JPS6346068B2 - - Google Patents
Info
- Publication number
- JPS6346068B2 JPS6346068B2 JP51072122A JP7212276A JPS6346068B2 JP S6346068 B2 JPS6346068 B2 JP S6346068B2 JP 51072122 A JP51072122 A JP 51072122A JP 7212276 A JP7212276 A JP 7212276A JP S6346068 B2 JPS6346068 B2 JP S6346068B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- represent
- alkenyl
- following formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 90
- -1 alkali metal cation Chemical class 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000000921 elemental analysis Methods 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 15
- 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 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 10
- ZTWMBHJPUJJJME-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)NC1=O ZTWMBHJPUJJJME-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical class NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- MEWMVMZALMGUJM-UHFFFAOYSA-N methyl(dipropoxy)silane Chemical compound CCCO[SiH](C)OCCC MEWMVMZALMGUJM-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- QJHLAWRHRBIINF-UHFFFAOYSA-N 1-(4-hydroxycyclohexyl)-3,4-dimethylpyrrole-2,5-dione Chemical compound O=C1C(C)=C(C)C(=O)N1C1CCC(O)CC1 QJHLAWRHRBIINF-UHFFFAOYSA-N 0.000 description 2
- HYAYPDUDDXSFBY-UHFFFAOYSA-N 1-amino-3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)N(N)C1=O HYAYPDUDDXSFBY-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 2
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000005048 methyldichlorosilane Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
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- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
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- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- NDPWCNORTYFYDW-UHFFFAOYSA-M triethyl(methyl)azanium;iodide Chemical compound [I-].CC[N+](C)(CC)CC NDPWCNORTYFYDW-UHFFFAOYSA-M 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
-
- 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
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/904—Monomer or polymer contains initiating group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH795175A CH599153A5 (en, 2012) | 1975-06-18 | 1975-06-18 | |
| CH1539075 | 1975-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS523055A JPS523055A (en) | 1977-01-11 |
| JPS6346068B2 true JPS6346068B2 (en, 2012) | 1988-09-13 |
Family
ID=25702497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51072122A Granted JPS523055A (en) | 1975-06-18 | 1976-06-18 | Imidyl compound and production thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4107174A (en, 2012) |
| JP (1) | JPS523055A (en, 2012) |
| CA (1) | CA1077490A (en, 2012) |
| DE (1) | DE2626795A1 (en, 2012) |
| FR (1) | FR2344536A1 (en, 2012) |
| GB (1) | GB1544840A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134970U (en, 2012) * | 1989-04-12 | 1990-11-08 | ||
| JPH0320959U (en, 2012) * | 1989-07-10 | 1991-02-28 |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH615912A5 (en, 2012) * | 1975-06-18 | 1980-02-29 | Ciba Geigy Ag | |
| CH619931A5 (en, 2012) * | 1976-08-12 | 1980-10-31 | Ciba Geigy Ag | |
| CH630089A5 (de) * | 1977-09-09 | 1982-05-28 | Ciba Geigy Ag | Verfahren zur herstellung von siliciummodifizierten imidyl-phthalsaeurederivaten. |
| JPS5472980U (en, 2012) * | 1977-10-28 | 1979-05-24 | ||
| DE2960956D1 (en) * | 1978-02-08 | 1981-12-24 | Ciba Geigy Ag | Tricyclic imide derivatives and process for their preparation |
| EP0003552B1 (de) * | 1978-02-08 | 1982-05-26 | Ciba-Geigy Ag | Unter der Einwirkung von Licht vernetzbare Polymere mit seitenständigen tricyclischen Imidylgruppen, ihre Herstellung und ihre Verwendung |
| CH641470A5 (de) | 1978-08-30 | 1984-02-29 | Ciba Geigy Ag | Imidgruppen enthaltende silane. |
| EP0014673B1 (de) * | 1979-01-30 | 1982-12-22 | Ciba-Geigy Ag | Durch Licht vernetzbare Polymere mit seitenständigen, sich vom Indenon ableitenden Gruppen, Herstellung und Verwendung derselben |
| US4331705A (en) * | 1979-05-11 | 1982-05-25 | Minnesota Mining And Manufacturing Company | Curing of polyamic acids or salts thereof by ultraviolet exposure |
| US4323701A (en) * | 1980-01-23 | 1982-04-06 | Ciba-Geigy Corporation | Process for the preparation of indenonecarboxylic acids |
| US4416975A (en) * | 1981-02-04 | 1983-11-22 | Ciba-Geigy Corporation | Photopolymerization process employing compounds containing acryloyl groups and maleimide groups |
| GB2101695B (en) * | 1981-07-10 | 1985-03-06 | British Gas Corp | Improvements in or relating to lubricated bearings |
| US4440850A (en) * | 1981-07-23 | 1984-04-03 | Ciba-Geigy Corporation | Photopolymerisation process with two exposures of a single layer |
| US4532332A (en) * | 1981-08-17 | 1985-07-30 | Ciba-Geigy Corporation | N-(hydroxypolyoxaalkylene)phthalimides and succinimides and acrylate esters thereof |
| EP0078233A1 (de) * | 1981-10-15 | 1983-05-04 | Ciba-Geigy Ag | Lichtempfindliches, Polymerbilder lieferndes Aufzeichnungsmaterial und Farbstoffe |
| US5367083A (en) * | 1987-09-03 | 1994-11-22 | The Boeing Company | Extended acid halide capping monomers |
| US5512676A (en) * | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5516876A (en) * | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| US5506060A (en) * | 1981-11-13 | 1996-04-09 | The Boeing Company | Method for making multidimensional ether or ester oligomers |
| US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| CH652729A5 (de) * | 1982-04-28 | 1985-11-29 | Ciba Geigy Ag | Lichtvernetzbare polymere mit seitenstaendigen thioaetherimidylgruppen. |
| US4656292A (en) * | 1982-05-19 | 1987-04-07 | Ciba-Geigy Corporation | 2,3-dimethylmaleimido-alkyl haloacetates |
| US4544621A (en) * | 1982-05-19 | 1985-10-01 | Ciba Geigy Corporation | Photocrosslinkable water-soluble polymers, containing maleimidyl and quaternary ammonium groups process for their preparation and use thereof |
| US4451971A (en) * | 1982-08-02 | 1984-06-05 | Fairchild Camera And Instrument Corporation | Lift-off wafer processing |
| US4552815A (en) * | 1982-10-01 | 1985-11-12 | Ciba Geigy Corporation | Prestressing elements coated with plastic material and process for making them |
| NL8303229A (nl) * | 1983-09-20 | 1985-04-16 | Dsm Resins Bv | Nieuwe maleimide-amide verbindingen en samenstellingen die deze bevatten, alsmede bereiding en toepassing daarvan. |
| US4481340A (en) * | 1982-12-03 | 1984-11-06 | Lourens Minnema | Photosensitive polyamic acid derivative, compound used in manufacture of derivative, method of manufacturing substrate having polyimide layer, and semiconductor device made from said method |
| DE3321157A1 (de) * | 1983-06-11 | 1984-12-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1h-pyrrol-2,5-dionen |
| US4542225A (en) * | 1984-08-29 | 1985-09-17 | Dana-Farber Cancer Institute, Inc. | Acid-cleavable compound |
| US4764368A (en) * | 1984-08-29 | 1988-08-16 | Dana-Farber Cancer Institute, Inc. | Acid-cleavable compound |
| US5082905A (en) * | 1984-09-18 | 1992-01-21 | The Boeing Company | Blended heterocycles |
| US5120819A (en) * | 1984-09-18 | 1992-06-09 | Boeing Company | High performance heterocycles |
| US4868270A (en) * | 1986-08-04 | 1989-09-19 | The Boeing Company | Heterocycle sulfone oligomers and blends |
| DE3443090A1 (de) * | 1984-11-27 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | Aromatische polyester mit dimethylmaleinimid-endgruppen, ihre herstellung und verwendung |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| FR2584069B1 (fr) * | 1985-07-01 | 1988-03-11 | Rhone Poulenc Spec Chim | Nouveaux maleimides et nouvelles compositions thermodurcissables les contenant. |
| US4654407A (en) * | 1985-08-02 | 1987-03-31 | Amoco Corporation | Aromatic bismaleimide and prepreg resin therefrom |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US5151487A (en) * | 1985-09-30 | 1992-09-29 | The Boeing Company | Method of preparing a crosslinking oligomer |
| US4935523A (en) * | 1985-09-30 | 1990-06-19 | The Boeing Company | Crosslinking imidophenylamines |
| US5087701A (en) * | 1985-09-30 | 1992-02-11 | The Boeing Company | Phthalimide acid halides |
| US4866185A (en) * | 1986-04-18 | 1989-09-12 | Ici Americas Inc. | Difunctional polyfluoroaromatic derivatives and a process of preparing the same |
| JPH0631226B2 (ja) * | 1986-05-01 | 1994-04-27 | 株式会社ヤマトヤ商会 | エポキシ化マレインイミド及びその製造方法 |
| EP0318162A3 (en) * | 1987-11-25 | 1990-11-07 | Texaco Development Corporation | Novel bismaleimide derivatives |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5021487A (en) * | 1988-05-27 | 1991-06-04 | Loctite Corporation | Thermally stabilized acrylic adhesive compositions and novel methacrylated malemide compounds useful therein |
| US5098982A (en) * | 1989-10-10 | 1992-03-24 | The B. F. Goodrich Company | Radiation curable thermoplastic polyurethanes |
| JP2627565B2 (ja) * | 1990-02-19 | 1997-07-09 | 富士写真フイルム株式会社 | 感光性平版印刷版 |
| US5196550A (en) * | 1990-04-30 | 1993-03-23 | The B. F. Goodrich Company | Maleimido group containing monomers |
| US5115037A (en) * | 1990-12-19 | 1992-05-19 | Monsanto Company | Hydrogenated cyclic alkyl polymers |
| US5208306A (en) * | 1991-03-25 | 1993-05-04 | The Dow Chemical Company | Mesogenic alkenyl functional maleimides and thermosets thereof |
| JPH05227952A (ja) * | 1991-04-05 | 1993-09-07 | Kuraray Co Ltd | ス−パ−オキシドジスムタ−ゼ誘導体 |
| US5446074A (en) * | 1993-12-17 | 1995-08-29 | International Business Machines Corporation | Photosensitive polyimide precursors |
| US6852814B2 (en) * | 1994-09-02 | 2005-02-08 | Henkel Corporation | Thermosetting resin compositions containing maleimide and/or vinyl compounds |
| US7645899B1 (en) | 1994-09-02 | 2010-01-12 | Henkel Corporation | Vinyl compounds |
| EP0813546B1 (en) * | 1995-03-07 | 2002-07-17 | Novartis AG | Photochemically cross-linked polysaccharide derivatives as supports for the chromatographic separation of enantiomers |
| US20080132695A1 (en) * | 1995-07-21 | 2008-06-05 | Eric Francotte | Cross-linked Polysaccharide Derivatives |
| EP0841353A1 (de) * | 1996-11-07 | 1998-05-13 | Witco GmbH | Verfahren zur Herstellung von polymeren Bindemitteln und deren Verwendung für Antifouling-Anstrichsysteme |
| EP1106659A1 (en) | 1999-12-03 | 2001-06-13 | Toagosei Co., Ltd. | Paint composition |
| CN100343305C (zh) * | 2002-12-31 | 2007-10-17 | 尼克塔治疗亚拉巴马公司 | 马来酰胺酸聚合物衍生物及其生物轭合物 |
| US9360759B2 (en) | 2014-09-12 | 2016-06-07 | Eastman Kodak Company | Forming conductive metal patterns using water-soluble polymers |
| JP6889873B2 (ja) * | 2018-11-21 | 2021-06-18 | 三菱瓦斯化学株式会社 | リソグラフィー用膜形成材料、リソグラフィー用膜形成用組成物、リソグラフィー用下層膜及びパターン形成方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2231905A (en) * | 1939-03-03 | 1941-02-18 | Du Pont | Aliphatic vinyl tertiary amides |
| US2686774A (en) * | 1951-08-31 | 1954-08-17 | Koppers Co Inc | Polymers and copolymers of nu-(dialkylamino aryl) imide of maleic and citraconic acids |
| US2727021A (en) * | 1951-10-30 | 1955-12-13 | American Cyanamid Co | Polymerizable and polymerized aminoethyl acrylate-acrylonitrile compositions |
| US2790787A (en) * | 1953-05-25 | 1957-04-30 | Us Rubber Co | Polymeric maleimide derivatives |
| US2743260A (en) * | 1953-05-25 | 1956-04-24 | Us Rubber Co | Polymeric methyeol maleimide and derivatives |
| US2958672A (en) * | 1956-11-19 | 1960-11-01 | Du Pont | Curing process for high molecular weight polymers involving the use of free radical generators and free radical acceptors and product thereof |
| US3265708A (en) * | 1961-03-01 | 1966-08-09 | Us Rubber Co | Nu-parahydroxyphenylmaleimide |
| US3151182A (en) * | 1961-03-17 | 1964-09-29 | Us Rubber Co | Nu-allyloxymethyl maleimide, and homopolymers and copolymers thereof |
| FR1317895A (en, 2012) * | 1961-03-21 | 1963-05-08 | ||
| US3129225A (en) * | 1961-06-07 | 1964-04-14 | Us Vitamin Pharm Corp | Novel 4-oxy-3-maleimidyl betaines |
| US3194812A (en) * | 1962-08-31 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-para amino-phenyl succinimide |
| GB1052137A (en, 2012) * | 1963-04-11 | |||
| US3301826A (en) * | 1964-04-24 | 1967-01-31 | Us Rubber Co | Vulcanizate of sulfur vulcanizable rubber with nu-maleimide derivatives |
| US3337583A (en) * | 1964-09-11 | 1967-08-22 | Squibb & Sons Inc | N-substituted maleimide compounds |
| US3397210A (en) * | 1966-01-17 | 1968-08-13 | Koppers Co Inc | Process for preparing maleimides using a solid phase acidic alumina-containing catalyst |
| US3465001A (en) * | 1966-03-31 | 1969-09-02 | Merck & Co Inc | Maleimido aryloxy alkanoic acids,alkyl esters and amides thereof |
| DE1288787B (de) * | 1966-09-08 | 1969-02-06 | Bayer Ag | Polyamidformmassen mit imidgruppenhaltigen Verbindungen als Entformungsmittel |
| US3337584A (en) * | 1967-01-06 | 1967-08-22 | Squibb & Sons Inc | N-substituted maleimide compounds |
| FR1594934A (en, 2012) * | 1968-12-05 | 1970-06-08 | ||
| US4045416A (en) * | 1971-01-21 | 1977-08-30 | Union Carbide Corporation | Amine acrylate addition reaction product compositions |
| DE2349948A1 (de) * | 1972-10-06 | 1974-05-02 | Agency Ind Science Techn | Neue photopolymere |
| US3948941A (en) * | 1973-10-26 | 1976-04-06 | Exxon Research And Engineering Company | Preparation of imides using CN- catalysts |
-
1976
- 1976-06-15 US US05/696,346 patent/US4107174A/en not_active Expired - Lifetime
- 1976-06-15 DE DE19762626795 patent/DE2626795A1/de active Granted
- 1976-06-16 CA CA255,016A patent/CA1077490A/en not_active Expired
- 1976-06-16 GB GB24963/76A patent/GB1544840A/en not_active Expired
- 1976-06-18 FR FR7618576A patent/FR2344536A1/fr active Granted
- 1976-06-18 JP JP51072122A patent/JPS523055A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134970U (en, 2012) * | 1989-04-12 | 1990-11-08 | ||
| JPH0320959U (en, 2012) * | 1989-07-10 | 1991-02-28 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2344536A1 (fr) | 1977-10-14 |
| CA1077490A (en) | 1980-05-13 |
| DE2626795A1 (de) | 1976-12-30 |
| DE2626795C2 (en, 2012) | 1991-08-08 |
| GB1544840A (en) | 1979-04-25 |
| US4107174A (en) | 1978-08-15 |
| FR2344536B1 (en, 2012) | 1981-01-23 |
| JPS523055A (en) | 1977-01-11 |
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