DE1620017A1 - 1,3-Disilyl-1,3.2-diazasilacycloalkanes and processes for their preparation - Google Patents
1,3-Disilyl-1,3.2-diazasilacycloalkanes and processes for their preparationInfo
- Publication number
- DE1620017A1 DE1620017A1 DE19661620017 DE1620017A DE1620017A1 DE 1620017 A1 DE1620017 A1 DE 1620017A1 DE 19661620017 DE19661620017 DE 19661620017 DE 1620017 A DE1620017 A DE 1620017A DE 1620017 A1 DE1620017 A1 DE 1620017A1
- Authority
- DE
- Germany
- Prior art keywords
- atom
- temperature
- groups
- heated
- reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 2
- -1 aliphatic diamine Chemical class 0.000 claims description 101
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 238000006384 oligomerization reaction Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YZQDCQBEYAKPDV-UHFFFAOYSA-N 1,2,3-triphenoxybenzene Chemical compound C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 YZQDCQBEYAKPDV-UHFFFAOYSA-N 0.000 description 1
- ASSBNKVXAKLHJI-UHFFFAOYSA-N 1,2,4-triphenoxybenzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C(OC=2C=CC=CC=2)=CC=1OC1=CC=CC=C1 ASSBNKVXAKLHJI-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- WZZSMXWYVCFISC-UHFFFAOYSA-N 1,3-diphenoxy-2-phenylbenzene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1 WZZSMXWYVCFISC-UHFFFAOYSA-N 0.000 description 1
- 239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
- PUQUSTFASRRVPU-UHFFFAOYSA-N 1,4-diphenoxy-2-phenylbenzene Chemical group O(C1=CC=CC=C1)C1=CC(=C(OC2=CC=CC=C2)C=C1)C1=CC=CC=C1 PUQUSTFASRRVPU-UHFFFAOYSA-N 0.000 description 1
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- RHQQHZQUAMFINJ-GKWSUJDHSA-N 1-[(3s,5s,8s,9s,10s,11s,13s,14s,17s)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC[C@H]21 RHQQHZQUAMFINJ-GKWSUJDHSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- QKHCUKLDPPXGFA-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenoxy)benzene Chemical compound C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 QKHCUKLDPPXGFA-UHFFFAOYSA-N 0.000 description 1
- HKPKPIBLJRBFCT-UHFFFAOYSA-N 1-phenoxy-2-(2-phenylphenoxy)benzene Chemical compound C=1C=CC=C(OC=2C(=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1 HKPKPIBLJRBFCT-UHFFFAOYSA-N 0.000 description 1
- APPKHSCJIQLOMM-UHFFFAOYSA-N 1-phenoxy-2-(3-phenylphenoxy)benzene Chemical compound C1(=CC(=CC=C1)OC1=C(C=CC=C1)OC1=CC=CC=C1)C1=CC=CC=C1 APPKHSCJIQLOMM-UHFFFAOYSA-N 0.000 description 1
- ABGWRHITXPRWLI-UHFFFAOYSA-N 1-phenoxy-2-(4-phenoxyphenyl)benzene Chemical group C=1C=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 ABGWRHITXPRWLI-UHFFFAOYSA-N 0.000 description 1
- YXODXFJTYOYBJD-UHFFFAOYSA-N 1-phenoxy-2-(4-phenylphenoxy)benzene Chemical compound C1(=CC=C(C=C1)OC1=C(C=CC=C1)OC1=CC=CC=C1)C1=CC=CC=C1 YXODXFJTYOYBJD-UHFFFAOYSA-N 0.000 description 1
- MVCITNPWSJQCBC-UHFFFAOYSA-N 1-phenoxy-3-(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 MVCITNPWSJQCBC-UHFFFAOYSA-N 0.000 description 1
- SEKQTPBJTSMNKU-UHFFFAOYSA-N 1-phenoxy-3-(3-phenoxyphenyl)benzene Chemical group C=1C=CC(C=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 SEKQTPBJTSMNKU-UHFFFAOYSA-N 0.000 description 1
- UOJBIUCWYZXEIP-UHFFFAOYSA-N 1-phenoxy-3-(3-phenylphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C=2C=CC=CC=2)=CC=1OC1=CC=CC=C1 UOJBIUCWYZXEIP-UHFFFAOYSA-N 0.000 description 1
- UIFPCJAUWOLAEN-UHFFFAOYSA-N 1-phenoxy-3-(4-phenylphenoxy)benzene Chemical compound C1(=CC=C(C=C1)OC1=CC(=CC=C1)OC1=CC=CC=C1)C1=CC=CC=C1 UIFPCJAUWOLAEN-UHFFFAOYSA-N 0.000 description 1
- DNBREAOUGAMGLA-UHFFFAOYSA-N 1-phenoxy-4-(2-phenylphenoxy)benzene Chemical compound C1(=C(C=CC=C1)OC1=CC=C(C=C1)OC1=CC=CC=C1)C1=CC=CC=C1 DNBREAOUGAMGLA-UHFFFAOYSA-N 0.000 description 1
- XGBRGISDQIIJFK-UHFFFAOYSA-N 1-phenoxy-4-(3-phenylphenoxy)benzene Chemical compound C1(=CC(=CC=C1)OC1=CC=C(C=C1)OC1=CC=CC=C1)C1=CC=CC=C1 XGBRGISDQIIJFK-UHFFFAOYSA-N 0.000 description 1
- GQGTXJRZSBTHOB-UHFFFAOYSA-N 1-phenoxy-4-(4-phenoxyphenoxy)benzene Chemical compound C=1C=C(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 GQGTXJRZSBTHOB-UHFFFAOYSA-N 0.000 description 1
- IPZGXTFRQUOUJU-UHFFFAOYSA-N 1-phenoxy-4-(4-phenylphenoxy)benzene Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 IPZGXTFRQUOUJU-UHFFFAOYSA-N 0.000 description 1
- GMRIWCLJJFNYSC-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenoxy)benzene Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1C1=CC=CC=C1 GMRIWCLJJFNYSC-UHFFFAOYSA-N 0.000 description 1
- CRANDWVUIZYCQG-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenoxy)benzene Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1OC(C=1)=CC=CC=1C1=CC=CC=C1 CRANDWVUIZYCQG-UHFFFAOYSA-N 0.000 description 1
- YFIYNWHZXYZPDZ-UHFFFAOYSA-N 1-phenyl-4-(4-phenylphenoxy)benzene Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OC(C=C1)=CC=C1C1=CC=CC=C1 YFIYNWHZXYZPDZ-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
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- MZBOFQKASKNTRJ-UHFFFAOYSA-N 2,2-diamino-1-phenylethanone Chemical compound NC(N)C(=O)C1=CC=CC=C1 MZBOFQKASKNTRJ-UHFFFAOYSA-N 0.000 description 1
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- NEXDVNWQTRAGPK-UHFFFAOYSA-N 2,4-diphenoxy-1-phenylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C(OC=2C=CC=CC=2)=CC=1OC1=CC=CC=C1 NEXDVNWQTRAGPK-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KQQQSVCIYVATTK-UHFFFAOYSA-N 2-phenylbutane-2,3-diamine Chemical compound CC(N)C(C)(N)C1=CC=CC=C1 KQQQSVCIYVATTK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005025 alkynylaryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- LJZJHELAFLRVSU-UHFFFAOYSA-N anthracene;phenanthrene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC=C2C3=CC=CC=C3C=CC2=C1 LJZJHELAFLRVSU-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 239000007862 dimeric product Substances 0.000 description 1
- WJKVFIFBAASZJX-UHFFFAOYSA-N dimethyl(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C)(C)C1=CC=CC=C1 WJKVFIFBAASZJX-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- PGAFCJWTBHYLDN-UHFFFAOYSA-N ethyne-1,2-diamine Chemical compound NC#CN PGAFCJWTBHYLDN-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GIGVICQLYWGMGW-UHFFFAOYSA-N methyl(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)C1=CC=CC=C1 GIGVICQLYWGMGW-UHFFFAOYSA-N 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical group O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- PZZICILSCNDOKK-UHFFFAOYSA-N propane-1,2,3-triamine Chemical compound NCC(N)CN PZZICILSCNDOKK-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003218 pyrazolidines Chemical class 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/62—Nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/549—Silicon-containing compounds containing silicon in a ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Description
München, den 5» 7. 1966 Mein Zeichen: HM - 195Munich, 5th July 1966 My reference: HM - 195
Be schrei bung zti der Patentanmeldung der Firma Monsanto Company, St. Louis (Mo., USA) betreffendDescription zti of the company's patent application Regarding Monsanto Company, St. Louis (Mo., USA)
1> 3-Disilyl-1„3 „2-diazasilacycloalkane und Verfahren zu ihrer Her- 1 > 3-Disilyl-1 "3" 2-diazasilacycloalkanes and process for their preparation
steilungsteepness
Priorität: Schweizerische Patentanmeldung 9979/65 vom 13.Juli 1965Priority: Swiss patent application 9979/65 of July 13, 1965
Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von 1,3-Disilyl-i ,3,Z-diazasilaci'cloalkanen der allgemeinen FormelThe present invention relates to a method of manufacture of 1,3-disilyl-i, 3, Z-diazasilaci'cloalkanen the general formula
XR1R2SiXR 1 R 2 Si
-JJ-YY
ε1 ε 1
1 2 '1 2 '
in welcher R und R , einzeln genommen, Wasserstoffatome, Fluoratome, gleiche oder verschiedene, gegebenenfalls substituierte und/oder äthylenisch oder acetylenisch ungesättigte Kohlenwasserstoff reste, heterocyclische Reste oder Silylgruppen, die aiicih durch ein Sauerstoffatom und die Silylgruppen überdies auch durch, einin which R and R, taken individually, are hydrogen atoms, fluorine atoms, identical or different, optionally substituted and / or ethylenically or acetylenically unsaturated hydrocarbon radicals, heterocyclic radicals or silyl groups that aiicih through an oxygen atom and the silyl groups, moreover, also through
1 2 Stickstoffatom gebunden sein können, R und R f zusammengenommen, mit ihrem Siliciumatom einen gegebenenfalls substituierten heterocyclischen Ring, R'* einen gegebener.falls substituierten und/oder äthylenisch oder acetylenisch ungesättigten zweiwertigen iCohien-1 2 nitrogen atom can be bonded, R and R f taken together, with their silicon atom an optionally substituted heterocyclic ring, R '* an optionally substituted and / or ethylenically or acetylenically unsaturated divalent alcohol
009812/1760009812/1760
wasserstoff rest, heterocyclischen Rest, 3.1 ne durch ein Kohlenstoffatom gebundens Aethergruppe oder el.ie entsprechende Gruppe, die S, SS, NH, NR (E «= organischer Eeet wie in Aminen vorkommend), SiR1ρ» HSiR', (E1 = organischer Rest wio in Silanen vorkommend), SO oder SO2 anstelle des ätherischen Säuerstoffatoms aufweist, welcher Rest R die beiden.Stickstoffatome des Diazasilacycloalkanringes in 1,2- oder 1,3-S.tellung bzw. ortho- oder periStellung gebunden hat, X ein Chloratom oder Bromatom und η eine ganze Zahl von 1 bis 10 bedeuten.hydrogen residue, heterocyclic residue, 3.1 ne through a carbon atom bound ether group or el. the corresponding group, the S, SS, NH, NR (E «= organic Eeet as occurring in amines), SiR 1 ρ» HSiR ', (E 1 = organic radical wio occurring in silanes), SO or SO 2 instead of the ethereal oxygen atom, which radical R has bonded the two nitrogen atoms of the diazasilacycloalkane ring in 1,2- or 1,3-S-position or ortho- or peri-position, X is a chlorine atom or a bromine atom and η is an integer from 1 to 10.
Es war bekannt, daß man aus z.B. Aethylendiamin und Dimethyldichlorsilan in einem molarsn Verhältnis von 1:1 in Benzollöeung bei tiefen Temperaturen das entsprechende 1,5-Bis(dimethylchlorsilyl)-2,2-dimethyl-1 ^-diaza-^-sila-cyclopentan in 605έ Ausbeute neben 15,6?b polymerem Rückstand erhält. Es war ferner auch bekannt, daß aus den erwähnten Reaktionskoiaponenten in einem molaren Verhältnis von 2:1 unter den gleichen Bedingungen ein lineares Polymeres mit der vermutlichen Struktur Zf-Si(CH5)21IHCH2CH2HH-J entsteht. (E.G. Rochow, Mh.Chem.£5, 750(759) 1964).It was known that one of, for example ethylenediamine and dimethyldichlorosilane in a molarsn ratio of 1: 1 in Benzollöeung at low temperatures the corresponding 1,5-bis (dimethylchlorosilyl) -2,2-dimethyl-1 ^ -diaza - ^ - Sila cyclopentane is obtained in 605έ yield in addition to 15.6? b of polymeric residue. It was also known that a linear polymer with the presumed structure Zf-Si (CH 5 ) 2 1IHCH 2 CH 2 HH-J is formed from the reaction components mentioned in a molar ratio of 2: 1 under the same conditions. (EG Rochow, Mh. Chem. £ 5, 750 (759) 1964).
Dieses Polymere ist unbeständig und epaltet schon bei.Raumtemperatur und schneller bei 4000C im Vakuum Aethylendiamin ab, wodurch eine weitere Kondensation stattfindet. Als Nebenprodukt bildet sich oei α einer Herstellung eine wesentliche Men&e des eueret genannten Monomeren. Mit diesen vorbekannten Verfahren ^lingt es nicht, definierte'"einheitliche Produkte heraus seilen-This polymer is unstable and epaltet already bei.Raumtemperatur and faster at 400 0 C in a vacuum from ethylenediamine, takes place whereby further condensation. A substantial amount of the monomer mentioned above is formed as a by-product during a production process. With these previously known processes, it is not possible to "rope out defined" uniform products.
009812/17.6*. ,:· a* OHiONAL 009812 / 17.6 *. ,: · A * OHiONAL
1620Q171620Q17
Es wurde gefunden, daß msn die Verbindungen 1 gehalt, "wenn man ein Bi&isin der .allgemeinen formel >'It was found that msn contained the compounds 1 "if one Bi & isin the .general formula> '
in welcher R·5wie frähiir definiert is-&f mit einem Halogensilan
der allgemeinen Borrasl ;
(III) R1A in which R · 5 as previously defined is- & f with a halosilane of the general Borrasl ;
(III) R 1 A
in welcher S", R" und X wie friüiei1 definisrt Bind, zuerst in einer liineielitlich des Halogennilans ungenügenden molaren Proport ion von vorzugövveise 1:0,5 in einem inerten Löaungsmittel, nötigenfalls unter Druokanvvend-ung bei einer unterhalb 1QO0C, z,B. bei £5°ö liegenden lemperatur iiraagtzt, diß Reäktiansmischung während einiger Seit, z.B* mindestens 10 Minuten^ auf eine höhere ale die zuerst angewandte Temperatur, s,B. auf 6QQO bis 13O0G erhitzt, dann die zur Erreichung des gewünschten Qligomerisä'fcionsgrades noch fehlende, theoretisch notwendige Menge Halogensilan. zur gegebenenfalls'" abgekühlten Iiosungλ zugesetzt und bis zur Beendigung der Reaktion mindestens bei der zuletzt angewandten Temperatur, z.B. 60° bis 250°C? gegebenenfalls ohne !Lösungsmittel, weiter erhitzt»in which S ', R "and X are as friüiei 1 definisrt Bind, first in one of the liineielitlich Halogennilans insufficient molar ProPort ion vorzugövveise of 1: 0.5 in an inert Löaungsmittel, if necessary with Druokanvvend-ung at a 1QO below 0 C, e.g. , B. The temperature is raised at £ 5 °, the reaction mixture for some time, e.g. at least 10 minutes, to a higher temperature than the first applied, s, B. heated to 6Q Q O to 13O 0 G, then to achieve the desired Qligomerisä'fcionsgrades missing, theoretically necessary amount of halosilane. added to the optionally cooled solution and heated further until the end of the reaction at least at the temperature last used, for example 60 ° to 250 ° C ? if necessary without! solvent.
in der ersten bekannten Realctionsstufe bildet sich ein hauptsächlich lineares Polymersa der iOrmel ' In the first known stage of the reaction, a mainly linear polymer of the iOrmel 'is formed
welches auch eine gewisse Anzähl cyclische Einheiten enthalten Rann. Ist das Halogensilan gut reaktionsfähig} wie z.B. ein ^ nie-?«res tialkvldiehlorsilanj vfirä dies3 Umsetzung z^eckmiißlg teei ηί.&?*ϊτ:&η TcTXX^Eiraturen, Ζι>Β. boi. C-G bis Baujiwhich also contain a certain number of cyclic units. Is the halosilane highly reactive} such as a ^ nie -? «Res tialkvldiehlorsilanj vfirä dies3 implementation z ^ eckmiißlg teei ηί. &? * Ϊτ : & η TcTXX ^ Eiraturen, Ζι> Β. boi. CG to Bauji
vorgenommen. JBs hat sich gezeigt, daß die Reakt.ionsmischung jetzt einige Zeit auf eine höhere Temperatur erhitzt werden mui3, bevor weiteres Halögensilan III zugegeben werden darf» Im allgemeinen genügt es, die Reaktionsmischung während etwa 1 Std. auf 800C au erhitzen. Man kunn aber auch während einer längeren Zeit auf eine niedrigere Temperatur, ZoB. 3 Stdo/60°0 oder während einer kürzeren Zeit auf eine höhere Temperatur, 2.B. 10 Min./i.30°"Ct erhitzen. Wird dieses nach.tragl.lch3 Erhitzen unterlass en 5 so entsteht als Endprodukt hauptsächlich das Monomere und nicht die erwünschten OliHomeren. Las Die.min und das Halögensilan III sind jetzt in der Reaktionumischung in einem molaren Verhältnis vcn * z.B, 1:0,5 anhörend, Hierbei ist die halbe Μβη,ξε dos Diamins zur Bindung der während der Reaktion abgespaltenen Halzsäure verbraucht worden,. En ist verständlich, daß man für diesen Zweck auch eine "entsprechende Menge eines anderen säurebindenöen Mittels anstatt Diaiuin susct^n kann= Tertiäre Amine, wie Trimethylamin, Triäthylamin.'Pyrxdin usw., deren Chlorhydrate--die nachfolgende Reaktion katalysieren, werden bevorzugt. In der zweiten sich anschließenden Reaktionsstufe wird eine weitere berechnete Men^e des DiorganodihalGgensilana zugegeben, wodurch bei weiterem Erhitzen die Bildung ~ron cyclischen Einheiten im Polymeren ur.ter gleichzeitigem "fCe'tteriabbau nach de:a" Schema /-Si (Ii1 R2) HH-R5 -NH-7—-^Xsi (R1 R2) ff~R5-N-Jperformed. JB has been found that the Reakt.ionsmischung now be heated for some time at a higher temperature mui3 before further Halögensilan III may be added "In general, it is sufficient to heat the reaction mixture for about 1 hour au. At 80 0 C. But you can also go to a lower temperature for a longer period of time, ZoB. 3 hours / 60 ° 0 or for a shorter time to a higher temperature, 2.B. 10 Min./i.30°"C t heat. If this nach.tragl.lch3 heating under let en 5 so formed as a final product is mainly the monomers and not the desired OliHomeren. Las Die.min Halögensilan and III are now Reaktionumischung in a molar ratio of, for example, 1: 0.5, here half the Μβη, ξε dos diamine has been consumed to bind the haloic acid split off during the reaction Another acid-binding agent instead of Diaiuin susct ^ n = tertiary amines, such as trimethylamine, triethylamine, pyrxdine, etc., whose chlorohydrates - catalyze the subsequent reaction, are preferred. In the second subsequent reaction stage a further calculated Men ^ e of DiorganodihalGgensilana is added, thereby further heating the formation ~ r on cyclic moieties in the polymer ur.ter simultaneous "fCe'tteriabbau after de: a" Schema / -Si (Ii 1 R 2 ) HH-R 5 -NH-7 - ^ Xsi (R 1 R 2 ) ff ~ R 5 -NJ
SiR1R*SiR 1 R *
errciicht wird. Diese- anreite Eeaktionestufe wirö normaler\?ßiee bei T eip er a tu ran ./Qn,etwa 80,bid 2000O oiurchgcifubrt, Je- m^h ders.is achieved. This initial stage of action is normal at T eip er a tu ran ./Qn, about 80, bid 200 0 O oiurchgcifubrt, each of the s .
Ten;:e; ι-"!;u.r" ka;'.-.n c :·ο 'irlij tKU.:iß{u><vre:? q-'u-ks.--10 *':..v ο5-3--_ Ten;: e; ι - "!;ur"ka;'.-. nc: · ο' irlij tKU.:iß Genealogieu><vre :? q-'u-ks. --10 * ': .. v ο5-3 --_
12/17^0 s ( BAD ORIGINAL12/17 ^ 0 s ( BAD ORIGINAL
bia raehrora dtunclen betragea, Hierbei wird eine weitere Menge des ursprünglich sin^üsetztsn Diainina suj: Bindung, der äbgespaVfcanen ilalzsäwre .verbrnuoht. V/eil dlaaoa Diamin nur -arao dem Polymeren zur Verfügung stellt, so 1st. diejao nachfolgende üiiisstaung swaa^alüuiHg mit einen Abbau:-ders Polymeren, d.h.. " jai-fe einer Verioitaung der 3i..la2ankßtbä verDtuiaenoDemaufolge ist daserfindungagemäiJe Verfahren besonders zu^.:itex>si1;elLuiig:v&a.-]m]:zke:htig&L oligoiiereii 1,3--Disil,yl-i ,ir^-ctidiiasi-lae^cloalltanem gseigne t, die in den endständigen exocyoIisehen Siiylgruppaa ein Chlor- oder BromatoEi enthalten. ": "bia raehrora dtunclen amount, Here a further amount of the originally sin ^ üsetztsn Diainina suj: bond, which is saved, is .brnuoht. V / eil dlaaoa diamine only makes available to the polymer, so 1st. diejao subsequent üiiisstaung swaa ^ alüuiHg with a breakdown: -der polymers, ie. "jai-fe a verioitaung of the 3i..la2ankstbä verDtuiaenoDemaufzugemäiJe method is particularly to ^ .: itex>si1; elLuiig: v & a .-] m]: zke : htig & L oligoiiereii 1 , 3 - Disil, yl-i, ir ^ -ctidiiasi-lae ^ cloalltanem gseigne t, which contain a chlorine or bromine egg in the terminal exocyoIisehen Siiylgruppaa. " : "
Mit den b-islier beJcannt gsvJOrdeiian Verfahren .connten aoXcke Oligoiiei'o nicht hergestellt y/eraent With the b-islier known gsvJOrdeiian Ve r drive. AoXcke Oligoiiei'o could not be produced y / weren t
ffenn das ■ Ilaloganailrui III ^venig reakbicnsfahig ist, wie z.B.If that is Ilaloganailrui III ^ venig responsive, such as
, öo. v/ard-in geeignete hÖ'iere Reaktions-, öo. v / ard-in suitable higher reaction
temperatursn gewählt. Die erste Eeaktionastufe kann 3.B. bei 50° bis IOO0C und die Beendigung der Reaktion bei z.B. 200° Ms-'2500S.. erfolgen, Die oberste Temperatürgrenze iat durch die Zer3et2ung3-teinpei-atui* des gebildeten SndprodukteB bestimmt. Diese Zersetaungs teaiperatur liegt h«i den be3tändigeren Typen etva zwischen 3CÖÖ und 4OQ0C. üül die aur Beendigung der Reaktion in gewissen Fällen notwendigen höheren Teraperatüren zu erreichen, kann es awerikmäßig seinj das Lösungsmittel zu entfernen.temperature sn selected. The first action stage can be 3.B. at 50 ° to IOO 0 C and the completion of the reaction, for example, at 200 ° Ms-'250 0 S .. take place, the top temperature limit door iat * of SndprodukteB formed determined by the Zer3et2ung3-teinpei-ATUI. This is Zersetaungs teaiperatur h "i the be3tändigeren types etva between 3CÖ Ö and 4OQ 0 C. üül the aur completion of the reaction in some cases to achieve the necessary higher Teraperatüren, it can awerikmäßig seinj to remove the solvent.
ffenn das uaziiaetzeiide Halo^eiisilan einen niedrigen Siedepunkt, z*B. weniger als oö°C, bseitsst, uo arbeitet man vp^teiliiait unter Druckanv/endung, Man kann, al)er auch anstelle von niedrig sieienden EalogunHilanen> wie z.B. DifluardichlorsilanIf the uaziiaetzeiide Halo ^ eiisilan has a low boiling point, z * B. less than oö ° C, besides, uo one works vp ^ partiiait under Pressure application, You can, al) er instead of low-weighting EalogunHilanes> such as difluardichlorosilane
BADORIGJNÄLBADORIGJNÄL
Diolilordinydrogensilan, Me thy Ifluordichlorsilan und Methylhydrogendichlorsilan die entsprechenden höher siedenden Bromide einsetzen. Diese sind in der Regel auch reaktionsfähiger als die Chloride.Diolilordinydrogensilan, Methy Ifluorodichlorosilan and Methylhydrogendichlorosilane the corresponding higher boiling bromides insert. As a rule, these are also more reactive than the chlorides.
Die in der zweiten E3aktionsatu:!e noch zuzusetzende und das vorzugsweise angewandte Verhältnis von 1:O,5'Übersteigende Menge Halogensilan ΙΙΓ ltßt «ich, auf ein Hol des eiegeüetzten Diiminn bezogen, aus der Formel 0,5p, +. J unö die Gesamtmenge 3eaThe Second E3aktionsatu: e still to be added, and preferably applied ratio of 1: O, 5'Übersteigende amount halosilane ΙΙΓ ltßt "I, based on a haul of eiegeüetzten Diiminn, from the formula 0, 5p +. J unö the total 3ea
notwendigen Halogensilane au« der Formel 2p + 1 berechnenCalculate the necessary halosilanes using the formula 2 p + 1
3p3p
Um die wertvollen Oligcmeren, bestehend aus einer Eauptfraktion mit η = 2 bis 10 zu erhalten, können die nachstehend aufgeführten molaren Proportionen eingehalten werden:About the valuable oligomers, consisting of a main fraction with η = 2 to 10, those listed below can be obtained molar proportions are observed:
Diaini.n HalogensilanDiaini.n halosilane
η Total 1. Stufe 2. Stufe Totalη Total 1st level 2nd level Total
009812/1760009812/1760
Im allgemeinen sind in den anfallenden Endproduktendie an die Hauptfraktion angrenzenden Fraktionen obenfalle Vertreten, bo daß im Endprodukt in der'Regel --verschiedene Oligömere vorhanden sind« Bei einem Ansatz entsprechend n=5 tritt das monomere Produkt nicht mehr wesentlich in Erscheinung. Die EnU-- ' produkte können in manchen Fällen durch Destillation-"in einheitliche Produkte aufgetrennt werden. Die anfallenden Mischungen können abei· auch direkt weiterverviendet werden. Die Reaktion wird in einem inerten Lösungsmittel durchgeführt* Geeignete Lösungsmittel sind besonders aliphatisehe, cycloaliphatische, aromatische und hydroaromatische Kohlenwasserstoffe, wie Hexan, Octan, Cyclohexan, Benzol, Toluol, Xylol, Biphenyl, Terphenyl, 1-Methylnaphthalin, 2-Methylnäphthalin, Decalin, Tetralin uewIn general, the resulting end products contain the parliamentary groups bordering on the main parliamentary group are represented, As a rule, there are various oligomers in the end product are present «With an approach corresponding to n = 5, this occurs monomeric product no longer significantly visible. The EnU-- ' products can in some cases by distillation- "into uniform Products are separated. The resulting mixtures can also be reused directly. The reaction is carried out in an inert solvent * Suitable solvents are especially aliphatic, cycloaliphatic, aromatic and hydroaromatic hydrocarbons, such as hexane, Octane, cyclohexane, benzene, toluene, xylene, biphenyl, terphenyl, 1-methylnaphthalene, 2-methylnäphthalin, decalin, tetralin and the like
Die zweite Realctionsutufe, die höhere Temperaturen erforöeri, kann zweckmäßig auch ohno Lösung!? mi ti el aus ge.führt werdeä. Zxia -i-c.-Btellung der erfindungsgeiBiäßen Produkte können Diatniße verwendei; werden, die zwei Aminogruppen entweder an einer aliphatiseheij Kette in 4..,2-.-. oder lr3- SteHung oder an einem Ring in ort.hc Stellung oder ?n einem polynttklearen Ring in■ peri-S-tellxmg ·-.-.anweisen c ;.... '. ..'.-'.' The second stage of implementation, which requires higher temperatures, can expediently also be a solution !? be carried out with. Zxia -ic.-Presentation of the products according to the invention can use diets; be the two amino groups either on an aliphatic chain in 4 .., 2 -.-. or lr 3- position or on a ring in ort.hc position or? in a polynttclear ring in ■ peri-S-tellxmg · -.-. instruct c ; .... '. ..'.- '.'
Bei den aliphatischen Vertretem kann der zweiwertige fioßt R' somit von einem der folgenden KohlenwaBserstoffe abgeleitet seins Methan. Aethan? Tropaa, Butan,-Pentanf K'~xan, Heptan, Octa.n. JTc:-i?.rijf Decan, Undecan, Dcdßcan und höhere Analoge mit bis zu 20 K'c]il-ii . stoffatjomen. Diese Alley lene köjnie.i al3 Sv.bfiöifcei'ter, Al'-r^ls *In the case of the aliphatic representatives, the divalent substance R 'can thus be derived from one of the following hydrocarbons: methane. Ethane ? Tropaa, butane, pentane f K'~ xane, heptane, Octa.n. J T c: -i? .Rijf Decane, Undecane, Dcdßcan and higher analogs with up to 20 K'c] il-ii. material atoms. This Alley lene köjnie.i al3 Sv.bfiöifcei'ter, Al'-r ^ ls *
009812/1760009812/1760
■ . -. ΆΆ-ν % ν; r';v-;! 7i; BAD ORIGINAL■. -. ΆΆ-ν% ν; r '; v- ; ! 7i; BATH ORIGINAL
Aralkyle und Aryle aufweisen, d.h. verzweigte aliphatische Diamine wie z.B. 1^-Diamino^-methyl-propan, 2|3-Diamino-2~ phenylbutan, 3,4-Diamino-3,4-Diraethylhexan, 4,4-Bis~arainomethyl-heptan, S-Amino^-aminoniethyl-nonan, 2,4-Diphenyl-6,6-big-aminomethyl~ootan usw. sind miteingeschlossen. Außer den beiden für die Cyclisierung notwendigen Aminogruppen können an einer anderen Stelle der aliphatischen Kette auch noch tertiäre Aminogruppen, wie Dimethylamino, Diäthylamino,Bi-n-propy!amino, Di-ieo-propylamino, Diallylamino, Di-η-butylamino, Di-iso-butylamino, Di~sec-butylaraino, Di-tert-buty!amino, Di-3-butenylamino, Di-2-butenylamino, Di-n-amylamino, Di-iso-octylamino, Didodedylamino, Dicyclohexylamine, Dicyclohexenylamino, Dibenzylamino, Diphenylamino t Ditolylamino, Bie(biphenyiyl )amino, Bis(p-methoxyphenyl)amino, Bis(mphenox3rphenyl)amino, Bie(m-frifluor-niethylphenyl)amino, Ν,Ν,ίΓ-Triphenylberizidinö, Pyrroline Pyrrolidino, Pyrazolino, Piperidino, Morpholine, Thiazino, N-Trimethyleilylpiperazino, Tetrahydrochinolino oder Decahydrochinoline vorhanden sein.Aralkyls and aryls, ie branched aliphatic diamines such as, for example, 1 ^ -diamino ^ -methyl-propane, 2,3-diamino-2-phenylbutane, 3,4-diamino-3,4-diraethylhexane, 4,4-bis-arainomethyl -heptane, S-amino ^ -aminoniethyl-nonane, 2,4-diphenyl-6,6-big-aminomethyl-ootane, etc. are included. In addition to the two amino groups necessary for the cyclization, tertiary amino groups, such as dimethylamino, diethylamino, bi-n-propylamino, di-ieo-propylamino, diallylamino, di-η-butylamino, di- iso-butylamino, di ~ sec-butylaraino, di-tert-buty! amino, di-3-butenylamino, di-2-butenylamino, di-n-amylamino, di-iso-octylamino, didodedylamino, dicyclohexylamine, dicyclohexenylamino, dibenzylamino, Diphenylamino t Ditolylamino, Bie (biphenyiyl) amino, Bis (p-methoxyphenyl) amino, Bis (mphenox3 r phenyl) amino, Bie (m-frifluoro-niethylphenyl) amino, Ν, Ν, ίΓ-Triphenylberizidinö, Pyrroline Pyrrolidino, Pyidrazolino, , Morpholines, thiazino, N-trimethyleilylpiperazino, tetrahydroquinolino or decahydroquinolines may be present.
Beispiele für einfachste Vertreter von Tri- und Tetraaminen sind 1,2,3-Triaminopropan, 1^,J-Triamino^-methylpropan, 1,1,I-Trieaminomethy 1-äthan, 1 ^,S-Triamino-S-phenyl-propan uevr. Wie der Fachmann leicht erkennen wird, können entsprechende blcyclische Endprodukte erhalten werden, wenn vier Aminogruppen vorhanden sind, wovon je zwei sich in der definierten Stellung befinden« wie z.B. beim tCetraaraino-neopentaii und 1,2,3-l!riamino~2--aminomethylpropah* Es iet verständlich, daß in solchem Mllen die umzueetiBehde Halogensilanmeiige III entsprechend grÖOör eu wählen lsi.Examples of the simplest representatives of tri- and tetraamines are 1,2,3-triaminopropane, 1 ^, J-triamino ^ -methylpropane, 1,1, I-trieaminomethy 1-ethane, 1 ^, S-triamino-S-phenyl- propane uevr. As the person skilled in the art will easily recognize, corresponding cyclic end products can be obtained if four amino groups are present, two of which are in the defined position, for example in the case of tCetraaraino-neopentaii and 1,2,3-l ! riamino ~ 2 - aminomethylpropah * It is understandable that in such trash the halosilane compound III to be converted should be selected correspondingly larger.
BAD. ORlGSNALBATH. ORIGSNAL
00.9812/176000.9812 / 1760
-9' - ■-■ -■■■-.;"■-9 '- ■ - ■ - ■■■ - .; "■
• Weitere geeignete Diamine haben cyclischen Charakter und enthalten die Aminogruppen in ortho-Steilung. Die cycloaliphatlachen Vertreter können vom Cyclobutan, Gyclopentan, Gyclohexan, Bicyolopentan, Bicyclohexan, Spiro-(5,4)-deean usw. abgeleitet sein. .. ■■·■"·"■;. " : ..:"■'""■" '/ ' ■ ..-".-" • Other suitable diamines are cyclic in character and contain the amino groups in the ortho position. The cycloaliphatlachen representatives may from cyclobutane, Gyclopentan, Gyclohexan, Bicyolopentan, bicyclohexane, spiro (5,4) -deean etc. derived. .. ■■ · ■ "·"■;.":..:" ■ '"" ■ "' / ' ■ ..-" .- "
Geeignete aromatische Diamine basieren auf Benzol, Toluol, Xylolen, Naphthalin, 1-Methylnaphthalin, 1,4-Dimethylnaphthalln, Phenanthren Anthracen, Acenaphthene Acenaphthylen, Diphenyl, Diphenylmethan, Triphenylmethan, Te trapheny line than, Dinaphthyl, Diphenylamin, Triphenylamin, Phenyl-trimethylailan, Diphenyldimethylsilan, Triphenylmethylsilan, Tetraphenylsilan, piphenyloxyd, Diphenylsulfid, Diphpnyleulfon, DiphenylBulfoxyd usw.Suitable aromatic diamines are based on benzene, toluene, xylenes, Naphthalene, 1-methylnaphthalene, 1,4-dimethylnaphthalene, phenanthrene Anthracene, Acenaphthene, Acenaphthylene, Diphenyl, Diphenylmethane, Triphenylmethane, Te trapheny line than, Dinaphthyl, Diphenylamine, Triphenylamine, phenyl-trimethylsilane, diphenyldimethylsilane, Triphenylmethylsilane, tetraphenylsilane, piphenyloxyd, diphenylsulfide, Diphpnyleulfon, DiphenylBulfoxyd etc.
Geeignete heterocyclische Diamine basieren auf Pyrrol, Pyrrolin, Pyrrolidin, Furan, Tetrahydrofuran, Thiophen, Pyrazol, Pyrazolin, Pyrazolidine Imidazol, Imidazolin, Imidazolidin, Benaimidazol, Thiazol, Oxazol, Triazol, Benzotriazol, Pyrrol, Pyrrolin, Pyrrolidin, Pyran, Pyridin, Thiopyran, Piperidin, Piperazin, Morpholin, Triazin, Indazol, Ghinolin, Ghinazolin, Chinoxalin, Phenazin, Carbazol usw. Miteingeschlossen sind die Derivate, die am Stickstoffatom des heterocyclischen Ringes gegebenenfalls alkyliert, phenyliert oder silyeiert Bind.Suitable heterocyclic diamines are based on pyrrole, pyrroline, Pyrrolidine, furan, tetrahydrofuran, thiophene, pyrazole, pyrazoline, Pyrazolidines imidazole, imidazoline, imidazolidine, benaimidazole, Thiazole, oxazole, triazole, benzotriazole, pyrrole, pyrroline, Pyrrolidine, pyran, pyridine, thiopyran, piperidine, piperazine, morpholine, triazine, indazole, ghinoline, ghinazoline, quinoxaline, Phenazine, carbazole, etc. Also included are the derivatives that may be present on the nitrogen atom of the heterocyclic ring alkylated, phenylated or silylated Bind.
Von den cyclischen Diaminen sind aber auch diejenigen verwendbar, die in -oftlio-Stellung eine Aminogruppe und eine"-OC-Amiiioalky!gruppe enthalten, wie z.B. ortho-Aminobenzylamin, 1-Amino-2-0<!— äminoäthyl-cyclohexan und 1-Amino-2-e(-aminopropylbenzol.Of the cyclic diamines, however, those can also be used the in -oflio position is an amino group and an "-OC-Amiiioalky! group contain, such as ortho-aminobenzylamine, 1-amino-2-0 <! - aminoethyl-cyclohexane and 1-amino-2-e (-aminopropylbenzene.
0098127 17600098 127 1760
BADBATH
Ferner sind auch Diaraine verwendbar, welche die beiden Aminogruppen in peri-Stellung enthalten, wie »«"?« 1,8-Diaminonaphthalin, 1 ,ß-Diaminotlecalin, 1,9-Anthracen, 4,5-Ghinolin und 1,9-Carbazol.Furthermore, diaraines can also be used, which contain the two amino groups contained in the peri position, such as "" "?" 1,8-diaminonaphthalene, 1, ß-diaminotlecalin, 1,9-anthracene, 4,5-ghinolin and 1,9-carbazole.
Außer teriären Aninogruppen kommen als weitere Substituenten in Betracht: Halogen (z.B. 1,3~Diamino-2-chlorpropan, 1,2-Diainino-4-chlorbenzol, 4»5-Diamino-2~chlorp3fridin, 2,3-Diamino-5- (bzw. 6-) chlorpyridiri, 2,3-Diamino-4,5-(bsw. 5»6-)dichlorpyridin ubw.), Sauerstoff (z.B. Diarninoaceton, Diaminoacetophenone, Diaminobenzophenone), Schwefel (z.B. Diaminothioketone), SO (z.B. Diaminosulfoxyde) und SOp (z.B. Diarainoeulfone).Except teriären Aninogruppen as further substituents are: halogen (for example, 1,3 ~ diamino-chloropropane-2, 1,2-Diainino-4-chlorobenzene, 4 »5-diamino-2 ~ ridin chlorp3 f, 2,3-diamino -5- (or 6-) chlorpyridiri, 2,3-diamino-4,5- (e.g. 5 »6-) dichloropyridine etc.), oxygen (e.g. diarninoacetone, diaminoacetophenone, diaminobenzophenone), sulfur (e.g. diaminothioketone), SO (e.g. Diaminosulfoxyde) and SOp (e.g. Diarainoeulfone).
Als Substituent kann ferner ein weiterer Diaza-sila-cycloalkan-rest vorhanden sein, bzw. in der Reaktion gebildet werden.A further diaza-sila-cycloalkane radical can also be used as a substituent be present or be formed in the reaction.
Besonders temperaturbeständige Endprodukte mit einem hohen Siede- ' punkt enthalten einen von einer der folgenden Verbindungen abgeleiteten zweiwertigen Rest R : Phenoxybenzol, Toloxybenzol, 2-BiphenyIylather,3-BiphenyIylather, 4-Biphenylyläther, 2-BiphenyIy1-4-biphenyIylather, J-Biphenylyl-^-biphenylyläther, 1-(2-Biphenylyloxy)-2-phenoxybenzol, 1-(2-Biphenylylcxy)-3-Phenoxybenzol, 1-(2-Biphenylyloxy)-4-phenoxybenzol, 1-(3-Biphenylyloxy)-2-phenoxybenzol, 1-(3-Biphenylyloxy)-3-phenoxybenzol, 1-(3-Biphenylyloxy)-4-phenoxybenzol,Particularly temperature-resistant end products with a high boiling point point contain a divalent radical R derived from one of the following compounds: phenoxybenzene, toloxybenzene, 2-biphenylyl ether, 3-biphenylyl ether, 4-biphenylyl ether, 2-BiphenyIy1-4-biphenyIylather, J-Biphenylyl - ^ - biphenylylether, 1- (2-biphenylyloxy) -2-phenoxybenzene, 1- (2-biphenylylxy) -3-phenoxybenzene, 1- (2-biphenylyloxy) -4-phenoxybenzene, 1- (3-biphenylyloxy) -2-phenoxybenzene, 1- (3-biphenylyloxy) -3-phenoxybenzene, 1- (3-biphenylyloxy) -4-phenoxybenzene,
•t . . -■_"-■• t. . - ■ _ "- ■
1-(4-Biphenylyloxy)-2-phenoxybenzol, 1-(4-Biphenylyloxy)-3-phenoxybenzol, 1- (4-biphenylyloxy) -2-phenoxybenzene, 1- (4-biphenylyloxy) -3-phenoxybenzene,
1-(4-Biphenylyloxy)-4-phenoxybenzol, 2,2'-I)iphenoxybiphenyl,1- (4-biphenylyloxy) -4-phenoxybenzene, 2,2'-I) iphenoxybiphenyl,
BAD ORIGINAL 00 98 12/ 1760 BATH ORIGINAL 00 98 12/1760
162D017162D017
3,3'-Diphenoxybipheny 1, 4,4' -BiphenoxybipiiSHylg 2,3' phenyl, 2,4'-Diphenoxybiphenyl, 3,4 Iphenoxybiphenyl, 2,4-Diphenoxybipiieiiyl, 2.,5-Diphenox3rM;"j^Sia„ 1, 2,6-Diphenoxybiphenyl, 3,4-Diphenoxjüipilek:r^* '??5-Biphenoxybiphenyl, 1,2,3-Triphenoxybenzol, 1,2,4-Triphenoxybenzol, 1,3,5-Iriphenoxybenzol, 2-Phenoxyphenylather, 3-Phenoxyphenylather, 4-Phenoxyphenyläther,, 2*Phenoxypheuyl-3-phenoxyphenylather, 2-Phenoxy-4'-phenoxyphenylather, 3-Phenoxypheny1-4'-phenoxyphenyläther, 1-Phenoxynaphthalin, 2-Pheiioxynaphthalin, 1,1 '-Binaphthalinäther, 2,2I-Dinaphthalinäther, 1,2'-Pinaphthalinäther usw., ferner längerkettige Pölyäroxyaryle ArO (ArO)0Ar, worin Ar ein gegebenenfalls nieaeralfcylsübstituiertes Phenyl, Biphenyl oder Naphthyl bedeutet und a eine gänsje Zähl 1 bis 10 ist. Die Aroxygruppen können in Bezug auf die Stickstoffatome des Diamins in ortho- ,para- oder meta-Steilung sich befinden* In den aufgezählten Ary!resten können ferner ein bis mehrere Wasserstoff atome durch FlUoratome ersetzt sein, wodurch der Fliissigkeitsbereich der Endprodukte erhöht werden kann, ffliteirigesehiossen sind die entsprechenden Schwefeläther, die Sauerstoff'-anstelle von Schwefel enthalten.3,3'-diphenoxybiphenyl, 4,4'-biphenoxybiphenylg 2,3'-phenyl, 2,4'-diphenoxybiphenyl, 3,4'-Iphenoxybiphenyl, 2,4-diphenoxybiphenyl, 2, 5-diphenoxybiphenyl ; "j ^ Si a " 1, 2,6-Diphenoxybiphenyl, 3,4-Diphenoxjüipilek: r ^ * '?? 5-Biphenoxybiphenyl, 1,2,3-Triphenoxybenzol, 1,2,4-Triphenoxybenzol, 1,3, 5-iriphenoxybenzene, 2-phenoxyphenyl ether, 3-phenoxyphenyl ether, 4-phenoxyphenyl ether, 2 * phenoxypheuyl-3-phenoxyphenyl ether, 2-phenoxy-4'-phenoxyphenyl ether, 3-phenoxypheny1-4'-phenoxyphenyl ether, 1-phenoxynaphthalene-phthalene , 1,1'-binaphthalene ether, 2,2 I- dinaphthalene ether, 1,2'-pinaphthalene ether, etc., also longer-chain polyacrylic aryls ArO (ArO) 0 Ar, where Ar is an optionally substituted phenyl, biphenyl or naphthyl and a is a whole 1 to 10. The aroxy groups can be in the ortho, para or meta position with respect to the nitrogen atoms of the diamine End products can be increased, the corresponding sulfur ethers are included, which contain oxygen instead of sulfur.
Beispiele für die Reste R1 und R , wie sie in Haiogehsilän III an Silicium gebunden vorkommen können, sind: Alkylev Alkenyle und Alkinyle wie Methyl, Aethy 1, Vinyl, Aethinjrl, h-Prbpyl, isö-Propyl, Allyl, Prcpsnyl, ieo-Propenyl, Propargyl, Propinylf ii-Bittyl, ißo-Butyl, sec~3ui;yl, Ter-ii-Butyl, Methallyl, !--BUtenyl, Grotyl, 3~Buteayl, Butadienyl, 1-Butinyl, 2-Butinj-l, 3-Butinyl, l-Buten-2-Ittyl und höhere aliphatische Reste mit bis zu 24 kohlenstoff atomenExamples of the radicals R 1 and R, as they can occur in Haiogehsilän III bonded to silicon, are: alkyls v alkenyls and alkynyls such as methyl, ethy 1, vinyl, ethynyl, h-prbpyl, iso-propyl, allyl, prcpsnyl, ieo -Propenyl, propargyl, propynyl-bittyl, iso-butyl, sec ~ 3ui; yl, ter-ii-butyl, methallyl,! -Btenyl, grotyl, 3- buteayl, butadienyl, 1-butynyl, 2-butinyl , 3-butynyl, l-butene-2-ittyl and higher aliphatic radicals with up to 24 carbon atoms
1309012/17601309012/1760
trie ündecenyl, Dodecyl, Myrietyl, Oleyl, Tetraoosyl; ferner Cycloalkyle, Cycloalkenyl© und Cycloalkinyle wie Cyclobutyl, Cyclopentyl, Cyclopentenyl, Cyclopentadidnyi, Cyclohexyl, Cyclohexenyl, Gyclohexadienyi, Cyclohexinyl und größere alicyelieohe, Beete wie Cyclocctyl, Cycloqctatrienyl» Cyclododecyl, Cyclododecatrienyle Bicyclohexyl, ferner Aralkyle, Aralkenyle und Aralfcinyle wie Bensyl, Cuminyl, Phenylfithyl, Styryl, Phenyläthinyl, Phenylpropyl, i-PhenylalJyl, 2-Phenylallyl, Cinnaoiylt Pnenylpropinyl, 1~Pheny!propargyl, 3-Phenylpropargyl, Diphenylmethyl» Triphenylmethyl, <A.-Kaphthylmethyl,· ß-Haphthylmethyl, "kjC-Naphthylathyl, 2-oC-Napnthylätny 1, 1 -.*c-iraphthylöthenyl, 2-^-Haphthy lätbeny 1, 1 -0-liaphthyläthy 1, 2-ß-Naplithyläthy 1, 1 ·<- HaphthylÄthinyl 2-ß-Naphthyläthinyij ferner AlkaryIe, Alkenylaryle und Alkinylaryle wie Oiölyl, Xylyl, Mesityl, Duryl, Aethylphenyl, Ctunyl, Vinylphenyl, Aethinylphenyl, Propargylphenyl, Propiny!phenyl, tert-Bu ty !phenyl, tr-Vinylnaphthyl, 2-Viny lnaphthyl, 1-Aethinylnaphthyl, 2-*Aethinylnaphthyl; ferner Aryle wie Phenyl, ο-BiphenyIyI, m-Biphenylyl, p-Biphenylyl, m-ierphenylyl, p-Terphenylyl, 1-Haphthyl, 2-ITaphthyl, 2-Anthryl, 9-Anthryl, 1-Phenanthryl, 2-Phenanthryl, 3-Phenanthryl, 4-Phenanthryl, 9-Phenanthryl, Indan5rl, Indenyl j Ferner gegebenenfalls N-Bubstituierte heterocyclische Reste wie Pyrryl, Puryl, Tetrahydrofuryl, Benzofuryl, Thienyl, Pyrralidyl, Pyrazolyl, Pyrazolidyl, Imidazolyl, Imidasolidyl, Benzlmidazolyl, Thiajsolyl, Oxazolyl, ieo-Oxazolyl, Triazolyl, Pyrazinyl, P3rj?imidyl, Pyridazinyl, Pyridyl, Pyranyl, iPhiopyranyl* Piperidyl, Morpholinyli Thiazinyl, !Priazinyl, Chinolyl, Chinazolyl, Chinoxalyl# Indolyl, Carbazolyl uew,trie ündecenyl, dodecyl, myrietyl, oleyl, tetraoosyl; Further, cycloalkyls, cycloalkenyl © and cycloalkynyls as cyclobutyl, cyclopentyl, cyclopentenyl, Cyclopentadidnyi, cyclohexyl, cyclohexenyl, Gyclohexadienyi, cyclohexynyl and larger alicyelieohe, flower beds as Cyclocctyl, Cycloqctatrienyl "cyclododecyl, Cyclododecatrienyl e bicyclohexyl further aralkyls aralkenyls and Aralfcinyle as Bensyl, Cuminyl, Phenylfithyl, styryl, phenylethinyl, phenylpropyl, i-phenylalyl, 2-phenylallyl, cinnamonylt pnenylpropynyl, 1-phenylpropargyl, 3-phenylpropargyl, diphenylmethyl, triphenylmethyl, <A.-kaphthylmethyl, -oC-Napnthylätny 1, 1 -. * c-iraphthylöthenyl, 2 - ^ - Haphthy lätbeny 1, 1 -0-liaphthyläthy 1, 2-ß-Naplithyläthy 1, 1 · <- Haphthyläthynyl 2-ß-Naphthyläthinyij also Alkylarylee, Alkenylarylee and alkynylaryls such as ollyl, xylyl, mesityl, duryl, ethylphenyl, ctunyl, vinylphenyl, ethynylphenyl, propargylphenyl, propynylphenyl, tert-butylphenyl, tr-vinylnaphthyl, 2-vinylnaphthyl, 1-ethynylnaphthyl, 2- * thyl; also aryls such as phenyl, ο-biphenyIyI, m-biphenylyl, p-biphenylyl, m-ierphenylyl, p-terphenylyl, 1-haphthyl, 2-ITaphthyl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3 -Phenanthryl, 4-phenanthryl, 9-phenanthryl, indan5 r l, indenyl j Furthermore, optionally N-B-substituted heterocyclic radicals such as pyrryl, puryl, tetrahydrofuryl, benzofuryl, thienyl, pyrralidyl, pyrazolyl, pyrazolidyl, imidazolyl, thiajazolyl, benzidazolyl , ieo-oxazolyl, triazolyl, pyrazinyl, P3rj? imidyl, pyridazinyl, pyridyl, pyranyl, iphiopyranyl * piperidyl, morpholinyli thiazinyl,! priazinyl, quinolyl, quinazolyl, quinoxalyl # indolyl, carbazolyl etc.,
, BAD ORIGINAL, BAD ORIGINAL
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·- 15 ■-· - 15 ■ -
Diese organischen Reste können auch, durch ein Sauerstoffatom an dae Silicxumatom gebunden sein.These organic radicals can also, through an oxygen atom the silicon atom can be bonded.
Ea wurde gefunden, daß die aufgezählten Kohlenwasserstoffreste -Substituenten aufweisen können, die die erfindungsgemäße Reaktion nicht behindern.Ea has been found to be the hydrocarbon radicals enumerated -May have substituents that the reaction according to the invention do not hinder.
Beispiele für solche Substituenten sind Chlor*, Brom-, Fluor- und Jodatorae, organische Gruppen, die durch ein Sauerstoffatom oder Schwefelatom gebunden sind, Cyahogruppen,'stickstoffgruppen, Silylgruppen und tertiäre Aminogruppen.Examples of such substituents are chlorine *, bromine, fluorine and Jodatorae, organic groups formed by an oxygen atom or Sulfur atom are bound, cyahogroups, 'nitrogen groups, Silyl groups and tertiary amino groups.
Beispiele für einige einfache. Vertreter der großen Klasse von halogenierten Kohlenwasserstoffresten,sinds Chlormethyl, Mchlormethyl, Triohlormethyl, Brommethyl, Dibrommethyl, Tribrommethyl, Fluormethyl, 1-Chloräthyl, 2-Chloräthyl, 1-Bromäthyl, 2-Bromäthyl, 1-Pluoräthyl, 2-Fluoräthyi, 1,2-Dichloräthyi, 1,2-DifluQräthyl, 2-Trichlorlthyl, 2-TriflUQräthyl, Pentafluoräthyl, 2-Cblorvinyl, 1-Chlorvinyl, 1,2-Dichlorvinyl, Triehlorvinyl, Trifluorvinyl, Bromphenyl, Fluprphenyl, Difluorphenyl, Trifluorphenyl, Pentafluorphenyl, Triohlormethy!phenyl und Bis(trifluormethyl)phenyl. In^ ähnlicher Weise können auch andere wie oben aufgezählte ,Kohlenwasserstoffreste halogeniert sein. ... ,Examples of some simple. Representatives of the great class of halogenated hydrocarbon residues are chloromethyl, chloromethyl, Triohlomethyl, bromomethyl, dibromomethyl, tribromomethyl, Fluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, 2-bromoethyl, 1-pluoroethyl, 2-fluoroethyi, 1,2-dichloroethyi, 1,2-difluoriethyl, 2-trichloroethyl, 2-trifluorine, pentafluoroethyl, 2-chlorovinyl, 1-chlorovinyl, 1,2-dichlorovinyl, triehlorvinyl, trifluorovinyl, bromophenyl, Fluprphenyl, difluorophenyl, trifluorophenyl, pentafluorophenyl, Triohlomethyl phenyl and bis (trifluoromethyl) phenyl. In ^ similar Other hydrocarbon radicals as listed above can also be used be halogenated. ...,
Beispiele für Substituenten, die eine organische Gruppe darstellen, 'die durch ein Sauerstoffatom, oder Schwefelatom gebunden ist, werden bei der Konsultation <ier^ oben erwähnten organischen Gruppen ersichtlich. Examples of substituents which represent an organic group bonded through an oxygen atom or sulfur atom will become apparent upon consultation of the above-mentioned organic groups.
BAD ORIGINALBATH ORIGINAL
fj; 008β12ΛίφΟ f j; 008β12ΛίφΟ
-H --H -
Weitere Substituents"*! bestehen aus verzweigten oder geradkettig sich wiederholenden Aetäergruppierungen wie MetMoxymethylenoxy, Mefchoxyäthylenoxy, Aethoxyäthylenoxy , tert-Butoxy-tert-lsutylenoxy, Veratroxy, Anisoxy, 3,4-Dimethoxyphenenyloxy, 3-3?henoxy-4-methoxyphenenyloxy und rein aromatische Aethergruppierungsn, wie sie früher als Beispiele für denRest H aufgezählt worden sind.Further substituents "*!" Consist of branched or straight-chain repeating ether groups such as MetMoxymethyleneoxy, Mefchoxyäthylenoxy, Aethoxyäthylenoxy, tert-Butoxy-tert-Isutylenoxy, Veratroxy, anisoxy, 3,4-dimethoxyphenenyloxy, 3-3? Enoxy-4-methoxyphenenyloxy and purely aromatic ether groups, such as they have been enumerated earlier as examples of the remainder H.
Ferner Substituenten, die durch Anlagerung von Formaldehyd, Aethylenoxyd oder Propylenoxyd an eine Hydroxylgruppe und anschließende Verätherung, Veresterung oder sonstige Blockierung der endständigen Hydroxylgruppe hervorgegangen sind. Sie entsprechen den Formeln -O(OH2O)aOH2OB, -0(CH2OH2O)8CH2CH2OB oder -0(CH2CH2CH2O) CH2CH2CH2OB (B = Hydroxylendgruppen blockierender Rest wie er in solchen Ketten üblich istj a = 1 - 10).Furthermore, substituents which have arisen from the addition of formaldehyde, ethylene oxide or propylene oxide to a hydroxyl group and subsequent etherification, esterification or other blocking of the terminal hydroxyl group. They correspond to the formulas -O (OH 2 O) a OH 2 OB, -0 (CH 2 OH 2 O) 8 CH 2 CH 2 OB or -0 (CH 2 CH 2 CH 2 O) CH 2 CH 2 CH 2 OB (B = radical which blocks hydroxyl end groups, as is customary in such chains, j a = 1 - 10).
1 2 Gemäß der eingangs gegebenen Definition für R und R können diese Alkoxy- und Ar oxy gruppen auch direkt mit einem Siliciumatom verbunden seinο Ferner können ein bis mehrere Wasserstoffatome durch Fluoratome ersetzt sein, wodurch der Flüssigkeitsbereich der Endprodukte erhöht werden kann<>1 2 According to the definition given above for R and R, these Alkoxy and Aroxy groups can also be connected directly to a silicon atom. Furthermore, one or more hydrogen atoms can be used be replaced by fluorine atoms, creating the liquid area the end products can be increased <>
Beispiele für einige der einfachsten Vertreter der Klasse von cyanierten und nitrierten Resten sind 2-Cyanäthvl, 2-iTitroäthyl, 2-Cyan-n-propyl, 3-Cyan-n-propyl und 2,4-Dicyan-n-butyl, AnstelleExamples of some of the simplest representatives of the class of cyanated and nitrated residues are 2-Cyanäthvl, 2-iTitroäthyl, 2-cyano-n-propyl, 3-cyano-n-propyl and 2,4-dicyano-n-butyl, instead
'. BAD -ORlQINAL- '. BATHROOM -ORlQINAL-
009812/1760009812/1760
H620017H620017
erwähnten " Kohlenwasserstoffreste- kön^si -andere; Reste treten, wie sie früher für R und R auf"gez&i&i;worden sind*mentioned "hydrocarbon residues - can ^ si - other; residues occur, as they used to be "drawn" for R and R *
Die Reste R1 und B2 könöen^ auch SiIy!gruppen eein. JDer Begriff "Silylgruppen11 soll hier im weitesten Sinne aufgefaßt werden und mindestens die Gruppierungen SiR*,, SiR^gBiÄf^V Si(SiRV)2 Si(OSiR^i)2R*, SiCSiR*5), und Si(0SiR*j)3 (R* = Wassere toff atom, Pluoratöffl und/oder organischer Rest, der gegebenenfalls über ein Sauerstoffatom gebunden ist) umfassen»The radicals R 1 and B 2 can also form SiIy! Groups. The term "silyl groups 11 should be understood here in the broadest sense and at least the groupings SiR * ,, SiR ^ gBiÄf ^ V Si (SiRV) 2 Si (OSiR ^ i) 2 R *, SiCSiR * 5 ), and Si (0SiR * j) 3 (R * = Hydrogen atom, Pluoratöffl and / or organic residue, which is optionally bound via an oxygen atom) include »
Es ist für den Fachmann klar, daß besonders die zwei und mehr Siliciumatome enthaltenden SiIy!gruppen in der* Regel nicht ausschließlich Fluor- oder ffasserstoffatome enthalten, sondern eine Kombination mit gegebenenfalls Über Sauerstoff gebundenen organischen Resten, wie sie in solchen Gruppen vorkommen können. Diese Reste werden nachfolgend mit dem Symbol R' dargestellt.It is clear to those skilled in the art that especially the two and more SiIy groups containing silicon atoms generally do not contain only fluorine or carbon atoms, but one Combination with, if necessary, organic compounds bound via oxygen Remnants as they can occur in such groups. These residues are shown below with the symbol R '.
Beispiele für einige organische Silylgrüppen der allgemeinen Formel SiR1 ^ sind: ,Ecimethylsily.l, Triphenylsilyl, Trimethoxysilyl, !riphenoxysilylp Dimethaxy-phenoxysilyl, Methoxy-diphenoxysllyl, Methyi-diinethoxysilyl, . Diraethyl-methoxysilyl, Phenyl-dimethoxysilyl, Methyl-aiphenoxysilyl, üethyl-phenyl-methoxysilyl, Methyl-phenyl-phenoxysilyl usw., miteingeschlossen sind Silylgruppen» in denen Si ein Bestandteil des heterocyclischen Hxng&s ist wie in den Resten 1-Siiacyclopeiityl, 1-Silacyclopentenyl, I-Silacyclohexyl, 1-Siiacyclohexenyl, 1-Eilacyclohexadienyl usw., fernem Fluorsilylgrappeii der allgemeinen SOraiel SiF^, SiPgR' undExamples of some organic silyl groups of the general formula SiR 1 ^ are:, Ecimethylsily.l, triphenylsilyl, trimethoxysilyl,! Riphenoxysilylp dimethaxy-phenoxysilyl, methoxydiphenoxysllyl, methyldiinethoxysilyl,. Diraethyl-methoxysilyl, phenyl-dimethoxysilyl, methyl-aiphenoxysilyl, ethyl-phenyl-methoxysilyl, methyl-phenyl-phenoxysilyl, etc., including silyl groups in which Si is a component of the heterocyclic Hxng & s as in the radicals 1-siacyclopeiityl, 1-silacyclopentenoyl , I-Silacyclohexyl, 1-Siiacyclohexenyl, 1-Eilacyclohexadienyl etc., furthermore Fluorsilylgrappeii the general SOraiel SiF ^, SiPgR 'and
009812/1760 bad009812/1760 bathroom
SiI1R1 2, wie !Drifluorsilyl, Methyldifluorsilyl, Dimethylfluorsilyl, PhenyldifluorBilyL, Diphenylfluorsilyl, .SiI 1 R 1 2 , such as drifluorosilyl, methyldifluorosilyl, dimethylfluorosilyl, phenyldifluorobilyL, diphenylfluorosilyl,.
Methyl-phenylfluorsilyl, Methoxyfluorsilyl, DimethoxyfluoreiIyI, Methoxy-phenoxyfluoreilyl, Methoxy-phenylfluorsilyl, Phenoxymethylfluorsilyl usw., ferner Hydrogensilylgruppen der allgemeinen Formeln SiH*, SiB2^V, SiHR'2t SiEffi1, SiHF2, wie Srihydrogensilyl, iiethyläihydrogensilylf Dime thylhydrogensilyl, Piienyldinydrogeneilyl, Diphenyldihydrogen8ilyl, ftlethyl-phenylhydrogenBilyl, JlethoxydihydrogeiiBilyl^ Diraethoxyhydrogensilyl, Phenoxydihydrogenailyl, Diphenoxyhydrogensilyl, Methoxy-phenoxyhydrogeneilyl, Methoxyphenylhydrogensilyl, Phenylfluorhydrogensilyl ubw. Anstatt Methyl, Phenyl, Methoxy oder Phenoxy enthalten andere analogeMethyl-phenylfluorsilyl, Methoxyfluorsilyl, DimethoxyfluoreiIyI, methoxy-phenoxyfluoreilyl, methoxy-phenylfluorsilyl, Phenoxymethylfluorsilyl etc., and also Hydrogensilylgruppen the general formulas SiH *, SiB 2 ^ V, SiHR '2 t SiEffi 1, SiHF 2 as Srihydrogensilyl, iiethyläihydrogensilyl f Dime thylhydrogensilyl , Piienyldinydrogeneilyl, Diphenyldihydrogen8ilyl, ftlethyl-phenylhydrogenBilyl, JlethoxydihydrogeiiBilyl ^ Diraethoxyhydrogensilyl, Phenoxydihydrogenailyl, Diphenoxyhydrogensilyl, Methoxy-phenoxyhydrogeneilyl, Methoxyphenylhydrogensilyl, phenylfluorohydrogensilyl. Instead of methyl, phenyl, methoxy or phenoxy, contain others analogues
1 -2 Silylgruppen andere organische Heste wie sie für R usid S auf gegezählt worden sind»1 -2 silyl groups other organic residues as counted for R usid S on have been"
Gemäß der am Anfang gegebenen Definition für H und R können diese Silylgruppen auch an ein Sauerstoffatom oder Stickstoffatom gebunden sein« .According to the definition given at the beginning for H and R can these silyl groups also on an oxygen atom or nitrogen atom be bound" .
Die einfachsten Vertreter der Subetituenten mit Si—HBi- oder S -Si-Bindungen sind Pentamethyldieilanyl, 1 -IrimethylsiXyl-tetramethyldieilasa^i,, 1 "Bis (trimettiyiililyl) -iri-» methyldieilanyl, Pentamethoxydieilanylt PentaffletixoxydieiXoxanyl,The simplest representatives of the substituents with Si — HBi- or S-Si bonds are pentamethyldieilanyl, 1 -IrimethylsiXyl-tetramethyldieilasa ^ i ,, 1 "bis (trimettiyiililyl) -iri-» methyldieilanyl, pentamethoxydieilanyl pentaffletixoxydieiXoxanyl,
j 1-Bia (ti-imethoxysilyi)-trinethoxydisiloxanyl. Analoge Subetituenten enthalten ans belle von Methyl) gegebenenfalls teilweise, andere organische Beste wie sie tiiv R und R aufgezählt wtilti|n eind Wasserstoffatome oder PIuoratome. Gemäß der anfange iriähntenj 1-Bia (ti-imethoxysilyi) -trinethoxydisiloxanyl. Analogous substituents may contain, instead of methyl), some other organic components such as those listed for R and R, and hydrogen atoms or fluorine atoms. According to the beginning
.Definition können diese Dlsilanyl- und Disiloxany!gruppen direkt an das Siliciumatom des MazasiXacycloalkanringes gebunden sein.These Dlsilanyl and Disiloxany! Groups can be defined directly be bound to the silicon atom of the MazasiXacycloalkanringes.
Die Silylgruppen können auch ala Substituenten an den Kohlenwasserstoffresten oder heterocyclischen Beeten vorkommen.The silyl groups can also have ala substituents on the Hydrocarbon residues or heterocyclic beds occur.
Einige einfache Repräsentanten der über ein Stickstoffatom gebundenen Silylgruppen sind: Irifluorsilylaminoy Trifluorsilylmethylamino, Bis(trimethylsilyl)amino, Srimethoxysilylamino, Trimethoxysilylmethylamino, Bie(trimethoxysilyl)amino» !Eriphenyleilylamino, Methyl-äiphenyisilylamlno, Bis(dimethyl-phenylsilyl) amino, Pentamethyldlsilanylamino, PentamethyIdieilazanylamino, Pentamethyldisiloxanylamino, Pentamethoxydiailanylamino, Pentamethoxydisilazanylamino und Pentamethoxydisiloxanylamino.Some simple representatives of the bonded via a nitrogen atom silyl groups are: Irifluorsilylaminoy Trifluorsilylmethylamino, bis (trimethylsilyl) amino, Srimethoxysilylamino, Trimethoxysilylmethylamino, Bie (trimethoxysilyl) amino "Eriphenyleilylamino, methyl äiphenyisilylamlno, bis (dimethyl-phenylsilyl) amino, Pentamethyldlsilanylamino, PentamethyIdieilazanylamino, Pentamethyldisiloxanylamino , Pentamethoxydiailanylamino, pentamethoxydisilazanylamino and pentamethoxydisiloxanylamino.
Weitere Stickstoff und Silicium enthaltende Substituenten können durch die allgemeinen Formeln -Si(R*)2-NH-SiR*, und -Sx(R*2)-IT-ausgedruckt werden.Further nitrogen and silicon-containing substituents can be expressed by the general formulas -Si (R *) 2 -NH-SiR *, and -Sx (R * 2 ) -IT-.
Auch diese Substituenten können durch ein Sauerstoff'- oder Stickstoffatom» gegebenenfalls über einen Kohlenwasserstoffrest oder heterocyclischen Rest, mit einem Siliciumatom der Ringeinheiten verbunden sein. Einige einfache Repräsentanten sind: Pentamethyldlsilany!amino, Pentsuaethyldisilazanyl, Pentamethy 1-disilazajiylamino und Pentamethyldisilaaaiioxye These substituents can also be linked to a silicon atom of the ring units through an oxygen or nitrogen atom, optionally via a hydrocarbon radical or heterocyclic radical. Some simple representatives are: pentamethyldlsilany! Amino, pentsuaethyldisilazanyl, pentamethyl 1-disilazajiylamino and pentamethyldisilaaaiioxy e
Die erfindungagemäi3en Produkte sind wertvolle Zwischenprodukte, well die an ilen Kettenenden befindlichen Halogenatome in an sichThe products of the invention are valuable intermediate products, well the halogen atoms located at the ends of the chain in per se
v 0 09812/176 Ö v 0 09812/176 Ö
BAD ORiGlNALORIGlNAL BATHROOM
bekannter V/eiee gegen zahlreiche organische Reste ausgetauscht werden können. Bei Auswahl der entsprecher3@n Reste in den Ausgangsverbindungen und für den Ersatz der Halogenatome in den Endprodukten kann man Produkte erhalten* die in einem weiten Temperaturbereich flüssig und außerordentlich temperaturbeständig sind. Sie erfindungsgemäßen Produkte» in denen X ein Fluoratom ist, können direkt als hochtemperaturbeständige Flüssigkeiten für Hydrauliköle, Wärmeaustauscher, Schmiermittel und Oelzusätze verwendet werden.known species exchanged for numerous organic residues can be. When selecting the corresponding 3 @ n residues in the Starting compounds and for the replacement of the halogen atoms in the End products can be obtained products * which in a wide range Temperature range are liquid and extremely temperature resistant. You products according to the invention »in which X is a fluorine atom can be used directly as high-temperature-resistant fluids for hydraulic oils, heat exchangers, lubricants and oil additives be used.
Ebenfalls direkt verwendbar sind die höhermolekularen Bndprodukte. Die an den Kettenenden befindlichen Chloratome können durch Hydrolyse mit Wasser oder mit einem wässrigen organischen Lösungsmittel gegen Hydroxylgruppen getauscht werden. Durch Erhitzen, gegebenenfalls in Gegenwart eines mit Wasser ein Azeotrop bildenden Lösungsmittels, können diese Derivate, insbesondere die niederen Oligomeren, zu höhermolekularen Produkten weiterkondensiert werdenβ The higher molecular weight end products can also be used directly. The chlorine atoms at the chain ends can be exchanged for hydroxyl groups by hydrolysis with water or with an aqueous organic solvent. By heating, optionally in the presence of a solvent which forms an azeotrope with water, these derivatives, in particular the lower oligomers, can be further condensed to form higher molecular weight products β
Zu 120,1 g (2 Mol) Aetbylendiamin in 1000 ml Benzol gelöst werden bei Raumtemperatur 129 g (1 Mol) Dime thy ldi chlor si lan zugetropft. Anschließend wird während 1 Std, zum Rückfluss erhitzt, abge- . kühlt, weitere 85,1 g (0,66 Mol) auf einmal zugegeben und die Reaktionsmischung während einer weiteren Stunde zum Rückfluss erhitzt. Nach dem Abfiltrieren des Ghlorhydrates wird das Benzol unter vermindertem Druck abdestilliert und der Rückstand imTo 120.1 g (2 mol) of acetylenediamine are dissolved in 1000 ml of benzene 129 g (1 mol) of dimethyl chloride were added dropwise at room temperature. The mixture is then heated to reflux for 1 hour. cools, a further 85.1 g (0.66 mol) are added all at once and the reaction mixture is refluxed for a further hour heated. After filtering off the chlorohydrate, the benzene becomes distilled off under reduced pressure and the residue im
■' -"" . : '- ■■■ - - -^ ti . BAD ORIGINAL■ '- "". : '- ■■■ - - - ^ ti. BATH ORIGINAL
0098 12/176 00098 12/176 0
■- 19 >■ - 19>
Vakuum fraktioniert destilliert.Vacuum fractionally distilled.
Man erhält 4 Fraktionen! (Durclisol^u ■'jawerte sue 2 Versuchen)You get 4 factions! (Durclisol ^ u ■ 'jawerte sue 2 attempts)
I. 19»lg t*> ^I. 19 »lg t *> ^
Bila-cyclopeütaßf Sap, 87^9O0CZO,ImiaBila-cyclopeütaßf Sap, 87 ^ 9O 0 CZO, Imia
IX«46t4 g Dimeres Produkt; Sap. H8-15QQO/O»O5 Bm, farblosesIX «46 t 4 g of dimeric product; Sap. H8-15Q Q O / O »O5 Bm, colorless
20 : 20 :
leicht bewegliches OeI, η 1,4819*easily movable oil, η 1.4819 *
■ .. - ' - '. ■ ■■ D ..;■, :. ' ■. Analyse C1 ■ .. - '-'. ■ ■■ D ..; ■,:. '■. Analysis C 1
Ber. $ C 35,49 H"B,.08 N 11,82 Cl 14,96MoLGeW. 473,85 Ge?. $> C 35,94 H 7,93 H 11,62 Cl 14,40 Mol.Gew.Ber. $ C 35.49 H "B, .08 N 11.82 Cl 14.96 mol wt. 473.85 ge?. $> C 35.94 H 7.93 H 11.62 Cl 14.40 mol wt.
(Benzol)(Benzene)
III. 18,0 g Trimeres ProfiUkti Sdp, 225-227°Q/Qt% am, leicht gelbes, Ijewegliches OeI, ncu 1,487öIII. 18.0 g Trimeres ProfiUkti Sdp, 225-227 ° Q / Q t % am, slightly yellow, Ijewegliches OeI, n cu 1.487ö
Analyseanalysis
Ber.'g C 37,17 E 8,42 Ή 13,00 Cl 10,97 Mol.Gew.646,24 Gef* $ C 37,07 H 8,14 N 13,05 Cl 10,71 Hol,Gew.690Ber.'g C 37.17 E 8.42 Ή 13.00 Cl 10.97 mol. Wt. 646.24 Gef * $ C 37.07 H 8.14 N 13.05 Cl 10.71 Hol, wt. 690
(Benzol)(Benzene)
IV* 3,3 g Tetrameres Produkt} Sdp, 277-28Το0/0,,ΰ5 mm, gelbes,IV * 3.3 g tetrameric product} Sdp, 277-28Τ ο 0/0,, ΰ5 mm, yellow,
■ - · · Pci ■ - · · Pci
viskoses OeI, n"- 1,4910.viscous oil, n "- 1.4910.
Ber. i> 0 38,15 H 8t62 H 13S69 Cl 8,66 Mol.Gew. 818,6 % C 38,27 H 8,36 IT 13,49 Cl 8,76 Mol.Gew. 798Ber. i> 0 38.15 H 8 t 62 H 13 S 69 Cl 8.66 mole weight 818.6 % C 38.27 H 8.36 IT 13.49 Cl 8.76 mol wt. 798
00901^/1760 ν00901 ^ / 1760 ν
BADBATH
' In der folgenden Tabelle ist die Verteilung der Monomeren und Oligomeren in i» dargestellt. Das molare Verhältnis des Aethylendiarains zum DimethyldiChlorsilan ist variiert worden. Es wurde die gleiche Arbeitsweise wie in Beispiel 1 beschriebe», angewandt. Der Rückstand nach vollständiger Entfernung des Benzols wurde als 100 io angenommen. Die fehlende Menge, um nach der fraktionierung eine Ausbeute von 100 9δ zu erhalten, ist durch höhere Oligomere mit as 6 oder größer verursacht. Bei Verminderung der Dimethyldichlorsilanmenge in Bezug auf das Aethylendiarain erhöht eich die Menge der höheren Oiigomeren^Wie aus der Tabelle ersichtlich ist. Die höheren Oligomeren erleiden bei der Destillation eine weitere Kondensation, Eine teilweise Auftrennung ist z,B» durcix fraktionierte Ausfällung möglich»The following table shows the distribution of the monomers and oligomers in i » . The molar ratio of ethylenediarain to dimethyldichlorosilane has been varied. The same procedure as described in Example 1 was used. The residue after complete removal of the benzene was assumed to be 100 io. The lack of quantity to obtain a yield of 100 9δ after fractionation is caused by higher oligomers with as 6 or greater. When the amount of dimethyldichlorosilane is reduced in relation to the ethylenediarain, the amount of the higher oligomers increases, as can be seen from the table. The higher oligomers undergo further condensation during the distillation. Partial separation is possible, for example »by fractional precipitation»
Aethylendiamin/ DimethyldichlorsilanEthylenediamine / dimethyldichlorosilane
1,3-Bis-dimethylchlorsilyl-2,2-dimethyl-1,3,2-diazasilaeyelopentan $ Ausbeute (Durchschnittswerte aus1,3-bis-dimethylchlorosilyl-2,2-dimethyl-1,3,2-diazasilaeyelopentane $ Yield (averages from
2 Versuchen)2 attempts)
Um so viel als möglich Monomeree (η - 1.) eu erhalten, iei? es zwackmäßig, einen Überschuß an H&Iogensilan, z»B, einTo get as many monomers (η - 1.) eu as possible, iei? it Zack moderate, an excess of H & Iogensilan, z »B, a
008812/1780008812/1780
BAD ORSGlMALBAD ORSGlMAL
- 21 - ·- 21 -
von 1 : 2 zu verwenden. .„ _ ■ "of 1: 2 to be used. . "_ ■"
Pentameres Produkt} Sdp. 304~308oC/0,06 mm, braune wachsartige Substanz, die teilweise kristallieiert.Pentameric product} b.p. 304 ~ 308 o C / 0.06 mm, brown waxy substance that partially crystallizes.
Analyse C33H86N10Si1 Analysis C 33 H 86 N 10 Si 1
Ber. ^ C 38,87 H' 8,75 N 14,1-3 Mol,Gew. 991,0 Gef. <$> C 37,27 H 8,52 U-'. 14,39 Mol.Gew* 965Ber. ^ C 38.87 H '8.75 N 14.1-3 mol, wt. 991.0 found <$> C 37.27 H 8.52 U- '. 14.39 mole weight * 965
Zu 60,1 g (1 Mol) Aethylendiarain in 800 ml Benzol gelöst, werden bei Raumtemperatur tropfenweise 253»2 g (T Mol) Biphenyldichlorsiläa, in 200 ml Benzol gelöst, zugesetzt und die Reaktionsmischung während 2 Stunden zum Rückfluß erhitzt. Das Chlorhydrat wird abfiltriert. Nachdem das Benzol entfernt worden istr hinterbleibt ein gelblicher, polymerer Rückstand, der mit weiteren 10Ö g Diphenyldichlorsllan bei 150° bis 2000G. so lange erhitzt wird, bis die Abscheidung des Chlorhydrates vollständig ist (ca. 30 Minuten). Die abgekühlte Mischung wird mit 300 bis 400 mlBenzol erhitzt und das Hydrochlorid abfiltriert. Sas Flltrat wird so lange konzentriert, bis Kristall! abgeschieden werden. Hexan wird zugesetzt und die Kristalle abgetrenn-fct Ausbeute 220 g (98 ?6) j m.p, 218-2O0G (umkristallieiert in Hizan) * -'. -'To 60.1 g (1 mol) of ethylenediarain dissolved in 800 ml of benzene, 253 »2 g (T mol) of biphenyldichlorosiläa, dissolved in 200 ml of benzene, are added dropwise at room temperature and the reaction mixture is refluxed for 2 hours. The chlorohydrate is filtered off. After the benzene was removed r remains behind a yellowish polymeric residue which g with further 10Ö Diphenyldichlorsllan is heated at 150 ° to 200 0 G. until the deposition of the chlorine hydrate is complete (about 30 minutes). The cooled mixture is heated with 300 to 400 ml of benzene and the hydrochloride is filtered off. Sas Flltrat is concentrated until crystal! to be deposited. Hexane is added and the crystals are separated off. Yield 220 g (98.6) j mp, 218-2O 0 G (recrystallized in Hizane) * - '. - '
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH997965A CH486521A (en) | 1965-07-13 | 1965-07-13 | Process for the preparation of 1,3-disilyl-1,3,2-diazasilacycloalkanes |
| CH1184465 | 1965-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620017A1 true DE1620017A1 (en) | 1970-03-19 |
Family
ID=62527932
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620017 Pending DE1620017A1 (en) | 1965-07-13 | 1966-07-05 | 1,3-Disilyl-1,3.2-diazasilacycloalkanes and processes for their preparation |
| DE19661620025 Pending DE1620025A1 (en) | 1965-07-13 | 1966-08-04 | Process for the preparation of 1,3-disilyl-3,3,2-diazasilacycloalkanes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620025 Pending DE1620025A1 (en) | 1965-07-13 | 1966-08-04 | Process for the preparation of 1,3-disilyl-3,3,2-diazasilacycloalkanes |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH486521A (en) |
| DE (2) | DE1620017A1 (en) |
| GB (2) | GB1156881A (en) |
-
1965
- 1965-07-13 CH CH997965A patent/CH486521A/en not_active IP Right Cessation
-
1966
- 1966-07-05 DE DE19661620017 patent/DE1620017A1/en active Pending
- 1966-07-13 GB GB31411/66A patent/GB1156881A/en not_active Expired
- 1966-08-04 DE DE19661620025 patent/DE1620025A1/en active Pending
- 1966-08-19 GB GB37293/66A patent/GB1163425A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620025A1 (en) | 1970-02-19 |
| GB1156881A (en) | 1969-07-02 |
| CH486521A (en) | 1970-02-28 |
| GB1163425A (en) | 1969-09-04 |
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