NL8220418A - N-glycidyl-gesubstitueerde amideverbindingen. - Google Patents
N-glycidyl-gesubstitueerde amideverbindingen. Download PDFInfo
- Publication number
- NL8220418A NL8220418A NL8220418A NL8220418A NL8220418A NL 8220418 A NL8220418 A NL 8220418A NL 8220418 A NL8220418 A NL 8220418A NL 8220418 A NL8220418 A NL 8220418A NL 8220418 A NL8220418 A NL 8220418A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- methyl
- compounds
- substituted
- methylglycidyl
- Prior art date
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- -1 AMIDE COMPOUNDS Chemical class 0.000 title claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 3
- KYLWLAQWEGADAU-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(CC1OC1)CC1CO1 KYLWLAQWEGADAU-UHFFFAOYSA-N 0.000 claims description 3
- QHDYZRDITXKYFI-UHFFFAOYSA-N n-methyl-n-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound C=CC(=O)N(C)CC1CO1 QHDYZRDITXKYFI-UHFFFAOYSA-N 0.000 claims description 3
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 claims description 2
- TZVOXYUFAFSYPI-UHFFFAOYSA-N n,2-dimethyl-n-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound CC(=C)C(=O)N(C)CC1CO1 TZVOXYUFAFSYPI-UHFFFAOYSA-N 0.000 claims description 2
- XGSGNHHBZQDRSZ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)propanamide Chemical compound C1OC1CN(C(=O)CC)CC1CO1 XGSGNHHBZQDRSZ-UHFFFAOYSA-N 0.000 claims description 2
- VHNQBAQIWZCBQN-UHFFFAOYSA-N n-methyl-n-(oxiran-2-ylmethyl)acetamide Chemical compound CC(=O)N(C)CC1CO1 VHNQBAQIWZCBQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NMTOLIDBJZRQGJ-UHFFFAOYSA-N n-benzyl-n-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound C=1C=CC=CC=1CN(C(=O)C=C)CC1CO1 NMTOLIDBJZRQGJ-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 90
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000203 mixture Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 19
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000006467 substitution reaction Methods 0.000 description 16
- 125000005521 carbonamide group Chemical group 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 10
- 125000005577 anthracene group Chemical group 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 150000001470 diamides Chemical class 0.000 description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
- 229940080818 propionamide Drugs 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229950000688 phenothiazine Drugs 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000004450 alkenylene group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- NBCMPBXYXCYYCM-UHFFFAOYSA-N n-butyl-n-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound CCCCN(C(=O)C=C)CC1CO1 NBCMPBXYXCYYCM-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- YSBPNMOAQMQEHE-UHFFFAOYSA-N (2-methyloxiran-2-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(C)CO1 YSBPNMOAQMQEHE-UHFFFAOYSA-N 0.000 description 1
- JXQXQFZHCJIDRP-QHHAFSJGSA-N (e)-n-(oxiran-2-ylmethyl)-n-(2-phenylethyl)but-2-enamide Chemical compound C1OC1CN(C(=O)/C=C/C)CCC1=CC=CC=C1 JXQXQFZHCJIDRP-QHHAFSJGSA-N 0.000 description 1
- YUNOXMRWJCZRQI-HWKANZROSA-N (e)-n-ethyl-n-(oxiran-2-ylmethyl)but-2-enamide Chemical compound C/C=C/C(=O)N(CC)CC1CO1 YUNOXMRWJCZRQI-HWKANZROSA-N 0.000 description 1
- KZKZNTRZOKFXEN-OIXVIMQBSA-N (z)-2-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)but-2-enamide Chemical compound C1OC1CN(CC1OC1)C(=O)C(=C/C)/OCC1CO1 KZKZNTRZOKFXEN-OIXVIMQBSA-N 0.000 description 1
- JGDYDPGHXVFWIU-UPHRSURJSA-N (z)-n'-(oxiran-2-ylmethyl)but-2-enediamide Chemical compound NC(=O)\C=C/C(=O)NCC1CO1 JGDYDPGHXVFWIU-UPHRSURJSA-N 0.000 description 1
- XOQCINMUEFCOPA-UHFFFAOYSA-N 1,1,3,3-tetrakis(oxiran-2-ylmethyl)urea Chemical compound C1OC1CN(CC1OC1)C(=O)N(CC1OC1)CC1CO1 XOQCINMUEFCOPA-UHFFFAOYSA-N 0.000 description 1
- MMQCIBDBUNFKTQ-UHFFFAOYSA-N 1,2,2-trimethylcyclopentane-1,3-dicarboxamide Chemical compound CC1(C)C(C(N)=O)CCC1(C)C(N)=O MMQCIBDBUNFKTQ-UHFFFAOYSA-N 0.000 description 1
- HYYJOCXNESGFSB-UHFFFAOYSA-N 1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical class C1OC1CNCC1CO1 HYYJOCXNESGFSB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- QJTATFQHXUPTAP-UHFFFAOYSA-N 2,3,4-tribromobenzamide Chemical compound BrC1=C(C(=C(C(=O)N)C=C1)Br)Br QJTATFQHXUPTAP-UHFFFAOYSA-N 0.000 description 1
- KZKYRHRAVGWEAV-UHFFFAOYSA-N 2,3-dichlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1Cl KZKYRHRAVGWEAV-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- RXCAAWVVBSKSSR-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)propanamide Chemical compound C1OC1CN(CC1OC1)C(=O)C(C)OCC1CO1 RXCAAWVVBSKSSR-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RKWDBSSYCGTKHM-UHFFFAOYSA-N 2-bromobenzene-1,3-dicarboxamide Chemical compound BrC1=C(C(=O)N)C=CC=C1C(=O)N RKWDBSSYCGTKHM-UHFFFAOYSA-N 0.000 description 1
- GNIQTTVCYDGDIZ-UHFFFAOYSA-N 2-chloro-n,n-bis(oxiran-2-ylmethyl)acetamide Chemical compound C1OC1CN(C(=O)CCl)CC1CO1 GNIQTTVCYDGDIZ-UHFFFAOYSA-N 0.000 description 1
- FLUHPKQITFOOBC-UHFFFAOYSA-N 2-chloro-n,n-bis(oxiran-2-ylmethyl)prop-2-enamide Chemical compound C1OC1CN(C(=O)C(=C)Cl)CC1CO1 FLUHPKQITFOOBC-UHFFFAOYSA-N 0.000 description 1
- OEZPDHRXGCLGKB-UHFFFAOYSA-N 2-chloropropanamide Chemical compound CC(Cl)C(N)=O OEZPDHRXGCLGKB-UHFFFAOYSA-N 0.000 description 1
- FGFSHJRPXHNROK-UHFFFAOYSA-N 2-methyl-2-(phenoxymethyl)oxirane Chemical compound C=1C=CC=CC=1OCC1(C)CO1 FGFSHJRPXHNROK-UHFFFAOYSA-N 0.000 description 1
- FPFZKFZYQYTAHO-UHFFFAOYSA-N 2-methyl-2-[(2-methyloxiran-2-yl)methoxymethyl]oxirane Chemical class C1OC1(C)COCC1(C)CO1 FPFZKFZYQYTAHO-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 1
- ZKPAGIWPCLTTAD-UHFFFAOYSA-N 2-methyl-n-(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1NCC1OC1 ZKPAGIWPCLTTAD-UHFFFAOYSA-N 0.000 description 1
- CLKLLOQFHJTTNV-UHFFFAOYSA-N 2-methyl-n-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound CC(=C)C(=O)NCC1CO1 CLKLLOQFHJTTNV-UHFFFAOYSA-N 0.000 description 1
- XPYFMWUZBCWIJA-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)benzamide Chemical compound C=1C=C(OCC2OC2)C=CC=1C(=O)N(CC1OC1)CC1CO1 XPYFMWUZBCWIJA-UHFFFAOYSA-N 0.000 description 1
- USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 101000997784 Cucurbita maxima Trypsin inhibitor 1 Proteins 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- FBOOJWGPJKVGRN-UHFFFAOYSA-N N-but-1-enyl-2-methyl-N-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound C(=CCC)N(C(C(=C)C)=O)CC1CO1 FBOOJWGPJKVGRN-UHFFFAOYSA-N 0.000 description 1
- BMPJLCARILTLJG-UHFFFAOYSA-N N-but-1-enyl-N-(oxiran-2-ylmethyl)formamide Chemical compound C(=CCC)N(C=O)CC1CO1 BMPJLCARILTLJG-UHFFFAOYSA-N 0.000 description 1
- ALFOHYZFXWKJRF-UHFFFAOYSA-N N-decyl-N-(oxiran-2-ylmethyl)but-2-enamide Chemical compound C(CCCCCCCCC)N(C(C=CC)=O)CC1CO1 ALFOHYZFXWKJRF-UHFFFAOYSA-N 0.000 description 1
- ZCDVPIYNHAVMEL-UHFFFAOYSA-N N-hexyl-N-(oxiran-2-ylmethyl)dec-2-enamide Chemical compound C(CCCCC)N(C(C=CCCCCCCC)=O)CC1CO1 ZCDVPIYNHAVMEL-UHFFFAOYSA-N 0.000 description 1
- DSTUVFVLGSUIBM-UHFFFAOYSA-N N-methyl-N-(oxiran-2-ylmethyl)dec-2-enamide Chemical compound CN(C(C=CCCCCCCC)=O)CC1CO1 DSTUVFVLGSUIBM-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 238000006434 Ritter amidation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000006270 aryl alkenylene group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- VDBXLXRWMYNMHL-UHFFFAOYSA-N decanediamide Chemical compound NC(=O)CCCCCCCCC(N)=O VDBXLXRWMYNMHL-UHFFFAOYSA-N 0.000 description 1
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical class CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- IJKJMNOJSYDDMT-UHFFFAOYSA-N hept-2-ynamide Chemical compound CCCCC#CC(N)=O IJKJMNOJSYDDMT-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- SGJPLFYHNLROIO-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-2-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1C(=C)C(=O)N(CC1OC1)CC1CO1 SGJPLFYHNLROIO-UHFFFAOYSA-N 0.000 description 1
- FRVGELNPABKJEP-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)butanamide Chemical compound C1OC1CN(C(=O)CCC)CC1CO1 FRVGELNPABKJEP-UHFFFAOYSA-N 0.000 description 1
- FOCVVPMDFNTBGC-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)formamide Chemical compound C1OC1CN(C=O)CC1CO1 FOCVVPMDFNTBGC-UHFFFAOYSA-N 0.000 description 1
- UANNYTGIANOGIN-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)-n-(2-phenylethyl)acetamide Chemical compound C1OC1CN(C(=O)C)CCC1=CC=CC=C1 UANNYTGIANOGIN-UHFFFAOYSA-N 0.000 description 1
- MERIEQHLDYSVSR-UHFFFAOYSA-N n-[[2-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C(=CC=CC=1)CN(CC1OC1)CC1OC1)CC1CO1 MERIEQHLDYSVSR-UHFFFAOYSA-N 0.000 description 1
- GAVMDASBCQSYHZ-UHFFFAOYSA-N n-benzyl-n-(oxiran-2-ylmethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(CC=1C=CC=CC=1)CC1CO1 GAVMDASBCQSYHZ-UHFFFAOYSA-N 0.000 description 1
- BLBCLPDAIPRBSH-UHFFFAOYSA-N n-benzyl-n-(oxiran-2-ylmethyl)formamide Chemical compound C=1C=CC=CC=1CN(C=O)CC1CO1 BLBCLPDAIPRBSH-UHFFFAOYSA-N 0.000 description 1
- CJCUAFCCYLXLMG-UHFFFAOYSA-N n-butyl-n-(oxiran-2-ylmethyl)propanamide Chemical compound CCCCN(C(=O)CC)CC1CO1 CJCUAFCCYLXLMG-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- DZZUIPUQCRTAPL-UHFFFAOYSA-N n-methyl-n-(oxiran-2-ylmethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC1CO1 DZZUIPUQCRTAPL-UHFFFAOYSA-N 0.000 description 1
- JLPURIICJAIFGA-UHFFFAOYSA-N n-methyl-n-(oxiran-2-ylmethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)N(C)CC1CO1 JLPURIICJAIFGA-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18553481A JPS5888373A (ja) | 1981-11-20 | 1981-11-20 | Ｎ−グリシジル置換アミド化合物 |
| JP18553481 | 1981-11-20 | ||
| JP12588682A JPS5916883A (ja) | 1982-07-21 | 1982-07-21 | Ｎ−２−メチルグリシジル置換アミド化合物 |
| JP12588682 | 1982-07-21 | ||
| JP8200443 | 1982-11-19 | ||
| PCT/JP1982/000443 WO1983001776A1 (en) | 1981-11-20 | 1982-11-19 | N-glycidyl-substituted amide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8220418A true NL8220418A (nl) | 1983-10-03 |
Family
ID=26462189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8220418A NL8220418A (nl) | 1981-11-20 | 1982-11-19 | N-glycidyl-gesubstitueerde amideverbindingen. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0094436B1 (de) |
| AU (1) | AU556551B2 (de) |
| CH (1) | CH655720A5 (de) |
| DE (1) | DE3249185T1 (de) |
| GB (1) | GB2141703B (de) |
| NL (1) | NL8220418A (de) |
| WO (1) | WO1983001776A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60193979A (ja) * | 1984-03-15 | 1985-10-02 | Mitsui Toatsu Chem Inc | Ν−（ω−グリシドキシアルキル）置換アミド化合物及びその製造方法 |
| US7300986B2 (en) | 2001-10-12 | 2007-11-27 | Dow3Global Technologies Inc. | Polyepoxy compounds having an amide linkage |
| KR20050035137A (ko) * | 2001-10-12 | 2005-04-15 | 다우 글로벌 테크놀로지스 인크. | 아미드 연결기를 보유하는 폴리에폭시 화합물 |
| CN111909117B (zh) * | 2020-08-28 | 2022-05-03 | 南京林业大学 | 一种苯酐二异丙醇酰胺类环氧树脂及其制备方法与应用 |
| TWI891825B (zh) * | 2021-06-25 | 2025-08-01 | 奇美實業股份有限公司 | 液晶配向劑、液晶配向膜及液晶顯示元件 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2131120A (en) * | 1934-11-01 | 1938-09-27 | Ig Farbenindustrie Ag | Manufacture of organic compounds containing basic substituents |
| US2730531A (en) * | 1953-03-03 | 1956-01-10 | Shell Dev | Amides of epoxyamines |
| US3904658A (en) * | 1970-09-25 | 1975-09-09 | Ciba Geigy Ag | N,n'-diglycidyl-dicarboxylic acid dianilides |
| US3931058A (en) * | 1970-09-25 | 1976-01-06 | Ciba-Geigy Ag | Polyglycidyl compounds, processes for their manufacture and use |
| CH545284A (de) * | 1970-09-25 | 1973-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Polyglycidylverbindungen und deren Verwendung |
| CH541552A (de) * | 1970-09-29 | 1973-09-15 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Polyglycidylverbindungen |
| JPS479048A (de) * | 1971-09-26 | 1972-05-11 | ||
| JPS477398A (de) * | 1971-09-29 | 1972-04-21 |
-
1982
- 1982-11-19 AU AU91270/82A patent/AU556551B2/en not_active Ceased
- 1982-11-19 NL NL8220418A patent/NL8220418A/nl not_active Application Discontinuation
- 1982-11-19 EP EP82903587A patent/EP0094436B1/de not_active Expired
- 1982-11-19 GB GB08317104A patent/GB2141703B/en not_active Expired
- 1982-11-19 CH CH4065/83A patent/CH655720A5/de not_active IP Right Cessation
- 1982-11-19 WO PCT/JP1982/000443 patent/WO1983001776A1/ja not_active Ceased
- 1982-11-19 DE DE823249185T patent/DE3249185T1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2141703A (en) | 1985-01-03 |
| AU9127082A (en) | 1983-06-01 |
| EP0094436A4 (de) | 1984-04-27 |
| EP0094436A1 (de) | 1983-11-23 |
| DE3249185C2 (de) | 1989-11-02 |
| DE3249185T1 (de) | 1983-11-17 |
| CH655720A5 (de) | 1986-05-15 |
| EP0094436B1 (de) | 1988-03-30 |
| GB2141703B (en) | 1986-04-23 |
| GB8317104D0 (en) | 1983-07-27 |
| AU556551B2 (en) | 1986-11-06 |
| WO1983001776A1 (en) | 1983-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |