JPH03369B2 - - Google Patents
Info
- Publication number
- JPH03369B2 JPH03369B2 JP57104064A JP10406482A JPH03369B2 JP H03369 B2 JPH03369 B2 JP H03369B2 JP 57104064 A JP57104064 A JP 57104064A JP 10406482 A JP10406482 A JP 10406482A JP H03369 B2 JPH03369 B2 JP H03369B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydroxyphenyl
- hydrogen
- straight
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- -1 resorcinol Chemical class 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 11
- 229910052709 silver Inorganic materials 0.000 description 11
- 239000004332 silver Substances 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- PMHUPJRTEQENJD-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methylbut-2-ene Chemical compound COP(=O)(OC)CC=C(C)C PMHUPJRTEQENJD-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- QCSCNTGILDKNRW-UHFFFAOYSA-N 11-aminoundecan-1-ol Chemical compound NCCCCCCCCCCCO QCSCNTGILDKNRW-UHFFFAOYSA-N 0.000 description 2
- YPTJKHVBDCRKNF-UHFFFAOYSA-N 2',6'-Dihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=CC=C1O YPTJKHVBDCRKNF-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- XJVFDVKXQFIYCP-UHFFFAOYSA-N 2-ethylhexyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound CCCCC(CC)COC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O XJVFDVKXQFIYCP-UHFFFAOYSA-N 0.000 description 2
- FSSGJRZHNCCLND-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-5-methyl-n-octylhexanamide Chemical compound CCCCCCCCNC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O FSSGJRZHNCCLND-UHFFFAOYSA-N 0.000 description 2
- CZVYEUMUKFOXGP-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-5-methylhexanoic acid Chemical compound OC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O CZVYEUMUKFOXGP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HYNYDZQETMTEHW-UHFFFAOYSA-N [7-(2,4-dihydroxyphenyl)-3,7-dimethyloctyl] acetate Chemical compound CC(=O)OCCC(C)CCCC(C)(C)C1=CC=C(O)C=C1O HYNYDZQETMTEHW-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- UJKCMASNMQOLFP-UHFFFAOYSA-N hexyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound CCCCCCOC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O UJKCMASNMQOLFP-UHFFFAOYSA-N 0.000 description 2
- IAWZMQNZGDWHMU-UHFFFAOYSA-N methyl 5-(2,4-dihydroxy-3-methylphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(C)=C1O IAWZMQNZGDWHMU-UHFFFAOYSA-N 0.000 description 2
- MUHJFQDNLZVRIB-UHFFFAOYSA-N n-(6-hydroxy-6-methylheptan-2-yl)acetamide Chemical compound CC(=O)NC(C)CCCC(C)(C)O MUHJFQDNLZVRIB-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QTZNKZBDWZKNEX-UHFFFAOYSA-N (4-methylphenyl) 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound C1=CC(C)=CC=C1OC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O QTZNKZBDWZKNEX-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 1
- OLBXCHICOZRKFK-UHFFFAOYSA-N 11-amino-2,2,12-trimethyltridecan-1-ol Chemical compound CC(C)C(N)CCCCCCCCC(C)(C)CO OLBXCHICOZRKFK-UHFFFAOYSA-N 0.000 description 1
- NZGJFGWSZTUGIT-UHFFFAOYSA-N 2-(2,4-dihydroxyphenyl)-2-methylpropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)C1=CC=C(O)C=C1O NZGJFGWSZTUGIT-UHFFFAOYSA-N 0.000 description 1
- LRLDAUJFKBMGKF-UHFFFAOYSA-N 2-(2,4-dihydroxyphenyl)-N-icosyl-2-methylpropane-1-sulfonamide Chemical compound CCCCCCCCCCCCCCCCCCCCNS(=O)(=O)CC(C)(C)C1=CC=C(O)C=C1O LRLDAUJFKBMGKF-UHFFFAOYSA-N 0.000 description 1
- CKNVBUDCNSAMHC-UHFFFAOYSA-N 2-(2,4-dihydroxyphenyl)-n,2-dimethylpropane-1-sulfonamide Chemical compound CNS(=O)(=O)CC(C)(C)C1=CC=C(O)C=C1O CKNVBUDCNSAMHC-UHFFFAOYSA-N 0.000 description 1
- YMNZCAMXJYRXDO-UHFFFAOYSA-N 2-(2,4-dihydroxyphenyl)-n,n-diethyl-2-methylpropane-1-sulfonamide Chemical compound CCN(CC)S(=O)(=O)CC(C)(C)C1=CC=C(O)C=C1O YMNZCAMXJYRXDO-UHFFFAOYSA-N 0.000 description 1
- HKDMBSOJNQJYBF-UHFFFAOYSA-N 2-(2,4-dihydroxyphenyl)-n-dodecyl-2-methylpropane-1-sulfonamide Chemical compound CCCCCCCCCCCCNS(=O)(=O)CC(C)(C)C1=CC=C(O)C=C1O HKDMBSOJNQJYBF-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- MCELKPNYKMMNHU-UHFFFAOYSA-N 2-butoxyethyl 5-[2,4-dihydroxy-3-[(2-phenylacetyl)amino]phenyl]-5-methylhexanoate Chemical compound CCCCOCCOC(=O)CCCC(C)(C)C1=CC=C(O)C(NC(=O)CC=2C=CC=CC=2)=C1O MCELKPNYKMMNHU-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- IRZZDMCHRRNYHD-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonamide Chemical compound CC(=C)CS(N)(=O)=O IRZZDMCHRRNYHD-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YTTXWFJGCBZAQR-UHFFFAOYSA-N 4-(12-amino-3,13-dimethyltetradecan-2-yl)benzene-1,3-diol Chemical compound CC(C)C(N)CCCCCCCCC(C)C(C)C1=CC=C(O)C=C1O YTTXWFJGCBZAQR-UHFFFAOYSA-N 0.000 description 1
- SLUYFRGKYHFHTB-UHFFFAOYSA-N 4-(12-amino-3,13-dimethyltetradecan-3-yl)benzene-1,3-diol Chemical compound CC(C)C(N)CCCCCCCCC(C)(CC)C1=CC=C(O)C=C1O SLUYFRGKYHFHTB-UHFFFAOYSA-N 0.000 description 1
- QBRIXEPEXMMZIY-UHFFFAOYSA-N 4-(2-methyl-6-morpholin-4-ylheptan-2-yl)benzene-1,3-diol Chemical compound C1COCCN1C(C)CCCC(C)(C)C1=CC=C(O)C=C1O QBRIXEPEXMMZIY-UHFFFAOYSA-N 0.000 description 1
- XRRBIWQPSQTBOQ-UHFFFAOYSA-N 4-(4-diethoxyphosphoryl-2-methylbutan-2-yl)benzene-1,3-diol Chemical compound CCOP(=O)(OCC)CCC(C)(C)C1=CC=C(O)C=C1O XRRBIWQPSQTBOQ-UHFFFAOYSA-N 0.000 description 1
- DLLHIPJRXMMHFN-UHFFFAOYSA-N 4-(4-dimethoxyphosphoryl-2-methylbutan-2-yl)benzene-1,3-diol Chemical compound COP(=O)(OC)CCC(C)(C)C1=CC=C(O)C=C1O DLLHIPJRXMMHFN-UHFFFAOYSA-N 0.000 description 1
- IPLVOABIGNNKNI-UHFFFAOYSA-N 4-(8-hydroxy-2,6-dimethyloctan-2-yl)benzene-1,3-diol Chemical compound OCCC(C)CCCC(C)(C)C1=CC=C(O)C=C1O IPLVOABIGNNKNI-UHFFFAOYSA-N 0.000 description 1
- PGAXPCLVZGYKLK-UHFFFAOYSA-N 4-[4-[dodecoxy(methoxy)phosphoryl]-2-methylbutan-2-yl]benzene-1,3-diol Chemical compound CCCCCCCCCCCCOP(=O)(OC)CCC(C)(C)C1=CC=C(O)C=C1O PGAXPCLVZGYKLK-UHFFFAOYSA-N 0.000 description 1
- IWMRJSNSRKUKBI-UHFFFAOYSA-N 4-[6-(dimethylamino)-2-methylheptan-2-yl]benzene-1,3-diol Chemical compound CN(C)C(C)CCCC(C)(C)C1=CC=C(O)C=C1O IWMRJSNSRKUKBI-UHFFFAOYSA-N 0.000 description 1
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
- FWWFIYAXTAKOFH-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-5-methylhexanenitrile Chemical compound N#CCCCC(C)(C)C1=CC=C(O)C=C1O FWWFIYAXTAKOFH-UHFFFAOYSA-N 0.000 description 1
- ZXLQBVXBIWDHHC-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-n,5-dimethylhexanamide Chemical compound CNC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O ZXLQBVXBIWDHHC-UHFFFAOYSA-N 0.000 description 1
- WRPYJCVQPJTEEK-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-n,n,5-trimethylhexanamide Chemical compound CN(C)C(=O)CCCC(C)(C)C1=CC=C(O)C=C1O WRPYJCVQPJTEEK-UHFFFAOYSA-N 0.000 description 1
- ZWPGWVOFTGCNTO-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-n,n-diethyl-5-methylhexanamide Chemical compound CCN(CC)C(=O)CCCC(C)(C)C1=CC=C(O)C=C1O ZWPGWVOFTGCNTO-UHFFFAOYSA-N 0.000 description 1
- QEBFTRKKSKLZSQ-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-n-ethyl-5-methylhexanamide Chemical compound CCNC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O QEBFTRKKSKLZSQ-UHFFFAOYSA-N 0.000 description 1
- RSJZKEOFIYHKQM-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-n-hexyl-5-methylhexanamide Chemical compound CCCCCCNC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O RSJZKEOFIYHKQM-UHFFFAOYSA-N 0.000 description 1
- QHXGXJPMRPBUEQ-UHFFFAOYSA-N 5-(2,4-dihydroxyphenyl)-n-icosyl-5-methylhexanamide Chemical compound CCCCCCCCCCCCCCCCCCCCNC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O QHXGXJPMRPBUEQ-UHFFFAOYSA-N 0.000 description 1
- HCLVGAZUVMWYLF-UHFFFAOYSA-N 5-methyl-5-hexenoic acid Chemical compound CC(=C)CCCC(O)=O HCLVGAZUVMWYLF-UHFFFAOYSA-N 0.000 description 1
- MHPUGCYGQWGLJL-UHFFFAOYSA-M 5-methylhexanoate Chemical compound CC(C)CCCC([O-])=O MHPUGCYGQWGLJL-UHFFFAOYSA-M 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HJIVNXPDFJBPDH-UHFFFAOYSA-N cyclohexyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)CCCC(=O)OC1CCCCC1 HJIVNXPDFJBPDH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- DEBHWTLOYPRNGF-UHFFFAOYSA-N dodecyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O DEBHWTLOYPRNGF-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229960005402 heptaminol Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
- JQFVDVMUTKYJSL-UHFFFAOYSA-N icosyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O JQFVDVMUTKYJSL-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- JRHLOKKVPAZVGT-UHFFFAOYSA-N methyl 21-(2,4-dihydroxyphenyl)-21-methyldocosanoate Chemical compound COC(=O)CCCCCCCCCCCCCCCCCCCC(C)(C)C1=CC=C(O)C=C1O JRHLOKKVPAZVGT-UHFFFAOYSA-N 0.000 description 1
- FPRJKVWEENBRHC-UHFFFAOYSA-N methyl 4-(2,4-dihydroxyphenyl)-4-methylcyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1(C)C1=CC=C(O)C=C1O FPRJKVWEENBRHC-UHFFFAOYSA-N 0.000 description 1
- JNDBPUPULVCVFC-UHFFFAOYSA-N methyl 4-methylcyclohex-3-ene-1-carboxylate Chemical compound COC(=O)C1CCC(C)=CC1 JNDBPUPULVCVFC-UHFFFAOYSA-N 0.000 description 1
- DEWFACSJRYPQNH-UHFFFAOYSA-N methyl 5-(2,4-dihydroxy-3-pentylphenyl)-5-methylhexanoate Chemical compound CCCCCC1=C(O)C=CC(C(C)(C)CCCC(=O)OC)=C1O DEWFACSJRYPQNH-UHFFFAOYSA-N 0.000 description 1
- DMZJQKIBUVCYKE-UHFFFAOYSA-N methyl 5-(2,4-dihydroxy-5-methylsulfanylphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC(SC)=C(O)C=C1O DMZJQKIBUVCYKE-UHFFFAOYSA-N 0.000 description 1
- YZJDWIHKBIFXFA-UHFFFAOYSA-N methyl 5-(2,4-dihydroxy-5-pentylsulfanylphenyl)-5-methylhexanoate Chemical compound CCCCCSC1=CC(C(C)(C)CCCC(=O)OC)=C(O)C=C1O YZJDWIHKBIFXFA-UHFFFAOYSA-N 0.000 description 1
- DWSAXVPERYCMQT-UHFFFAOYSA-N methyl 5-(2,4-dihydroxy-5-phenylsulfanylphenyl)-5-methylhexanoate Chemical compound C1=C(O)C(C(C)(C)CCCC(=O)OC)=CC(SC=2C=CC=CC=2)=C1O DWSAXVPERYCMQT-UHFFFAOYSA-N 0.000 description 1
- KPXNIRJDYNWYLS-UHFFFAOYSA-N methyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O KPXNIRJDYNWYLS-UHFFFAOYSA-N 0.000 description 1
- SUOQCERZIULJHA-UHFFFAOYSA-N methyl 5-(3,5-dibromo-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC(Br)=C(O)C(Br)=C1O SUOQCERZIULJHA-UHFFFAOYSA-N 0.000 description 1
- ZDTIENBELYANNI-UHFFFAOYSA-N methyl 5-(3,5-dichloro-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1O ZDTIENBELYANNI-UHFFFAOYSA-N 0.000 description 1
- AIFGFNSJWKJGNF-UHFFFAOYSA-N methyl 5-(3-acetamido-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(NC(C)=O)=C1O AIFGFNSJWKJGNF-UHFFFAOYSA-N 0.000 description 1
- BEYIROARARZPJF-UHFFFAOYSA-N methyl 5-(3-acetyl-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(C(C)=O)=C1O BEYIROARARZPJF-UHFFFAOYSA-N 0.000 description 1
- NPJUOHDECLAZCM-UHFFFAOYSA-N methyl 5-(3-bromo-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(Br)=C1O NPJUOHDECLAZCM-UHFFFAOYSA-N 0.000 description 1
- DBWSLQSSMOPTDQ-UHFFFAOYSA-N methyl 5-(3-chloro-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(Cl)=C1O DBWSLQSSMOPTDQ-UHFFFAOYSA-N 0.000 description 1
- GHYUBMPOKYQDPE-UHFFFAOYSA-N methyl 5-(5-bromo-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC(Br)=C(O)C=C1O GHYUBMPOKYQDPE-UHFFFAOYSA-N 0.000 description 1
- BKJVCJYGNMDDGW-UHFFFAOYSA-N methyl 5-(5-chloro-2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC(Cl)=C(O)C=C1O BKJVCJYGNMDDGW-UHFFFAOYSA-N 0.000 description 1
- PFVQWSUTHKSKRA-UHFFFAOYSA-N methyl 5-[2,4-dihydroxy-3-(prop-2-enoylamino)phenyl]-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(NC(=O)C=C)=C1O PFVQWSUTHKSKRA-UHFFFAOYSA-N 0.000 description 1
- FUPYWABTEQUONU-UHFFFAOYSA-N methyl 5-[3-(cyclohexanecarbonylamino)-2,4-dihydroxyphenyl]-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=C(O)C(NC(=O)C2CCCCC2)=C1O FUPYWABTEQUONU-UHFFFAOYSA-N 0.000 description 1
- ULJWOYASSOTGGQ-UHFFFAOYSA-N methyl 5-[3-(dodecanoylamino)-2,4-dihydroxyphenyl]-5-methylhexanoate Chemical compound CCCCCCCCCCCC(=O)NC1=C(O)C=CC(C(C)(C)CCCC(=O)OC)=C1O ULJWOYASSOTGGQ-UHFFFAOYSA-N 0.000 description 1
- JVZAOFWHBUUONL-UHFFFAOYSA-N methyl 5-[3-(hexanoylamino)-2,4-dihydroxyphenyl]-5-methylhexanoate Chemical compound CCCCCC(=O)NC1=C(O)C=CC(C(C)(C)CCCC(=O)OC)=C1O JVZAOFWHBUUONL-UHFFFAOYSA-N 0.000 description 1
- XUUOSBRRQHFVNM-UHFFFAOYSA-N methyl 5-methylhex-5-enoate Chemical compound COC(=O)CCCC(C)=C XUUOSBRRQHFVNM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FZQKKUPVFOGQGR-UHFFFAOYSA-N n,2-dimethylprop-2-ene-1-sulfonamide Chemical compound CNS(=O)(=O)CC(C)=C FZQKKUPVFOGQGR-UHFFFAOYSA-N 0.000 description 1
- QCRYSDZPKYQJBD-UHFFFAOYSA-N n,n,2-trimethylprop-2-ene-1-sulfonamide Chemical compound CN(C)S(=O)(=O)CC(C)=C QCRYSDZPKYQJBD-UHFFFAOYSA-N 0.000 description 1
- FUNQUBKTHQDOPQ-UHFFFAOYSA-N n,n-dibutyl-5-(2,4-dihydroxyphenyl)-5-methylhexanamide Chemical compound CCCCN(CCCC)C(=O)CCCC(C)(C)C1=CC=C(O)C=C1O FUNQUBKTHQDOPQ-UHFFFAOYSA-N 0.000 description 1
- WTSBTMVLSCNWIL-UHFFFAOYSA-N n-(4-butylphenyl)-5-(2,4-dihydroxyphenyl)-5-methylhexanamide Chemical compound C1=CC(CCCC)=CC=C1NC(=O)CCCC(C)(C)C1=CC=C(O)C=C1O WTSBTMVLSCNWIL-UHFFFAOYSA-N 0.000 description 1
- DWPRGJBRAALJCG-UHFFFAOYSA-N n-(6-hydroxy-6-methylheptan-2-yl)hexanamide Chemical compound CCCCCC(=O)NC(C)CCCC(C)(C)O DWPRGJBRAALJCG-UHFFFAOYSA-N 0.000 description 1
- JZEZTAZIRDGKNF-UHFFFAOYSA-N n-(6-methylhept-5-en-2-yl)acetamide Chemical compound CC(=O)NC(C)CCC=C(C)C JZEZTAZIRDGKNF-UHFFFAOYSA-N 0.000 description 1
- SHDRVWPBMISXRE-UHFFFAOYSA-N n-[5-(2,4-dihydroxyphenyl)-5-methylhexyl]acetamide Chemical compound CC(=O)NCCCCC(C)(C)C1=CC=C(O)C=C1O SHDRVWPBMISXRE-UHFFFAOYSA-N 0.000 description 1
- PHXKAOBULXOVOK-UHFFFAOYSA-N n-[6-(2,4-dihydroxyphenyl)-6-methylheptan-2-yl]acetamide Chemical compound CC(=O)NC(C)CCCC(C)(C)C1=CC=C(O)C=C1O PHXKAOBULXOVOK-UHFFFAOYSA-N 0.000 description 1
- VDBNVSLESOFLID-UHFFFAOYSA-N n-[6-(2,4-dihydroxyphenyl)-6-methylheptan-2-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C)CCCC(C)(C)C1=CC=C(O)C=C1O VDBNVSLESOFLID-UHFFFAOYSA-N 0.000 description 1
- AKGJPBVRNBJTNL-UHFFFAOYSA-N n-[6-(2,4-dihydroxyphenyl)-6-methylheptan-2-yl]hexanamide Chemical compound CCCCCC(=O)NC(C)CCCC(C)(C)C1=CC=C(O)C=C1O AKGJPBVRNBJTNL-UHFFFAOYSA-N 0.000 description 1
- XLZLOQNYHPGIQJ-UHFFFAOYSA-N n-benzyl-2-(2,4-dihydroxyphenyl)-2-methylpropane-1-sulfonamide Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)CS(=O)(=O)NCC1=CC=CC=C1 XLZLOQNYHPGIQJ-UHFFFAOYSA-N 0.000 description 1
- XMYDKFSMUJKERZ-UHFFFAOYSA-N n-benzyl-5-(2,4-dihydroxyphenyl)-5-methylhexanamide Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)CCCC(=O)NCC1=CC=CC=C1 XMYDKFSMUJKERZ-UHFFFAOYSA-N 0.000 description 1
- JGYKYVUPEFJVNB-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dihydroxyphenyl)-2-methylpropane-1-sulfonamide Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)CS(=O)(=O)NC1CCCCC1 JGYKYVUPEFJVNB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- NUHKIPUNLZPKQY-UHFFFAOYSA-N phenyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)CCCC(=O)OC1=CC=CC=C1 NUHKIPUNLZPKQY-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [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])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/245—Halogenated derivatives monocyclic polyhydroxylic containing halogens bound to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/18—Acetic acid esters of trihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
- G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
- G03C7/30523—Phenols or naphtols couplers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
- G03C7/346—Phenolic couplers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8119011 | 1981-06-19 | ||
| GB8119011 | 1981-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58925A JPS58925A (ja) | 1983-01-06 |
| JPH03369B2 true JPH03369B2 (OSRAM) | 1991-01-07 |
Family
ID=10522666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57104064A Granted JPS58925A (ja) | 1981-06-19 | 1982-06-18 | レゾルシノ−ル化合物およびその製法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4661601A (OSRAM) |
| EP (1) | EP0069066B1 (OSRAM) |
| JP (1) | JPS58925A (OSRAM) |
| CA (1) | CA1240689A (OSRAM) |
| DE (1) | DE3260883D1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3362618D1 (en) * | 1982-10-07 | 1986-04-24 | Ciba Geigy Ag | Phenols and their preparation |
| US5202458A (en) * | 1987-09-28 | 1993-04-13 | Ciba-Geigy Ag | Stabilizers for color photographic recording materials |
| EP0309957B1 (de) * | 1987-09-28 | 1992-05-27 | Ciba-Geigy Ag | Stabilisatoren für farbphotographische Aufzeichnungsmaterialien |
| EP1467248A1 (en) * | 2003-04-11 | 2004-10-13 | Fuji Photo Film B.V. | Photographic colour material containing a resorcinol derivative as black coupler |
| WO2022195364A1 (en) | 2021-03-17 | 2022-09-22 | 3M Innovative Properties Company | Polymerizable 4,4'-spirobi[chromane]-2,2'-diones and curable compositions including the same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2008337A (en) * | 1932-05-09 | 1935-07-16 | Rohm & Haas | Condensation product of dhsobutylene and polyhydric phenols |
| US2050188A (en) * | 1932-07-20 | 1936-08-04 | Sharples Solvents Corp | Method of producing derivatives of hydroxy aryl compounds |
| US2051473A (en) * | 1933-04-29 | 1936-08-18 | Shell Dev | Production of alkylated phenolic bodies |
| US2099738A (en) * | 1934-06-30 | 1937-11-23 | Universal Oil Prod Co | Alkylation of trihydric phenols |
| US2191240A (en) * | 1936-12-05 | 1940-02-20 | Gulf Oil Corp | Manufacture of stabilized gasoline |
| FR1468342A (fr) * | 1965-03-11 | 1967-02-03 | Mira Lanza Spa | Procédé de préparation d'esters d'acides aliphatiques hydroxy-arylés |
| US4323714A (en) * | 1980-11-20 | 1982-04-06 | Uop Inc. | Alkylation of hydroxy-substituted aromatic compounds |
| CA1247632A (en) * | 1981-06-19 | 1988-12-28 | Frederick H. Howell | Hydroquinones |
-
1982
- 1982-06-14 EP EP82810255A patent/EP0069066B1/de not_active Expired
- 1982-06-14 DE DE8282810255T patent/DE3260883D1/de not_active Expired
- 1982-06-17 CA CA000405366A patent/CA1240689A/en not_active Expired
- 1982-06-18 JP JP57104064A patent/JPS58925A/ja active Granted
-
1985
- 1985-04-03 US US06/719,184 patent/US4661601A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0069066A1 (de) | 1983-01-05 |
| US4661601A (en) | 1987-04-28 |
| CA1240689A (en) | 1988-08-16 |
| EP0069066B1 (de) | 1984-10-03 |
| JPS58925A (ja) | 1983-01-06 |
| DE3260883D1 (en) | 1984-11-08 |
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