JPH0524142B2 - - Google Patents
Info
- Publication number
- JPH0524142B2 JPH0524142B2 JP13829884A JP13829884A JPH0524142B2 JP H0524142 B2 JPH0524142 B2 JP H0524142B2 JP 13829884 A JP13829884 A JP 13829884A JP 13829884 A JP13829884 A JP 13829884A JP H0524142 B2 JPH0524142 B2 JP H0524142B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- isocyanate
- reaction
- hydroxyl
- 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 - Lifetime
Links
- -1 Carbamate ester Chemical class 0.000 claims description 76
- 239000012948 isocyanate Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001302 tertiary amino group Chemical group 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 238000007259 addition reaction Methods 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- 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 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 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
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- FLLHZLOYVPKTTJ-UHFFFAOYSA-N dibenzyl tetrasulphide Natural products C=1C=CC=CC=1CSSSSCC1=CC=CC=C1 FLLHZLOYVPKTTJ-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VKKTUDKKYOOLGG-UHFFFAOYSA-N 1-(diethylamino)propan-1-ol Chemical compound CCC(O)N(CC)CC VKKTUDKKYOOLGG-UHFFFAOYSA-N 0.000 description 1
- AOTFMTHVPXAIEJ-UHFFFAOYSA-N 1-(n-methylanilino)ethanol Chemical compound CC(O)N(C)C1=CC=CC=C1 AOTFMTHVPXAIEJ-UHFFFAOYSA-N 0.000 description 1
- NOGZHGRZRLPDMX-UHFFFAOYSA-N 1-(n-methylanilino)propan-1-ol Chemical compound CCC(O)N(C)C1=CC=CC=C1 NOGZHGRZRLPDMX-UHFFFAOYSA-N 0.000 description 1
- PXMOPWBGTCWBRS-UHFFFAOYSA-N 1-[2-(diethylamino)ethoxy]propan-1-ol Chemical compound CCC(O)OCCN(CC)CC PXMOPWBGTCWBRS-UHFFFAOYSA-N 0.000 description 1
- UTVIFPWRUNMEHM-UHFFFAOYSA-N 1-[2-(dimethylamino)ethoxy]propan-1-ol Chemical compound CCC(O)OCCN(C)C UTVIFPWRUNMEHM-UHFFFAOYSA-N 0.000 description 1
- AHZFVSZAGIRWAC-UHFFFAOYSA-N 1-[benzyl(ethyl)amino]ethanol Chemical compound CCN(C(C)O)CC1=CC=CC=C1 AHZFVSZAGIRWAC-UHFFFAOYSA-N 0.000 description 1
- SKUYVURWAOKGNB-UHFFFAOYSA-N 1-[benzyl(methyl)amino]ethanol Chemical compound CC(O)N(C)CC1=CC=CC=C1 SKUYVURWAOKGNB-UHFFFAOYSA-N 0.000 description 1
- XTDRUISJXKCLRO-UHFFFAOYSA-N 1-[ethyl(2-phenylethyl)amino]propan-1-ol Chemical compound CCC(O)N(CC)CCC1=CC=CC=C1 XTDRUISJXKCLRO-UHFFFAOYSA-N 0.000 description 1
- XXOLIEQZMLCJCA-UHFFFAOYSA-N 1-[ethyl(methyl)amino]propan-1-ol Chemical compound CCC(O)N(C)CC XXOLIEQZMLCJCA-UHFFFAOYSA-N 0.000 description 1
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical group CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 description 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 description 1
- GQERPJMMKFVYHE-UHFFFAOYSA-N 1-morpholin-4-ylpropan-1-ol Chemical compound CCC(O)N1CCOCC1 GQERPJMMKFVYHE-UHFFFAOYSA-N 0.000 description 1
- MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 description 1
- YIJAXVWJZJYWPI-UHFFFAOYSA-N 1-piperidin-1-ylpropan-1-ol Chemical compound CCC(O)N1CCCCC1 YIJAXVWJZJYWPI-UHFFFAOYSA-N 0.000 description 1
- SLRACUOCNBFRPC-UHFFFAOYSA-N 1-pyrrolidin-1-ylpropan-1-ol Chemical compound CCC(O)N1CCCC1 SLRACUOCNBFRPC-UHFFFAOYSA-N 0.000 description 1
- QFNXZXVIPZYRTF-UHFFFAOYSA-N 2-(dimethylamino)ethyl n-(2-methylprop-2-enoyl)carbamate Chemical compound CN(C)CCOC(=O)NC(=O)C(C)=C QFNXZXVIPZYRTF-UHFFFAOYSA-N 0.000 description 1
- AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- JEHFRMABGJJCPF-UHFFFAOYSA-N 2-methylprop-2-enoyl isocyanate Chemical compound CC(=C)C(=O)N=C=O JEHFRMABGJJCPF-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- REUJCMPVVNETJW-UHFFFAOYSA-N 6-tert-butyl-2-[(3-tert-butyl-2-hydroxy-6-methylphenyl)methyl]-3-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1CC1=C(C)C=CC(C(C)(C)C)=C1O REUJCMPVVNETJW-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- XQKRYBXCYCKQLL-UHFFFAOYSA-N dimethylaminomethanol Chemical compound CN(C)CO XQKRYBXCYCKQLL-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010801 sewage sludge Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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[Industrial Application Fields] The present invention relates to carbamate esters and their production methods, which have a wide range of uses as raw materials in the fields of organic synthesis and polymer production, particularly due to their excellent reactivity. [wherein R is a lower alkyl group (e.g. methyl,
A represents an organic group having a tertiary amino group (e.g., di(lower)alkylamino(lower)alkyl, di(lower)alkylaminophenyl, lower alkyl-phenylamino(lower)alkyl, lower Alkyl-phenyl (lower)
Alkylamino (lower) alkyl, pyrrolidino,
piperidino, morpholino, pyrrolidino(lower)alkyl, piperidino(lower)alkyl, morpholino(lower)alkyl, di(lower)alkylamino(lower)alkoxy(lower)alkyl, etc.). ] The present invention relates to a novel carbamate ester represented by the following and a method for producing the same. [Prior Art] Compounds having isocyanate groups are widely used in the field of polymer chemistry because of their excellent reactivity. In particular, compounds that have both a polymerizable carbon-carbon unsaturated group and an isocyanate group in the same molecule are used in a wide range of industrial technology fields because both of these functional groups participate in various reactions with different reaction mechanisms. I can do it. Focusing on such usefulness, the present inventors previously provided an isocyanate compound represented by the following formula [Patent Application No. 58-225226]
issue]: [In the formula, R has the same meaning as above. ]. The isocyanate symbol () is generally a stable liquid at room temperature and easy to handle. However, it not only has a polymerizable carbon-carbon unsaturated group and an isocyanate group in its molecule, but also has both of these functional groups. Since a carbonyl group exists between the groups adjacent to them, the activity of the carbon-carbon unsaturated group is increased, and the activity of the isocyanate group is also increased, and it is in a state where it can carry out various addition reactions. . That is, the isocyanate compound () can be used for various reactions based on the A part (conjugated double bond structure) and B part (acyl isocyanate structure) of the following formula, such as radical polymerization, anionic polymerization, dimerization, trimerization, polar addition, Active hydrogen addition, etc. can be carried out: Therefore, isocyanate compounds () are expected to have a wide range of uses as raw materials for industrial production. For example, the isocyanate compound () has the formula: Râ²OH (â²) [wherein Râ² represents a residue obtained by excluding the hydroxyl group from a hydroxyl compound. ] When reacted with a hydroxyl compound represented by the formula, the addition reaction proceeds preferentially between the isocyanate group of the former and the hydroxyl group of the latter, and the formula: [In the formula, R and R' have the same meanings as above. ] A carbamate ester represented by the following is obtained.
Therefore, isocyanate compounds () are generally useful as reagents for introducing polymerizable conjugated double bonds into hydroxyl compounds [Patent Application No.
No. 87606 (hereinafter referred to as "Application A")]. As mentioned above, isocyanate compounds ()
has the potential to carry out various reactions, so when the hydroxyl compound (') is reacted with it, in addition to and/or in place of the addition reaction between the isocyanate compound () and the hydroxyl compound ('), Isocyanate compounds ()
Dimerization, trimerization, multimerization (polymerization), etc.
Polymerization of the produced carbamate ester ('), amide form of the produced carbamate ester (')
It was predicted that various side reactions would proceed, such as the reaction between the NH group and the isocyanate compound (), but in reality, it was confirmed that essentially only the above addition reactions proceed preferentially at temperatures not exceeding 100°C. It was done. [Purpose of the Invention] By the way, the introduction of a polymerizable conjugated double bond using the isocyanate compound () according to the invention of Application A above is generally applicable to compounds having a hydroxyl group. When some kind of functional group is further present in the compound having the above, the possibility that some kind of side reaction originating from this functional group will proceed cannot be denied. Therefore, based on the invention of Application A, we will further develop this to determine whether side reactions will proceed with hydroxyl compounds in which such functional groups exist, and even if they do, whether it is possible to select conditions to avoid this. We conducted research on this topic. That is, a hydroxyl compound having a tertiary amino group was selected as a hydroxyl compound having a functional group, and research was conducted to clarify how the reaction with an isocyanate compound () proceeds. As a result, under the same conditions as the invention of Application A (100â
It has been found that the addition reaction between the hydroxyl group and the isocyanate group proceeds preferentially at a temperature not exceeding 100% (temperature not exceeding 100%) without being affected by any effects derived from the tertiary amino group. [Structure of the Invention] The gist of the present invention is to provide a carbamate represented by the formula () and an isocyanate compound represented by the formula (), and the formula: A-OH () [wherein A has the same meaning as above]. ] A process for producing a carbamate ester, characterized by reacting a hydroxyl compound represented by the following to obtain a carbamate ester represented by the formula (). Both isocyanate compounds () and hydroxyl compounds () have various functional groups and have the potential to carry out many reactions. Therefore, when the isocyanate compound () is reacted with the hydroxyl compound (), not only is there an addition reaction between the isocyanate compound () and the hydroxyl compound (), but also an addition reaction between the isocyanate compound () and the isocyanate compound (). Progress of various side reactions such as quantification, trimerization, multimerization (polymerization), polymerization of the produced carbamate ester (), and reaction between the amide NH group of the produced carbamate ester () and the isocyanate compound (). However, in reality, the addition reaction between the isocyanate group of the isocyanate compound () and the hydroxyl group of the hydroxyl compound () actually proceeds preferentially in a temperature range that does not exceed at least 100°C. confirmed. That is,
At a relatively low temperature not exceeding 100°C, only the desired reaction proceeds, and various predicted side reactions can be substantially avoided. According to the invention, carbamate ester ()
can be produced by reacting an isocyanate compound () with a hydroxyl compound (). Typical examples of hydroxyl compounds () include di(lower) alkylamino(lower) alkanols (e.g. dimethylamino methanol,
dimethylaminoethanol, dimethylaminopropanol, diethylaminoethanol, diethylaminopropanol, N-methyl-N-ethylaminopropanol), di(lower) alkylaminophenols (e.g. o-dimethylaminophenol, m-dimethylaminophenol, p-dimethylamino Phenol, m-diethylaminophenol), lower alkyl-phenylamino (lower)
Alkanols (e.g. N-methyl-N-phenylaminoethanol, N-methyl-N-phenylaminopropanol), lower alkyl-phenyl (lower) alkylamino (lower) alkanols (e.g. N-methyl-N-benzylaminoethanol) , N-ethyl-N-benzylaminoethanol, N-ethyl-N-phenethylaminopropanol), N-hydroxypyrrolidine, N-hydroxypiperidine, N-hydroxymorpholine,
pyrrolidino (lower) alkanols (e.g. pyrrolidinoethanol, pyrrolidinopropanol),
piperidino (lower) alkanols (e.g. piperidinoethanol, piperidinopropanol),
morpholino (lower) alkanols (e.g. morpholinoethanol, morpholinopropanol),
Examples include di(lower)alkylamino(lower)alkoxy(lower)alkanols (eg, dimethylaminoethoxyethanol, dimethylaminoethoxypropanol, diethylaminoethoxypropanol), atropine, and the like. If the hydroxyl compound () is liquid at room temperature, it can itself serve as a reaction medium;
Whether the hydroxyl compound () is a liquid or a solid, it is common to use an inert solvent. There are no particular restrictions on the inert solvent as long as it does not adversely affect the reaction, and various solvents can be used, including aliphatic hydrocarbons such as pentane, hexane, and heptane, aromatic solvents such as benzene, toluene, and xylene. Hydrocarbons, alicyclic hydrocarbons such as cyclohexane, methylcyclohexane and decalin, hydrocarbon solvents such as petroleum ether and petroleum benzine, carbon tetrachloride, chloroform,
Halogenated hydrocarbon solvents such as 1,2-dichloroethane, ether solvents such as ethyl ether, isopropyl ether, anisole, dioxane, and tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, acetophenone, and isophorone, acetic acid It may be appropriately selected from esters such as ethyl and butyl acetate, acetonitrile, dimethylformamide, dimethyl sulfoxide, and the like. These may be used alone or in mixtures. The reaction may generally be carried out at temperatures not exceeding 100°C, but it is particularly advantageous to carry out the reaction near room temperature (0-30°C) or under ice-cooling. If the temperature exceeds 100°C, side reactions may occur, while if the temperature is too low, the reaction rate will decrease, which is disadvantageous. Although the use of a tin-based catalyst may be considered during the reaction, the necessity of using a catalyst is usually not recognized. In addition, when carrying out the reaction, the hydroxyl compound () may be added to the isocyanate compound (), or the isocyanate compound () may be added to the hydroxyl compound ().
From the viewpoint of preventing the progress of side reactions, it is preferable to dissolve the hydroxyl compound () in an inert solvent, and then add a solution of the isocyanate compound () in an inert solvent little by little dropwise to the solution under ice cooling. [Operation and Effect] As is clear from the above explanation, the isocyanate group of the isocyanate compound () easily and selectively reacts with the hydroxyl group of the hydroxyl compound () to give the carbamate ester (). Carbamate ester obtained here ()
generally has high solubility and is soluble in most common organic solvents. In addition, when A is a dimethylaminoethyl group, for example, this product has various active structures or groups as shown in the formula below, so it is highly reactive, and therefore, it cannot be stored without polymerization. It is preferable to add inhibitors or store in a cool and dark place: In the above formula, the conjugated double bond structure A' has polymerization reactivity, and therefore the carbamate ester () can be used for producing homopolymers and copolymers. For example, it can be used to modify synthetic fibers, synthetic resins, natural polymers, etc. by graft polymerization, or it can be used by itself or with other polymerizable monomers (such as styrene, alkyl acrylates,
varnish by polymerizing with alkyl methacrylate),
Used in the production of paints, adhesives, plastics, elastomers, etc. In the polymerization, it is advantageous to use a radical polymerization catalyst such as azobisisobutyronitrile. Since the acyl urethane structure B' has high intermolecular cohesive force and intermolecular hydrogen bond forming ability, polymers obtained using carbamate ester () have excellent properties in terms of toughness, adhesion, and dispersibility. contribute to waste disposal. The tertiary amino group-containing structure C' is basic and highly reactive, or exhibits strong cationic properties when quaternized. Therefore, the reaction product obtained using carbamate ester (2) is highly water-soluble or hydrophilic, has good dyeability with acid dyes, and has reactivity or adsorption to anions. In addition, it exhibits cohesive properties against negative colloids such as sewage sludge and cellulose, has excellent electrical properties such as chargeability and conductivity, and has good adhesion and dispersibility. In this way, carbamate ester () is
It has a wide range of uses as a raw material for industrial production. In addition, the isocyanate compound () which is a raw material can be manufactured by the reaction of α-alkylacrylamide and oxalyl halide. The reaction is usually carried out in the presence of an inert solvent such as a halogenated hydrocarbon at a temperature of 0 to 80°C. In addition, in order to avoid unnecessary polymerization of terminal double bonds, a polymerization inhibitor may be present in the reaction system. Specific examples of polymerization inhibitors used here or during storage of the carbamate ester () are hydroquinone, p-methoxyphenol, 2,6-di-t-butyl-4-methylphenol, 4-t -butylcatechol, bisdihydroxybenzylbenzene, 2,2'-methylenebis(6-t-butyl-3-methylphenol), 4,
4'-Butyldenbis(6-t-butyl-3-methylphenol), 4,4'-thiobis(6-t-butyl-3-methylphenol), p-nitrosophenol, diisopropylxanthogen sulfide, N-nitro Sophenylhydroxylamineã»
Ammonium salt, 1,1-diphenyl-2-picrylhydrazyl, 1,3,5-triphenylferdazyl, 2,6-di-t-butyl-α-(3,
5-di-t-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-trioxy, 2,2,6,6-tetramethyl-4-piperidone-1-oxyl, dithiobenzoylsulfur phide, p, p'-ditolyltrisulfide, p, p'-
Examples include ditolyltetrasulfide, dibenzyltetrasulfide, and tetraethylthiuram disulfide. [Example] Examples are given below to specifically explain the method for producing carbamate ester (2). Example 1 N-methacryloylcarbamic acid dimethylaminoethyl ester dimethylaminoethylethanol 0.89g
(10 mmol) was dissolved in 20 ml of dry chloroform,
Ice cold. A solution of 1.11 g (10 mmol) of methacryloyl isocyanate in 5 ml of 1,2-dichloroethane was added dropwise to this solution in a nitrogen stream. After the dropwise addition, chloroform and 1,2-dichloroethane were distilled off under reduced pressure to obtain 2.00 g of N-methacryloylcarbamic acid dimethylaminoethyl ester. Recrystallization from benzene-hexane gives colorless needles with a melting point of 71-73°C. Examples 2-7 The compounds shown in Table 1 were obtained in essentially the same manner as in Example 1. The viscosity is a value measured at 25°C using an E-type viscometer EHD (for high viscosity) manufactured by Tokyo Keiki Co., Ltd.
ãè¡šããtableã
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ãã[Table] As understood from the above explanation, the present invention utilizes the technical idea of the invention of Application A described above in that a specific isocyanate compound () is used to introduce a polymerizable conjugated double bond into a hydroxyl compound. However, in that the target hydroxyl compound has an active group, that is, a tertiary amino group, in addition to a hydroxyl group, it can be said that the technical idea of the invention of Application A is further expanded.
Claims (1)
ããåºãæã€ãææ©åºã瀺ãã ã§è¡šããããã«ã«ããã³é žãšã¹ãã«ã ïŒ åŒïŒ åŒäžãã¯äœçŽã¢ã«ãã«åºã瀺ãã ã§è¡šããããã€ãœã·ã¢ããŒãååç©ãš åŒïŒ âOH åŒäžãã¯äžçŽã¢ããåºãæã€ãææ©åºã瀺
ãã ã§è¡šããããããããã·ã«ååç©ãåå¿ãã㊠åŒïŒ åŒäžãããã³ïŒ¡ã¯åèšãšåæ矩ã ã§è¡šããããã«ã«ããã³é žãšã¹ãã«ãåŸãããšã
ç¹åŸŽãšããã«ã«ããã³é žãšã¹ãã«ã®è£œæ³ã ïŒ åå¿ãäžæŽ»æ§æº¶åªäžã§å®æœããç¹èš±è«æ±ã®ç¯
å²ç¬¬ïŒé èšèŒã®è£œæ³ã[Claims] 1 Formula: [In the formula, R represents a lower alkyl group, and A represents an organic group having a tertiary amino group. ] Carbamate ester represented by. 2 formula: [In the formula, R represents a lower alkyl group. ] An isocyanate compound represented by the formula: A-OH [wherein A represents an organic group having a tertiary amino group. ] By reacting a hydroxyl compound represented by the formula: [In the formula, R and A have the same meanings as above. ] A method for producing a carbamate ester, characterized by obtaining a carbamate ester represented by the following. 3. The production method according to claim 2, wherein the reaction is carried out in an inert solvent.
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59138298A JPS6117554A (en) | 1984-07-03 | 1984-07-03 | Carbamic ester and its preparation |
AT85304739T ATE74349T1 (en) | 1984-07-03 | 1985-07-03 | ACRYLAMIDE DERIVATIVES. |
EP85304739A EP0177122B1 (en) | 1984-07-03 | 1985-07-03 | Acrylamide derivatives |
CA000486249A CA1310958C (en) | 1984-07-03 | 1985-07-03 | Physical property-improving reagent |
ES544849A ES8703831A1 (en) | 1984-07-03 | 1985-07-03 | New acrylamide derivs. |
KR1019850004779A KR930006196B1 (en) | 1984-07-03 | 1985-07-03 | Physical property-improving reagent |
DE8585304739T DE3585763D1 (en) | 1984-07-03 | 1985-07-03 | ACRYLAMIDE DERIVATIVES. |
ES552694A ES8704451A1 (en) | 1984-07-03 | 1986-03-05 | New acrylamide derivs. |
US07/058,782 US4935413A (en) | 1984-07-03 | 1987-06-05 | Carbamate physical property-improving reagent |
US07/486,864 US5354495A (en) | 1984-07-03 | 1990-03-01 | Alkenoylcarbamate compounds as elasticity, adhesion, and dispersibility enhancer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59138298A JPS6117554A (en) | 1984-07-03 | 1984-07-03 | Carbamic ester and its preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6117554A JPS6117554A (en) | 1986-01-25 |
JPH0524142B2 true JPH0524142B2 (en) | 1993-04-06 |
Family
ID=15218608
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59138298A Granted JPS6117554A (en) | 1984-07-03 | 1984-07-03 | Carbamic ester and its preparation |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6117554A (en) |
-
1984
- 1984-07-03 JP JP59138298A patent/JPS6117554A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6117554A (en) | 1986-01-25 |
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