SK283404B6 - Tris-aryl-s-triazíny, spôsob ich prípravy, kompozícia stabilizovaná týmito triazínmi, ich použitie a spôsob ochrany organického polyméru proti degradácii - Google Patents

Tris-aryl-s-triazíny, spôsob ich prípravy, kompozícia stabilizovaná týmito triazínmi, ich použitie a spôsob ochrany organického polyméru proti degradácii Download PDF

Info

Publication number: SK283404B6
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; alkyl; phenyl; bis
Prior art date: 1994-07-27

Application number

SK935-95A

Other languages

English (en)

Slovak (sk)

Other versions

SK93595A3 (en

Inventor

Tyler Arthur Stevenson

Ramanathan Ravichandran

Mark Stephen Holt

Thuy Ngoc Phan

Jean-Luc Birbaum

Vien Van Toan

Original Assignee

Ciba Specialty Chemicals Holding Inc.

Priority date (The priority date 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 date listed.)

1994-07-27

Filing date

1995-07-25

Publication date

2003-07-01

1995-07-25 Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.

1996-02-07 Publication of SK93595A3 publication Critical patent/SK93595A3/sk

2003-07-01 Publication of SK283404B6 publication Critical patent/SK283404B6/sk

Links

239000000203 mixture Substances 0.000 title claims description 163
125000000217 alkyl group Chemical group 0.000 claims abstract description 137
229910052736 halogen Inorganic materials 0.000 claims abstract description 49
150000002367 halogens Chemical class 0.000 claims abstract description 48
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 18
239000000758 substrate Substances 0.000 claims abstract description 9
-1 2,2,6,6-tetramethylpiperidinyl Chemical group 0.000 claims description 172
150000001875 compounds Chemical class 0.000 claims description 141
125000004432 carbon atom Chemical group C* 0.000 claims description 137
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 96
125000002947 alkylene group Chemical group 0.000 claims description 79
125000000753 cycloalkyl group Chemical group 0.000 claims description 56
239000007787 solid Substances 0.000 claims description 47
238000000034 method Methods 0.000 claims description 41
239000000126 substance Substances 0.000 claims description 41
125000003545 alkoxy group Chemical group 0.000 claims description 34
238000000576 coating method Methods 0.000 claims description 34
229920000642 polymer Polymers 0.000 claims description 30
150000001412 amines Chemical class 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 24
239000011248 coating agent Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 20
229920005989 resin Polymers 0.000 claims description 19
239000011347 resin Substances 0.000 claims description 19
239000003381 stabilizer Substances 0.000 claims description 17
230000000087 stabilizing effect Effects 0.000 claims description 16
230000005855 radiation Effects 0.000 claims description 14
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 13
239000002184 metal Substances 0.000 claims description 13
229920000877 Melamine resin Polymers 0.000 claims description 11
239000006096 absorbing agent Substances 0.000 claims description 11
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
125000002993 cycloalkylene group Chemical group 0.000 claims description 11
125000004956 cyclohexylene group Chemical group 0.000 claims description 11
125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 10
239000011230 binding agent Substances 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 10
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
229910052727 yttrium Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 8
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 7
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 7
229920001187 thermosetting polymer Polymers 0.000 claims description 7
239000004593 Epoxy Substances 0.000 claims description 6
150000001336 alkenes Chemical class 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
230000015556 catabolic process Effects 0.000 claims description 6
238000006731 degradation reaction Methods 0.000 claims description 6
125000003700 epoxy group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
125000001769 aryl amino group Chemical group 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 5
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
239000003973 paint Substances 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 4
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 4
238000003547 Friedel-Crafts alkylation reaction Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
239000004305 biphenyl Substances 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
229940098779 methanesulfonic acid Drugs 0.000 claims description 4
229920000620 organic polymer Polymers 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000005628 tolylene group Chemical group 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
239000008199 coating composition Substances 0.000 claims description 3
150000001925 cycloalkenes Chemical class 0.000 claims description 3
125000006839 xylylene group Chemical group 0.000 claims description 3
XIIJQVXWEHBGTQ-UHFFFAOYSA-N 1-[5-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2,4-dihydroxyphenyl]propan-1-one Chemical compound C1=C(O)C(C(=O)CC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O XIIJQVXWEHBGTQ-UHFFFAOYSA-N 0.000 claims description 2
BYTDJFWMBNWPHB-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-hexyl-5-(2-hydroxy-3-nonoxypropoxy)phenol Chemical compound C1=C(CCCCCC)C(OCC(O)COCCCCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 BYTDJFWMBNWPHB-UHFFFAOYSA-N 0.000 claims description 2
ZUKRRNURZPMYFF-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-hexyl-5-methoxyphenol Chemical compound C1=C(OC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1O ZUKRRNURZPMYFF-UHFFFAOYSA-N 0.000 claims description 2
VYBOVBLHRYWRDU-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxy-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 VYBOVBLHRYWRDU-UHFFFAOYSA-N 0.000 claims description 2
WATQWOIVOVTGAU-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCC(O)COCCCCCCCCCCCC)=CC(O)=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 WATQWOIVOVTGAU-UHFFFAOYSA-N 0.000 claims description 2
XOEDSKNCBPKBJK-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-hexoxy-4-(2-phenylpropan-2-yl)phenol Chemical compound CCCCCCOC1=CC(O)=C(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)C=C1C(C)(C)C1=CC=CC=C1 XOEDSKNCBPKBJK-UHFFFAOYSA-N 0.000 claims description 2
ROJJGXXZFGBZBA-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-hexoxy-4-hexylphenol Chemical compound CCCCCCOc1cc(O)c(cc1CCCCCC)-c1nc(nc(n1)-c1ccc(C)cc1C)-c1ccc(C)cc1C ROJJGXXZFGBZBA-UHFFFAOYSA-N 0.000 claims description 2
JQYYVSXZAIWYSF-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-hexoxy-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC(C)=CC=2)=NC(C=2C=CC(C)=CC=2)=N1 JQYYVSXZAIWYSF-UHFFFAOYSA-N 0.000 claims description 2
FIWCBWRTLBJGOE-UHFFFAOYSA-N 3-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-phenylthiophene-2,4-diol Chemical compound OC=1SC(=C(C1C1=NC(=NC(=N1)C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C)O)C1=CC=CC=C1 FIWCBWRTLBJGOE-UHFFFAOYSA-N 0.000 claims description 2
CKKYBCOKWOYIPX-UHFFFAOYSA-N 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-6-hexylbenzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1O CKKYBCOKWOYIPX-UHFFFAOYSA-N 0.000 claims description 2
KBMCOOMAMATYHQ-UHFFFAOYSA-N 4-(benzenesulfonyl)-6-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound Cc1ccc(c(C)c1)-c1nc(nc(n1)-c1cc(c(O)cc1O)S(=O)(=O)c1ccccc1)-c1ccc(C)cc1C KBMCOOMAMATYHQ-UHFFFAOYSA-N 0.000 claims description 2
LNWQRUNTXDGNLU-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-(1-hydroxypropyl)benzene-1,3-diol Chemical compound C1=C(O)C(C(O)CC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O LNWQRUNTXDGNLU-UHFFFAOYSA-N 0.000 claims description 2
BINPLUADTPSKCM-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-[3-(2-methylpropylamino)propyl]benzene-1,3-diol Chemical compound C1=C(O)C(CCCNCC(C)C)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O BINPLUADTPSKCM-UHFFFAOYSA-N 0.000 claims description 2
LGXTZRACBVFXPU-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-[3-(2-methylpropylimino)propyl]benzene-1,3-diol Chemical compound C1=C(O)C(CCC=NCC(C)C)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O LGXTZRACBVFXPU-UHFFFAOYSA-N 0.000 claims description 2
IDNMOCZVCKKPQW-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-chlorobenzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=C(Cl)C=2)O)=N1 IDNMOCZVCKKPQW-UHFFFAOYSA-N 0.000 claims description 2
DGJDPVINDQRXKS-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-hexylbenzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O DGJDPVINDQRXKS-UHFFFAOYSA-N 0.000 claims description 2
APXVALWQCJACEN-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-prop-1-enylbenzene-1,3-diol Chemical compound CC=Cc1cc(c(O)cc1O)-c1nc(nc(n1)-c1ccc(C)cc1C)-c1ccc(C)cc1C APXVALWQCJACEN-UHFFFAOYSA-N 0.000 claims description 2
CQYHODPINUKJFS-UHFFFAOYSA-N 4-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-6-hexylbenzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C1O CQYHODPINUKJFS-UHFFFAOYSA-N 0.000 claims description 2
ROMOVEOVEAWFBS-UHFFFAOYSA-N 4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound C1=C(Cl)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 ROMOVEOVEAWFBS-UHFFFAOYSA-N 0.000 claims description 2
IRVMGEAXNIMINM-UHFFFAOYSA-N 4-hexyl-6-[4-(5-hexyl-2,4-dihydroxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C(=CC(O)=C(CCCCCC)C=2)O)=C1O IRVMGEAXNIMINM-UHFFFAOYSA-N 0.000 claims description 2
RNPMCTYVUSAJCK-UHFFFAOYSA-N 5-hexoxy-2-[4-(4-hexoxy-5-hexyl-2-hydroxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC(OCCCCCC)=C(CCCCCC)C=2)O)=N1 RNPMCTYVUSAJCK-UHFFFAOYSA-N 0.000 claims description 2
QNBMOSPYOAEHDK-UHFFFAOYSA-N [5-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2,4-dihydroxyphenyl]-phenylmethanone Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=C(C(=O)C=3C=CC=CC=3)C=2)O)=N1 QNBMOSPYOAEHDK-UHFFFAOYSA-N 0.000 claims description 2
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
239000001023 inorganic pigment Substances 0.000 claims description 2
239000012860 organic pigment Substances 0.000 claims description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
IGSZLCRLLROOEG-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-4-hexyl-5-(2-hydroxy-3-phenoxypropoxy)phenol Chemical compound CCCCCCC1=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C(O)C=C1OCC(O)COC1=CC=CC=C1 IGSZLCRLLROOEG-UHFFFAOYSA-N 0.000 claims 1
PQSSARCHBGYLPE-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)-4-hexylphenol Chemical compound C1=C(OCC(O)COCCCC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O PQSSARCHBGYLPE-UHFFFAOYSA-N 0.000 claims 1
ZOQBTWAAZMIHRQ-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)-4-hexylphenol Chemical compound C1=C(OCC(O)COCCCC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C1O ZOQBTWAAZMIHRQ-UHFFFAOYSA-N 0.000 claims 1
KLKCGQRWVCBXEA-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-[hydroxy(phenyl)methyl]benzene-1,3-diol Chemical compound Cc1ccc(c(C)c1)-c1nc(nc(n1)-c1cc(C(O)c2ccccc2)c(O)cc1O)-c1ccc(C)cc1C KLKCGQRWVCBXEA-UHFFFAOYSA-N 0.000 claims 1
PFSDKNGWYYIJGH-UHFFFAOYSA-N 5-(3-butoxy-2-hydroxypropoxy)-2-[4-[4-(3-butoxy-2-hydroxypropoxy)-5-hexyl-2-hydroxyphenyl]-6-phenyl-1,3,5-triazin-2-yl]-4-hexylphenol Chemical compound C1=C(OCC(O)COCCCC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C(=CC(OCC(O)COCCCC)=C(CCCCCC)C=2)O)=C1O PFSDKNGWYYIJGH-UHFFFAOYSA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
230000009931 harmful effect Effects 0.000 claims 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 35
230000006641 stabilisation Effects 0.000 abstract description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 2
230000002939 deleterious effect Effects 0.000 abstract 1
125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
238000002211 ultraviolet spectrum Methods 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
239000000047 product Substances 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 42
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
229920001577 copolymer Polymers 0.000 description 37
229910052757 nitrogen Inorganic materials 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 28
238000001819 mass spectrum Methods 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
238000006467 substitution reaction Methods 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
238000001914 filtration Methods 0.000 description 19
150000003918 triazines Chemical class 0.000 description 19
239000012043 crude product Substances 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
239000012299 nitrogen atmosphere Substances 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
230000002829 reductive effect Effects 0.000 description 16
239000002904 solvent Substances 0.000 description 16
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ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000011990 phillips catalyst Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
239000012994 photoredox catalyst Substances 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920001643 poly(ether ketone) Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002312 polyamide-imide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920002480 polybenzimidazole Polymers 0.000 description 1
229920006393 polyether sulfone Polymers 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
238000012667 polymer degradation Methods 0.000 description 1
239000002897 polymer film coating Substances 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000069 polyphenylene sulfide Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
QVKOLZOAOSNSHQ-UHFFFAOYSA-N prop-1-ene;prop-2-enoic acid Chemical compound CC=C.OC(=O)C=C QVKOLZOAOSNSHQ-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000007342 radical addition reaction Methods 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
230000008439 repair process Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
239000006254 rheological additive Substances 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229940045870 sodium palmitate Drugs 0.000 description 1
229940074404 sodium succinate Drugs 0.000 description 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000003068 static effect Effects 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
125000005591 trimellitate group Chemical group 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
229920006163 vinyl copolymer Polymers 0.000 description 1
UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
238000004804 winding Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
239000011590 β-tocopherol Substances 0.000 description 1
235000007680 β-tocopherol Nutrition 0.000 description 1
239000002478 γ-tocopherol Substances 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
239000002446 δ-tocopherol 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Paints Or Removers (AREA)
Compositions Of Macromolecular Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Epoxy Resins (AREA)
Medicinal Preparation (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)

SK935-95A 1994-07-27 1995-07-25 Tris-aryl-s-triazíny, spôsob ich prípravy, kompozícia stabilizovaná týmito triazínmi, ich použitie a spôsob ochrany organického polyméru proti degradácii SK283404B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/281,381 US5556973A (en)	1994-07-27	1994-07-27	Red-shifted tris-aryl-s-triazines and compositions stabilized therewith

Publications (2)

Publication Number	Publication Date
SK93595A3 SK93595A3 (en)	1996-02-07
SK283404B6 true SK283404B6 (sk)	2003-07-01

Family

ID=23077052

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK935-95A SK283404B6 (sk)	1994-07-27	1995-07-25	Tris-aryl-s-triazíny, spôsob ich prípravy, kompozícia stabilizovaná týmito triazínmi, ich použitie a spôsob ochrany organického polyméru proti degradácii

Country Status (12)

Country	Link
US (7)	US5556973A (fr)
EP (1)	EP0704437B1 (fr)
JP (1)	JP3965603B2 (fr)
KR (1)	KR100346064B1 (fr)
AT (1)	ATE224880T1 (fr)
BR (1)	BR9503460A (fr)
CA (1)	CA2154626A1 (fr)
CZ (1)	CZ192595A3 (fr)
DE (1)	DE69528331T2 (fr)
ES (1)	ES2181760T3 (fr)
SK (1)	SK283404B6 (fr)
TW (1)	TW308602B (fr)

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Also Published As

Publication number	Publication date
EP0704437B1 (fr)	2002-09-25
US5684070A (en)	1997-11-04
SK93595A3 (en)	1996-02-07
EP0704437A2 (fr)	1996-04-03
KR960004328A (ko)	1996-02-23
US5675004A (en)	1997-10-07
CA2154626A1 (fr)	1996-01-28
ATE224880T1 (de)	2002-10-15
US5681955A (en)	1997-10-28
ES2181760T3 (es)	2003-03-01
US5556973A (en)	1996-09-17
KR100346064B1 (ko)	2002-11-16
DE69528331T2 (de)	2003-05-15
JPH0853427A (ja)	1996-02-27
US5637706A (en)	1997-06-10
DE69528331D1 (de)	2002-10-31
TW308602B (fr)	1997-06-21
CZ192595A3 (en)	1996-02-14
EP0704437A3 (fr)	1996-10-23
BR9503460A (pt)	1996-02-27
JP3965603B2 (ja)	2007-08-29
US5543518A (en)	1996-08-06
US5648488A (en)	1997-07-15

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EP0815089B1 (fr)	2002-09-25	Triazines a substitution biphenyle a titre de photostabilisant
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EP1034169B1 (fr)	2004-02-11	Absorbeurs de rayons ultraviolets au trisaryl-1,3,5-triazine
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JP5497077B2 (ja)	2014-05-21	トリスレゾリシニルトリアジン
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FR2753447A1 (fr)	1998-03-20	Hydroxyphenyltriazines comme agents stabilisants de matieres organiques
SK284174B6 (sk)	2004-10-05	Synergická zmes stabilizátorov, kompozícia obsahujúca túto zmes a organický materiál a použitie tejto zmesi
AU1592499A (en)	1999-06-15	Trisaryl-1,3,5-triazine ultraviolet light absorbers
US5488112A (en)	1996-01-30	Dimeric benzotriazoles as UV absorbers
KR20010053057A (ko)	2001-06-25	비황변 파라-3급-알킬 페닐 치환된 트리아진 및 피리미딘자외선 흡수제
KR100517489B1 (ko)	2006-05-03	광안정화제로서의 아미노-및 하이드록시 치환된 트리페닐-s-트리아진
MXPA97006950A (en)	1998-11-12	Combination of stabilization
MXPA00012420A (en)	2001-11-21	Poly-trisaryl-1,3,5-triazine carbamate ultraviolet light absorbers