TWI236472B - Novel methods for the preparation of tris-phenyl-s-triazines wherein at least one phenyl group is o-hydroxyphenyl - Google Patents
Novel methods for the preparation of tris-phenyl-s-triazines wherein at least one phenyl group is o-hydroxyphenyl Download PDFInfo
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- TWI236472B TWI236472B TW088103143A TW88103143A TWI236472B TW I236472 B TWI236472 B TW I236472B TW 088103143 A TW088103143 A TW 088103143A TW 88103143 A TW88103143 A TW 88103143A TW I236472 B TWI236472 B TW I236472B
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- 238000000034 method Methods 0.000 title claims abstract description 97
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 36
- -1 o-hydroxyphenyl Chemical group 0.000 title claims description 27
- HBQUOLGAXBYZGR-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5-triazine Chemical class C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 HBQUOLGAXBYZGR-UHFFFAOYSA-N 0.000 title 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000002841 Lewis acid Substances 0.000 claims abstract description 23
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 23
- 239000003377 acid catalyst Substances 0.000 claims abstract description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- HPJKLCJJNFVOEM-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine;hydrochloride Chemical group Cl.NC1=NC(N)=NC(N)=N1 HPJKLCJJNFVOEM-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002989 phenols Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- RXELBMYKBFKHSM-UHFFFAOYSA-N 2-phenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC=N1 RXELBMYKBFKHSM-UHFFFAOYSA-N 0.000 claims 1
- 244000131316 Panax pseudoginseng Species 0.000 claims 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims 1
- 235000003140 Panax quinquefolius Nutrition 0.000 claims 1
- 244000028344 Primula vulgaris Species 0.000 claims 1
- 235000016311 Primula vulgaris Nutrition 0.000 claims 1
- 241000489455 Sitta europaea Species 0.000 claims 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 235000008434 ginseng Nutrition 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 22
- 125000003118 aryl group Chemical group 0.000 abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 abstract description 9
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract description 3
- 239000006096 absorbing agent Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000000269 nucleophilic effect Effects 0.000 abstract description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 230000002411 adverse Effects 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 125000005023 xylyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 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 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 230000002079 cooperative effect Effects 0.000 description 12
- 239000007789 gas Substances 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000008096 xylene 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
- 150000002431 hydrogen Chemical group 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003828 vacuum filtration Methods 0.000 description 10
- 150000001412 amines Chemical group 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 229940098779 methanesulfonic acid Drugs 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 125000003884 phenylalkyl group Chemical group 0.000 description 6
- 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
- 239000000543 intermediate Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 241000208140 Acer Species 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000003756 stirring Methods 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
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [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
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical class 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-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 Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 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
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001308 synthesis method Methods 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
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- JBQVAAZCTJXHJX-UHFFFAOYSA-N 1-[[3-(9H-fluoren-1-ylmethyl)phenyl]methyl]-9H-fluorene Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC1=2)CC1=CC(=CC=C1)CC1=CC=CC=2C3=CC=CC=C3CC1=2 JBQVAAZCTJXHJX-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
- 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
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- UQCAPYSJNAXJTN-UHFFFAOYSA-N 4-(triazin-4-yl)benzene-1,3-diol Chemical compound OC1=C(C=CC(=C1)O)C1=NN=NC=C1 UQCAPYSJNAXJTN-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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- ARWYOUJLSRGJSW-UHFFFAOYSA-N CN.ClCC1=CC=CC=C1 Chemical compound CN.ClCC1=CC=CC=C1 ARWYOUJLSRGJSW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 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
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910010165 TiCu Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- RMTNSIBBWXZNDC-UHFFFAOYSA-N argon;hydrochloride Chemical compound Cl.[Ar] RMTNSIBBWXZNDC-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 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
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000002699 waste material Substances 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3326698A | 1998-03-02 | 1998-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI236472B true TWI236472B (en) | 2005-07-21 |
Family
ID=21869434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088103143A TWI236472B (en) | 1998-03-02 | 1999-03-02 | Novel methods for the preparation of tris-phenyl-s-triazines wherein at least one phenyl group is o-hydroxyphenyl |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6242598B1 (enExample) |
| EP (1) | EP0941989B1 (enExample) |
| JP (1) | JP4629814B2 (enExample) |
| KR (1) | KR100555072B1 (enExample) |
| CN (1) | CN1202090C (enExample) |
| CA (1) | CA2263090A1 (enExample) |
| DE (1) | DE69941073D1 (enExample) |
| IN (1) | IN188425B (enExample) |
| TW (1) | TWI236472B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI837270B (zh) * | 2019-01-08 | 2024-04-01 | 德商巴地斯顏料化工廠 | Uv吸收劑之製備方法 |
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| 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 |
| 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 (enExample) * | 1962-10-30 | |||
| NL130993C (enExample) * | 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI837270B (zh) * | 2019-01-08 | 2024-04-01 | 德商巴地斯顏料化工廠 | Uv吸收劑之製備方法 |
| US12291509B2 (en) | 2019-01-08 | 2025-05-06 | Basf Se | Process for the preparation of UV absorbers |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2263090A1 (en) | 1999-09-02 |
| 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 (enExample) | 2002-09-21 |
| EP0941989A3 (en) | 2000-01-12 |
| US6242598B1 (en) | 2001-06-05 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |