und stabilen homöotropen Orientierung flüssigkristalliner Phasen war bisher technologisch recht schwierig. So wurde die verwendete flüssigkristalline Phase mit oberflächenaktiven Stoffen wie Lecithinen, langkettigen aliphatischen Aminen, quartären Ammonium- oder Phosphoniumsalzen oder Carboxylatochrom-Komplexen (Appl.Phys.Lett 27, 268 (1975) dotiert. Üblich war auch eine Beschichtung von Glasoberflächen mit den genannten Stoffen vor der Einfüllung der flüssigkristallinen Phase. Gleichmäßigkeit und Stabilität der so erzeugten homöotropen Orientierung der flüssigkristallinen Phasen lassen jedoch zu wünschen übrig.The creation of a uniform and stable homeotropic orientation Liquid-crystalline phases have hitherto been very difficult technologically. So it became liquid crystalline phase used with surface-active substances such as lecithins, long-chain aliphatic amines, quaternary ammonium or phosphonium salts or Carboxylatochrome complexes (Appl.Phys.Lett 27, 268 (1975). It was also common a coating of glass surfaces with the substances mentioned before filling the liquid crystalline phase. Uniformity and stability of the homeotropic However, the orientation of the liquid-crystalline phases leaves something to be desired.
Aus der deutschen Patentanmeldung P 33 31 515 sind Trisalkanoyloxysilane zur Erzeugung einer hömootropen Orientierung flüssigkristalliner Phasen auf Oberflächen bekannt. Diese Verbindungen besitzen jedoch eine Reihe von Nachteilen. So bilden sich bei ihrer Darstellung aus Säureanhydriden und Trichlorsilanen oft dunkelbraune Nebenprodukte, die sich von dem gewünschten Trisalkanoyloxysilan nicht abtrennen lassen. Derart verunreinigte Produkte sind zur Oberflächenbehandlung nicht mehr geeignet, da sie die optische Durchlässigkeit des Trägermaterials herabsetzen. Des weiteren führt die Hydrolyse der Trisalkanoyloxyverbindungen auf der Trägeroberfläche nach dem in der P 33 31 515 angegebenen Verfahren häufig nur zu niedermolekularen Hydrolyseprodukten, die mit dem angewandten Wasserdampf flüchtig sind und somit zur Modifikation der behandelten Qberfläche nicht beitragen, was eine unvollständige oder nur teilweise Oberflächenorientierung aufgebrachter flüssigkristalliner Phasen zur Folge hat.From the German patent application P 33 31 515 are trisalkanoyloxysilanes for generating a homootropic orientation of liquid-crystalline phases on surfaces known. However, these compounds have a number of disadvantages. So form When they are made from acid anhydrides and trichlorosilanes, they often turn dark brown By-products that do not separate from the desired trisalkanoyloxysilane permit. Such contaminated products are no longer suitable for surface treatment suitable because they reduce the optical transmittance of the carrier material. Of the hydrolysis of the trisalkanoyloxy compounds on the carrier surface also leads to it according to the method specified in P 33 31 515 often only to low molecular weight Hydrolysis products that are volatile with the applied water vapor and thus do not contribute to the modification of the treated surface, which is incomplete or only partial surface orientation of applied liquid-crystalline phases has the consequence.
Der Erfindung lag daher die Aufgabe zugrunde, eine bessere, insbesondere gleichmäßigere und stabilere homöotrope Orientierung flüssigkristalliner Phasen auf Oberflächen zu ermöglichen. Diese Aufgabe wurde durch die Bereitstellung der Verbindungen der Formel I gelöst.The invention was therefore based on the object of a better, in particular more uniform and more stable homeotropic orientation of liquid-crystalline phases to enable on surfaces. This task was accomplished by providing the Compounds of formula I dissolved.
Gegenstand der Erfindung sind somit die Verbindungen der Formel I sowie ein Verfahren zu ihrer Herstellung, dadurch gekennzeichnet, daß man eine ungesättigte Verbindung der Formel II, R¹-A¹-A²-O-CnH2n-1 II mit einem Silan H-SiXaYbzc, worin R1, A1, A2, X, Y, Z, a, b, c und n die in Anspruch 1 angegebene Bedeutung haben, umsetzt, oder daß man ein Halogenid der Formel IV, R 112 IV R -A -A -O-CnH2n-Hal IV mit einem Silan H-SiXaYbZC, worin R1, A1, A2, X, Y, Z, a, b, c und n die in Anspruch 1 angegebene Bedeutung haben und Hal C1, Br oder I bedeutet, umsetzt, oder daß man eine Siliciumverbindung der Formel I nach Anspruch 1, in der mindestens einer der Substituenten X, Y und Z H, C1, Br oder I bedeutet, mit einem Alkali-, Erdalkali-oder Silbersalz der Anionen CN-, NC , OCN-, NCO , SCN NCS oder N3, oder mit deren zugehörigen Säuren HCN, HOCN, HNCO, HSCN, HNCS oder HN3 oder zur Herstellung von Isocyanaten mit Harnstoff oder von Isothiocyanaten mit Thioharnstoff umsetzt.The invention thus relates to the compounds of the formula I and a process for their preparation, characterized in that one unsaturated Compound of formula II, R¹-A¹-A²-O-CnH2n-1 II with a silane H-SiXaYbzc, wherein R1, A1, A2, X, Y, Z, a, b, c and n have the meaning given in claim 1, implements, or that a halide of the formula IV, R 112 IV R -A -A -O-CnH2n-Hal IV with a silane H-SiXaYbZC, where R1, A1, A2, X, Y, Z, a, b, c and n have the meaning given in claim 1 and Hal is C1, Br or I, converts, or that a silicon compound of the formula I according to Claim 1, in which at least one of the substituents X, Y and Z is H, C1, Br or I, with one Alkali, alkaline earth or silver salt of the anions CN-, NC, OCN-, NCO, SCN or NCS N3, or with their associated acids HCN, HOCN, HNCO, HSCN, HNCS or HN3 or for the production of isocyanates with urea or of isothiocyanates with thiourea implements.
Weiterhin sind Gegenstand der Erfindung die Verwendung der Verbindungen der Formel I als Komponenten flüssigkristalliner Dielektrika für elektrooptische Anzeigeelemente sowie ihre Verwendung zur Erzeugung einer homöotropen Orientierung flüssigkristalliner Phasen auf Oberflächen. Gegenstand der Erfindung sind ferner flüssigkristalline Dielektrika mit einem Gehalt an mindestens einer Verbindung der Formel I sowie elektrooptische Anzeigeelemente, die derartige Dielektrika enthalten und/ oder die Oberflächen enthalten, welche mit einer Verbindung der Formel I behandelt worden sind.The invention also relates to the use of the compounds of the formula I as components of liquid-crystalline dielectrics for electro-optical Display elements and their use to generate a homeotropic orientation liquid crystalline phases on surfaces. The invention also provides liquid-crystalline dielectrics containing at least one compound of the Formula I and electro-optical display elements that contain such dielectrics and / or the surfaces which have been treated with a compound of the formula I. have been.
Vor- und nachstehend haben R1, R2, A1, A2 und n die angegebene Bedeutung, sofern nicht ausdrücklich etwas anderes vermerkt ist.Above and below, R1, R2, A1, A2 and n have the meaning given, unless expressly stated otherwise.
Nach der Definition der Gruppen A¹ und A2 umfassen die Verbindungen der Formel I solche der Teilformeln Ia bis Id: Rl~phe-Phe-O-CnH2n~SiXaYbZC Ia R¹-Cy-Phe-O-CnH2nSiXaYbZc Ib R¹-Phe-Cy-O-CnH2n-SiXaYbZc Ic R¹-Cy-Cy-O-CnH2n-SiXaYbZc Id.According to the definition of groups A1 and A2, the compounds include of the formula I those of the sub-formulas Ia to Id: Rl ~ phe-Phe-O-CnH2n ~ SiXaYbZC Ia R¹-Cy-Phe-O-CnH2nSiXaYbZc Ib R¹-Phe-Cy-O-CnH2n-SiXaYbZc Ic R¹-Cy-Cy-O-CnH2n-SiXaYbZc Id.
In diesen Formeln bedeuten Phe 1,4-Phenylen und Cy 1,4-Cyclohexylen. Verbindungen der Formeln Ia und Ib sind bevorzugt.In these formulas, Phe is 1,4-phenylene and Cy is 1,4-cyclohexylene. Compounds of the formulas Ia and Ib are preferred.
In den Verbindungen der vor- und nachstehenden Formeln bedeuten R1 vorzugsweise Alkyl, ferner Alkoxy (insbesondere wenn dieser Rest an einer Phe-Gruppe steht) oder eine andere Oxaalkylgruppe.In the compounds of the formulas above and below, R1 is preferably alkyl, furthermore alkoxy (especially if this radical is on a Phe group stands) or another oxaalkyl group.
In den Verbindungen der vor- und nachstehenden Formeln sind X, Y und Z vorzugsweise gleich (a = b = c = 1) und bedeuten vorzugsweise Halogen, insbesondere Chlor.In the compounds of the formulas above and below, X, Y and Z is preferably the same (a = b = c = 1) and is preferably halogen, in particular Chlorine.
Der Parameter n hat vorzugsweise den Wert 3. Der Rest CnH2n ist vorzugsweise geradkettig und steht dementsprechend insbesondere für -(CH2)3-, ferner insbesondere für -(CH2)2-, -(CH2)4-, -(CH2)5- oder -(CH2)6-.The parameter n preferably has the value 3. The remainder CnH2n is preferably straight-chain and accordingly stands in particular for - (CH2) 3 -, furthermore in particular for - (CH2) 2-, - (CH2) 4-, - (CH2) 5- or - (CH2) 6-.
In den Verbindungen der vor- und nachstehenden Formeln können die Alkylreste geradkettig oder verzweigt sein.In the compounds of the formulas above and below, the Alkyl radicals can be straight-chain or branched.
Vorzugsweise sind sie geradkettig, haben 1, 2, 3, 4, 5, 6 oder 7 C-Atome und bedeuten demnach bevorzugt Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl oder Heptyl. R1 kann auch eine Alkylgruppe bedeuten, worin eine ("Alkoxy" bzw. "Oxaalkyl") oder 2 ("AlkoxyalkoxyZ' bzw. "Dioxaalkyl") nicht benachbarte CH2-Gruppen durch O-Atome ersetzt sein können, bevorzugt Methoxy, Ethoxy, Propoxy, Butoxy, Pentoxy, Hexoxy, Heptoxy, 2-Oxapropyl (= Methoxymethyl), 2- (= Ethoxymethyl) oder 3-Oxabutyl (= 3-Methoxyethyl), 2-, 3-, 4-, 5- oder 6-Oxaheptyl.They are preferably straight-chain and have 1, 2, 3, 4, 5, 6 or 7 carbon atoms and are accordingly preferably methyl, ethyl, propyl, butyl, pentyl, hexyl or Heptyl. R1 can also mean an alkyl group in which a ("alkoxy" or "oxaalkyl") or 2 ("alkoxyalkoxyZ 'or" dioxaalkyl ") non-adjacent CH2 groups can be replaced by O atoms, preferably methoxy, ethoxy, propoxy, butoxy, pentoxy, Hexoxy, heptoxy, 2-oxapropyl (= methoxymethyl), 2- (= ethoxymethyl) or 3-oxabutyl (= 3-methoxyethyl), 2-, 3-, 4-, 5- or 6-oxaheptyl.
R1 kann ferner beispielsweise bedeuten Octyl, Nonyl, Decyl, Octoxy, Nonoxy, Decoxy, 2-, 3-, 4-, 5-, 6- oder 7-Oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- oder 8-Oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- oder 9-Oxadecyl, 1,3-Dioxabutyl (= Methoxymethoxy), 1,3-, 1,4- oder 2,4-Dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,5 oder 3,5-Dioxahexyl, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- oder 4,6 Dioxaheptyl. Bevorzugte Bedeutungen des Restes R1 sind ferner F, C1, Br oder CN.R1 can also mean, for example, octyl, nonyl, decyl, octoxy, Nonoxy, decoxy, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl, 1,3-dioxabutyl (= methoxymethoxy), 1,3-, 1,4- or 2,4-dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,5 or 3,5-dioxahexyl, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- or 4,6- dioxaheptyl. Preferred Meanings of the radical R1 are also F, C1, Br or CN.
Verbindungen der Formeln I sowie Ia bis Id mit verzweigtem Rest R1 können gelegentlich wegen einer besseren Löslichkeit in den üblichen flüssigkristallinen Basismaterialien von Bedeutung sein, ferner auch als Dotierstoffe, wenn sie optisch aktiv sind. Verzweigte Gruppen dieser Art enthalten in der Regel nicht mehr als eine Kettenverzweigung. Bevorzugte verzweigte Reste R1 sind Isopropyl, 2-Butyl (= 1 Methylpropyl), Isobutyl (= 2-Methylpropyl), 2-Methylbutyl, Isopentyl (= 3-Methylbutyl); R1 kann ferner bedeuten 2-Methylpentyl, 3-Methylpentyl, 2-Ethylhexyl, 2-Propylpentyl, Isopropoxy, 2-Methylpropoxy, 2-Methylbutoxy, 3-Methylbutoxy, 2-Methylpentoxy, 3-Methylpentoxy, l-Methylhexoxy, l-Methylheptoxy, 2-Ethylhexoxy, 2-Oxa-3-methylbutyl, 3-Oxa-4-methylpentyl.Compounds of the formulas I and Ia to Id with a branched radical R1 can occasionally because of a better solubility in the usual liquid crystalline Base materials are important, furthermore as dopants, if they are optical are active. Branched groups of this type usually contain no more than a chain branch. Preferred branched radicals R1 are isopropyl, 2-butyl (= 1 methylpropyl), isobutyl (= 2-methylpropyl), 2-methylbutyl, isopentyl (= 3-methylbutyl); R1 can also mean 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, Isopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 1-methylhexoxy, 1-methylheptoxy, 2-ethylhexoxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl.
Falls die Gruppen A und/oder A2 in 1- und 4-Stellung disubstituierte Cyclohexylengruppen bedeuten, so können die Substituenten in cis- oder trans-Stellung stehen. Die Verbindungen mit trans-Konfiguration sind bevorzugt.If the groups A and / or A2 are disubstituted in the 1- and 4-positions Cyclohexylene groups mean, the substituents can be in the cis or trans position stand. The compounds with the trans configuration are preferred.
Verbindungen der Formel I mit optisch-aktiven C-Atomen umschließen sowohl die Racemate als auch die entsprechenden optisch-aktiven Enantiomeren sowie deren Gemische.Enclose compounds of the formula I with optically active carbon atoms both the racemates and the corresponding optically active enantiomers as well their mixtures.
Die Verbindungen der Formel I können nach an sich bekannten Methoden hergestellt werden, wie sie in der Literatur (z.B. in den Standard-Werken wie Houben-Weyl, Methoden der Organischen Chemie, Bd. XIII, 5, Georg-Thieme-Verlag, Stuttgart) beschrieben sind, und zwar unter Reaktionsbedingungen, die für die genannten Umsetzungen bekannt und geeignet sind. Dabei kann man auch von an sich bekannten, hier nicht näher erwähnten Varianten Gebrauch machen.The compounds of the formula I can be prepared according to methods known per se as they are in the literature (e.g. in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Vol. XIII, 5, Georg-Thieme-Verlag, Stuttgart) are, under the reaction conditions known for the reactions mentioned and are suitable. One can also use something known per se, but not mentioned here in more detail Make use of variants.
Sie können beispielsweise hergestellt werden, indem man einen ungesättigten Ether der Formel II, Rl-Al-A2-o-CnH2n-l II mit einem Silan H-SiXaYbZC, worin R1, A1, A2, X, Y, Z, a, b, c und n die in Anspruch 1 angegebene Bedeutung haben, umsetzt.For example, they can be made by making an unsaturated one Ether of the formula II, Rl-Al-A2-o-CnH2n-l II with a silane H-SiXaYbZC, in which R1, A1, A2, X, Y, Z, a, b, c and n have the meaning given in claim 1.
Die Silane der Formel H-SiXaXbZc sind bekannt, oder können nach bekannten Methoden wie sie beispielsweise in der voranstehenden Literatur beschrieben sind, hergestellt werden.The silanes of the formula H-SiXaXbZc are known or can be prepared according to known Methods as described, for example, in the literature above, getting produced.
Die Ether der Formel II können ihrerseits durch Alkenylierung von Hydroxyverbindungen der Formel R1-A1-A2 -OH III mit einem entsprechenden Alkenylhalogenid der Formeln CnH2n~lCl oder CnH2n1Br oder einem Alkenylsulfonat der Formel Alkyl-S02-C 2n-1 oder Aryl-SO2-CnH2n-1 hergestellt werden.The ethers of the formula II can in turn by alkenylation of Hydroxy compounds of the formula R1-A1-A2 -OH III with a corresponding alkenyl halide of the formulas CnH2n ~ lCl or CnH2n1Br or an alkenyl sulfonate of the formula alkyl-SO2-C 2n-1 or aryl-SO2-CnH2n-1 can be produced.
Die Addition der Silane H-SiXaYbZc an die ungesättigten Ether der Formel II gelingt zweckmäßig in Gegenwart eines inerten Lösungsmittels, z.B. eines halogenierten Kohlenwasserstoffs wie Dichlormethan bei Temperaturen zwischen etwa 0 und etwa 1000, zweckmäßig bei Siedetemperatur. Das Silan wird vorteilhaft im Überschuß eingesetzt. Der Zusatz eines Edelmetallkatalysators, beispielsweise einer Lösung von H2PtC16 in Isopropanol, ist dabei vorteilhaft. Auch durch Zusatz von Peroxiden wie Diacetylperoxid und/oder Bestrahlung mit Licht läßt sich die Umsetzung beschleunigen.The addition of the silanes H-SiXaYbZc to the unsaturated ethers of the Formula II expediently succeeds in the presence of an inert solvent, e.g. halogenated hydrocarbon such as dichloromethane at temperatures between about 0 and about 1000, expediently at boiling temperature. The silane is advantageously used in excess used. The addition of a noble metal catalyst, such as a solution of H2PtC16 in isopropanol is advantageous. Also by adding peroxides like diacetyl peroxide and / or irradiation with light, the reaction can be accelerated.
Weiterhin können Silane der Formel H-SiXaYbZC auch mit einem Halogenid der Formel IV, E¹-A¹-A²-O-CnH2n-Hal IV worin R1, A1, A2, X, Y, Z, a, b, c und n die in Anspruch 1 angegebene Bedeutung haben und Hal Cl, Br oder I bedeutet, umgesetzt werden. Die Reaktion der Silane mit den Halogeniden der Formel IV erfolgt zweckmäßig in Gegenwart eines inerten Lösungsmittel wie beispielsweise einem Ether oder einem Kohlenwasserstoff wie Benzol oder Toluol. Vorzugsweise setzt man dem Reaktionsgemisch eine Base, z.B. in Form eines organischen Amins wie Pyridin, Triethylamin oder Butylamin, zur Entfernung des entstehenden Halogenwasserstoffs zu. Die Reaktionstemperaturen liegen zwischen etwa 0° und etwa 1500, zweckmäßigerweise bei Siedetemperatur.Furthermore, silanes of the formula H-SiXaYbZC can also be used with a halide of formula IV, E¹-A¹-A²-O-CnH2n-Hal IV wherein R1, A1, A2, X, Y, Z, a, b, c and n have the meaning given in claim 1 and Hal means Cl, Br or I, implemented will. The reaction of the silanes with the halides of the formula IV is expedient in the presence of an inert solvent such as an ether or a Hydrocarbons such as benzene or toluene. Preference is given to adding the reaction mixture a base, e.g. in Form of an organic amine such as pyridine, triethylamine or butylamine, to remove the hydrogen halide formed. The reaction temperatures lie between about 0 ° and about 1500, expediently at the boiling point.
Des weiteren können Siliciumverbindungen der Formel 1 nach Anspruch 1, in der mindestens einer der Substituenten X, Y und Z H, C1, Br oder I bedeutet mit einem Alkali-, Erdalkali- oder Silbersalz der Anionen CN-, NC , OCN , NCO , SCN , NCS oder N3 oder mit deren zugehörigen Säuren HCN, HOCN, HCNO, HSCN oder HN3 oder zur Herstellung von Isocyanaten mit Harnstoff oder von Isothiocyanaten mit Thioharnstoff umgesetzt werden.Furthermore, silicon compounds of the formula 1 according to claim 1, in which at least one of the substituents X, Y and Z is H, C1, Br or I. with an alkali, alkaline earth or silver salt of the anions CN-, NC, OCN, NCO, SCN, NCS or N3 or with their associated acids HCN, HOCN, HCNO, HSCN or HN3 or for the production of isocyanates with urea or of isothiocyanates with Thiourea are implemented.
Man führt die Umsetzung der Alkali-, Erdalkali- oder Silbersalze mit den Silanen der Formel I zweckmäßig in einem inerten Lösungsmittel wie Tetrahydrofuran oder Pyridin bei Temperaturen zwischen etwa 0° und etwa 150 durch. Besonders vorteilhaft gelingt die Umsetzung in Salzschmelzen aus beispielsweise Lithium-, Kalium- und/ oder Zinkchlorid bei Temperaturen von etwa 100 bis etwa 500°, insbesondere zwischen 1500 und 350 OC.The reaction of the alkali, alkaline earth or silver salts is carried out the silanes of the formula I expediently in an inert solvent such as tetrahydrofuran or pyridine at temperatures between about 0 ° and about 150. Particularly beneficial if the conversion succeeds in molten salts from, for example, lithium, potassium and / or zinc chloride at temperatures from about 100 to about 500 °, especially between 1500 and 350 OC.
Die Verbindungen der Formel I können unmittelbar zur Beschichtung der zu behandelnden Oberflächen verwendet werden. Zur Beschichtung eignen sich insbesondere oxidische Oberflächen, z.B. solche von Metall-, Halbmetall- oder Nichtmetalloxiden, vor allem aber Glasoberflächen.The compounds of the formula I can be used directly for coating of the surfaces to be treated. Are particularly suitable for coating oxidic surfaces, e.g. those of metal, semi-metal or non-metal oxides, but above all glass surfaces.
Man beschichtet zweckmäßig, indem man die vorher gereinigten Oberflächen mit einer etwa 0,1 bis 1 %igen Lösung einer Verbindung der Formel I in einem inerten Lösungsmittel, z.B. einem halogenierten Kohlenwasserstoff wie Dichlormethan oder l,l,l-Trichlorethan, benetzt und das Lösungsmittel an der Luft verdampft. Ein Erhitzen oder Nachbehandeln mit Wasserdampf der so modifizierten Oberfläche wie bei den in der DE-OS 33 31 515 beanspruchten Verbindungen ist bei den Verbindungen der Formel I im allgemeinen nicht erforderlich. Es entsteht ein gleichmäßiger, hochmolekularer Film, der flüssigkristalline Phasen homöotrop zu orientieren vermag. Zur Erleichterung der Handhabung von Verbindungen der Formel I können diese unmittelbar nach ihrer Herstellung und nach destillativer Entfernung flüchtiger Reaktionskomponenten in einem geeigneten inerten Lösungsmittel wie z.B. l,l,l-Trichlorethan gelöst und in einer mit einem Septum verschlossenen Flasche aufbewahrt werden.It is expedient to coat by applying the previously cleaned surfaces with an about 0.1 to 1% solution of a compound of the formula I in an inert Solvent, e.g. a halogenated hydrocarbon such as dichloromethane or l, l, l-trichloroethane, wetted and the solvent evaporates in the air. A heating or aftertreatment with steam of the surface modified in this way as with the in the DE-OS 33 31 515 claimed compounds is in the compounds of the formula I generally not required. The result is a more uniform, high molecular weight Film capable of orienting liquid-crystalline phases homeotropically. To make things easier the handling of compounds of the formula I can these immediately after their Production and after removal of volatile reaction components by distillation in a suitable inert solvent such as l, l, l-trichloroethane and dissolved in in a bottle closed with a septum.
Mit einer Spritze wird nur die jeweils benötigte Menge aus der Vorratsflasche entnommen, so daß die restliche Lösung vor Hydrolyse durch Luftfeuchtigkeit geschützt bleibt.With a syringe, only the required amount is dispensed from the supply bottle removed so that the remaining solution is protected from hydrolysis by humidity remain.
Mit den Verbindungen der Formel II steht somit ein wirkungsvolles Mittel zur Erzeugung einer homöotropen Orientierung flüssigkristalliner Phasen auf Oberflächen zur Verfügung.With the compounds of formula II there is thus an effective one Means for generating a homeotropic orientation of liquid-crystalline phases Finishes available.
Man kann aber auch eine oder mehrere Verbindungen der Formel I als Dotierstoffe flüssigkristallinen Dielektrika zusetzen, wobei diese Dielektrika etwa 0,01 bis 1, vorzugsweise etwa 0,05 bis 0,5 %, an I enthalten. Die erfindungsgemäßen Dielektrika bestehen aus 2 bis 25, vorzugsweise 3 bis 15 Komponenten, darunter mindestens einer Verbindung der Formel I. Die anderen Bestandteile werden vorzugsweise ausgewählt aus den nematischen oder nematogenen Substanzen, insbesondere den bekannten Substanzen, aus den Klassen der Azoxybenzole, Benyzlidenaniline, Biphenyle, Terphenyle, Phenyl- oder Cyclohexylbenzoate, Cyclohexan-carbonsäurephenyl- oder -cyclohexyl-ester, Phenylcyclohexane, Cyclohexylbiphenyle, Cyclohexylcyclohexane, Cyclohexylnaphthaline, 1,4-Bis-cyclohexylbenzole, 4,4' -Bis-cyclohexylbiphenyle, Phenyl- oder Cyclohexylpyrimidine, Phenyl- oder Cyclohexyldioxane, Phenyl- oder Cyclohexyldithiane, 1, 2-Bis-cyclohexylethane, 1, 2-Bis-phenylethane, l-Cyclohexyl-2-phenylethane, gegebenenfalls halogenierten Stilbene, Benzylphenylether, Tolane und substituierten Zimtsäuren.But you can also use one or more compounds of the formula I as Add dopants to liquid-crystalline dielectrics, these dielectrics about 0.01 to 1, preferably about 0.05 to 0.5%, of I. the Dielectrics according to the invention consist of 2 to 25, preferably 3 to 15 components, including at least one compound of formula I. The other ingredients are preferably selected from the nematic or nematogenic substances, in particular the known substances from the classes of azoxybenzenes, benyzlideneanilines, biphenyls, Terphenyls, phenyl or cyclohexyl benzoates, cyclohexane-carboxylic acid phenyl or -cyclohexyl esters, phenylcyclohexanes, cyclohexylbiphenyls, cyclohexylcyclohexanes, Cyclohexylnaphthalenes, 1,4-bis-cyclohexylbenzenes, 4,4'-bis-cyclohexylbiphenyls, Phenyl or cyclohexyl pyrimidines, phenyl or cyclohexyl dioxanes, phenyl or Cyclohexyldithiane, 1, 2-bis-cyclohexylethane, 1, 2-bis-phenylethane, l-cyclohexyl-2-phenylethane, optionally halogenated stilbenes, benzyl phenyl ethers, tolanes and substituted ones Cinnamic acids.
Die wichtigsten als Bestandteile derartiger flüssigkristillen Dielektrika in Frage kommenden Verbindungen lassen sich durch die Formel V charakterisieren, R'-L-G-E-R" V worin L und E je ein carbo- oder heterocyclisches Ringsystem aus der aus 1,4-disubstituierten Benzol- und Cyclohexanringen, 4,4'-disubstituierten Biphenyl-, Phenylcyclohexan- und Cyclohexylcyclohexansystemen, 2,5-disubstituierten Pyrimidin- und 1,3-Dioxanringen, 2,6-disubstituiertem Naphthalin, Di- und Tetrahydronaphthalin, Chinazolin und Tetrahydrochinazolin gebildeten Gruppe, G -CH=CH--CH=CY- -CH=N(O)--C=C- -CH2CH2 --CO-O- -CH2 -0--CO-S- -CH2-S--CH=N- -COO-Phe-COO-oder eine C-C-Einfachbindung, Y Halogen, vorzugsweise Chlor, oder -CN, und R' und R" Alkyl, Alkoxy, Alkanoyloxy oder Alkoxycarbonylolxy mit bis zu 18, vorzugsweise bis zu 8 Kohlenstoffatomen, oder einer dieser Reste auch CN, NC, NO2, CF3, F, C1 oder Br bedeuten.The most important as components of such liquid crystal dielectrics Compounds in question can be characterized by the formula V, R'-L-G-E-R "V wherein L and E are each a carbo- or heterocyclic ring system from the from 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyl, Phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidine and 1,3-dioxane rings, 2,6-disubstituted naphthalene, di- and tetrahydronaphthalene, Quinazoline and tetrahydroquinazoline formed group, G -CH = CH - CH = CY- -CH = N (O) - C = C- -CH2CH2 --CO-O- -CH2 -0 - CO-S- -CH2-S - CH = N- -COO-Phe-COO- or a C-C single bond, Y halogen, preferably chlorine, or -CN, and R 'and R "alkyl, Alkoxy, alkanoyloxy or alkoxycarbonylolxy with up to 18, preferably up to 8 Carbon atoms, or one of these radicals also CN, NC, NO2, CF3, F, C1 or Br mean.
Die Benzol- und Cyclohexanringe können auch durch F, C1, -CN oder -CH3 substituiert sein.The benzene and cyclohexane rings can also be replaced by F, C1, -CN or -CH3 be substituted.
Bei den meisten dieser Verbindungen sind R' und R'' voneinander verschieden, wobei einer dieser Reste meist eine Alkyl- oder Alkoxygruppe ist. Aber auch andere Varianten der vorgesehenen Substituenten sind gebräuchlich.In most of these compounds, R 'and R' 'are different from one another, one of these radicals is usually an alkyl or alkoxy group. But others too Variants of the intended substituents are common.
Viele solcher Substanzen oder auch Gemische davon im Handel erhältlich.Many such substances or mixtures thereof are commercially available.
Die Herstellung der erfindungsgemäßen Dielektrika erfolgt in an dich üblicher Weise. In der Regel werden die Komponenten ineinander gelöst, zweckmäßig bei erhöhter Temperatur.The dielectrics according to the invention are produced in to you usual way. As a rule, the components are dissolved in one another, expediently at elevated temperature.
Durch geeignete Zusätze können die flüssigkristallinen Dielektrika nach der Erfindung so modifiziert werden, daß sie in allen bisher bekannt gewordenen Arten von Flüssigkristallanzeigeelementen verwendet werden können.With suitable additives, the liquid-crystalline dielectrics be modified according to the invention so that they are in all previously known Types of liquid crystal display elements can be used.
Derartige Zusätze sind dem Fachmann bekannt und in der Literatur ausführlich beschrieben. Beispielsweise können Leitsalze, vorzugsweise Ethyl-dimethyl-dodecylammonium-4-hexyloxybenzoat, Tetrabutylammonium-tetraphenylboranat oder Komplexsalze von Kronenethern (vgl.Such additives are known to the person skilled in the art and are detailed in the literature described. For example, electrolyte salts, preferably ethyl dimethyl dodecylammonium 4-hexyloxybenzoate, Tetrabutylammonium tetraphenylboranate or complex salts of crown ethers (cf.
z.B. I. Haller et al., Mol.Cryst.Liq. Band 24, Seiten 249 - 258 (1973)) zur Verbesserung der Leitfähigkeit, dichroitische Farbstoffe zur Herstellung farbiger Guest-Host-Systeme oder Substanzen zur Veränderung der dielektrischen Anisotropie, der Viskosität und/oder der Orientierung der nematischen Phasen zugesetzt werden. Derartige Substanzen sind z.B. in den DE-OS 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, 28 53 728 und 29 02 l beschrieben.e.g. I. Haller et al., Mol.Cryst.Liq. Volume 24, pages 249-258 (1973)) to improve conductivity, dichroic dyes to produce colored ones Guest-host systems or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases are added. Such substances are e.g. in DE-OS 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, 28 53 728 and 29 02 l.
Die folgenden Beispiele sollen die Erfindung erläutern, ohne sie zu begrenzen. F. = Schmelzpunkt, K. = Klärpunkt. Vor- und nachstehend bedeuten Prozentangaben Gewichtsprozent; alle Temperaturen sind in Grad Celsius angegeben.The following examples are intended to illustrate the invention without limiting it limit. F. = melting point, K. = clearing point. Above and below denote percentages Weight percent; all temperatures are given in degrees Celsius.
Beispiel 1 20 g Dichlorsilan werden bei -20 "C in 30 ml Dichlormethan gelöst. Dazu gibt man eine Lösung von 25.8 g 3- (p-trans-4-Propylcyclohexylphenoxy) -propen (F. 25 - 280, erhältlich durch Reaktion von Na-p-trans-4-Propylcyclohexylphenolat mit Allylbromid) in 20 ml Dichlormethan und 0,2 ml einer 0,1 molaren Lösung von Hexachlorplatin(IV)-Säure in Isopropanol. Man rührt zwei Tage unter Rückfluß und destilliert darauf das Lösungsmittel und überschüssiges Dichlorsilan ab. Der aus l-Dichlorsilyl-3- (p-trans-4-propylcyclohexylphenoxy) -propan bestehende Rückstand wird in einer 0,1 bis 1 %igen Lösung in l,l,l-Trichlorethan zur Oberflächenbehandlung eingesetzt.Example 1 20 g of dichlorosilane are dissolved in 30 ml of dichloromethane at -20 ° C solved. A solution of 25.8 g of 3- (p-trans-4-propylcyclohexylphenoxy) is added -propene (F. 25-280, obtainable by reaction of Na-p-trans-4-propylcyclohexylphenolate with allyl bromide) in 20 ml of dichloromethane and 0.2 ml of a 0.1 molar solution of Hexachloroplatinum (IV) acid in isopropanol. The mixture is stirred under reflux and for two days the solvent and excess dichlorosilane are then distilled off. The out l-dichlorosilyl-3- (p-trans-4-propylcyclohexylphenoxy) propane existing residue is used in a 0.1 to 1% solution in l, l, l-trichloroethane for surface treatment used.
Analog werden enthalten: 1-Dichlorsilyl-3-p-cyclohexylphenoxy-propan 1-Dichlorsilyl-3-(p-trans-4-methylcyclohexylphenoxy)-propan 1-Dichlorsilyl-3- (p-trans-4-ethylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3-(p-trans-4-butylcyclohexylphenoxy)-propan 1-Dichlorsilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3- (p-trans-4-sek.-butylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3-(p-trans-4w-pentylcyclohexylphenoxy)-propan 1-Dichlorsilyl-3- (p-trans-4-hexylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3- (p-trans-4-heptylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3- (p-trans-4-octylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3- (p-trans-4-nonylcyclohexylphenoxy) -propan 1-Dichlorsilyl-3-(p-trans-4-decylcyclohexylphenoxy)-propan 1-Dichlorsilyl-3-p-biphenyloxy-propan 1-Dichlorsilyl-3-(4'-methyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-ethyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-propyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-butyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-pentyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-hexyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-heptyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-octyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-nonyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-decyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-methoxy-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-ethoxy-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-propoxy-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-butoxy-biphenylyl-4-oxy)-propan l-Dichlorsilyl-3-(4'-pentoxy-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-hexoxy-biphenylyl-4-oxy)-propan l-Dichlorsilyl-3-(4'-heptoxy-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4f-methoxymethyl-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-methoxymethoxy-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-fluor-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-chlor-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-brom-biphenylyl-4-oxy)-propan 1-Dichlorsilyl-3-(4'-cyan-biphenylyl-4-oxy)-propan l-Dichlorsilyl-3-(trans-4-phenylcyclohexoxy)-propan 1-Dichlorsilyl-3-(trans-4-p-tolylcyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4-p-ethylphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-propylphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-butylphenylcyclohexoxy) -propan l-Dichlorsilyl-3- (trans-4-p-pentylphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-hexylphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-heptylphenylcyclohexoxy) -propan 1-Dichlorsily1-3-(trans-4-p-methoxyphenylcyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4-p-ethoxyphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-propoxyphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-butoxyphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-pentoxyphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-fluorphenylcyclohexoxy) -propan 1-Dichlorsilyl-3- (trans-4-p-chlorphenylcyclohexoxy) -propan 1-Dichlorsilyl-3-(trans-4-p-bromphenylcyclohexoxy)-propan 1-Dichlorsilyl-3-(trans-4-p-cyanphenylcyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4- (trans-4-butylcyclohexyl) -cyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4- (trans-4-pentylcyclohexyl) -cyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy)-propan 1-Dichlorsilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy)-propan 1-Dichlorsilyl-4- (p-trans-4-propylcyclohexylphenoxy) -butan 1-Dichlorsilyl-5-(p-trans-4-propylcyclohexylphenoxy)-pentan 1-Dichlorsilyl-6-(p-trans-4-propylcyclohexylphenoxy)-hexan 1-Dichlorsilyl-2-methyl-3-(p-trans-4-propylcycloheXylphenoxy)-propan.The following are also contained: 1-dichlorosilyl-3-p-cyclohexylphenoxy-propane 1-dichlorosilyl-3- (p-trans-4-methylcyclohexylphenoxy) propane 1-dichlorosilyl-3- (p-trans-4-ethylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-butylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-sec-butylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4w-pentylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-hexylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-heptylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-octylcyclohexylphenoxy) -propane 1-dichlorosilyl-3- (p-trans-4-nonylcyclohexylphenoxy) propane 1-dichlorosilyl-3- (p-trans-4-decylcyclohexylphenoxy) propane 1-dichlorosilyl-3-p-biphenyloxy-propane 1-dichlorosilyl-3- (4'-methyl-biphenylyl-4-oxy) propane 1-dichlorosilyl-3- (4'-ethyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-propyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-butyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-pentyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-hexyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-heptyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-octyl-biphenylyl-4-oxy) propane 1-dichlorosilyl-3- (4'-nonyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-decyl-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-methoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-ethoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-propoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-butoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-pentoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-hexoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-heptoxy-biphenylyl-4-oxy) propane 1-dichlorosilyl-3- (4f-methoxymethyl-biphenylyl-4-oxy) propane 1-dichlorosilyl-3- (4'-methoxymethoxy-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-fluoro-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-chloro-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-bromo-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (4'-cyano-biphenylyl-4-oxy) -propane 1-dichlorosilyl-3- (trans-4-phenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-tolylcyclohexoxy) propane 1-dichlorosilyl-3- (trans-4-p-ethylphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-propylphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-butylphenylcyclohexoxy) -propane l-dichlorosilyl-3- (trans-4-p-pentylphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-hexylphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-heptylphenylcyclohexoxy) -propane 1-Dichlorsily1-3- (trans-4-p-methoxyphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-ethoxyphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-propoxyphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-butoxyphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-pentoxyphenylcyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4-p-fluorophenylcyclohexoxy) propane 1-dichlorosilyl-3- (trans-4-p-chlorophenylcyclohexoxy) propane 1-dichlorosilyl-3- (trans-4-p-bromophenylcyclohexoxy) propane 1-dichlorosilyl-3- (trans-4-p-cyanophenylcyclohexoxy) propane 1-dichlorosilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4- (trans-4-butylcyclohexyl) -cyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4- (trans-4-pentylcyclohexyl) -cyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy) -propane 1-dichlorosilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy) -propane 1-dichlorosilyl-4- (p-trans-4-propylcyclohexylphenoxy) -butane 1-dichlorosilyl-5- (p-trans-4-propylcyclohexylphenoxy) pentane 1-dichlorosilyl-6- (p-trans-4-propylcyclohexylphenoxy) hexane 1-dichlorosilyl-2-methyl-3- (p-trans-4-propylcyclohexylphenoxy) propane.
Beispiel 2 Man gibt zu einer Lösung von 25,8 g 3-(p-trans-4-propylcyclohexyl-phenoxy)-propen in 50 ml Dichlormethan 19,9 ml Tribromsilan und 0,2 ml einer 0,1 molaren Lösung von Hexachlorplatin(IV)-Säure in Isopropanol. Man rührt zwei Tage unter Rückfluß und destilliert dann das Lösungsmittel und das überschüssige Tribromsilan ab. So erhaltenes rohes 1-Tribromsilyl-3- (p-trans-4-propylcyclohexylphenoxy>-propan wird in einer 0,1 bis 1 %igen Lösung in 1,1,1-Trichlorethan zur Oberflächenbehandlung eingesetzt.Example 2 A solution of 25.8 g of 3- (p-trans-4-propylcyclohexylphenoxy) propene is added in 50 ml of dichloromethane 19.9 ml of tribromosilane and 0.2 ml of a 0.1 molar solution of hexachloroplatinum (IV) acid in isopropanol. The mixture is stirred under reflux for two days and then distilling off the solvent and the excess tribromosilane. So obtained crude 1-tribromosilyl-3- (p-trans-4-propylcyclohexylphenoxy> -propane is used in a 0.1 to 1% solution in 1,1,1-trichloroethane for surface treatment used.
Analog werden enthalten: 1-Tribromsilyl-3-p-cyclohexylphenoxy-propan 1-Tribromsilyl-3- (p-trans-4-methylcyclohexylphenoxy) -propan 1-Tribromsilyl-3- (p-trans-4-ethylcyclohexylphenoxy) -propan 1-Tribromsilyl-3- (p-trans-4-butylcyclohexylphenoxy) -propan 1-Tribromsilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) -propan 1-Tribromsilyl-3- (p-trans-4-sek. -butylcyclohexylphenoxy) -propan 1-Tribromsilyl-3-(p-trans-4-pentylcyclohexylphenoxy)-propan 1-Tribromsilyl-3-(p-trans-4-hexylcyclohexylphenoxy)-propan 1-Tribromsilyl-3- (p-trans-4-heptylcyclohexylphenoxy) -propan 1-Tribromsilyl-3-(p-trans-4-octylcyclohexylphenoxy)-propan l-Tribromsilyl-3- (p-trans-4-nonylcyclohexylphenoxy) -propan l-Tribromsilyl-3-(p-trans-4-decylcyclohexylphenoxy)-propan 1-Tribromsilyl-3-p-biphenyloxy-propan l-Tribromsilyl-3-(4'-methyl-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-ethyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-propyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-butyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-pentyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-hexyl-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-heptyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-octyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-nonyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-decyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-methoxy-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-ethoxy-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3- (4' -propoxy-biphenylyl-4-oxy) -propan l-Tribromsilyl-3-(4'-butoxy-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-pentoxy-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-hexoxy-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-heptoxy-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(4'-methoxymethyl-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3- (4' -methoxymethoxy-biphenylyl-4-oxy) -propan 1-Tribromsilyl-3- (4' -fluor-biphenylyl-4-oxy) -propan l-Tribromsilyl-3-(4'-chlor-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-brom-biphenylyl-4-oxy)-propan 1-Tribromsilyl-3-(4'-cyan-biphenylyl-4-oxy)-propan l-Tribromsilyl-3-(trans-4-phenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-tolylcyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4-p-ethylphenylcyclohexoxy) -propan l-Tribromsilyl-3-(trans-4-p-propylphenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-butylphenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-pentylphenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-hexylphenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-heptylphenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-methoxyphenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-ethoxypenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-propoxypenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-butoxypenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-pentoxypenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-fluorpenylcyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4-p-chlorpenylcyclohexoxy) -propan l-Tribromsilyl-3-(trans-4-p-brompenylcyclohexoxy)-propan l-Tribromsilyl-3-(trans-4-p-cyanpenylcyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4- (trans-4-butylcyclohexyl) -cyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4- (trans-4-pentylcyclohexyl) -cyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy)-propan 1-Tribromsilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy)-propan l-Tribromsilyl-4-(p-trans-4-propylcyclohexylphenoxy)-butan l-Tribromsilyl-5-(p-trans-4-propylcyclohexylphenoxy)-pentan l-Tribromsilyl-6- (p-trans-4-propylcyclohexylphenoxy) -hexan 1-Tribromsilyl-2-methyl-3-(p-trans-4-propylcycloheXylphenoxy)-propan.The following are also contained: 1-tribromosilyl-3-p-cyclohexylphenoxy-propane 1-tribromosilyl-3- (p-trans-4-methylcyclohexylphenoxy) propane 1-tribromosilyl-3- (p-trans-4-ethylcyclohexylphenoxy) -propane 1-tribromosilyl-3- (p-trans-4-butylcyclohexylphenoxy) -propane 1-tribromosilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) -propane 1-tribromosilyl-3- (p-trans-4-sec-butylcyclohexylphenoxy) propane 1-tribromosilyl-3- (p-trans-4-pentylcyclohexylphenoxy) propane 1-tribromosilyl-3- (p-trans-4-hexylcyclohexylphenoxy) propane 1-tribromosilyl-3- (p-trans-4-heptylcyclohexylphenoxy) propane 1-tribromosilyl-3- (p-trans-4-octylcyclohexylphenoxy) propane l-tribromosilyl-3- (p-trans-4-nonylcyclohexylphenoxy) propane 1-tribromosilyl-3- (p-trans-4-decylcyclohexylphenoxy) propane 1-tribromosilyl-3-p-biphenyloxy-propane 1-tribromosilyl-3- (4'-methyl-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-ethyl-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-propyl-biphenylyl-4-oxy) -propane 1-Tribromosilyl-3- (4'-butyl-biphenylyl-4-oxy) -propane 1-Tribromosilyl-3- (4'-pentyl-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-hexyl-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-heptyl-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-octyl-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-nonyl-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-decyl-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-methoxy-biphenylyl-4-oxy) -propane l-tribromosilyl-3- (4'-ethoxy-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-propoxy-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-butoxy-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-pentoxy-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-hexoxy-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4'-heptoxy-biphenylyl-4-oxy) -propane l-tribromosilyl-3- (4'-methoxymethyl-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4 ' -methoxymethoxy-biphenylyl-4-oxy) -propane 1-tribromosilyl-3- (4 '-fluor-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-chlorobiphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-bromo-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (4'-cyano-biphenylyl-4-oxy) propane 1-tribromosilyl-3- (trans-4-phenylcyclohexoxy) propane l-tribromosilyl-3- (trans-4-p-tolylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-ethylphenylcyclohexoxy) -propane 1-tribromosilyl-3- (trans-4-p-propylphenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-butylphenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-pentylphenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-hexylphenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-heptylphenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-methoxyphenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-ethoxypenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-propoxypenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-butoxypenylcyclohexoxy) propane l-tribromosilyl-3- (trans-4-p-pentoxypenylcyclohexoxy) propane l-tribromosilyl-3- (trans-4-p-fluoropenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-chloropenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4-p-bromopenylcyclohexoxy) propane l-tribromosilyl-3- (trans-4-p-cyanpenylcyclohexoxy) propane 1-tribromosilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy) -propane 1-tribromosilyl-3- (trans-4- (trans-4-butylcyclohexyl) -cyclohexoxy) -propane 1-tribromosilyl-3- (trans-4- (trans-4-pentylcyclohexyl) -cyclohexoxy) -propane 1-Tribromosilyl-3- (trans-4- (trans-4-hexylcyclohexyl) cyclohexoxy) propane 1-tribromosilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy) -propane 1-tribromosilyl-4- (p-trans-4-propylcyclohexylphenoxy) -butane l-tribromosilyl-5- (p-trans-4-propylcyclohexylphenoxy) pentane l-tribromosilyl-6- (p-trans-4-propylcyclohexylphenoxy) -hexane 1-tribromosilyl-2-methyl-3- (p-trans-4-propylcyclohexylphenoxy) propane.
Beispiel 3 Man gibt zu einer Lösung von 25,8 g 3-(p-trans-4-propylcyclohexylphenoxy)-propen in 50 ml Dichlormethan 15,5 ml Iodsilan und 0,2 ml einer 0,1 molaren Lösung von Hexachloroplatin(IV)-Säure in Isopropanol. Man rührt zwei Tage unter Rückfluß und destilliert anschließend das Lösungsmittel und überschüssiges Iodsilan ab. Das erhaltene l-Iodsilyl-3-(p-trans-4-propylcyclohexylphenoxy)-propan wird in einer 0,1 bis 1 %igen Lösung in l,l,l-Trichlorethan zur Oberflächenbehandlung eingesetzt.Example 3 A solution of 25.8 g of 3- (p-trans-4-propylcyclohexylphenoxy) propene is added in 50 ml of dichloromethane 15.5 ml of iodosilane and 0.2 ml of a 0.1 molar solution of Hexachloroplatinum (IV) acid in isopropanol. The mixture is stirred under reflux and for two days the solvent and excess iodosilane are then distilled off. The received l-Iodosilyl-3- (p-trans-4-propylcyclohexylphenoxy) propane is used in a 0.1 to 1 % solution in l, l, l-trichloroethane used for surface treatment.
Analog werden enthalten: 1-Iodsilylsilyl-3-p-cyclohexylphenoxy-propan l-Iodsilylsilyl-3-(p-trans-4-methylcyclohexylphenoxy)-propan 1-Iodsilylsilyl-3-(p-trans-4-ethylcyclohexylphenoxy)-propan 1-Iodsilylsily1-3-(p-trans-4-butylcyclohexylphenoxy)-propan 1-Iodsilylsilyl-3-(p-trans-4-isobutylcyclohexylphenoxy)-propan l-Iodsilylsilyl-3-(p-trans-4-sek.-butylcycloheXylphenoxy)-propan l-Iodsilylsilyl-3-(p-trans-4-pentylcyclohexylphenoxy)-propan l-Iodsilylsily1-3-(p-trans-4-hexylcyclohexylphenoxy)-propan l-Iodsilylsilyl-3-(p-trans-4-heptylcyclohexylphenoxy)-propan l-Iodsilylsilyl-3- (p-trans-4-octylcyclohexylphenoxy) -propan 1-Iodsilylsilyl-3-(p-trans-4-nonylcyclohexylphenoxy)-propan l-Iodsilylsilyl-3-(p-trans-4-decylcyclohexylphenoxy}-propan l-Iodsilylsily1-3-p-biphenyloxy-propan 1-Iodsilylsilyl-3-(4'-methyl-biphenylyl-4-oxy)-propan 1-Iodsilylsily1-3-(4'-ethyl-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-propyl-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-butyl-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-pentyl-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-hexyl-biphenyly1-4-oxy)-propan l-Iodsilylsilyl-3-(4'-heptyl-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-octyl-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-nonyl-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-decyl-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-methoxy-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-ethoxy-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-propoxy-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-butoxy-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-pentoxy-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3-(4'-hexoxy-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-heptoxy-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-methoxymethyl-biphenylyl-4-oxy)-propan 1-Iodsilylsilyl-3- (4' -methoxymethoxy-biphenylyl-4-oxy) -propan 1-Iodsilylsilyl-3-(4'-fluor-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-chlor-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-brom-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(4'-cyan-biphenylyl-4-oxy)-propan l-Iodsilylsilyl-3-(trans-4-phenylcyclohexoxy)-propan 1-Iodsilylsilyl-3-(trans-4-p-tolylcyclohexoxy)-propan l-Iodsilylsilyl-3- (trans-4-p-ethylphenylcyclohexoxy) -propan 1-Iodsilylsilyl-3-(trans-4-p-propylphenylcyclohexoxy)-propan l-Iodsilylsilyl-3-(trans-4-p-butylphenylcyclohexoxy)-propan 1-Iodsilylsilyl-3-(trans-4-p-pentylphenylcyclohexoxy)-propan 1-Iodsilylsilyl-3- (trans-4-p-hexylphenylcyclohexoxy) -propan 1-Iodsilylsilyl-3- (trans-4-p-heptylphenylcyclohexoxy) -propan 1-Iodsilylsilyl-3- (trans-4-p-methoxyphenylcyclohexoxy) -propan 1-Iodsilylsilyl-3-(trans-4-p-ethoxypenylcyclohexoxy)-propan 1-Iodsilylsilyl-3-(trans-4-p-propoxypenylcyclohexoxy)-propan l-Iodsilylsilyl-3-(trans-4-p-butoxypenylcyclohexoxy)-propan 1-Iodsiylolsilyl-3-(trans-4-p-pentoxypenylcyclohexoxy)-propan 1-Iodsilylsilyl-3-(trans-4-p-fluorpenylcyclohexoxy)-propan 1-Iodsilylsilyl-3- (trans-4-p-chlorpenylcyclohexoxy) -propan l-Iodsiylylsilyl-3-(trans-4-p-brompenylcyclohexoxy)-propan l-Iodsilylsily1-3-(trans-4-p-cyanpenylcyclohexoxy)-propan 1-Iodsilylsilyl-3-(trans-4-(trans-4-propylcycloheXyl)-cyclohexoxy)-propan l-Iodsilylsilyl-3-(trans-4-(trans-4-butylcycloheXyl)-cyclohexoxy)-propan l-Iodsilylsily1-3-(trans-4-(trans-4-pentylcycloheXyl)-cyclohexoxy)-propan 1-Iodsilylsilyl-3- (trans-4-(trans-4-hexylcyclohexyl) -cyclohexoxy)-propan l-Iodsilylsilyl-3-(trans-4-(trans-4-heptylcycloheXyl)-cyclohexoxy)-propan l-Iodsilylsilyl-4-(p-trans-4-propylcyclohexylphenoxy)-butan l-Iodsilylsilyl-5-(p-trans-4-propylcyclohexylphenoxy)-pentan l-Iodsilylsilyl-6-(p-trans-4-propylcyclohexylphenoxy)-hexan l-Iodsilylsilyl-2-methyl-3- (p-trans-4-propylcyclohexylphenoxy)-propan.The following are analogously included: 1-iodosilylsilyl-3-p-cyclohexylphenoxy-propane 1-iodosilylsilyl-3- (p-trans-4-methylcyclohexylphenoxy) propane 1-iodosilylsilyl-3- (p-trans-4-ethylcyclohexylphenoxy) propane 1-iodosilylsily1-3- (p-trans-4-butylcyclohexylphenoxy) propane 1-iodosilylsilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) propane l-iodosilylsilyl-3- (p-trans-4-sec-butylcyclohexylphenoxy) propane 1-iodosilylsilyl-3- (p-trans-4-pentylcyclohexylphenoxy) propane 1-iodosilylsily1-3- (p-trans-4-hexylcyclohexylphenoxy) propane l-iodosilylsilyl-3- (p-trans-4-heptylcyclohexylphenoxy) propane l-iodosilylsilyl-3- (p-trans-4-octylcyclohexylphenoxy) propane 1-iodosilylsilyl-3- (p-trans-4-nonylcyclohexylphenoxy) propane l-iodosilylsilyl-3- (p-trans-4-decylcyclohexylphenoxy} propane l-iodosilylsily1-3-p-biphenyloxy-propane 1-iodosilylsilyl-3- (4'-methyl-biphenylyl-4-oxy) -propane 1-iodosilylsily1-3- (4'-ethyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-propyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-butyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-pentyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-hexyl-biphenyly1-4-oxy) -propane 1-iodosilylsilyl-3- (4'-heptyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-octyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-nonyl-biphenylyl-4-oxy) propane 1-iodosilylsilyl-3- (4'-decyl-biphenylyl-4-oxy) propane 1-iodosilylsilyl-3- (4'-methoxy-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-ethoxy-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-propoxy-biphenylyl-4-oxy) propane 1-iodosilylsilyl-3- (4'-butoxy-biphenylyl-4-oxy) propane 1-iodosilylsilyl-3- (4'-pentoxy-biphenylyl-4-oxy) propane 1-iodosilylsilyl-3- (4'-hexoxy-biphenylyl-4-oxy) propane 1-iodosilylsilyl-3- (4'-heptoxy-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-methoxymethyl-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-methoxymethoxy-biphenylyl-4-oxy) -propane 1-iodosilylsilyl-3- (4'-fluoro-biphenylyl-4-oxy) -propane l-iodosilylsilyl-3- (4'-chlorobiphenylyl-4-oxy) propane l-iodosilylsilyl-3- (4'-bromo-biphenylyl-4-oxy) propane l-iodosilylsilyl-3- (4'-cyano-biphenylyl-4-oxy) propane l-iodosilylsilyl-3- (trans-4-phenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-tolylcyclohexoxy) -propane l-iodosilylsilyl-3- (trans-4-p-ethylphenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-propylphenylcyclohexoxy) propane l-iodosilylsilyl-3- (trans-4-p-butylphenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-pentylphenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-hexylphenylcyclohexoxy) -propane 1-iodosilylsilyl-3- (trans-4-p-heptylphenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-methoxyphenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-ethoxypenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4-p-propoxypenylcyclohexoxy) -propane 1-iodosilylsilyl-3- (trans-4-p-butoxypenylcyclohexoxy) -propane 1-iodosilylsilyl-3- (trans-4-p-pentoxypenylcyclohexoxy) -propane 1-iodosilylsilyl-3- (trans-4-p-fluoropenylcyclohexoxy) -propane 1-iodosilylsilyl-3- (trans-4-p-chloropenylcyclohexoxy) propane l-iodosiylylsilyl-3- (trans-4-p-bromopenylcyclohexoxy) propane 1-iodosilylsily1-3- (trans-4-p-cyanopenylcyclohexoxy) propane 1-iodosilylsilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy) propane l-iodosilylsilyl-3- (trans-4- (trans-4-butylcycloheXyl) -cyclohexoxy) -propane l-iodosilylsily1-3- (trans-4- (trans-4-pentylcycloheXyl) -cyclohexoxy) -propane 1-iodosilylsilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy) -propane l-iodosilylsilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy) -propane 1-iodosilylsilyl-4- (p-trans-4-propylcyclohexylphenoxy) butane 1-iodosilylsilyl-5- (p-trans-4-propylcyclohexylphenoxy) pentane l-iodosilylsilyl-6- (p-trans-4-propylcyclohexylphenoxy) -hexane l-iodosilylsilyl-2-methyl-3- (p-trans-4-propylcyclohexylphenoxy) propane.
Beispiel 4 48,6 g Ammoniumisothiocyanat werden in 50 ml Tetrahydrofuran suspendiert. Dazu gibt man eine Lösung von 39,4 g 1-Trichlorsilyl-3- (p-trans-4-propylcyclohexylphenoxy) -propan (hergestellt analog Beispiel 2 aus Trichlorsilan und 3- (p-trans-4-Propylcyclohexylphenoxy) -propen) in 40 ml Tetrahydrofuran. Es wird 24 Stdn. unter Rückfluß gerührt. Man filtriert unter Stickstoff über eine Fritte und destilliert das Lösungsmittel ab. So erhaltenes l-Triisothiocyanatosilyl-3-(p-trans-4-propylcycloheXylphenoxy)-propan wird als 0,1 bis 1 %ige Lösung direkt zur Oberflächenbehandlung eingesetzt.Example 4 48.6 g of ammonium isothiocyanate are dissolved in 50 ml of tetrahydrofuran suspended. A solution of 39.4 g of 1-trichlorosilyl-3- (p-trans-4-propylcyclohexylphenoxy) is added propane (prepared analogously to Example 2 from trichlorosilane and 3- (p-trans-4-propylcyclohexylphenoxy) -propene) in 40 ml of tetrahydrofuran. It is stirred under reflux for 24 hours. Man filtered through a frit under nitrogen and distilled off the solvent. Thus obtained l-triisothiocyanatosilyl-3- (p-trans-4-propylcyclohexylphenoxy) propane is used as a 0.1 to 1% solution directly for surface treatment.
Analog werden enthalten: l-Triisothiocyanatosilyl-3-p-cyclohexylphenoxy-propan l-Triisothiocyanatosilyl-3-(p-trans-4-methylcycloheXylphenoxy)-propan l-Triisothiocyanatosilyl-3-(p-trans-4-ethylcycloheXylphenoxy)-propan 1-Triisothiocyanatosilyl-3- (p-trans-4-butylcyclohexylphenoxy)-propan 1-Triisothiocyanatosilyl-3- (p-trans-4-isobutylcyclohexylphenoxy)-propan l-Triisothiocyanatosilyl-3-(p-trans-4-sek.-butylcyclohexylphenoxy)-propan l-Triisothiocyanatosilyl-3-(p-trans-4-pentylcycloheXylphenoxy)-propan 1-Triisothiocyanatosilyl-3-(p-trans-4-hexylcycloheXylphenoxy)-propan 1-Triisothiocyanatosilyl-3-(p-trans-4-heptylcycloheXylphenoxy)-propan 1-Triisothiocyanatosilyl-3-(p-trans-4-octylcycloheXylphenoxy)-propan 1-Triisothiocyanatosilyl-3-(p-trans-4-nonylcycloheXylphenoxy)-propan 1-Triisothiocyanatosilyl-3-(p-trans-4-decylcycloheXylphenoxy)-propan l-Triisothiocyanatosilyl-3-p-biphenyloxy-propan 1-Triisothiocyanatosilyl-3-(4'-methyl-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-ethyl-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-propyl-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-butyl-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-pentyl-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-hexyl-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-heptyl-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-octyl-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-nonyl-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-decyl-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-methoxy-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-ethoxy-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3- (4' -propoxy-biphenylyl-4-oxy) -propan 1-Triisothiocyanatosilyl-3-(4'-butoxy-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-pentoxy-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-hexoxy-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-heptoxy-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-methoxymethyl-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-methoxymethoxy-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-fluor-biphenylyl-4-oxy)-propan l-Triisothiocyanatosilyl-3-(4'-chlor-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-brom-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3-(4'-cyan-biphenylyl-4-oxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-phenylcyclohexoxy) -propan l-Triisothiocyanatosilyl-3-(trans-4-p-tolylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-ethylphenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3-(trans-4-p-propylphenylcyclohexoxy)-propan l-Triisothiocyanatosilyl-3-(trans-4-p-butylphenylcyclohexoxy)-propan l-Triisothiocyanatosilyl-3-(trans-4-p-pentylphenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-hexylphenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-heptylphenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-methoxyphenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-ethoxypenylcyclohexoxy)-propan l-Triisothiocyanatosilyl-3-(trans-4-p-propoxypenylcyclohexoxy)-propan l-Triisothiocyanatosilyl-3-(trans-4-p-butoxypenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-pentoxypenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-fluorpenylcyclohexoxy)-propan l-Triisothiocyanatosilyl-3- (trans-4-p-chlorpenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4-p-brompenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3-(trans-4-p-cyanpenylcyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4- (trans-4-propylcyclohexyl)-cyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4- (trans-4-butylcyclohexyl)-cyclohexoxy)-propan 1-Triisothiocyanatosilyl-3- (trans-4- (trans-4-pentylcyclohexyl) -cyclohexoxy) -propan 1-Triisothiocyanatosilyl-3- (trans-4- (trans-4-hexylcyclohexyl)-cyclohexoxy)-propan l-Triisothiocyanatosilyl-3- (trans-4- (trans-4-heptylcyclohexyl)-cyclohexoxy)-propan l-Triisothiocyanatosilyl-4-(p-trans-4-propylcycloheXylphenoxy)-butan l-Triisothìocyanatosily1-5-(p-trans-4-propylcycloheXylphenoxy)-pentan 1 -Triisothiocyanatosilyl-6- (p-trans-4-propylcyclohexylphenoxy)-hexan l-Triisothiocyanatosilyl-2-methyl-3-(p-trans-4-propylcyclohexylphenoxy)-propan.The following are analogously included: l-triisothiocyanatosilyl-3-p-cyclohexylphenoxy-propane 1-triisothiocyanatosilyl-3- (p-trans-4-methylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-ethylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-butylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-sec-butylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-pentylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-hexylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-heptylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-octylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-nonylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3- (p-trans-4-decylcyclohexylphenoxy) propane 1-triisothiocyanatosilyl-3-p-biphenyloxy-propane 1-triisothiocyanatosilyl-3- (4'-methyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-ethyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-propyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-butyl-biphenylyl-4-oxy) propane 1-triisothiocyanatosilyl-3- (4'-pentyl-biphenylyl-4-oxy) propane 1-triisothiocyanatosilyl-3- (4'-hexyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-heptyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-octyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-nonyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-decyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-methoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-ethoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-propoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-butoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-pentoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-hexoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-heptoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-methoxymethyl-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-methoxymethoxy-biphenylyl-4-oxy) -propane 1-triisothiocyanatosilyl-3- (4'-fluoro-biphenylyl-4-oxy) -propane l-triisothiocyanatosilyl-3- (4'-chlorobiphenylyl-4-oxy) propane 1-triisothiocyanatosilyl-3- (4'-bromobiphenylyl-4-oxy) propane 1-triisothiocyanatosilyl-3- (4'-cyano-biphenylyl-4-oxy) propane 1-triisothiocyanatosilyl-3- (trans-4-phenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-tolylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-ethylphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-propylphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-butylphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-pentylphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-hexylphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans -4-p-heptylphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans -4-p-methoxyphenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-ethoxypenylcyclohexoxy) -propane 1-triisothiocyanatosilyl-3- (trans-4-p-propoxypenylcyclohexoxy) -propane l-triisothiocyanatosilyl-3- (trans-4-p-butoxypenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-pentoxypenylcyclohexoxy) -propane 1-triisothiocyanatosilyl-3- (trans-4-p-fluoropenylcyclohexoxy) -propane l-triisothiocyanatosilyl-3- (trans-4-p-chloropenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-bromopenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4-p-cyanpenylcyclohexoxy) propane 1-triisothiocyanatosilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy) -propane 1-triisothiocyanatosilyl-3- (trans-4- (trans-4-butylcyclohexyl) -cyclohexoxy) -propane 1-triisothiocyanatosilyl-3- (trans-4- (trans-4-pentylcyclohexyl) -cyclohexoxy) -propane 1-triisothiocyanatosilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy) -propane l-triisothiocyanatosilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy) -propane 1-triisothiocyanatosilyl-4- (p-trans-4-propylcyclohexylphenoxy) -butane l-triisothiocyanatosily1-5- (p-trans-4-propylcyclohexylphenoxy) pentane 1 -triisothiocyanatosilyl-6- (p-trans -4-propylcyclohexylphenoxy) -hexane 1-triisothiocyanatosilyl-2-methyl-3- (p-trans-4-propylcyclohexylphenoxy) propane.
Beispiel 5 Eine Lösung von 100 g 3-(4-Phenylphenoxy)-propen (F.Example 5 A solution of 100 g of 3- (4-phenylphenoxy) propene (F.
84 - 850; erhältlich durch Reaktion von 4-Phenylphenol mit Allylbromid ) in 230 ml Dichlormethan wird mit 99 g Trichlorsilan und 1 ml einer 0,1 molaren Lösung von Hexachloroplatin(IV)-Säure in Isopropanol versetzt.84-850; obtainable by reacting 4-phenylphenol with allyl bromide ) in 230 ml of dichloromethane is combined with 99 g of trichlorosilane and 1 ml of a 0.1 molar Solution of hexachloroplatinum (IV) acid in isopropanol.
Nach Rückflußkochen über Nacht werden das Lösungsmittel und überschüssiges Trichlorsilan abdestilliert.After refluxing overnight, remove the solvent and excess Trichlorosilane distilled off.
Es hinterbleibt 1-Trichlorsilyl-3- (4-phenylphenoxy) -propan (F. 24 - 26°), das als 0,1 bis 1 %ige Lösung zur Oberflächenbehandlung verwendet wird.What remains is 1-trichlorosilyl-3- (4-phenylphenoxy) propane (F. 24 - 26 °), which is used as a 0.1 to 1% solution for surface treatment.
Analog werden enthalten: l-Trichlorsilyl-3-p-cyclohexylphenoxy-propan 1-Trichlorsilyl-3-(p-trans-4-methylcyclohexylphenoxy)-propan 1-Trichlorsilyl-3- (p-trans-4-ethylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-butylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3-(p-trans-4-isobutylcyclohexylphenoxy)= propan 1-Trichlorsilyl-3- (p-trans-4-sek. -butylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-pentylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-hexylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-heptylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-octylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-nonylcyclohexylphenoxy) -propan 1-Trichlorsilyl-3- (p-trans-4-decylcyclohexylphenoxy) -propan l-Trichlorsilyl-3-p-biphenyloxy-propan 1-Trichlorsilyl-3-(4'-methyl-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-ethyl-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3- (4 -propyl-biphenylyl-4-oxy) -propan 1-Trichlorsilyl-3-(4'-butyl-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-pentyl-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-hexyl-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-heptyl-biphenylyl-4-oxy)-propan l-Trichlorsilyl-3-(4'-octyl-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-nonyl-biphenylyl-4-oxy)-propan l-Trichlorsilyl-3-(4'-decyl-biphenylyl-4-oxy)-propan l-Trichlorsilyl-3-(4'-methoxy-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3- (4 -ethoxy-biphenylyl-4-oxy) -propan 1-Trichlorsilyl-3-(4'-propoxy-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-butoxy-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-pentoxy-biphenylyl-4-oxy)-propan l-Trichlorsilyl-3-(4'-hexoxy-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-heptoxy-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3- (4 -methoxymethyl-biphenylyl-4-oxy) -propan 1-Trichlorsilyl-3-(4'-methoxymethoxy-biphenylyl-4-oxy)-propan l-Trichlorsilyl-3-(4'-fluor-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3-(4'-chlor-biphenylyl-4-oxy)-propan 1-Trichlorsilyl-3- (4 -brom-biphenylyl-4-oxy) -propan 1-Trichlorsilyl-3- (4 -cyan-biphenylyl-4-oxy) -propan 1-Trichlorsilyl-3-(trans-4-phenylcyclohexoxy)-propan 1-Trichlorsilyl-3-(trans-4-p-tolylcyclohexoxy)-propan l-Trichlorsilyl-3- (trans-4-p-ethylphenylcyclohexoxy) -propan l-Trichlorsilyl-3-(trans-4-p-propylphenylcyclohexoxy)-propan 1-Trichlorsilyl-3- (trans-4-p-butylphenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-pentylphenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-hexylphenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-heptylphenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-methoxyphenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-ethoxypenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-propoxypenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-butoxypenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-pentoxypenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-fluorpenylcyclohexoxy) -propan 1-Trichlorsilyl-3- (trans-4-p-chlorpenylcyclohexoxy) -propan 1-Trichlorsilyl-3-(trans-4-p-brompenylcyclohexoxy)-propan 1-Trichlorsilyl-3-(trans-4-p-cyanpenylcyclohexoxy)-propan 1-Trichlorsilyl-3-(trans-4-(trans-4-propylcycloheXyl)-cyclohexoxy)-propan 1-Trichlorsilyl-3-(trans-4-(trans-4-butylcycloheXyl)-cyclohexoxy)-propan 1-Trichlorsily1-3-(trans-4-(trans-4-pentylcycloheXyl)-cyclohexoxy)-propan 1-Trichlorsilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy)-propan 1-Trichlorsilyl-3-(trans-4-(trans-4-heptylcycloheXyl)-cyclohexoxy)-propan 1-Trichlorsilyl-4- (p-trans-4-propylcyclohexylphenoxy) -butan 1-Trichlorsily1-5-(p-trans-4-propylcyclohexylphenoxy)-pentan 1-Trichlorsily1-6-(p-trans-4-propylcyclohexylphenoxy)-hexan 1-Trichlorsilyl-2-methyl-3-(p-trans-4-propylcycloheXylphenoxy)-propan.The following are also contained: l-Trichlorosilyl-3-p-cyclohexylphenoxy-propane 1-trichlorosilyl-3- (p-trans-4-methylcyclohexylphenoxy) propane 1-trichlorosilyl-3- (p-trans-4-ethylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-butylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-isobutylcyclohexylphenoxy) = propane 1-trichlorosilyl-3- (p-trans-4-sec-butylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-pentylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-hexylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-heptylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-octylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-nonylcyclohexylphenoxy) -propane 1-trichlorosilyl-3- (p-trans-4-decylcyclohexylphenoxy) propane 1-trichlorosilyl-3-p-biphenyloxy-propane 1-Trichlorosilyl-3- (4'-methyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-ethyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4-propyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-butyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-pentyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-hexyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-heptyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-octyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-nonyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-decyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-methoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4-ethoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-propoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-butoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-pentoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-hexoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-heptoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4-methoxymethyl-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-methoxymethoxy-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-fluoro-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4'-chloro-biphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4-bromobiphenylyl-4-oxy) -propane 1-Trichlorosilyl-3- (4 -cyan-biphenylyl-4-oxy) propane 1-trichlorosilyl-3- (trans-4-phenylcyclohexoxy) propane 1-trichlorosilyl-3- (trans-4-p-tolylcyclohexoxy) propane 1-Trichlorosilyl-3- (trans-4-p-ethylphenylcyclohexoxy) propane 1-Trichlorosilyl-3- (trans-4-p-propylphenylcyclohexoxy) propane 1-trichlorosilyl-3- (trans-4-p-butylphenylcyclohexoxy) propane 1-trichlorosilyl-3- (trans-4-p-pentylphenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-hexylphenylcyclohexoxy) propane 1-trichlorosilyl-3- (trans-4-p-heptylphenylcyclohexoxy) propane 1-trichlorosilyl-3- (trans-4-p-methoxyphenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-ethoxypenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-propoxypenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-butoxypenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-pentoxypenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-fluoropenylcyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4-p-chloropenylcyclohexoxy) propane 1-trichlorosilyl-3- (trans-4-p-bromopenylcyclohexoxy) propane 1-Trichlorosilyl-3- (trans-4-p-cyanopenylcyclohexoxy) -propane 1-Trichlorosilyl-3- (trans-4- (trans-4-propylcyclohexyl) -cyclohexoxy) -propane 1-Trichlorosilyl-3- (trans-4- (trans-4-butylcycloheXyl) -cyclohexoxy) -propane 1-Trichlorsily1-3- (trans-4- (trans-4-pentylcycloheXyl) -cyclohexoxy) -propane 1-Trichlorosilyl-3- (trans-4- (trans-4-hexylcyclohexyl) -cyclohexoxy) -propane 1-trichlorosilyl-3- (trans-4- (trans-4-heptylcyclohexyl) -cyclohexoxy) -propane 1-Trichlorosilyl-4- (p-trans-4-propylcyclohexylphenoxy) -butane 1-Trichlorsily1-5- (p-trans-4-propylcyclohexylphenoxy) -pentane 1-Trichlorsily1-6- (p-trans-4-propylcyclohexylphenoxy) -hexane 1-trichlorosilyl-2-methyl-3- (p-trans-4-propylcyclohexylphenoxy) -propane.
Formulierungsbeispiel Ein Gemisch aus 51,8 % Buttersäure-(p-trans-4-propylcyclohexyl-phenylester) 26,0 % p-trans-4-Butylcyclohexylbenzoesäure- (trans-4-propylcyclohexylester) 22,1 % p-trans-4-Propylcyclohexylbenzoesäure- (trans-4-propylcyclohexylester) und 0,1 % 1-Triacetoxysilyl-3- (p-trans-4-propylcyclohexylphenoxy)-propan eignet sich als flüssigkristallines Dielektrikum.Formulation example A mixture of 51.8% butyric acid (p-trans-4-propylcyclohexyl-phenyl ester) 26.0% p-trans-4-butylcyclohexylbenzoic acid (trans-4-propylcyclohexyl ester) 22.1 % p-trans-4-propylcyclohexylbenzoic acid (trans-4-propylcyclohexyl ester) and 0.1 % 1-Triacetoxysilyl-3- (p-trans-4-propylcyclohexylphenoxy) propane is suitable as liquid crystalline dielectric.
Anwendungsbeispiel: Beschichtung von Glasoberflächen Die in l,l,l-Trichlorethan-Dampf sorgfältig gereinigten Gläser werden mit einer 0,5 %igen Lösung von l-Trichlorsily1-3-(p-trans-4-propylcyclohexylphenoxy)-propan in 1,1,1-Trichlorethan benetzt und das Lösungsmittel an der Luft verdampft.Application example: Coating of glass surfaces Die in l, l, l-trichloroethane vapor Carefully cleaned glasses are mixed with a 0.5% solution of l-Trichlorsily1-3- (p-trans-4-propylcyclohexylphenoxy) propane wetted in 1,1,1-trichloroethane and the solvent evaporated in the air.
Die Orientierung flüssigkristalliner Phasen auf mit Verbindungen der Formel I behandelten Oberflächen ist in allen Fällen besser als die durch die in der DE-OS 3331515 beanspruchten Trialkanoylsilane bewirkte Orientierung.The orientation of liquid-crystalline phases with compounds of the Formula I treated surfaces is in all cases better than that by the in the DE-OS 3331515 claimed trialkanoylsilanes caused orientation.
Claims (7)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853521201 DE3521201A1 (en) | 1985-06-13 | 1985-06-13 | Organosilicon compounds |
| DE19863601742 DE3601742A1 (en) | 1985-06-13 | 1986-01-22 | ORGANOSILICIUM COMPOUNDS |
| JP61136379A JPS61286393A (en) | 1985-06-13 | 1986-06-13 | Organosilicon compound |
| US06/873,913 US4730904A (en) | 1985-06-13 | 1986-06-13 | Organosilicon compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853521201 DE3521201A1 (en) | 1985-06-13 | 1985-06-13 | Organosilicon compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3521201A1 true DE3521201A1 (en) | 1986-12-18 |
Family
ID=6273174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853521201 Withdrawn DE3521201A1 (en) | 1985-06-13 | 1985-06-13 | Organosilicon compounds |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS61286393A (en) |
| DE (1) | DE3521201A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163495A2 (en) * | 1984-05-28 | 1985-12-04 | Toray Silicone Company Limited | Liquid crystalline organosilicon compounds |
| EP0355008A2 (en) | 1988-08-13 | 1990-02-21 | Hoechst Aktiengesellschaft | Organosilylalkyl or -alkenyl compounds, process for their preparation and their use in liquid-crystal mixtures |
| EP0872484A1 (en) * | 1995-07-27 | 1998-10-21 | Chisso Corporation | Organosilicon compounds, liquid-crystal composition, and liquid-crystal display element |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59707681D1 (en) * | 1996-10-28 | 2002-08-14 | Rolic Ag Zug | Crosslinkable, photoactive silane derivatives |
| JP4655387B2 (en) * | 2001-03-01 | 2011-03-23 | チッソ株式会社 | Silicon compound, liquid crystal composition, and liquid crystal display device |
| CN105452262A (en) | 2013-06-06 | 2016-03-30 | 日产化学工业株式会社 | Alkoxysilane compound, liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
-
1985
- 1985-06-13 DE DE19853521201 patent/DE3521201A1/en not_active Withdrawn
-
1986
- 1986-06-13 JP JP61136379A patent/JPS61286393A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163495A2 (en) * | 1984-05-28 | 1985-12-04 | Toray Silicone Company Limited | Liquid crystalline organosilicon compounds |
| EP0163495A3 (en) * | 1984-05-28 | 1988-09-21 | Toray Silicone Company Limited | Liquid crystalline organosilicon compounds |
| EP0355008A2 (en) | 1988-08-13 | 1990-02-21 | Hoechst Aktiengesellschaft | Organosilylalkyl or -alkenyl compounds, process for their preparation and their use in liquid-crystal mixtures |
| EP0872484A1 (en) * | 1995-07-27 | 1998-10-21 | Chisso Corporation | Organosilicon compounds, liquid-crystal composition, and liquid-crystal display element |
| EP0872484A4 (en) * | 1995-07-27 | 1998-12-23 | Chisso Corp | Organosilicon compounds, liquid-crystal composition, and liquid-crystal display element |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61286393A (en) | 1986-12-16 |
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