CA1055958A - Polyacrylamides containing silyl groups - Google Patents
Polyacrylamides containing silyl groupsInfo
- Publication number
- CA1055958A CA1055958A CA182,409A CA182409A CA1055958A CA 1055958 A CA1055958 A CA 1055958A CA 182409 A CA182409 A CA 182409A CA 1055958 A CA1055958 A CA 1055958A
- Authority
- CA
- Canada
- Prior art keywords
- silyl groups
- bis
- formula
- containing silyl
- radical
- 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.)
- Expired
Links
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 title claims abstract description 33
- 229920002401 polyacrylamide Polymers 0.000 title claims abstract description 20
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- NCVVWUXRTGEEOD-UHFFFAOYSA-N 3,3-bis(trimethylsilyl)prop-2-enamide Chemical compound C[Si](C)(C)C(=CC(=O)N)[Si](C)(C)C NCVVWUXRTGEEOD-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- SZKMQLSOCJEGGP-UHFFFAOYSA-N n-[[prop-2-enoyl(trimethylsilyl)amino]methyl]-n-trimethylsilylprop-2-enamide Chemical compound C=CC(=O)N([Si](C)(C)C)CN(C(=O)C=C)[Si](C)(C)C SZKMQLSOCJEGGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000004817 gas chromatography Methods 0.000 abstract description 5
- 238000004949 mass spectrometry Methods 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- -1 aralkyl radical Chemical class 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000006884 silylation reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
- 239000005051 trimethylchlorosilane Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 241001248539 Eurema lisa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 1
- OZSLNVMOKRIJKG-UHFFFAOYSA-N 1,3-dimethyl-1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)N(C)C(=O)N(C)[Si](C)(C)C OZSLNVMOKRIJKG-UHFFFAOYSA-N 0.000 description 1
- QMICENZLPUNUGH-UHFFFAOYSA-N 1,3-diphenyl-1,3-bis(trimethylsilyl)urea Chemical compound C=1C=CC=CC=1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=CC=CC=C1 QMICENZLPUNUGH-UHFFFAOYSA-N 0.000 description 1
- LLFPRAAWYLMXJE-UHFFFAOYSA-N 2,2-bis(triethylsilyl)acetamide Chemical compound CC[Si](CC)(CC)C(C(N)=O)[Si](CC)(CC)CC LLFPRAAWYLMXJE-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical compound CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 description 1
- WBINOCGONULFGY-UHFFFAOYSA-N 2-methyl-3,3-bis(triethylsilyl)prop-2-enamide Chemical compound C(C)[Si](CC)(CC)C(=C(C(=O)N)C)[Si](CC)(CC)CC WBINOCGONULFGY-UHFFFAOYSA-N 0.000 description 1
- NRWLIVSNUTZFSQ-UHFFFAOYSA-N 2-methyl-3-trimethylsilylprop-2-enamide Chemical compound C[Si](C)(C)C=C(C(=O)N)C NRWLIVSNUTZFSQ-UHFFFAOYSA-N 0.000 description 1
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 description 1
- UIGHARXPLDWFHA-UHFFFAOYSA-N 2-trimethylsilylphenol Chemical compound C[Si](C)(C)C1=CC=CC=C1O UIGHARXPLDWFHA-UHFFFAOYSA-N 0.000 description 1
- VBPANMIPLOLNQO-UHFFFAOYSA-N 3,3-bis(dipropoxysilyl)prop-2-enamide Chemical compound C(CC)O[SiH](OCCC)C(=CC(=O)N)[SiH](OCCC)OCCC VBPANMIPLOLNQO-UHFFFAOYSA-N 0.000 description 1
- WXHFSSRVIOCFIF-UHFFFAOYSA-N 3,3-bis(trimethoxysilyl)prop-2-enamide Chemical compound CO[Si](OC)(OC)C(=CC(=O)N)[Si](OC)(OC)OC WXHFSSRVIOCFIF-UHFFFAOYSA-N 0.000 description 1
- ZAWQXWZJKKICSZ-UHFFFAOYSA-N 3,3-dimethyl-2-methylidenebutanamide Chemical compound CC(C)(C)C(=C)C(N)=O ZAWQXWZJKKICSZ-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- MBRVKEJIEFZNST-UHFFFAOYSA-N 3-methyl-2-methylidenebutanoic acid Chemical compound CC(C)C(=C)C(O)=O MBRVKEJIEFZNST-UHFFFAOYSA-N 0.000 description 1
- YYNIIASHTJWCCN-UHFFFAOYSA-N 4-nitro-2,3,6-triphenylphenol Chemical compound C=1C=CC=CC=1C=1C(O)=C(C=2C=CC=CC=2)C=C([N+]([O-])=O)C=1C1=CC=CC=C1 YYNIIASHTJWCCN-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IVKTVSJBRPBZFZ-UHFFFAOYSA-N CC1=C(C(=C(C=C1)[Si](C)(C)C)[Si](C)(C)C)N Chemical compound CC1=C(C(=C(C=C1)[Si](C)(C)C)[Si](C)(C)C)N IVKTVSJBRPBZFZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 241000562429 Jamides Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- MQBIDSQPVADEHG-UHFFFAOYSA-N N-ethyl-2-methyl-3-trimethylsilylprop-2-enamide Chemical compound C[Si](C)(C)C=C(C(=O)NCC)C MQBIDSQPVADEHG-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229940117913 acrylamide Drugs 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- INXWKRGKKYNACQ-UHFFFAOYSA-N bromo(tridodecyl)silane Chemical compound CCCCCCCCCCCC[Si](Br)(CCCCCCCCCCCC)CCCCCCCCCCCC INXWKRGKKYNACQ-UHFFFAOYSA-N 0.000 description 1
- VSCMNSZBNLOXNR-UHFFFAOYSA-N bromo(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Br)C1=CC=CC=C1 VSCMNSZBNLOXNR-UHFFFAOYSA-N 0.000 description 1
- KDZANFSNYFDMFR-UHFFFAOYSA-N bromo-diethyl-methylsilane Chemical compound CC[Si](C)(Br)CC KDZANFSNYFDMFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- SXVYREKZKGKJIO-UHFFFAOYSA-N chloro(propoxy)silane Chemical compound CCCO[SiH2]Cl SXVYREKZKGKJIO-UHFFFAOYSA-N 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- RZVDZQLEAUDZLO-UHFFFAOYSA-N chloro-dimethyl-naphthalen-1-ylsilane Chemical compound C1=CC=C2C([Si](C)(Cl)C)=CC=CC2=C1 RZVDZQLEAUDZLO-UHFFFAOYSA-N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- FRCLVJBDJNNNGI-UHFFFAOYSA-N n,n-bis(trimethylsilyl)formamide Chemical compound C[Si](C)(C)N(C=O)[Si](C)(C)C FRCLVJBDJNNNGI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- QHUOBLDKFGCVCG-UHFFFAOYSA-N n-methyl-n-trimethylsilylacetamide Chemical compound CC(=O)N(C)[Si](C)(C)C QHUOBLDKFGCVCG-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UTXPCJHKADAFBB-UHFFFAOYSA-N tribenzyl(chloro)silane Chemical compound C=1C=CC=CC=1C[Si](CC=1C=CC=CC=1)(Cl)CC1=CC=CC=C1 UTXPCJHKADAFBB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/04—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F30/08—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1573172A CH578592A5 (OSRAM) | 1972-10-27 | 1972-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055958A true CA1055958A (en) | 1979-06-05 |
Family
ID=4411474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA182,409A Expired CA1055958A (en) | 1972-10-27 | 1973-10-02 | Polyacrylamides containing silyl groups |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4980189A (OSRAM) |
| CA (1) | CA1055958A (OSRAM) |
| CH (1) | CH578592A5 (OSRAM) |
| DE (1) | DE2353356A1 (OSRAM) |
| FR (1) | FR2204635B1 (OSRAM) |
| GB (1) | GB1441939A (OSRAM) |
| NL (1) | NL7314555A (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101231181B1 (ko) * | 2007-06-25 | 2013-02-07 | 남택인 | 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에의해 제조된 연질 콘텍트렌즈 |
| US8079703B2 (en) * | 2008-07-21 | 2011-12-20 | Novartis Ag | Silicone-containing polymeric materials with hydrolyzable groups |
| JP6170074B2 (ja) | 2012-02-09 | 2017-07-26 | ライフ テクノロジーズ コーポレーション | 親水性ポリマー粒子およびその製造方法 |
| WO2017004556A1 (en) | 2015-07-02 | 2017-01-05 | Life Technologies Corporation | Polymer substrates formed from carboxy functional acrylamide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595654A1 (de) * | 1966-07-26 | 1969-10-02 | Bayer Ag | Verfahren zur Herstellung von selbstvernetzbaren Polymerisaten mit N-Methyloltrialkylsilylaethergruppen |
-
1972
- 1972-10-27 CH CH1573172A patent/CH578592A5/xx not_active IP Right Cessation
-
1973
- 1973-10-02 CA CA182,409A patent/CA1055958A/en not_active Expired
- 1973-10-18 GB GB4866673A patent/GB1441939A/en not_active Expired
- 1973-10-23 NL NL7314555A patent/NL7314555A/xx not_active Application Discontinuation
- 1973-10-24 DE DE19732353356 patent/DE2353356A1/de active Pending
- 1973-10-26 FR FR7338247A patent/FR2204635B1/fr not_active Expired
- 1973-10-27 JP JP12115573A patent/JPS4980189A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH578592A5 (OSRAM) | 1976-08-13 |
| GB1441939A (en) | 1976-07-07 |
| FR2204635A1 (OSRAM) | 1974-05-24 |
| FR2204635B1 (OSRAM) | 1978-02-24 |
| DE2353356A1 (de) | 1974-05-09 |
| NL7314555A (OSRAM) | 1974-05-01 |
| JPS4980189A (OSRAM) | 1974-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4812588A (en) | Polyorganosiloxane-bridged bisbenzocyclobutene monomers | |
| US4581461A (en) | Maleated siloxane derivatives | |
| GB1573170A (en) | Halosilyl carbamates and preparation of isocyanates therefrom | |
| CA1055958A (en) | Polyacrylamides containing silyl groups | |
| US4841083A (en) | Ladder polysilanes | |
| US4105648A (en) | Crosslinked polyacrylamides containing silyl groups | |
| US4159383A (en) | N,N-Disubstituted acryl- and methacrylamides | |
| JPS63267791A (ja) | 環状シルエチニルポリマーの製造方法 | |
| CA1235137A (en) | Silylation process | |
| US4107196A (en) | N-tertiarybutyl organosilylamides | |
| JP2787343B2 (ja) | アゾ化合物 | |
| US3839387A (en) | Process for preparing n-trimethyl-silylacetamide | |
| US4758623A (en) | Trifluoroacetylation of unhindered primary and secondary amines and polymer-bound trifluoroacetylation reagents | |
| JPH0813821B2 (ja) | ビニルシラン化合物 | |
| JPH10182584A (ja) | エチレン性不飽和イソシアナートを製造する方法 | |
| KR20040029461A (ko) | α-할로엔아민 시약 | |
| AU2002323122A1 (en) | (Alpha)-haloenamine reagents | |
| JPS58206611A (ja) | トリアルキルシリルアセチレン類の重合方法 | |
| JPS63253090A (ja) | トリメチルシロキシ基含有シリル（メタ）アクリレ−ト | |
| JPS61286394A (ja) | オレフイン性シラザンの製造方法 | |
| JP2774362B2 (ja) | ジ（メタ）アクリロキシアルキル基を有するシロキサン化合物 | |
| JPH02250888A (ja) | α―トリフルオロメチルアクリル酸トリオルガノシリルメチルエステル | |
| SU1666462A1 (ru) | Способ получени аминоацилполимеров | |
| JPH0156083B2 (OSRAM) | ||
| SU1126577A1 (ru) | Способ получени полинитрилов и политиоцианатов |