JP4778041B2 - 両性スチルベン組成物 - Google Patents
両性スチルベン組成物 Download PDFInfo
- Publication number
- JP4778041B2 JP4778041B2 JP2008509230A JP2008509230A JP4778041B2 JP 4778041 B2 JP4778041 B2 JP 4778041B2 JP 2008509230 A JP2008509230 A JP 2008509230A JP 2008509230 A JP2008509230 A JP 2008509230A JP 4778041 B2 JP4778041 B2 JP 4778041B2
- Authority
- JP
- Japan
- Prior art keywords
- stilbene
- diamino
- disulfonic acid
- composition
- amphoteric
- 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 - Fee Related
Links
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 38
- 239000000203 mixture Substances 0.000 title claims description 36
- 235000021286 stilbenes Nutrition 0.000 title claims description 36
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 title claims description 34
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 claims description 20
- 125000005841 biaryl group Chemical group 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 11
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 10
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- -1 biaryl disulfide Chemical compound 0.000 description 10
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QHDAFTKIEDDTPV-SEPHDYHBSA-N 4,4'-Diaminostilbene dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC([NH3+])=CC=C1\C=C\C1=CC=C([NH3+])C=C1 QHDAFTKIEDDTPV-SEPHDYHBSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical class C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920006317 cationic polymer Polymers 0.000 description 3
- VUJGKADZTYCLIL-YHPRVSEPSA-L disodium;5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfonatophenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 VUJGKADZTYCLIL-YHPRVSEPSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 0 *CC*1CCCC1 Chemical compound *CC*1CCCC1 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000005588 protonation Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000001629 stilbenes Chemical class 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NTTLKRPWPKPUAI-UHFFFAOYSA-N (1e)-1-[amino(anilino)methylidene]-2-phenylguanidine Chemical compound C=1C=CC=CC=1N=C(N)\N=C(/N)NC1=CC=CC=C1 NTTLKRPWPKPUAI-UHFFFAOYSA-N 0.000 description 1
- QZFUJXGLCPJZFN-UHFFFAOYSA-N 1,1-dibutylguanidine Chemical compound CCCCN(C(N)=N)CCCC QZFUJXGLCPJZFN-UHFFFAOYSA-N 0.000 description 1
- MTZUNDSWFIDAOO-UHFFFAOYSA-N 1,2-di(propan-2-yl)guanidine Chemical compound CC(C)NC(=N)NC(C)C MTZUNDSWFIDAOO-UHFFFAOYSA-N 0.000 description 1
- VEGSEUJMFASKPM-UHFFFAOYSA-N 1,2-dibenzylguanidine Chemical compound C=1C=CC=CC=1CNC(=N)NCC1=CC=CC=C1 VEGSEUJMFASKPM-UHFFFAOYSA-N 0.000 description 1
- MPUAUPQFSLHOHQ-UHFFFAOYSA-N 1,2-dicyclohexylguanidine Chemical compound C1CCCCC1NC(=N)NC1CCCCC1 MPUAUPQFSLHOHQ-UHFFFAOYSA-N 0.000 description 1
- MCMBEBOHGREEOP-UHFFFAOYSA-N 1,2-diethylguanidine Chemical compound CCNC(=N)NCC MCMBEBOHGREEOP-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- HGMDNMBBCKDWTQ-UHFFFAOYSA-N 1,4-diguanidinobutane Chemical compound NC(=N)NCCCCNC(N)=N HGMDNMBBCKDWTQ-UHFFFAOYSA-N 0.000 description 1
- XWFPIJRFFLYWRN-UHFFFAOYSA-N 1-(diaminomethylidene)-2-ethylguanidine Chemical compound CCN=C(N)N=C(N)N XWFPIJRFFLYWRN-UHFFFAOYSA-N 0.000 description 1
- UUBZPMKBMHXGNE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-naphthalen-1-ylguanidine Chemical compound C1=CC=C2C(N=C(N)N=C(N)N)=CC=CC2=C1 UUBZPMKBMHXGNE-UHFFFAOYSA-N 0.000 description 1
- UBBHRFLEDZWRNR-UHFFFAOYSA-N 1-(diaminomethylidene)-2-propan-2-ylguanidine Chemical compound CC(C)N=C(N)N=C(N)N UBBHRFLEDZWRNR-UHFFFAOYSA-N 0.000 description 1
- LFYYWNBMKVGMPJ-UHFFFAOYSA-N 2-(1-adamantyl)guanidine Chemical compound C1C(C2)CC3CC2CC1(N=C(N)N)C3 LFYYWNBMKVGMPJ-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- PGJJYXPMHZOQHJ-UHFFFAOYSA-N 2-[1,2-diamino-2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound C=1C=CC=C(S(O)(=O)=O)C=1C(N)=C(N)C1=CC=CC=C1S(O)(=O)=O PGJJYXPMHZOQHJ-UHFFFAOYSA-N 0.000 description 1
- ICBVWIUIDVBAFX-UHFFFAOYSA-N 2-[1-(diaminomethylideneamino)propan-2-yl]guanidine Chemical compound NC(=N)NC(C)CNC(N)=N ICBVWIUIDVBAFX-UHFFFAOYSA-N 0.000 description 1
- MRXYVMXWTBRRSB-UHFFFAOYSA-N 2-[2-(diaminomethylideneamino)ethyl]guanidine Chemical compound NC(N)=NCCN=C(N)N MRXYVMXWTBRRSB-UHFFFAOYSA-N 0.000 description 1
- BBXYBXZOUMQIBH-UHFFFAOYSA-N 2-[2-(diaminomethylideneamino)phenyl]guanidine Chemical compound NC(=N)NC1=CC=CC=C1NC(N)=N BBXYBXZOUMQIBH-UHFFFAOYSA-N 0.000 description 1
- UKKLLWZIENSJBD-UHFFFAOYSA-N 2-[2-[[amino-(diaminomethylideneamino)methylidene]amino]ethyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCCN=C(N)N=C(N)N UKKLLWZIENSJBD-UHFFFAOYSA-N 0.000 description 1
- FWAYARHRNJZASC-UHFFFAOYSA-N 2-[2-[[amino-(diaminomethylideneamino)methylidene]amino]phenyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1N=C(N)N=C(N)N FWAYARHRNJZASC-UHFFFAOYSA-N 0.000 description 1
- MEUHWVQPQDPQTB-UHFFFAOYSA-N 2-[4-[[amino-(diaminomethylideneamino)methylidene]amino]butyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCCCCN=C(N)N=C(N)N MEUHWVQPQDPQTB-UHFFFAOYSA-N 0.000 description 1
- FIHKQNOFFQZHRM-UHFFFAOYSA-N 2-[5-(diaminomethylideneamino)pentyl]guanidine Chemical compound NC(N)=NCCCCCN=C(N)N FIHKQNOFFQZHRM-UHFFFAOYSA-N 0.000 description 1
- GEPXLDLVTRMBJJ-UHFFFAOYSA-N 2-[5-[[amino-(diaminomethylideneamino)methylidene]amino]pentyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCCCCCN=C(N)N=C(N)N GEPXLDLVTRMBJJ-UHFFFAOYSA-N 0.000 description 1
- WBLYUCKTWSGGBI-UHFFFAOYSA-N 2-[6-(diaminomethylideneamino)hexyl]guanidine Chemical compound NC(N)=NCCCCCCN=C(N)N WBLYUCKTWSGGBI-UHFFFAOYSA-N 0.000 description 1
- RXGSAYBOEDPICZ-UHFFFAOYSA-N 2-[6-[[amino-(diaminomethylideneamino)methylidene]amino]hexyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)N RXGSAYBOEDPICZ-UHFFFAOYSA-N 0.000 description 1
- OEYZRZQNTMPUOQ-UHFFFAOYSA-N 2-[7-(diaminomethylideneamino)heptyl]guanidine Chemical compound NC(=N)NCCCCCCCNC(N)=N OEYZRZQNTMPUOQ-UHFFFAOYSA-N 0.000 description 1
- BYUZHFUCTUWAJS-UHFFFAOYSA-N 2-[7-[[amino-(diaminomethylideneamino)methylidene]amino]heptyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCCCCCCCN=C(N)N=C(N)N BYUZHFUCTUWAJS-UHFFFAOYSA-N 0.000 description 1
- VUUYNASTGNDRSQ-UHFFFAOYSA-N 2-[8-(diaminomethylideneamino)octyl]guanidine Chemical compound NC(N)=NCCCCCCCCN=C(N)N VUUYNASTGNDRSQ-UHFFFAOYSA-N 0.000 description 1
- NVCXIHMOEIDCKV-UHFFFAOYSA-N 2-[8-[[amino-(diaminomethylideneamino)methylidene]amino]octyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCCCCCCCCN=C(N)N=C(N)N NVCXIHMOEIDCKV-UHFFFAOYSA-N 0.000 description 1
- ABSNGNUGFQIDDO-UHFFFAOYSA-N 2-benzylguanidine Chemical compound NC(N)=NCC1=CC=CC=C1 ABSNGNUGFQIDDO-UHFFFAOYSA-N 0.000 description 1
- CGWBIHLHAGNJCX-UHFFFAOYSA-N 2-butylguanidine Chemical compound CCCCNC(N)=N CGWBIHLHAGNJCX-UHFFFAOYSA-N 0.000 description 1
- USGCMNLQYSXCDU-UHFFFAOYSA-N 2-cyclohexyl-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1CCCCC1 USGCMNLQYSXCDU-UHFFFAOYSA-N 0.000 description 1
- AJGAPBXTFUSKNJ-UHFFFAOYSA-N 2-cyclohexylguanidine Chemical compound NC(=N)NC1CCCCC1 AJGAPBXTFUSKNJ-UHFFFAOYSA-N 0.000 description 1
- CMEIYVWWZREFEM-UHFFFAOYSA-N 2-ethyl-1-(n'-ethylcarbamimidoyl)guanidine Chemical compound CCN=C(N)NC(N)=NCC CMEIYVWWZREFEM-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- YXYNPIWENOTEHZ-UHFFFAOYSA-N 2-nitramidoguanidine Chemical compound NC(=N)NN[N+]([O-])=O YXYNPIWENOTEHZ-UHFFFAOYSA-N 0.000 description 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- YTZWQUYIRHGHMJ-UHFFFAOYSA-N 3-(1,2-diamino-2-phenylethenyl)benzene-1,2-disulfonic acid Chemical compound NC(=C(C1=C(C(=CC=C1)S(=O)(=O)O)S(=O)(=O)O)N)C1=CC=CC=C1 YTZWQUYIRHGHMJ-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- DUUBGMMYIDBKQK-UHFFFAOYSA-N N1=CNC2=C1C=CC=C2.NC(=N)N Chemical compound N1=CNC2=C1C=CC=C2.NC(=N)N DUUBGMMYIDBKQK-UHFFFAOYSA-N 0.000 description 1
- VLCLRBWUQVKYAN-UHFFFAOYSA-N NC(=N)NC(=N)N.NC(=N)NC(=N)N.C=CC Chemical compound NC(=N)NC(=N)N.NC(=N)NC(=N)N.C=CC VLCLRBWUQVKYAN-UHFFFAOYSA-N 0.000 description 1
- TXIJNGXOSNIPNO-UHFFFAOYSA-N NC(=N)NC(=N)N.NC(=N)NC(=N)N.N1CCNCC1 Chemical compound NC(=N)NC(=N)N.NC(=N)NC(=N)N.N1CCNCC1 TXIJNGXOSNIPNO-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 229920002413 Polyhexanide Polymers 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- WKMDUBICDHCAFD-UHFFFAOYSA-N n,n'-bis(diaminomethylidene)butanediamide Chemical compound NC(N)=NC(=O)CCC(=O)N=C(N)N WKMDUBICDHCAFD-UHFFFAOYSA-N 0.000 description 1
- ZOBNKERGXPIREC-UHFFFAOYSA-N n,n'-bis(diaminomethylidene)octanediamide Chemical compound NC(N)=NC(=O)CCCCCCC(=O)N=C(N)N ZOBNKERGXPIREC-UHFFFAOYSA-N 0.000 description 1
- UOIDVBITUXAYQD-UHFFFAOYSA-N n,n'-bis(diaminomethylidene)oxamide Chemical compound NC(N)=NC(=O)C(=O)N=C(N)N UOIDVBITUXAYQD-UHFFFAOYSA-N 0.000 description 1
- UJIRDWWFZPFOJG-UHFFFAOYSA-N n,n'-bis(diaminomethylidene)pentanediamide Chemical compound NC(N)=NC(=O)CCCC(=O)N=C(N)N UJIRDWWFZPFOJG-UHFFFAOYSA-N 0.000 description 1
- ICVDHYBHEGEATP-UHFFFAOYSA-N n,n'-bis(diaminomethylidene)propanediamide Chemical compound NC(N)=NC(=O)CC(=O)N=C(N)N ICVDHYBHEGEATP-UHFFFAOYSA-N 0.000 description 1
- NMOQKZKGHMEEDX-UHFFFAOYSA-N n,n'-bis[amino-(diaminomethylideneamino)methylidene]butanediamide Chemical compound NC(N)=NC(N)=NC(=O)CCC(=O)N=C(N)N=C(N)N NMOQKZKGHMEEDX-UHFFFAOYSA-N 0.000 description 1
- CYERAWIJKVFPDL-UHFFFAOYSA-N n,n'-bis[amino-(diaminomethylideneamino)methylidene]octanediamide Chemical compound NC(N)=NC(N)=NC(=O)CCCCCCC(=O)N=C(N)N=C(N)N CYERAWIJKVFPDL-UHFFFAOYSA-N 0.000 description 1
- NBENMUYGJTYGIQ-UHFFFAOYSA-N n,n'-bis[amino-(diaminomethylideneamino)methylidene]oxamide Chemical compound NC(N)=NC(N)=NC(=O)C(=O)N=C(N)N=C(N)N NBENMUYGJTYGIQ-UHFFFAOYSA-N 0.000 description 1
- VKVHQPPKQCGELM-UHFFFAOYSA-N n,n'-bis[amino-(diaminomethylideneamino)methylidene]pentanediamide Chemical compound NC(N)=NC(N)=NC(=O)CCCC(=O)N=C(N)N=C(N)N VKVHQPPKQCGELM-UHFFFAOYSA-N 0.000 description 1
- LSNCRLSFWFMRSA-UHFFFAOYSA-N n,n'-bis[amino-(diaminomethylideneamino)methylidene]propanediamide Chemical compound NC(N)=NC(N)=NC(=O)CC(=O)N=C(N)N=C(N)N LSNCRLSFWFMRSA-UHFFFAOYSA-N 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229920002851 polycationic polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Images
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/614—Optical bleaching or brightening in aqueous solvents
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/09—Sulfur-containing compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/919—Paper
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24934—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including paper layer
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Claims (8)
- 両性スチルベン組成物(12)であって:
式:
を持つ4,4’−ジアミノ−2,2’−スチルベンジスルホン酸(16)、
式:
を持つビアリールスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16’)、
式:
を持つビアリールジスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16”)〔これらの式中、M及びM’は同じものとも異なるものともし得、そして、H+、Na+、K+、及び/又はN(R) 4 +(ここで、Rは、H、アルキル基、又はアリール基)からなる群より選択され、R1、R2、R3、及びR4もまた、同じものとも異なるものともし得、そして、H、アルキル基、アリール基、又は複素環式環からなる群より選択される〕、それらの誘導体、それらの塩、及びそれらの混合物のうちの少なくとも1つを0.1gsmから5gsmの範囲の量で;
及び
ポリグアニジン、グアニジン、ビグアニジン、ジグアニジン、ポリアルキルビグアニド、ポリアルキルイミン、ポリアリールイミン、ポリアルキルグアニジン、ポリアリールグアニジン、ポリモノグアニジン及びそれらの混合物のうちの少なくとも1つである定着剤(18)を含み、
4から10までの間の範囲のpHを持つ、両性スチルベン組成物(12)。 - 前記定着剤(18)が、ポリ(ヘキサメチレンビグアニド)ヒドロクロリドである、請求項1に記載の両性スチルベン組成物(12)。
- 前記定着剤(18)が、0.1gsm〜10gsmの範囲の量にて存在する、請求項1〜2の何れか1つに記載の両性スチルベン組成物(12)。
- 4,4’−ジアミノ−2,2’−スチルベンジスルホン酸(16)、ビアリールスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16’)、ビアリールジスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16”)、それらの誘導体、それらの塩、及びそれらの混合物のうちの少なくとも1つが、前記定着剤(18)と、均一にもしくは不均一に混合されているうちの少なくとも1つである、請求項1〜3の何れか1つに記載の両性スチルベン組成物(12)。
- 4,4’−ジアミノ−2,2’−スチルベンジスルホン酸(16)、ビアリールスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16’)、ビアリールジスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16”)、それらの誘導体、それらの塩、及びそれらの混合物のうちの少なくとも1つが、その上に前記組成物が配置されることになる基材(14)の190,000から205,000の範囲のμM当たりの蛍光強度を示す、請求項1〜4の何れか1つに記載の両性スチルベン組成物(12)。
- 高い蛍光性を有する媒体基材(14)を製造する方法であって:
式:
を持つ4,4’−ジアミノ−2,2’−スチルベンジスルホン酸(16)、
式:
を持つビアリールスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16’)、
式:
を持つビアリールジスルホナート−4、4’−ジアミノ−2,2’−スチルベンジスルホン酸(16”)〔これらの式中、M及びM’は同じものとも異なるものともし得、そして、H+、Na+、K+、及び/又はN(R) 4 +(ここで、Rは、H、アルキル基、又はアリール基)からなる群より選択され、R1、R2、R3、及びR4もまた、同じものとも異なるものともし得、そして、H、アルキル基、アリール基、又は複素環式環からなる群より選択される〕、それらの誘導体、それらの塩、及びそれらの混合物のうちの少なくとも1つを0.1gsmから5gsmの範囲の量で;
ポリグアニジン、グアニジン、ビグアニジン、ジグアニジン、ポリアルキルビグアニド、ポリアルキルイミン、ポリアリールイミン、ポリアルキルグアニジン、ポリアリールグアニジン、ポリモノグアニジン及びそれらの混合物のうちの少なくとも1つである定着剤(18)と混合して溶液を形成すること;
前記溶液を前記媒体基材(14)上に配置すること;
を包含し、前記溶液が4から10までの間の範囲のpHであり、前記媒体基材(14)の蛍光性を高める、方法。 - 前記溶液を配置することが、インクジェット装置による射出、ディップコーティング、ドローコーティング、及びそれらの組合せのうちの1つによって達成される、請求項6に記載の方法。
- 請求項1〜5の何れか1つに記載の両性スチルベン組成物によって印刷された媒体基材。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/117,823 | 2005-04-29 | ||
| US11/117,823 US20060246383A1 (en) | 2005-04-29 | 2005-04-29 | Amphoteric stilbene composition |
| PCT/US2006/016651 WO2006119201A1 (en) | 2005-04-29 | 2006-04-27 | Amphoteric stilbene composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008540700A JP2008540700A (ja) | 2008-11-20 |
| JP4778041B2 true JP4778041B2 (ja) | 2011-09-21 |
Family
ID=36943988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008509230A Expired - Fee Related JP4778041B2 (ja) | 2005-04-29 | 2006-04-27 | 両性スチルベン組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20060246383A1 (ja) |
| EP (1) | EP1885938B1 (ja) |
| JP (1) | JP4778041B2 (ja) |
| CN (1) | CN101263256B (ja) |
| WO (1) | WO2006119201A1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5788013B2 (ja) | 2010-10-29 | 2015-09-30 | ヒューレット−パッカード デベロップメント カンパニー エル.ピー.Hewlett‐Packard Development Company, L.P. | 塩化カルシウムを低減した紙強化処理 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002348494A (ja) * | 2001-03-22 | 2002-12-04 | Nippon Kayaku Co Ltd | 染色特性に優れる蛍光増白剤の水性液状組成物 |
| US20030089888A1 (en) * | 2001-10-05 | 2003-05-15 | Erwin Bacher | Use of aqueous brightener preparations for brightening natural and synthetic materials |
| JP2004181955A (ja) * | 2002-12-03 | 2004-07-02 | Hewlett-Packard Development Co Lp | インクジェット印刷に使用されるフルオロ界面活性剤パッケージ及びインクジェットペンにおけるパドリングを制御する方法 |
| JP2007536133A (ja) * | 2004-05-03 | 2007-12-13 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | インクジェット印刷基材用蛍光増白剤 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157644A (en) * | 1956-04-04 | 1964-11-17 | Gen Aniline & Film Corp | Brightening agents |
| US3909266A (en) * | 1966-04-14 | 1975-09-30 | Canon Kk | Recording member of photocolor developing and eliminating material and the recording method |
| US3575866A (en) * | 1969-11-19 | 1971-04-20 | Gaf Corp | New brighteners,compositions thereof and processes for using same |
| DE2060762A1 (de) * | 1970-12-10 | 1972-06-22 | Henkel & Cie Gmbh | Mittel zur Herstellung von Kaltbleichflotten,insbesondere von kaltbleichwirksamen Waschlaugen |
| GB8711105D0 (en) * | 1987-05-11 | 1987-06-17 | Ici Plc | Information device |
| GB9412590D0 (en) * | 1994-06-23 | 1994-08-10 | Sandoz Ltd | Organic compounds |
| DE19646759C2 (de) * | 1996-11-04 | 2003-01-09 | Schuelke & Mayr Gmbh | Verwendung eines optischen Aufhellers in einem Desinfektionsmittel |
| AU2599499A (en) * | 1998-02-12 | 1999-08-30 | Surfacine Development Company, Llc | Disinfectant compositions providing sustained biocidal action |
| US6066673A (en) * | 1998-03-12 | 2000-05-23 | The Procter & Gamble Company | Enzyme inhibitors |
| US20030147925A1 (en) * | 1998-09-11 | 2003-08-07 | Samuel P. Sawan | Topical dermal antimicrobial compositions, methods for generating same, and monitoring methods utilizing same |
| GB9930247D0 (en) * | 1999-12-22 | 2000-02-09 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| US9028852B2 (en) * | 2004-09-07 | 2015-05-12 | 3M Innovative Properties Company | Cationic antiseptic compositions and methods of use |
-
2005
- 2005-04-29 US US11/117,823 patent/US20060246383A1/en not_active Abandoned
-
2006
- 2006-04-27 JP JP2008509230A patent/JP4778041B2/ja not_active Expired - Fee Related
- 2006-04-27 WO PCT/US2006/016651 patent/WO2006119201A1/en not_active Ceased
- 2006-04-27 CN CN2006800144016A patent/CN101263256B/zh not_active Expired - Fee Related
- 2006-04-27 EP EP06752017.1A patent/EP1885938B1/en not_active Expired - Lifetime
-
2008
- 2008-08-05 US US12/186,079 patent/US7789917B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002348494A (ja) * | 2001-03-22 | 2002-12-04 | Nippon Kayaku Co Ltd | 染色特性に優れる蛍光増白剤の水性液状組成物 |
| US20030089888A1 (en) * | 2001-10-05 | 2003-05-15 | Erwin Bacher | Use of aqueous brightener preparations for brightening natural and synthetic materials |
| JP2004181955A (ja) * | 2002-12-03 | 2004-07-02 | Hewlett-Packard Development Co Lp | インクジェット印刷に使用されるフルオロ界面活性剤パッケージ及びインクジェットペンにおけるパドリングを制御する方法 |
| JP2007536133A (ja) * | 2004-05-03 | 2007-12-13 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | インクジェット印刷基材用蛍光増白剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20060246383A1 (en) | 2006-11-02 |
| CN101263256A (zh) | 2008-09-10 |
| EP1885938B1 (en) | 2013-06-26 |
| JP2008540700A (ja) | 2008-11-20 |
| WO2006119201A1 (en) | 2006-11-09 |
| US7789917B2 (en) | 2010-09-07 |
| CN101263256B (zh) | 2011-07-06 |
| EP1885938A1 (en) | 2008-02-13 |
| US20080290320A1 (en) | 2008-11-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1423444B1 (en) | Amphoteric polymer resins that increase the rate of sizing development | |
| AU2006278119B2 (en) | Storage stable solutions of optical brighteners | |
| TWI484083B (zh) | 雙磺基型螢光增白劑組成物 | |
| TWI300065B (en) | Improvements relating to optical brighteners | |
| US4251410A (en) | Reaction products of a polyacrylamide formaldehyde, a secondary amine and an-nh group-containing functional derivative of an acid | |
| CN102057106B (zh) | 荧光增白剂组合物 | |
| US7731820B2 (en) | Compositions of fluorescent whitening agents | |
| US9415620B2 (en) | Optical brightening compositions for high quality ink jet printing | |
| US9376405B2 (en) | Bis-(triazinylamino)-stilbene derivatives | |
| CN1926120A (zh) | 浓荧光增白剂溶液 | |
| US20090081475A1 (en) | Aqueous Solutions of Optical Brighteners | |
| CN1498250A (zh) | 具有极好染色特性的荧光增白剂水成液组合物 | |
| JP4778041B2 (ja) | 両性スチルベン組成物 | |
| TW201245542A (en) | Fluorescent whitening agent compositions | |
| EP2781648B1 (en) | Optical brightening agents for high quality ink-jet printing | |
| JPS59101395A (ja) | カラ−受像体 | |
| CN1369030A (zh) | 增白纸张涂料组合物的增白颜料的应用 | |
| CN1208059A (zh) | 直接双偶氮染料 | |
| JP4768349B2 (ja) | アルカノールアンモニウム含有トリアジニルフラボネート漂白剤 | |
| CH548484A (de) | Aufhellpraeparat. | |
| AU2018387075B2 (en) | Optical brightener for whitening paper | |
| EP0662634B1 (en) | Ballasted optical brighteners | |
| JPH04502034A (ja) | 光学的増白剤および光安定剤の塩 | |
| JP2005238613A (ja) | インクジェット記録用紙用塗料組成物の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100701 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100713 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101013 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101020 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110113 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110308 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110608 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110628 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110630 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4778041 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140708 Year of fee payment: 3 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |