JP2009209112A - New gemini type phenol compound - Google Patents
New gemini type phenol compound Download PDFInfo
- Publication number
- JP2009209112A JP2009209112A JP2008056019A JP2008056019A JP2009209112A JP 2009209112 A JP2009209112 A JP 2009209112A JP 2008056019 A JP2008056019 A JP 2008056019A JP 2008056019 A JP2008056019 A JP 2008056019A JP 2009209112 A JP2009209112 A JP 2009209112A
- Authority
- JP
- Japan
- Prior art keywords
- phenol compound
- type phenol
- compound
- gemini type
- 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.)
- Granted
Links
- -1 phenol compound Chemical class 0.000 title claims abstract description 29
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 230000003712 anti-aging effect Effects 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000004597 plastic additive Substances 0.000 description 5
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- SHDKPHGPBNHILS-UHFFFAOYSA-N 1-chloroheptacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCl SHDKPHGPBNHILS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ALZARSJEJMWPOM-UHFFFAOYSA-N n,n'-didodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCCCCCCCCCCC ALZARSJEJMWPOM-UHFFFAOYSA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- RBBNTRDPSVZESY-UHFFFAOYSA-N 1,10-dichlorodecane Chemical compound ClCCCCCCCCCCCl RBBNTRDPSVZESY-UHFFFAOYSA-N 0.000 description 1
- SIBVHGAPHVRHMJ-UHFFFAOYSA-N 1,11-dibromoundecane Chemical compound BrCCCCCCCCCCCBr SIBVHGAPHVRHMJ-UHFFFAOYSA-N 0.000 description 1
- FFYJIEDNUOXZJY-UHFFFAOYSA-N 1,11-dichloroundecane Chemical compound ClCCCCCCCCCCCCl FFYJIEDNUOXZJY-UHFFFAOYSA-N 0.000 description 1
- ZJJATABWMGVVRZ-UHFFFAOYSA-N 1,12-dibromododecane Chemical compound BrCCCCCCCCCCCCBr ZJJATABWMGVVRZ-UHFFFAOYSA-N 0.000 description 1
- RNXPZVYZVHJVHM-UHFFFAOYSA-N 1,12-dichlorododecane Chemical compound ClCCCCCCCCCCCCCl RNXPZVYZVHJVHM-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- LBKDGROORAKTLC-UHFFFAOYSA-N 1,5-dichloropentane Chemical compound ClCCCCCCl LBKDGROORAKTLC-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- LVWSZGCVEZRFBT-UHFFFAOYSA-N 1,7-dibromoheptane Chemical compound BrCCCCCCCBr LVWSZGCVEZRFBT-UHFFFAOYSA-N 0.000 description 1
- PSEMXLIZFGUOGC-UHFFFAOYSA-N 1,7-dichloroheptane Chemical compound ClCCCCCCCCl PSEMXLIZFGUOGC-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WXYMNDFVLNUAIA-UHFFFAOYSA-N 1,8-dichlorooctane Chemical compound ClCCCCCCCCCl WXYMNDFVLNUAIA-UHFFFAOYSA-N 0.000 description 1
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 1
- JMGRNJZUQCEJDB-UHFFFAOYSA-N 1,9-dichlorononane Chemical compound ClCCCCCCCCCCl JMGRNJZUQCEJDB-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- QYOXLKAKUAASNA-UHFFFAOYSA-N 1-bromodocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCBr QYOXLKAKUAASNA-UHFFFAOYSA-N 0.000 description 1
- ABHHLNIVRZCBKH-UHFFFAOYSA-N 1-bromohenicosane Chemical compound [H]C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])Br ABHHLNIVRZCBKH-UHFFFAOYSA-N 0.000 description 1
- NKLFQHQMCURNDI-UHFFFAOYSA-N 1-bromoheptacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCBr NKLFQHQMCURNDI-UHFFFAOYSA-N 0.000 description 1
- HHSDZLLPIXMEIU-UHFFFAOYSA-N 1-bromoheptadecane Chemical compound CCCCCCCCCCCCCCCCCBr HHSDZLLPIXMEIU-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- CCSZHMUGOPQUDX-UHFFFAOYSA-N 1-bromohexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCBr CCSZHMUGOPQUDX-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- CZASMUMJSKOHFJ-UHFFFAOYSA-N 1-bromoicosane Chemical compound CCCCCCCCCCCCCCCCCCCCBr CZASMUMJSKOHFJ-UHFFFAOYSA-N 0.000 description 1
- GWESGLGUMMNXDU-UHFFFAOYSA-N 1-bromononadecane Chemical compound CCCCCCCCCCCCCCCCCCCBr GWESGLGUMMNXDU-UHFFFAOYSA-N 0.000 description 1
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- DDEOKNGWYRTQDY-UHFFFAOYSA-N 1-bromopentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCBr DDEOKNGWYRTQDY-UHFFFAOYSA-N 0.000 description 1
- JKOTZBXSNOGCIF-UHFFFAOYSA-N 1-bromopentadecane Chemical compound CCCCCCCCCCCCCCCBr JKOTZBXSNOGCIF-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- ZGPCRVNHYNSDIH-UHFFFAOYSA-N 1-bromotetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCBr ZGPCRVNHYNSDIH-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- SFVIZKWTUKBDIY-UHFFFAOYSA-N 1-bromotriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCBr SFVIZKWTUKBDIY-UHFFFAOYSA-N 0.000 description 1
- CUGDSQNIRNDFDX-UHFFFAOYSA-N 1-bromotricosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCBr CUGDSQNIRNDFDX-UHFFFAOYSA-N 0.000 description 1
- BFDNZQUBFCYTIC-UHFFFAOYSA-N 1-bromotridecane Chemical compound CCCCCCCCCCCCCBr BFDNZQUBFCYTIC-UHFFFAOYSA-N 0.000 description 1
- IKPSIIAXIDAQLG-UHFFFAOYSA-N 1-bromoundecane Chemical compound CCCCCCCCCCCBr IKPSIIAXIDAQLG-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- OACXFSZVCDOBKF-UHFFFAOYSA-N 1-chlorodocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCl OACXFSZVCDOBKF-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- LGRRXTJABQMXHY-UHFFFAOYSA-N 1-chlorohenicosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCl LGRRXTJABQMXHY-UHFFFAOYSA-N 0.000 description 1
- FGIOHOBVUCNHBY-UHFFFAOYSA-N 1-chloroheptadecane Chemical compound CCCCCCCCCCCCCCCCCCl FGIOHOBVUCNHBY-UHFFFAOYSA-N 0.000 description 1
- DZMDPHNGKBEVRE-UHFFFAOYSA-N 1-chloroheptane Chemical compound CCCCCCCCl DZMDPHNGKBEVRE-UHFFFAOYSA-N 0.000 description 1
- OMQRHANPZIOLFM-UHFFFAOYSA-N 1-chlorohexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCl OMQRHANPZIOLFM-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- AFGNVSCTEXUEJE-UHFFFAOYSA-N 1-chloroicosane Chemical compound CCCCCCCCCCCCCCCCCCCCCl AFGNVSCTEXUEJE-UHFFFAOYSA-N 0.000 description 1
- GQUCGTSGWMJXSA-UHFFFAOYSA-N 1-chlorononacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCl GQUCGTSGWMJXSA-UHFFFAOYSA-N 0.000 description 1
- ZPHKHTAJPZOPHM-UHFFFAOYSA-N 1-chlorononadecane Chemical compound CCCCCCCCCCCCCCCCCCCCl ZPHKHTAJPZOPHM-UHFFFAOYSA-N 0.000 description 1
- RKAMCQVGHFRILV-UHFFFAOYSA-N 1-chlorononane Chemical compound CCCCCCCCCCl RKAMCQVGHFRILV-UHFFFAOYSA-N 0.000 description 1
- VPEHIEKEZIRMSJ-UHFFFAOYSA-N 1-chlorooctacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCl VPEHIEKEZIRMSJ-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- BSXQWKIEASRPLY-UHFFFAOYSA-N 1-chloropentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCl BSXQWKIEASRPLY-UHFFFAOYSA-N 0.000 description 1
- WFDSCHJVWDKDFK-UHFFFAOYSA-N 1-chloropentadecane Chemical compound CCCCCCCCCCCCCCCCl WFDSCHJVWDKDFK-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- SUSHJBUUCQMSOK-UHFFFAOYSA-N 1-chlorotetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCl SUSHJBUUCQMSOK-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- VTFGODLCXIRDGH-UHFFFAOYSA-N 1-chlorotricosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCl VTFGODLCXIRDGH-UHFFFAOYSA-N 0.000 description 1
- ASZMYJSJEOGSBR-UHFFFAOYSA-N 1-chlorotridecane Chemical compound CCCCCCCCCCCCCCl ASZMYJSJEOGSBR-UHFFFAOYSA-N 0.000 description 1
- ZHKKNUKCXPWZOP-UHFFFAOYSA-N 1-chloroundecane Chemical compound CCCCCCCCCCCCl ZHKKNUKCXPWZOP-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 1
- HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 1
- ZRHQRWXPUVMKHW-UHFFFAOYSA-N BrCCCCCCCCCCCCCCCCCCCCCCCCCCCCC.BrCCCCCCCCCCCCCCCCCCCCCCCCCCCC Chemical compound BrCCCCCCCCCCCCCCCCCCCCCCCCCCCCC.BrCCCCCCCCCCCCCCCCCCCCCCCCCCCC ZRHQRWXPUVMKHW-UHFFFAOYSA-N 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 1
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- 239000000417 fungicide Substances 0.000 description 1
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- FUJXKFCTVKZXTJ-UHFFFAOYSA-N hexacosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCN FUJXKFCTVKZXTJ-UHFFFAOYSA-N 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QCENGKPIBJNODL-UHFFFAOYSA-N n'-dodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCN QCENGKPIBJNODL-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- QETVFNWBXURDPO-UHFFFAOYSA-N nonacosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCN QETVFNWBXURDPO-UHFFFAOYSA-N 0.000 description 1
- INAMEDPXUAWNKL-UHFFFAOYSA-N nonadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCN INAMEDPXUAWNKL-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- DZLRGXSUDHQIOZ-UHFFFAOYSA-N octacosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCN DZLRGXSUDHQIOZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
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- 229940100684 pentylamine Drugs 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- QHKIWQPIFXRUOW-UHFFFAOYSA-N tetracosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCN QHKIWQPIFXRUOW-UHFFFAOYSA-N 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- WFLJHDLVVWUGGZ-UHFFFAOYSA-N triacontan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN WFLJHDLVVWUGGZ-UHFFFAOYSA-N 0.000 description 1
- ASLXNOZOXWPTNG-UHFFFAOYSA-N tricosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCN ASLXNOZOXWPTNG-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明は新規ジェミニ型フェノール化合物に関する。 The present invention relates to a novel gemini-type phenol compound.
従来、フェノール化合物は酸化防止剤、耐熱安定剤、重合禁止剤、紫外線吸収剤等のプラスチック添加剤や、老化防止剤等のゴム添加剤、医薬品、界面活性剤、除草剤、殺虫剤、殺菌剤、可塑剤、安定剤等の中間物質、感熱記録媒体の顕色剤、電子材料、液晶材料等として用いられるフェノール樹脂原料等として利用され、例えば特許文献１にはフェノール誘導体がゴム老化防止剤として用いられることが記載され、特許文献２、３にはフェノール化合物を感熱記録媒体の顕色剤として用いる技術が開示されている。 Conventionally, phenol compounds are antioxidants, heat stabilizers, polymerization inhibitors, plastic additives such as UV absorbers, rubber additives such as anti-aging agents, pharmaceuticals, surfactants, herbicides, insecticides, fungicides. It is used as an intermediate material such as a plasticizer and a stabilizer, a developer for a heat-sensitive recording medium, a phenol resin raw material used as an electronic material, a liquid crystal material, etc. For example, in Patent Document 1, a phenol derivative is used as a rubber aging inhibitor. Patent Documents 2 and 3 disclose techniques using a phenol compound as a color developer for a thermal recording medium.
しかしながら従来のフェノール化合物からなるプラスチック添加剤、ゴム添加剤は、熱的安定性が乏しかったり、老化防止効果等が不十分であるという問題があった。また従来のフェノール化合物からなる顕色剤を用いた感熱記録媒体は、安定な発色性と良好な消色性とを有する可逆性感熱記録媒体であるが、顕色剤であるフェノール化合物は１分子あたり、４−ヒドロキシフェニル基を１個しか持たないためモル比で発色剤の３〜４倍もの顕色剤を添加しなければならなかった。
本発明者等は研究の結果、プラスチック添加剤、ゴム添加剤、顕色剤等としての利用が可能な、１分子当たり４−ヒドロキシフェニル基２個を有する新規ジェミニ型フェノール化合物を得ることに成功し、本発明を完成するに至った。
However, conventional plastic additives and rubber additives made of phenolic compounds have a problem of poor thermal stability and insufficient anti-aging effect. A conventional thermosensitive recording medium using a developer composed of a phenol compound is a reversible thermosensitive recording medium having stable color development and good decoloring properties. Since only one 4-hydroxyphenyl group is present, the developer had to be added 3 to 4 times as much as the color former in a molar ratio.
As a result of research, the present inventors have succeeded in obtaining a novel gemini-type phenol compound having two 4-hydroxyphenyl groups per molecule that can be used as a plastic additive, a rubber additive, a developer, and the like. Thus, the present invention has been completed.
即ち本発明は、下記一般式（１）で示される新規ジェミニ型フェノール化合物である。 That is, the present invention is a novel gemini-type phenol compound represented by the following general formula (1).
ジェミニ型化合物は、１鎖型化合物２分子がスペーサーを介して対象に結合した構造を有し、一般的に１鎖型化合物に比べて、熱的に安定であり、また分子同士が規則的な配列を組みやすいため、より大きな官能基効果が得られることが知られている。本発明の新規ジェミニ型フェノール化合物はジェミニ型の構造を持ち、且つ、主鎖に官能基を持つことにより、さらに分子の規則的配列及び熱的安定性が向上し、特に、酸化防止剤、耐熱安定剤、重合禁止剤、紫外線吸収剤等のプラスチック添加剤、老化防止剤等のゴム添加剤、感熱記録媒体の顕色剤分野に効果が期待される。また、酸化防止剤、重合防止剤、紫外線吸収剤、老化防止剤等としては、４−ヒドロキシフェニル基のパラ位にアミド、尿素基を有することで、電子受容性能の向上も期待される。
顕色剤の分野では、本発明の新規ジェミニ型フェノール化合物は、主鎖部分中にアミド基、尿素基等の水素結合性会合基を有する１鎖型フェノール化合物が、スペーサーを介して対象に結合したジェミニ型構造を有しているため、従来の１鎖型フェノール化合物に比べ、分子間凝集力への寄与が高まり、より規則的な分子集合構造をとって安定化するため、発色状態が安定し、画像保存性の向上が期待されるとともに、低い運動エネルギーでロイコ染料と作用でき、ロイコ染料の発色に大きなエネルギーを必要とせず、感熱記録媒体へのダメージが軽減される。また、従来のフェノール化合物からなる顕色剤に比べ、発色効率が向上し、半分程度のモル比で安定な発色性を有する可逆性感熱記録媒体を得ることが可能である。
Gemini-type compounds have a structure in which two molecules of a single-chain compound are bound to a target via a spacer, are generally more thermally stable than single-chain compounds, and the molecules are regular. It is known that a larger functional group effect can be obtained because the arrangement can be easily assembled. The novel gemini-type phenol compound of the present invention has a gemini-type structure and has a functional group in the main chain, so that the regular arrangement of molecules and thermal stability are further improved. It is expected to be effective in the field of color additives such as stabilizers, polymerization inhibitors, plastic additives such as UV absorbers, rubber additives such as anti-aging agents, and thermal recording media. Moreover, as an antioxidant, a polymerization inhibitor, an ultraviolet absorber, an anti-aging agent, and the like, an electron accepting performance is expected to be improved by having an amide or urea group at the para position of the 4-hydroxyphenyl group.
In the field of color developers, the novel gemini-type phenol compound of the present invention is a 1-chain type phenol compound having a hydrogen-bonding association group such as an amide group or a urea group in the main chain portion, which binds to the target via a spacer. Compared to conventional single-chain phenolic compounds, it contributes to intermolecular cohesion and is stabilized by taking a more regular molecular assembly structure, resulting in a stable colored state. In addition, an improvement in image storability is expected, and it can act with a leuco dye with low kinetic energy, so that a large amount of energy is not required for color development of the leuco dye, and damage to the heat-sensitive recording medium is reduced. In addition, it is possible to obtain a reversible thermosensitive recording medium having improved color development efficiency and having stable color developability at a molar ratio of about half compared to a conventional developer composed of a phenol compound.
一般式（１）で示される本発明の新規ジェミニ型フェノール化合物は、具体的には下記式（２）、式（３）で示される化合物である。 The novel gemini-type phenol compound of the present invention represented by the general formula (1) is specifically a compound represented by the following formula (2) or formula (3).
上記式（２）で示すフェノール化合物を得るには、例えばまず炭素数１〜３０のハロゲン化アルキルと、炭素数１〜１２の第１級ジアミンとを反応させるか、炭素数１〜３０の第１級アミンと、炭素数１〜１２のジハロゲン化アルキルと反応させて第１の中間体を合成する（第１工程）。次に、縮合剤、縮合助剤を用い、第１の中間体とｐ−ヒドロキシ安息香酸との縮合反応（第２工程）によって、上記式（２）で示すフェノール化合物を得ることができる。 In order to obtain the phenol compound represented by the above formula (2), for example, first, an alkyl halide having 1 to 30 carbon atoms is reacted with a primary diamine having 1 to 12 carbon atoms, A first intermediate is reacted with a primary amine and an alkyl halide having 1 to 12 carbon atoms to synthesize a first intermediate (first step). Next, a phenol compound represented by the above formula (2) can be obtained by a condensation reaction (second step) between the first intermediate and p-hydroxybenzoic acid using a condensing agent and a condensing aid.
上記式（３）で示すフェノール化合物を得るには、例えばまず炭素数１〜３０のハロゲン化アルキルと、炭素数１〜１２の第１級ジアミンとを反応させるか、炭素数１〜３０の第１級アミンと、炭素数１〜１２のジハロゲン化アルキルと反応させて第１の中間体を合成する（第１工程）。次に、ｐ−ヒドロキシ安息香酸とアジド化合物を用いたクルチウス転移反応を行ない、この転移生成物と第１の中間体とを反応させ（第２工程）、上記式（３）で示すフェノール化合物を得ることができる。 In order to obtain the phenol compound represented by the above formula (3), for example, first, an alkyl halide having 1 to 30 carbon atoms is reacted with a primary diamine having 1 to 12 carbon atoms, A first intermediate is reacted with a primary amine and an alkyl halide having 1 to 12 carbon atoms to synthesize a first intermediate (first step). Next, a Curtius rearrangement reaction using p-hydroxybenzoic acid and an azide compound is performed, the transfer product and the first intermediate are reacted (second step), and the phenol compound represented by the above formula (3) is obtained. Obtainable.
上記第１工程に用いられる炭素数１〜３０のハロゲン化アルキルとしては、例えばブロモメタン、ブロモエタン、１−ブロモプロパン、１−ブロモブタン、１−ブロモペンタン、１−ブロモへキサン、１−ブロモヘプタン、１−ブロモオクタン、１−ブロモノナン、１−ブロモデカン、１−ブロモウンデカン、１−ブロモドデカン、１−ブロモトリデカン、１−ブロモテトラデカン、１−ブロモペンタデカン、１−ブロモヘキサデカン、１−ブロモヘプタデカン、１−ブロモオクタデカン、１−ブロモノナデカン、１−ブロモエイコサン、１−ブロモへニコサン、１−ブロモドコサン、１−ブロモトリコサン、１−ブロモテトラコサン、１−ブロモペンタコサン、１−ブロモヘキサコサン、１−ブロモヘプタコサン、１−ブロモオクタコサン、１−ブロモノナコサン、１−ブロモトリアコンタン、クロロメタン、クロロエタン、１−クロロプロパン、１−クロロブタン、１−クロロペンタン、１−クロロへキサン、１−クロロヘプタン、１−クロロオクタン、１−クロロノナン、１−クロロデカン、１−クロロウンデカン、１−クロロドデカン、１−クロロトリデカン、１−クロロテトラデカン、１−クロロペンタデカン、１−クロロヘキサデカン、１−クロロヘプタデカン、１−クロロオクタデカン、１−クロロノナデカン、１−クロロエイコサン、１−クロロへニコサン、１−クロロドコサン、１−クロロトリコサン、１−クロロテトラコサン、１−クロロペンタコサン、１−クロロヘキサコサン、１−クロロヘプタコサン、１−クロロオクタコサン、１−クロロノナコサン、１−クロロトリアコンタン等が挙げられ、炭素数1〜１２の第１級ジアミンとしては、メチレンジアミン、エチレンジアミン、１，３−プロパンジアミン、１，４−ブタンジアミン、１，５−ペンタンジアミン、１，６−ヘキサンジアミン、１，７−ヘプタンジアミン、１，８−オクタンジアミン、１，９−ノナンジアミン、１，１０−デカンジアミン、１，１１−ウンデカンジアミン、１，１２−ドデカンジアミン等が挙げられる。また炭素数１〜３０の第１級アミンとしてはメチルアミン、エチルアミン、プロピルアミン、ブチルアミン、ペンチルアミン、ヘキシルアミン、ヘプチルアミン、オクチルアミン、ノニルアミン、デシルアミン、ウンデシルアミン、ドデシルアミン、トリデシルアミン、テトラデシルアミン、ペンタデシルアミン、ヘキサデシルアミン、ヘプタデシルアミン、オクタデシルアミン、ノナデシルアミン、エイコシルアミン、ヘニコシルアミン、ドコシルアミン、トリコシルアミン、テトラコシルアミン、ペンタコシルアミン、ヘキサコシルアミン、ヘプタコシルアミン、オクタコシルアミン、ノナコシルアミン、トリアコンチルアミン等が挙げられ、炭素数１〜１２のジハロゲン化アルキルとしてはジブロモメタン、１，２−ジブロモエタン、１，３−ジブロモプロパン、１，４−ジブロモブタン、１，５−ジブロモペンタン、１，６−ジブロモヘキサン、１，７−ジブロモヘプタン、１，８−ジブロモオクタン、１，９−ジブロモノナン、１，１０−ジブロモデカン、１，１１−ジブロモウンデカン、１，１２−ジブロモドデカン、ジクロロメタン、１，２−ジクロロエタン、１，３−ジクロロプロパン、１，４−ジクロロブタン、１，５−ジクロロペンタン、１，６−ジクロロヘキサン、１，７−ジクロロヘプタン、１，８−ジクロロオクタン、１，９−ジクロロノナン、１，１０−ジクロロデカン、１，１１−ジクロロウンデカン、１，１２−ジクロロドデカン等が挙げられる。 Examples of the alkyl halide having 1 to 30 carbon atoms used in the first step include bromomethane, bromoethane, 1-bromopropane, 1-bromobutane, 1-bromopentane, 1-bromohexane, 1-bromoheptane, 1 1-bromooctane, 1-bromononane, 1-bromodecane, 1-bromoundecane, 1-bromododecane, 1-bromotridecane, 1-bromotetradecane, 1-bromopentadecane, 1-bromohexadecane, 1-bromoheptadecane, 1 -Bromooctadecane, 1-bromononadecane, 1-bromoeicosane, 1-bromohenicosane, 1-bromodocosane, 1-bromotricosane, 1-bromotetracosane, 1-bromopentacosane, 1-bromohexacosane, 1- Bromoheptacosane, 1-bromooctacosane 1-bromononacosane, 1-bromotriacontane, chloromethane, chloroethane, 1-chloropropane, 1-chlorobutane, 1-chloropentane, 1-chlorohexane, 1-chloroheptane, 1-chlorooctane, 1-chlorononane, 1- Chlorodecane, 1-chloroundecane, 1-chlorododecane, 1-chlorotridecane, 1-chlorotetradecane, 1-chloropentadecane, 1-chlorohexadecane, 1-chloroheptadecane, 1-chlorooctadecane, 1-chlorononadecane, 1- Chloroeicosane, 1-chlorohenicosane, 1-chlorodocosane, 1-chlorotricosane, 1-chlorotetracosane, 1-chloropentacosane, 1-chlorohexacosane, 1-chloroheptacosane, 1-chlorooctacosane, 1-chlorononacosane, -Chlorotriacontane and the like, and as the primary diamine having 1 to 12 carbon atoms, methylene diamine, ethylene diamine, 1,3-propane diamine, 1,4-butane diamine, 1,5-pentane diamine, 1, Examples include 6-hexanediamine, 1,7-heptanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1,11-undecanediamine, and 1,12-dodecanediamine. Examples of the primary amine having 1 to 30 carbon atoms include methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, Tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, nonadecylamine, eicosylamine, henicosylamine, docosylamine, tricosylamine, tetracosylamine, pentacosylamine, hexacosylamine, heptacosylamine, octacosylamine Ruamine, nonacosylamine, triacontylamine and the like. Examples of the dihalogenated alkyl having 1 to 12 carbon atoms include dibromomethane, 1,2-dibromoethane, , 3-dibromopropane, 1,4-dibromobutane, 1,5-dibromopentane, 1,6-dibromohexane, 1,7-dibromoheptane, 1,8-dibromooctane, 1,9-dibromononane, 1, 10-dibromodecane, 1,11-dibromoundecane, 1,12-dibromododecane, dichloromethane, 1,2-dichloroethane, 1,3-dichloropropane, 1,4-dichlorobutane, 1,5-dichloropentane, 1, Examples include 6-dichlorohexane, 1,7-dichloroheptane, 1,8-dichlorooctane, 1,9-dichlorononane, 1,10-dichlorodecane, 1,11-dichloroundecane, and 1,12-dichlorododecane. .
式（２）で示されるフェノール化合物を得るために、第２工程において、第１の中間体とｐ−ヒドロキシ安息香酸とを縮合反応させるために用いる縮合剤としては、例えばＮ，Ｎ′−ジイソプロピルカルボジイミド、Ｎ，Ｎ′−ジシクロヘキシルカルボジイミド、Ｎ−エチル−Ｎ′−3−ジメチルアミノプロピルカルボジイミド、（１−ヒドロキシベンゾトリアゾール−１−イルオキシ）トリス（ジメチルアミノ）ホスホニウムヘキサフルオロホスファート、１−［ビス（ジメチルアミノ）メチレン］−１−ヒドロキシベンゾトリアゾリウム−３−オキシドヘキサフルオロホスファート等が挙げられる。また縮合助剤としては、１−ヒドロキシベンゾトリアゾール、Ｎ−ヒドロキシスクシンイミド、３−ヒドロキシ−４−オキソ−３，４−ジヒドロ−１，２，３−ベンゾトリアジン、１−ヒドロキシ−７−アザベンゾトリアゾール等が挙げられる。式（３）で示されるフェノール化合物を得るために、第２工程において、ｐ−ヒドロキシ安息香酸と反応させるアジド化合物は、例えばアジ化ナトリウム、アジ化ジフェニルホスホリル等が挙げられる。なお、これら第１工程から第２工程までのすべての合成法は、本発明のフェノール化合物を得るための一例であり、本発明は何らこれら製造方法に限定されるものではない。 In order to obtain the phenol compound represented by the formula (2), as a condensing agent used for the condensation reaction of the first intermediate and p-hydroxybenzoic acid in the second step, for example, N, N′-diisopropyl is used. Carbodiimide, N, N'-dicyclohexylcarbodiimide, N-ethyl-N'-3-dimethylaminopropylcarbodiimide, (1-hydroxybenzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate, 1- [bis (Dimethylamino) methylene] -1-hydroxybenzotriazolium-3-oxide hexafluorophosphate and the like. Further, as the condensation assistant, 1-hydroxybenzotriazole, N-hydroxysuccinimide, 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine, 1-hydroxy-7-azabenzotriazole Etc. In order to obtain the phenol compound represented by formula (3), examples of the azide compound to be reacted with p-hydroxybenzoic acid in the second step include sodium azide and diphenylphosphoryl azide. In addition, all the synthesis methods from these 1st processes to a 2nd process are examples for obtaining the phenolic compound of this invention, and this invention is not limited to these manufacturing methods at all.
本発明のジェミニ型フェノール化合物は、顕色剤として用いた場合、１分子中に４−ヒドロキシフェニル基を１個有する１鎖型のフェノール化合物に比べ、より低いエネルギーでロイコ染料と反応するため、感熱記録媒体への熱ダメージも少なくすることができる。 When the gemini-type phenol compound of the present invention is used as a developer, it reacts with a leuco dye at a lower energy than a one-chain type phenol compound having one 4-hydroxyphenyl group in one molecule. Thermal damage to the heat-sensitive recording medium can be reduced.
以下、実施例を挙げて本発明を更に詳細に説明する。
実施例１
１−プロパノール２５００ｇに、１−ブロモドデカン２５０．０ｇ、エチレンジアミン２０．１ｇを加え、還流下８時間攪拌した。室温に冷却した後、結晶を濾別、乾燥後、トルエンで加熱洗浄し、室温で結晶を濾別した。得られた結晶を水酸化ナトリウム水溶液で攪拌、洗浄した。結晶を濾別、水洗、乾燥し、式（４）に示すＮ，Ｎ′−ジドデシルエチレンジアミン３４．７ｇを得た。この化合物においては、赤外線吸収スペクトル（ＫＢｒ錠剤法）の１１３４ｃｍ−１に第２級アミンのＣ−Ｎ伸縮振動、３２４４ｃｍ−１に第２級アミンのＮ−Ｈ伸縮振動に基づく吸収が認められた。この化合物の元素分析結果を表１に示す。
Hereinafter, the present invention will be described in more detail with reference to examples.
Example 1
To 2500 g of 1-propanol, 250.0 g of 1-bromododecane and 20.1 g of ethylenediamine were added and stirred for 8 hours under reflux. After cooling to room temperature, the crystals were separated by filtration, dried, washed with toluene, and the crystals were separated by filtration at room temperature. The obtained crystals were stirred and washed with an aqueous sodium hydroxide solution. The crystals were separated by filtration, washed with water, and dried to obtain 34.7 g of N, N′-didodecylethylenediamine represented by the formula (4). In this compound, absorption based on the C—N stretching vibration of the secondary amine was observed at 1134 cm −1 and the N—H stretching vibration of the secondary amine was observed at 3244 cm −1 of the infrared absorption spectrum (KBr tablet method). . The elemental analysis results of this compound are shown in Table 1.
（表１）
メチルエチルケトン１００ｇに、ｐ−ヒドロキシ安息香酸３．８ｇ、１−ヒドロキシベンゾトリアゾール４．２ｇ、Ｎ，Ｎ′−ジイソプロピルカルボジイミド３．５ｇ、上記Ｎ，Ｎ′−ジドデシルエチレンジアミン５．０ｇを加え、還流下３時間攪拌した。室温に冷却後、結晶を濾別、メタノールで再結晶し、化合物１を６．４ｇ得た。融点は１９０℃であり、赤外線吸収スペクトル（ＫＢｒ錠剤法）の１６５２ｃｍ−１に第３アミドのＣ＝Ｏ伸縮振動に基づく吸収が認められた。この化合物１の元素分析結果を表２に示す。元素分析の結果は、化合物１は式（２）におけるｌ＝１１、ｍ＝２、で示されるフェノール化合物と一致しており、赤外線吸収スペクトル及び元素分析結果より、化合物１が式（２）で示す構造のフェノール化合物であることが確認された。 To 100 g of methyl ethyl ketone, 3.8 g of p-hydroxybenzoic acid, 4.2 g of 1-hydroxybenzotriazole, 3.5 g of N, N′-diisopropylcarbodiimide, and 5.0 g of N, N′-didodecylethylenediamine are added under reflux. Stir for 3 hours. After cooling to room temperature, the crystals were separated by filtration and recrystallized from methanol to obtain 6.4 g of Compound 1. The melting point was 190 ° C., and absorption based on the C═O stretching vibration of the third amide was observed at 1652 cm −1 in the infrared absorption spectrum (KBr tablet method). Table 2 shows the elemental analysis results of Compound 1. As a result of elemental analysis, Compound 1 is consistent with the phenol compound represented by l = 11, m = 2 in Formula (2). From the infrared absorption spectrum and the results of elemental analysis, Compound 1 is represented by Formula (2). It was confirmed to be a phenol compound having the structure shown.
（表２）
実施例２
トルエン２００ｇに、p−ヒドロキシ安息香酸を１２．６ｇ、トリエチルアミン９．２ｇ、アジ化ジフェニルホスホリル２５．１ｇを加え、８０℃で２時間攪拌した後、実施例１で得たＮ，Ｎ′−ジドデシルエチレンジアミン１６．５ｇを加え、８０℃で２時間攪拌した。室温に冷却後、結晶を濾別、メタノールで再結晶し、ジエチルエーテルにて洗浄することで、化合物２を２．２ｇ得た。化合物２の融点は１６５℃であり、赤外線吸収スペクトル（ＫＢｒ錠剤法）の１６４１ｃｍ−１に尿素のＣ＝Ｏ伸縮振動に基づく吸収が認められた。この化合物２の元素分析結果を表３に示す。元素分析の結果は、化合物２は式（３）におけるｌ＝１１、ｍ＝２で示されるフェノール化合物と一致しており、赤外線吸収スペクトル及び元素分析結果より、化合物２が式（３）で示す構造のフェノール化合物であることが確認された。
Example 2
To 200 g of toluene, 12.6 g of p-hydroxybenzoic acid, 9.2 g of triethylamine, and 25.1 g of diphenylphosphoryl azide were added and stirred at 80 ° C. for 2 hours, and then the N, N′-di-acid obtained in Example 1 was used. 16.5 g of dodecylethylenediamine was added and stirred at 80 ° C. for 2 hours. After cooling to room temperature, the crystals were separated by filtration, recrystallized from methanol, and washed with diethyl ether to obtain 2.2 g of Compound 2. Compound 2 had a melting point of 165 ° C., and absorption based on C═O stretching vibration of urea was observed at 1641 cm −1 in the infrared absorption spectrum (KBr tablet method). Table 3 shows the elemental analysis results of Compound 2. As a result of elemental analysis, compound 2 is consistent with the phenol compound represented by l = 11, m = 2 in formula (3), and from the infrared absorption spectrum and the result of elemental analysis, compound 2 is represented by formula (3). It was confirmed to be a phenolic compound having a structure.
（表３）
本発明のジェミニ型フェノール化合物は、酸化防止剤、耐熱安定剤、重合禁止剤、紫外線吸収剤等のプラスチック添加剤や、ゴム老化防止剤等のゴム添加剤、医薬品、界面活性剤、除草剤、殺虫剤、殺菌剤、可塑剤、安定剤等の中間物質、感熱記録媒体の顕色剤等としての利用が期待され、顕色剤として用いた場合、従来のフェノール化合物からなる顕色剤に比べ、発色効率が向上し、半分程度のモル比で安定な発色性を有する可逆性感熱記録媒体を得ることが可能である。 The gemini-type phenolic compound of the present invention includes antioxidants, heat stabilizers, polymerization inhibitors, plastic additives such as UV absorbers, rubber additives such as rubber anti-aging agents, pharmaceuticals, surfactants, herbicides, Expected to be used as an intermediate for insecticides, bactericides, plasticizers, stabilizers, etc., and as a developer for heat-sensitive recording media. When used as a developer, compared to conventional developers made of phenolic compounds It is possible to obtain a reversible thermosensitive recording medium having improved color development efficiency and stable color development at a molar ratio of about half.
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| US20050181455A1 (en) * | 2000-04-03 | 2005-08-18 | Cerno Biosciences Llc | Generation of combinatorial synthetic libraries and screening for novel proadhesins and nonadhesins |
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| US2683083A (en) * | 1950-12-09 | 1954-07-06 | Ethyl Corp | Nu-alkyl-nu'-(p-hydroxyphenyl) ureas as antioxidants for petroleum hydrocarbon fuels |
| JPH04267183A (en) * | 1991-02-22 | 1992-09-22 | Fuji Photo Film Co Ltd | Development sheet for pressure sensitive recording |
| JPH05249641A (en) * | 1991-12-06 | 1993-09-28 | Eastman Kodak Co | Dye diffusing thermal solvent for image separating system |
| US20050181455A1 (en) * | 2000-04-03 | 2005-08-18 | Cerno Biosciences Llc | Generation of combinatorial synthetic libraries and screening for novel proadhesins and nonadhesins |
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