CA2263090A1 - Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines - Google Patents
Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines Download PDFInfo
- Publication number
- CA2263090A1 CA2263090A1 CA002263090A CA2263090A CA2263090A1 CA 2263090 A1 CA2263090 A1 CA 2263090A1 CA 002263090 A CA002263090 A CA 002263090A CA 2263090 A CA2263090 A CA 2263090A CA 2263090 A1 CA2263090 A1 CA 2263090A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- carbon atoms
- alkyl
- halogen
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 91
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 45
- 239000002841 Lewis acid Substances 0.000 claims abstract description 29
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 29
- 239000003377 acid catalyst Substances 0.000 claims abstract description 20
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical group 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 29
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 150000002989 phenols Chemical class 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 27
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 16
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 12
- 125000003118 aryl group Chemical group 0.000 abstract description 9
- 239000000758 substrate Substances 0.000 abstract description 9
- 230000000269 nucleophilic effect Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 239000006096 absorbing agent Substances 0.000 abstract description 2
- 230000002411 adverse Effects 0.000 abstract description 2
- BEOWAMYAXCGDMK-UHFFFAOYSA-N 4-(1,3,5-triazin-2-yl)benzene-1,2,3-triol Chemical compound Oc1ccc(c(O)c1O)-c1ncncn1 BEOWAMYAXCGDMK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 150000003918 triazines Chemical class 0.000 abstract 1
- 125000005023 xylyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 12
- 229940098779 methanesulfonic acid Drugs 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003828 vacuum filtration Methods 0.000 description 10
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- -1 hydrogen halides Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003444 phase transfer catalyst Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- WPAYYYDSSCOEHN-UHFFFAOYSA-N 2-chloro-4,6-diphenoxy-1,3,5-triazine Chemical compound N=1C(OC=2C=CC=CC=2)=NC(Cl)=NC=1OC1=CC=CC=C1 WPAYYYDSSCOEHN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000011575 calcium Chemical class 0.000 description 2
- 229910052791 calcium Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011591 potassium Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- ZQBKITVCWRWZPS-UHFFFAOYSA-N 1,1'-biphenyl 4-(1,3,5-triazin-2-yl)benzene-1,3-diol Chemical compound OC1=C(C=CC(=C1)O)C1=NC=NC=N1.C1=C(C=CC=C1)C1=CC=CC=C1 ZQBKITVCWRWZPS-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WWASTWQYXXOELT-UHFFFAOYSA-N 2,4-bis(2,4-dimethylphenyl)-4-propoxy-1h-1,3,5-triazine Chemical compound N=1C(OCCC)(C=2C(=CC(C)=CC=2)C)NC=NC=1C1=CC=C(C)C=C1C WWASTWQYXXOELT-UHFFFAOYSA-N 0.000 description 1
- LPOJIRJXGOALES-UHFFFAOYSA-N 2,4-bis(2,4-dimethylphenyl)-6-phenoxy-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC(OC=2C=CC=CC=2)=NC(C=2C(=CC(C)=CC=2)C)=N1 LPOJIRJXGOALES-UHFFFAOYSA-N 0.000 description 1
- ONJNUTGHRYVYHO-UHFFFAOYSA-N 2,4-dichloro-4-[3-[(2,4-dichloro-1h-1,3,5-triazin-4-yl)oxy]phenoxy]-1h-1,3,5-triazine Chemical compound N1C=NC(Cl)=NC1(Cl)OC1=CC=CC(OC2(Cl)N=C(Cl)N=CN2)=C1 ONJNUTGHRYVYHO-UHFFFAOYSA-N 0.000 description 1
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 1
- UOBCMPHSRPQQIT-UHFFFAOYSA-N 2,4-diphenoxy-6-(2,4,6-trimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC(C)=C1C1=NC(OC=2C=CC=CC=2)=NC(OC=2C=CC=CC=2)=N1 UOBCMPHSRPQQIT-UHFFFAOYSA-N 0.000 description 1
- MRGNHBPLBXQZRA-UHFFFAOYSA-N 2-[3-[[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]oxy]phenoxy]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC(OC=2C=C(OC=3N=C(N=C(N=3)C=3C(=CC(C)=CC=3)C)C=3C(=CC(C)=CC=3)C)C=CC=2)=NC(C=2C(=CC(C)=CC=2)C)=N1 MRGNHBPLBXQZRA-UHFFFAOYSA-N 0.000 description 1
- LVWOBZPDFCTAOU-UHFFFAOYSA-N 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC(Cl)=NC(C=2C(=CC(C)=CC=2)C)=N1 LVWOBZPDFCTAOU-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- VQHGZBRYGMNULJ-UHFFFAOYSA-N 4-[4-(2,4-dihydroxyphenyl)-6-(2,4,6-trimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC(C)=C1C1=NC(C=2C(=CC(O)=CC=2)O)=NC(C=2C(=CC(O)=CC=2)O)=N1 VQHGZBRYGMNULJ-UHFFFAOYSA-N 0.000 description 1
- GZCHMQTWICRCLR-UHFFFAOYSA-N 4-[4-(2,4-dihydroxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC(O)=CC=2)O)=N1 GZCHMQTWICRCLR-UHFFFAOYSA-N 0.000 description 1
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical class OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 238000010485 C−C bond formation reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000010842 Sarcandra glabra Nutrition 0.000 description 1
- 240000004274 Sarcandra glabra Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- XMHAFYSAMZJJDN-UHFFFAOYSA-N benzene-1,3-diol;1,3,5-triazine Chemical class C1=NC=NC=N1.OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1 XMHAFYSAMZJJDN-UHFFFAOYSA-N 0.000 description 1
- PGTXRVQSJHKGSN-UHFFFAOYSA-N benzene-1,3-diol;2-(1,3,5-triazin-2-yl)-1,3,5-triazine Chemical compound OC1=CC=CC(O)=C1.C1=NC=NC(C=2N=CN=CN=2)=N1 PGTXRVQSJHKGSN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3326698A | 1998-03-02 | 1998-03-02 | |
| US09/033,266 | 1998-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2263090A1 true CA2263090A1 (en) | 1999-09-02 |
Family
ID=21869434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002263090A Abandoned CA2263090A1 (en) | 1998-03-02 | 1999-02-26 | Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6242598B1 (enFirst) |
| EP (1) | EP0941989B1 (enFirst) |
| JP (1) | JP4629814B2 (enFirst) |
| KR (1) | KR100555072B1 (enFirst) |
| CN (1) | CN1202090C (enFirst) |
| CA (1) | CA2263090A1 (enFirst) |
| DE (1) | DE69941073D1 (enFirst) |
| IN (1) | IN188425B (enFirst) |
| TW (1) | TWI236472B (enFirst) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI259182B (en) | 1998-11-17 | 2006-08-01 | Cytec Tech Corp | Process for preparing triazines using a combination of Lewis acids with reaction promoters |
| JP4744754B2 (ja) * | 1999-06-18 | 2011-08-10 | チバ ホールディング インコーポレーテッド | ミクロ顔料からなる混合物 |
| WO2001057124A2 (en) | 2000-02-01 | 2001-08-09 | Ciba Specialty Chemicals Holding Inc. | Method of content protection with durable uv absorbers |
| JP4181413B2 (ja) | 2001-03-22 | 2008-11-12 | チバ ホールディング インコーポレーテッド | キナクリドン顔料用の相配向剤及び粒子サイズ減少剤としての芳香族化合物の使用 |
| US6632944B2 (en) | 2001-06-22 | 2003-10-14 | Cytec Technology Corp. | Process for isolation of monophenolic-bisaryl triazines |
| TWI318208B (en) * | 2001-07-02 | 2009-12-11 | Ciba Sc Holding Ag | Highly compatible hydroxyphenyltriazine uv-absorbers |
| US7015227B2 (en) | 2002-06-21 | 2006-03-21 | Cgi Pharmaceuticals, Inc. | Certain amino-substituted monocycles as kinase modulators |
| JP4850694B2 (ja) | 2003-02-26 | 2012-01-11 | チバ ホールディング インコーポレーテッド | 水融和性立体阻害されたヒドロキシ置換アルコキシアミン類 |
| MX267068B (es) | 2003-03-24 | 2009-05-29 | Ciba Sc Holding Ag | Derivados simetricos de triazina. |
| US7595011B2 (en) | 2004-07-12 | 2009-09-29 | Ciba Specialty Chemicals Corporation | Stabilized electrochromic media |
| WO2006131469A1 (en) | 2005-06-10 | 2006-12-14 | Ciba Specialty Chemicals Holding Inc. | Tris(hydroxyphenyl) triazines |
| CN101636455B (zh) | 2007-03-15 | 2013-11-27 | 巴斯夫欧洲公司 | 基于间苯二酚基三嗪衍生物的热敏涂料组合物 |
| EP2167570A1 (en) | 2007-06-29 | 2010-03-31 | Basell Poliolefine Italia S.R.L. | An irradiated polyolefin composition comprising a non - phenolic stabilizer |
| EP2181163B1 (en) | 2007-08-22 | 2011-12-21 | DataLase Ltd | Laser-sensitive coating composition |
| CA2702732A1 (en) | 2007-11-07 | 2009-05-14 | Basf Se | New fiber products |
| CN102056906B (zh) * | 2008-06-04 | 2014-02-12 | 株式会社Adeka | 2,4,6-三(羟苯基)-1,3,5-三嗪化合物的制造方法 |
| WO2010026230A1 (de) | 2008-09-05 | 2010-03-11 | Thor Gmbh | Flammschutzzusammensetzung enthaltend ein phosphonsäurederivat |
| US20120045624A1 (en) | 2008-10-27 | 2012-02-23 | Basf Se | Aqueous laser-sensitive composition for marking substrates |
| CN102264825B (zh) | 2008-12-22 | 2014-07-02 | 巴斯夫欧洲公司 | 改善耐刮性的方法及相关产品和用途 |
| JP5675647B2 (ja) | 2009-01-19 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 有機黒色顔料およびその製造 |
| JP5719528B2 (ja) | 2009-06-09 | 2015-05-20 | 富士フイルム株式会社 | 新規なトリアジン誘導体、紫外線吸収剤及び樹脂組成物 |
| JP5422269B2 (ja) | 2009-06-23 | 2014-02-19 | 富士フイルム株式会社 | 紫外線吸収剤組成物及び樹脂組成物 |
| KR101782173B1 (ko) | 2009-07-07 | 2017-10-23 | 바스프 에스이 | 칼륨 세슘 텅스텐 브론즈 입자 |
| JP5613481B2 (ja) | 2009-07-29 | 2014-10-22 | 富士フイルム株式会社 | 新規なトリアジン誘導体、紫外線吸収剤 |
| US8748520B2 (en) | 2009-09-28 | 2014-06-10 | Fujifilm Corporation | Polycarbonate resin composition containing triazine compound and molded article using the same |
| JP5647872B2 (ja) | 2010-01-19 | 2015-01-07 | 富士フイルム株式会社 | ポリエステル樹脂組成物 |
| JP2012072125A (ja) | 2010-08-31 | 2012-04-12 | Fujifilm Corp | トリアジン系化合物、及び紫外線吸収剤 |
| US9481670B2 (en) * | 2011-01-25 | 2016-11-01 | Sphaera Pharma Pte. Ltd. | Triazine compounds |
| US8663457B2 (en) | 2011-11-23 | 2014-03-04 | General Electric Company | Methods and compounds for improving sulfide scavenging activity |
| US9108899B2 (en) | 2011-12-30 | 2015-08-18 | General Electric Company | Sulfide scavengers, methods for making and methods for using |
| EP2912017A4 (en) | 2012-10-23 | 2016-07-20 | Basf Se | ETHYLENICALLY UNSATURATED OLIGOMERS WITH POLYMER STABILIZATION GROUPS |
| KR102294024B1 (ko) | 2013-09-27 | 2021-08-27 | 바스프 에스이 | 건축 재료를 위한 폴리올레핀 조성물 |
| US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| US9850208B2 (en) | 2014-01-27 | 2017-12-26 | Vertellus Holdings Llc | Process for making 2-chloro-5-methylpyridine |
| WO2017013028A1 (en) | 2015-07-20 | 2017-01-26 | Basf Se | Flame retardant polyolefin articles |
| EP3645527A1 (de) * | 2017-06-26 | 2020-05-06 | Merck Patent GmbH | Verfahren zur herstellung substituierter stickstoffhaltiger heterocyclen |
| PL3841166T5 (pl) | 2018-08-22 | 2025-08-18 | Basf Se | Stabilizowana poliolefina wytwarzana w procesie formowania rotacyjnego |
| US12289992B2 (en) | 2018-10-05 | 2025-04-29 | Samsung Display Co., Ltd. | Display apparatus and light absorber included in display apparatus |
| WO2020144094A1 (en) | 2019-01-08 | 2020-07-16 | Basf Se | A process for the preparation of uv absorbers |
| US20230220239A1 (en) | 2019-03-18 | 2023-07-13 | Basf Se | Uv curable compositions for dirt pick-up resistance |
| US20220282064A1 (en) | 2019-07-30 | 2022-09-08 | Basf Se | Stabilizer composition |
| CN112647319B (zh) * | 2020-11-24 | 2022-11-01 | 长胜纺织科技发展(上海)有限公司 | 转移染色活性染料墨水及其应用 |
| CN120379973A (zh) | 2022-12-19 | 2025-07-25 | 巴斯夫欧洲公司 | 机械处理以获得取代的三嗪产物 |
| CN116143715B (zh) * | 2023-02-28 | 2023-11-24 | 江苏极易新材料有限公司 | 一种2-(4,6-二苯基-1,3,5-三嗪-2-基)-5-正己烷氧基苯酚合成方法 |
| CN120590593B (zh) * | 2025-08-04 | 2025-10-24 | 湖南工程学院 | 一种杂原子修饰的自具微孔聚合物材料、制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118887A (en) * | 1961-03-06 | 1964-01-21 | American Cyanamid Co | O-hydroxy substituted tris aryl-s-triazines |
| NL299881A (enFirst) * | 1962-10-30 | |||
| NL130993C (enFirst) * | 1963-02-07 | |||
| CH473818A (de) * | 1964-03-18 | 1969-06-15 | Ciba Geigy | Verfahren zur Herstellung von neuen Hydroxyphenyl-1,3,5-triazinen und deren Verwendung |
| CH473604A (de) * | 1965-02-19 | 1969-06-15 | Ciba Geigy | Verwendung von neuen Aryl-1,3,5-triazinen als Stabilisierungsmittel für nicht-textile organische Materialien |
| EP0165608B1 (de) * | 1984-06-22 | 1991-01-02 | Ilford Ag | Hydroxyphenyltriazine, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber |
| ES2081868T3 (es) | 1989-04-21 | 1996-03-16 | Ciba Geigy Ag | Procedimiento para la preparacion de 2-(2',4'-dihidroxifenil)-4,6-diaril-s-triazinas. |
| US5556973A (en) * | 1994-07-27 | 1996-09-17 | Ciba-Geigy Corporation | Red-shifted tris-aryl-s-triazines and compositions stabilized therewith |
| JP3844307B2 (ja) * | 1995-08-11 | 2006-11-08 | 株式会社Ａｄｅｋａ | ２−（２’，４’−ジヒドロキシフェニル）−４，６−ジアリール−ｓ−トリアジン誘導体の製造方法 |
-
1999
- 1999-02-22 EP EP99810156A patent/EP0941989B1/en not_active Expired - Lifetime
- 1999-02-22 DE DE69941073T patent/DE69941073D1/de not_active Expired - Lifetime
- 1999-02-26 CA CA002263090A patent/CA2263090A1/en not_active Abandoned
- 1999-03-01 IN IN251MA1999 patent/IN188425B/en unknown
- 1999-03-02 CN CNB991031563A patent/CN1202090C/zh not_active Expired - Lifetime
- 1999-03-02 TW TW088103143A patent/TWI236472B/zh not_active IP Right Cessation
- 1999-03-02 JP JP05444399A patent/JP4629814B2/ja not_active Expired - Fee Related
- 1999-03-02 KR KR1019990006776A patent/KR100555072B1/ko not_active Expired - Fee Related
-
2000
- 2000-03-22 US US09/532,222 patent/US6242598B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| TWI236472B (en) | 2005-07-21 |
| KR100555072B1 (ko) | 2006-02-24 |
| KR19990077522A (ko) | 1999-10-25 |
| JPH11315072A (ja) | 1999-11-16 |
| DE69941073D1 (de) | 2009-08-20 |
| JP4629814B2 (ja) | 2011-02-09 |
| EP0941989A2 (en) | 1999-09-15 |
| CN1232823A (zh) | 1999-10-27 |
| CN1202090C (zh) | 2005-05-18 |
| EP0941989B1 (en) | 2009-07-08 |
| IN188425B (enFirst) | 2002-09-21 |
| EP0941989A3 (en) | 2000-01-12 |
| US6242598B1 (en) | 2001-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |