KR20050043791A - 2급 및 3급 아미노-작용성 실란, 이미노오가노실란및/또는 이미도오가노실란의 제조방법 - Google Patents
2급 및 3급 아미노-작용성 실란, 이미노오가노실란및/또는 이미도오가노실란의 제조방법 Download PDFInfo
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- KR20050043791A KR20050043791A KR1020047007479A KR20047007479A KR20050043791A KR 20050043791 A KR20050043791 A KR 20050043791A KR 1020047007479 A KR1020047007479 A KR 1020047007479A KR 20047007479 A KR20047007479 A KR 20047007479A KR 20050043791 A KR20050043791 A KR 20050043791A
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- Prior art keywords
- compound
- carbon atoms
- hydrocarbon group
- hydrogen
- alkoxy
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- 238000000034 method Methods 0.000 title claims description 27
- 150000004756 silanes Chemical class 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229910000077 silane Inorganic materials 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- -1 organo imine compound Chemical class 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract description 5
- 230000002829 reductive effect Effects 0.000 abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 abstract description 4
- 125000003277 amino group Chemical group 0.000 abstract 1
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- 239000000376 reactant Substances 0.000 abstract 1
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- 238000006722 reduction reaction Methods 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- 150000002576 ketones Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 150000003949 imides Chemical class 0.000 description 8
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 7
- CDRHUURBSOCCDK-UHFFFAOYSA-N 1-phenyl-n-(3-triethoxysilylpropyl)methanimine Chemical compound CCO[Si](OCC)(OCC)CCCN=CC1=CC=CC=C1 CDRHUURBSOCCDK-UHFFFAOYSA-N 0.000 description 6
- 239000002318 adhesion promoter Substances 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 5
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- 230000001588 bifunctional effect Effects 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- MDWZOAUWADLKNG-UHFFFAOYSA-N 1-phenyl-n-(3-trimethoxysilylpropyl)methanimine Chemical compound CO[Si](OC)(OC)CCCN=CC1=CC=CC=C1 MDWZOAUWADLKNG-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 125000004416 alkarylalkyl group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- UVEWQKMPXAHFST-SDNWHVSQSA-N chembl1256376 Chemical group C=1C=CC=CC=1/C=N/C1=CC=CC=C1 UVEWQKMPXAHFST-SDNWHVSQSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 239000013466 adhesive and sealant Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 150000004658 ketimines Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QLBIJVOHMKFIQB-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanimine Chemical compound CO[Si](OC)(OC)CCCN=C1CCCCC1 QLBIJVOHMKFIQB-UHFFFAOYSA-N 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N 1-methylpyrrolidine-2,5-dione Chemical compound CN1C(=O)CCC1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GVDZNWFGNHAZCX-UHFFFAOYSA-N 1-phenyl-n-propan-2-ylmethanimine Chemical compound CC(C)N=CC1=CC=CC=C1 GVDZNWFGNHAZCX-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 2-methylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C)C(=O)C2=C1 ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- BMZZGIWIRFMFOU-UHFFFAOYSA-N 4-cyclohexylidenebutan-1-amine Chemical group NCCCC=C1CCCCC1 BMZZGIWIRFMFOU-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
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- 238000010923 batch production Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
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- 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
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
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- XZRLSZCBYSWKMI-UHFFFAOYSA-N n-propan-2-ylcyclohexanimine Chemical compound CC(C)N=C1CCCCC1 XZRLSZCBYSWKMI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/990,959 US6586612B2 (en) | 2001-11-16 | 2001-11-16 | Process for the preparation of secondary and tertiary amino-functional silanes, iminoorganosilanes and/or imidoorganosilanes |
| US09/990,959 | 2001-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050043791A true KR20050043791A (ko) | 2005-05-11 |
Family
ID=25536688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020047007479A Ceased KR20050043791A (ko) | 2001-11-16 | 2002-11-04 | 2급 및 3급 아미노-작용성 실란, 이미노오가노실란및/또는 이미도오가노실란의 제조방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6586612B2 (https=) |
| EP (1) | EP1451198B1 (https=) |
| JP (1) | JP4436678B2 (https=) |
| KR (1) | KR20050043791A (https=) |
| AU (1) | AU2002354009A1 (https=) |
| BR (1) | BR0214262A (https=) |
| DE (1) | DE60209541T2 (https=) |
| WO (1) | WO2003044026A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100845520B1 (ko) * | 2007-02-08 | 2008-07-10 | 연세대학교 산학협력단 | 이방성 도전필름용 코어하드볼의 제조방법 |
| US8132305B2 (en) | 2006-08-30 | 2012-03-13 | Samsung Electronics Co., Ltd. | Equipment and method for cutting package |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005056051A1 (de) | 2005-11-24 | 2007-05-31 | Wacker Chemie Ag | Verfahren zur Herstellung von beta-Ketocarbonyl-funktionellen Organosiliciumverbindungen |
| US7442821B2 (en) * | 2005-11-28 | 2008-10-28 | Momentive Performance Materials Inc. | Process for preparing unsaturated imidoalkoxysilanes |
| US20090165676A1 (en) * | 2007-12-26 | 2009-07-02 | E.I. Du Pont De Nemours And Company | Bis(n-silylalkyl)aspartimides and processes therefor |
| US20090203826A1 (en) * | 2008-02-13 | 2009-08-13 | Michael Joseph Rachita | Methods of making siloxy-imine functionalized rubbery polymers and uses thereof in rubber compositions for tires |
| US8022159B2 (en) | 2008-11-24 | 2011-09-20 | The Goodyear Tire & Rubber Company | Terminating compounds, polymers, and their uses in rubber compositions and tires |
| EP2544768A4 (en) * | 2010-03-11 | 2016-02-24 | Agency Science Tech & Res | MEDICINE FOR THE ADMINISTRATION OF CANCER RELIEF WITH IMPROVED CARGO |
| KR101460352B1 (ko) * | 2014-02-28 | 2014-11-10 | 동우 화인켐 주식회사 | 점착제 조성물 |
| TWI716333B (zh) * | 2015-03-30 | 2021-01-11 | 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 | 碳矽烷與氨、胺類及脒類之觸媒去氫耦合 |
| FR3050207B1 (fr) * | 2016-04-15 | 2018-04-06 | Ecole Superieure De Physique Et De Chimie Industrielles De La Ville De Paris | Composition de polymeres comprenant des silicones reticules a points de reticulation echangeables, procede de preparation et utilisations |
| SG11201811355XA (en) * | 2016-06-24 | 2019-01-30 | Jsr Corp | Method for producing modified conjugated diene-based polymer, modified conjugated diene-based polymer, polymer composition, crosslinked body, tire and compound |
| CN109563111B (zh) | 2016-07-15 | 2022-04-12 | 莫门蒂夫性能材料股份有限公司 | 使亚氨基官能的硅烷稳定化的方法 |
| JP6947084B2 (ja) * | 2018-03-05 | 2021-10-13 | 信越化学工業株式会社 | イミン構造含有オルガノキシシラン化合物の製造方法 |
| WO2021033164A1 (en) | 2019-08-20 | 2021-02-25 | Shpp Global Technologies B.V. | Poly(phenylene ether) based compatibilizing material |
| JP2024169858A (ja) * | 2023-05-26 | 2024-12-06 | 信越化学工業株式会社 | オルガノキシシリルアルキルアミノ基で置換されたシリル基を有するビスシリル化合物およびその製造方法、並びにこれを含む組成物および硬化物 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513996A (en) | 1947-12-19 | 1950-07-04 | Shell Dev | Reaction of a primary amine with an imine |
| US2582128A (en) | 1950-02-11 | 1952-01-08 | Rohm & Haas | Aldimines |
| US2942019A (en) * | 1956-10-12 | 1960-06-21 | Union Carbide Corp | Organosilicon methylideneamino compounds and process for producing the same |
| US3755354A (en) * | 1969-05-05 | 1973-08-28 | Gen Electric | Amide acid and imido-substituted organosilanes |
| SU353547A1 (ru) * | 1970-11-16 | 1977-07-25 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | Способ получени кремнийорганических аминов |
| US3681287A (en) * | 1971-03-03 | 1972-08-01 | Quaker Oats Co | Siliceous materials bound with resin containing organosilane coupling agent |
| US3737430A (en) * | 1971-03-03 | 1973-06-05 | Quaker Oats Co | N,n'-bis((tri(substituted))silylalkylene)-1,4-xylene-alpha,alpha'-diimine |
| US3681420A (en) * | 1971-03-03 | 1972-08-01 | Quaker Oats Co | N,n{40 -bis{8 tri (substituted)silylalkylene{9 -1,4-xylene-{60 ,{60 {40 -diimine |
| DE2525295C3 (de) | 1975-06-06 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Azomethinen |
| US4088668A (en) * | 1977-07-01 | 1978-05-09 | Merrell Toraude Et Compagnie | Acetylene derivatives |
| US4378250A (en) | 1981-07-31 | 1983-03-29 | Treadway Gerald D | Organosilicone coating compositions |
| DE3414877A1 (de) * | 1984-04-19 | 1985-10-24 | Henkel KGaA, 4000 Düsseldorf | Polyurethanzubereitungen mit inkorporiertem haftvermittler |
| JPH0616179B2 (ja) * | 1984-12-24 | 1994-03-02 | 富士ゼロックス株式会社 | 電子写真現像剤 |
| US4832748A (en) * | 1986-10-21 | 1989-05-23 | Toagosei Chemical Industry Co., Ltd. | Coating composition |
| JP3483999B2 (ja) * | 1995-09-14 | 2004-01-06 | 東レ・ダウコーニング・シリコーン株式会社 | プリプレグおよびガラス繊維強化樹脂成形物 |
| US5866262A (en) | 1995-10-16 | 1999-02-02 | Galic Maus Ventures | Fully-hydrolized ketimine silane/epoxide silane copolymer liquid hardcoating compositions and processes for dipcoating polycarbonate spectacle lenses |
| JP3831437B2 (ja) * | 1995-11-15 | 2006-10-11 | 東レ・ダウコーニング株式会社 | シランカップリング剤およびその製造方法 |
| JP2000514809A (ja) * | 1996-07-12 | 2000-11-07 | ジー．ディー．サール アンド カンパニー | キラルβ―アミノ酸の不斉合成 |
| US6072085A (en) | 1997-09-30 | 2000-06-06 | Massachusetts Institute Of Technology | Imine hydrosilylation, uses and reagents related thereto |
| JP3427742B2 (ja) | 1998-07-30 | 2003-07-22 | 信越化学工業株式会社 | 硬化性樹脂組成物及び接着剤 |
| US6191286B1 (en) * | 1998-08-26 | 2001-02-20 | Osi Specialties Inc. | Imidosilane compositions |
| JP3969101B2 (ja) * | 2001-01-31 | 2007-09-05 | 日立化成工業株式会社 | 封止用エポキシ樹脂成形材料及び電子部品装置 |
-
2001
- 2001-11-16 US US09/990,959 patent/US6586612B2/en not_active Expired - Lifetime
-
2002
- 2002-11-04 AU AU2002354009A patent/AU2002354009A1/en not_active Abandoned
- 2002-11-04 EP EP02789413A patent/EP1451198B1/en not_active Expired - Lifetime
- 2002-11-04 BR BR0214262-7A patent/BR0214262A/pt not_active IP Right Cessation
- 2002-11-04 KR KR1020047007479A patent/KR20050043791A/ko not_active Ceased
- 2002-11-04 WO PCT/US2002/035350 patent/WO2003044026A1/en not_active Ceased
- 2002-11-04 DE DE60209541T patent/DE60209541T2/de not_active Expired - Lifetime
- 2002-11-04 JP JP2003545663A patent/JP4436678B2/ja not_active Expired - Fee Related
-
2003
- 2003-06-10 US US10/458,036 patent/US6998499B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8132305B2 (en) | 2006-08-30 | 2012-03-13 | Samsung Electronics Co., Ltd. | Equipment and method for cutting package |
| KR100845520B1 (ko) * | 2007-02-08 | 2008-07-10 | 연세대학교 산학협력단 | 이방성 도전필름용 코어하드볼의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60209541T2 (de) | 2006-12-21 |
| DE60209541D1 (de) | 2006-04-27 |
| JP2005509682A (ja) | 2005-04-14 |
| BR0214262A (pt) | 2004-09-21 |
| JP4436678B2 (ja) | 2010-03-24 |
| EP1451198B1 (en) | 2006-03-01 |
| WO2003044026A1 (en) | 2003-05-30 |
| EP1451198A1 (en) | 2004-09-01 |
| US20030220513A1 (en) | 2003-11-27 |
| US6998499B2 (en) | 2006-02-14 |
| AU2002354009A1 (en) | 2003-06-10 |
| US6586612B2 (en) | 2003-07-01 |
| US20030097014A1 (en) | 2003-05-22 |
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