JPS6353182B2 - - Google Patents
Info
- Publication number
- JPS6353182B2 JPS6353182B2 JP4765280A JP4765280A JPS6353182B2 JP S6353182 B2 JPS6353182 B2 JP S6353182B2 JP 4765280 A JP4765280 A JP 4765280A JP 4765280 A JP4765280 A JP 4765280A JP S6353182 B2 JPS6353182 B2 JP S6353182B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- vinylbenzyl
- compound
- acid
- compound represented
- 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 38
- -1 oxybis(dimethylene) group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000126 substance Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229960003237 betaine Drugs 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- CFAFEJHONLMPQY-UHFFFAOYSA-N 2-(dimethylazaniumyl)ethanesulfonate Chemical compound CN(C)CCS(O)(=O)=O CFAFEJHONLMPQY-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical class NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- CGQMSVZSAGRUJH-UHFFFAOYSA-N 1-(3-ethenylphenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(C=C)=C1 CGQMSVZSAGRUJH-UHFFFAOYSA-N 0.000 description 1
- FXLJHFCTYDFUER-UHFFFAOYSA-N 1-bromoprop-2-enylbenzene Chemical compound C=CC(Br)C1=CC=CC=C1 FXLJHFCTYDFUER-UHFFFAOYSA-N 0.000 description 1
- XOSWHKPBBJLUBE-UHFFFAOYSA-N 2-(1-phenylprop-2-enylamino)acetic acid Chemical compound OC(=O)CNC(C=C)C1=CC=CC=C1 XOSWHKPBBJLUBE-UHFFFAOYSA-N 0.000 description 1
- YPXRPPMJYNVONP-UHFFFAOYSA-N 2-(1-phenylprop-2-enylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC(C=C)C1=CC=CC=C1 YPXRPPMJYNVONP-UHFFFAOYSA-N 0.000 description 1
- OIXSOQOJISAETD-UHFFFAOYSA-N 2-(diethylamino)ethanesulfonic acid Chemical compound CCN(CC)CCS(O)(=O)=O OIXSOQOJISAETD-UHFFFAOYSA-N 0.000 description 1
- BMYCCWYAFNPAQC-UHFFFAOYSA-N 2-[dodecyl(methyl)azaniumyl]acetate Chemical compound CCCCCCCCCCCCN(C)CC(O)=O BMYCCWYAFNPAQC-UHFFFAOYSA-N 0.000 description 1
- TYYFOBPOUHHBNZ-UHFFFAOYSA-N 2-[dodecyl(methyl)azaniumyl]ethanesulfonate Chemical compound CCCCCCCCCCCCN(C)CCS(O)(=O)=O TYYFOBPOUHHBNZ-UHFFFAOYSA-N 0.000 description 1
- JCXVGKHPBDUOHN-UHFFFAOYSA-N 3-(1-phenylprop-2-enylamino)propanoic acid Chemical compound OC(=O)CCNC(C=C)C1=CC=CC=C1 JCXVGKHPBDUOHN-UHFFFAOYSA-N 0.000 description 1
- WVIVDMIARDUSDI-UHFFFAOYSA-N 3-(dibutylazaniumyl)propanoate Chemical compound CCCCN(CCCC)CCC(O)=O WVIVDMIARDUSDI-UHFFFAOYSA-N 0.000 description 1
- DIOYEFVIHLBWJX-UHFFFAOYSA-N 3-(diethylamino)propanoic acid Chemical compound CCN(CC)CCC(O)=O DIOYEFVIHLBWJX-UHFFFAOYSA-N 0.000 description 1
- KHCNLDMUKGVKDP-UHFFFAOYSA-N 3-[dodecyl(methyl)amino]propanoic acid Chemical compound CCCCCCCCCCCCN(C)CCC(O)=O KHCNLDMUKGVKDP-UHFFFAOYSA-N 0.000 description 1
- MALFKRUKALLGKG-UHFFFAOYSA-N 6-(diethylamino)hexanoic acid Chemical class CCN(CC)CCCCCC(O)=O MALFKRUKALLGKG-UHFFFAOYSA-N 0.000 description 1
- SWCSXNZBAVHUMT-UHFFFAOYSA-N 6-(dimethylamino)hexanoic acid Chemical class CN(C)CCCCCC(O)=O SWCSXNZBAVHUMT-UHFFFAOYSA-N 0.000 description 1
- FKDIYKIZGBVKNK-UHFFFAOYSA-N 6-[dodecyl(methyl)amino]hexanoic acid Chemical class CCCCCCCCCCCCN(C)CCCCCC(O)=O FKDIYKIZGBVKNK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYNZJZVQLMGGLB-UHFFFAOYSA-N C[N+](C)(CC([O-])=O)C(C=C)C1=CC=CC=C1 Chemical compound C[N+](C)(CC([O-])=O)C(C=C)C1=CC=CC=C1 OYNZJZVQLMGGLB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
- JMOXSQYGVIXBBZ-UHFFFAOYSA-N N,N-dimethyl-beta-alanine Chemical compound CN(C)CCC(O)=O JMOXSQYGVIXBBZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 108700003601 dimethylglycine Proteins 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- UGECPXXEZQMPHE-UHFFFAOYSA-N n,n-diethyl-1-phenylprop-2-en-1-amine Chemical compound CCN(CC)C(C=C)C1=CC=CC=C1 UGECPXXEZQMPHE-UHFFFAOYSA-N 0.000 description 1
- 229940078490 n,n-dimethylglycine Drugs 0.000 description 1
- LPUZAWOYVYGQIV-UHFFFAOYSA-N n-ethyl-n-methyl-1-phenylprop-2-en-1-amine Chemical compound CCN(C)C(C=C)C1=CC=CC=C1 LPUZAWOYVYGQIV-UHFFFAOYSA-N 0.000 description 1
- RYFQCJLCNVFPIK-UHFFFAOYSA-N n-octyl-n-(1-phenylprop-2-enyl)octan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)C(C=C)C1=CC=CC=C1 RYFQCJLCNVFPIK-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4765280A JPS56145250A (en) | 1980-04-10 | 1980-04-10 | Polymerizable quaternary ammonium compound |
| GB8111045A GB2075970B (en) | 1980-04-10 | 1981-04-08 | Polymerisable amino acid compounds and their production |
| DE19813114360 DE3114360A1 (de) | 1980-04-10 | 1981-04-09 | Polymerisierbare aminosaeureverbindungen und ihre herstellung |
| CA000375135A CA1161436A (en) | 1980-04-10 | 1981-04-09 | Polymerizable amino acid compounds and their production |
| US06/372,729 US4452746A (en) | 1980-04-10 | 1982-04-28 | Polymerizable amino acid compounds and their production |
| US06/594,826 US4543216A (en) | 1980-04-10 | 1984-03-29 | Polymerizable amino acid compounds and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4765280A JPS56145250A (en) | 1980-04-10 | 1980-04-10 | Polymerizable quaternary ammonium compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56145250A JPS56145250A (en) | 1981-11-11 |
| JPS6353182B2 true JPS6353182B2 (enrdf_load_stackoverflow) | 1988-10-21 |
Family
ID=12781176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4765280A Granted JPS56145250A (en) | 1980-04-10 | 1980-04-10 | Polymerizable quaternary ammonium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56145250A (enrdf_load_stackoverflow) |
-
1980
- 1980-04-10 JP JP4765280A patent/JPS56145250A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56145250A (en) | 1981-11-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2024505911A (ja) | アミド形成によるサルカプロジン酸の新規合成 | |
| IE41482B1 (en) | The preparation of esters of aminocarboxylic acids | |
| CN115340476B (zh) | 一种含氟三子季铵盐化合物及其制备方法和应用 | |
| EP2334635B1 (en) | Process for producing n-alkyl (alkyl)acrylamides | |
| CN110903344B (zh) | 一种四硅氧烷改性谷胱甘肽及其制备方法 | |
| JPS6353182B2 (enrdf_load_stackoverflow) | ||
| US4543216A (en) | Polymerizable amino acid compounds and their production | |
| JPS5973560A (ja) | 重合性スルホベタイン化合物ならびにその製法 | |
| JPS5838475B2 (ja) | 含フッ素界面活性剤 | |
| JPS6353181B2 (enrdf_load_stackoverflow) | ||
| JP4737788B2 (ja) | ポリビニルアミン塩とその用途 | |
| JPH04298533A (ja) | ポリ−γ−グルタミン酸グラフト化物の製造法 | |
| JPS5826906B2 (ja) | 重合性アミノ酸化合物 | |
| US3335167A (en) | beta-cyanoallylox ybenzene sulfonic acid and alkali metal salts thereof | |
| JP2520384B2 (ja) | ３，５―ジカルボキシベンゼンスルホン酸ホスホニウム塩の製造方法 | |
| JPH0469141B2 (enrdf_load_stackoverflow) | ||
| JPH03271265A (ja) | 新規アスパラギン酸誘導体及びその製造方法並びにその製造中間体 | |
| JP2979143B1 (ja) | カルボキシベタイン型構造を側鎖に有するアミノ酸重合体及びその製造方法 | |
| US4127732A (en) | Monomers and polymers containing the reactive aromatic system and method for their preparation | |
| CN119390687A (zh) | 一种含咪唑的氨基酸-n-硫代羧酸酐单体的制备和聚合方法 | |
| KR970001536B1 (ko) | 트리요오도벤젠 유도체의 제조방법 | |
| JPH09124567A (ja) | ２，２’−ジメチルイミノ二酢酸誘導体およびそのアルカリ金属塩を含む生分解性キレート剤とその製造方法 | |
| GB2179654A (en) | Acrylamido- and methacrylamido-n-disubstituted sulfonic acids | |
| RU1794941C (ru) | N(3-Нитро-4-хлорфенилсульфонил)-5-хлор-антранилова кислота в качестве промежуточного продукта дл получени N-(4-хлорфенил)-2(3-нитро-4-хлор-фенилсульфонил)амино-5-хлорбензамида, обладающего противотрихоцефалезной активностью | |
| US6437181B1 (en) | Method for producing (S,S)-N,N′-ethylenediaminedisuccinic acid, analogous compounds or salts thereof |