BE1012428A3

BE1012428A3 - Hydroxyphenyltriazines et compositions de polymeres organiques stabilisees par des hydroxyphenyltriazines.

Hydroxyphenyltriazines et compositions de polymeres organiques stabilisees par des hydroxyphenyltriazines. Download PDF

Info

Publication number: BE1012428A3
Authority: BE; Belgium
Prior art keywords: sep; alkyl; phenyl; residue; formula
Prior art date: 1996-03-26

Application number

BE9700253A

Other languages

English (en)

French (fr)

Original Assignee

Ciba Sc Holding Ag

Priority date

1996-03-26

Filing date

1997-03-21

Publication date

2000-11-07

1997-03-21 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

2000-11-07 Application granted granted Critical

2000-11-07 Publication of BE1012428A3 publication Critical patent/BE1012428A3/fr

Links

239000000203 mixture Substances 0.000 title claims abstract description 84
VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title description 4
229920000620 organic polymer Polymers 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 145
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
239000001301 oxygen Substances 0.000 claims abstract description 18
229920005613 synthetic organic polymer Polymers 0.000 claims abstract description 11
230000009931 harmful effect Effects 0.000 claims abstract description 6
-1 alkyl radical Chemical class 0.000 claims description 164
125000000217 alkyl group Chemical group 0.000 claims description 85
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
239000003381 stabilizer Substances 0.000 claims description 37
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 35
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
125000003342 alkenyl group Chemical group 0.000 claims description 26
238000000034 method Methods 0.000 claims description 23
125000003884 phenylalkyl group Chemical group 0.000 claims description 23
150000001412 amines Chemical class 0.000 claims description 20
125000002947 alkylene group Chemical group 0.000 claims description 19
239000011230 binding agent Substances 0.000 claims description 19
238000000576 coating method Methods 0.000 claims description 19
125000003302 alkenyloxy group Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 13
239000000470 constituent Substances 0.000 claims description 10
239000004611 light stabiliser Substances 0.000 claims description 10
150000001602 bicycloalkyls Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
229920001169 thermoplastic Polymers 0.000 claims description 9
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 6
230000015556 catabolic process Effects 0.000 claims description 6
125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
238000006731 degradation reaction Methods 0.000 claims description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
125000003547 cyclohexylalkoxy group Chemical group 0.000 claims description 5
239000011368 organic material Substances 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
230000006641 stabilisation Effects 0.000 claims description 5
238000011105 stabilization Methods 0.000 claims description 5
230000000087 stabilizing effect Effects 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
230000009471 action Effects 0.000 claims description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 3
HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 2
MHPIFHORTBEEEF-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(2-hydroxycyclohexyl)oxyphenol Chemical compound CC1=C(C=CC(=C1)C)C1=NC(=NC(=N1)C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)OC1C(CCCC1)O)O MHPIFHORTBEEEF-UHFFFAOYSA-N 0.000 claims description 2
RIOZSIUZXTUMAM-UHFFFAOYSA-N 5-(2-hydroxycyclohexyl)oxy-2-[4-[2-hydroxy-4-(2-hydroxycyclohexyl)oxyphenyl]-6-phenyl-1,3,5-triazin-2-yl]phenol Chemical compound C1(=CC=CC=C1)C1=NC(=NC(=N1)C1=C(C=C(C=C1)OC1C(CCCC1)O)O)C1=C(C=C(C=C1)OC1C(CCCC1)O)O RIOZSIUZXTUMAM-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
NUENSZMSNYAUJH-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(2-hydroxycyclohexyl)oxyphenol Chemical compound OC1CCCCC1Oc1ccc(c(O)c1)-c1nc(nc(n1)-c1ccccc1)-c1ccccc1 NUENSZMSNYAUJH-UHFFFAOYSA-N 0.000 claims 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 50
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 47
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
239000002966 varnish Substances 0.000 description 41
229920001577 copolymer Polymers 0.000 description 39
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239000008199 coating composition Substances 0.000 description 22
239000003054 catalyst Substances 0.000 description 21
238000012512 characterization method Methods 0.000 description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
229910052757 nitrogen Inorganic materials 0.000 description 20
239000000047 product Substances 0.000 description 19
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NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
239000005977 Ethylene Substances 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical group 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000004952 Polyamide Substances 0.000 description 11
239000003973 paint Substances 0.000 description 11
229920002647 polyamide Polymers 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000000463 material Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
229920000877 Melamine resin Polymers 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
239000004743 Polypropylene Substances 0.000 description 9
239000011248 coating agent Substances 0.000 description 9
150000004820 halides Chemical class 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229920002857 polybutadiene Polymers 0.000 description 9
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
239000004417 polycarbonate Substances 0.000 description 8
230000008569 process Effects 0.000 description 8
239000008096 xylene Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
125000001309 chloro group Chemical group Cl* 0.000 description 7
239000012043 crude product Substances 0.000 description 7
150000001993 dienes Chemical class 0.000 description 7
229920001971 elastomer Polymers 0.000 description 7
229920001903 high density polyethylene Polymers 0.000 description 7
239000004700 high-density polyethylene Substances 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000004925 Acrylic resin Substances 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
150000001252 acrylic acid derivatives Chemical class 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
229910052782 aluminium Inorganic materials 0.000 description 6
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
150000002739 metals Chemical class 0.000 description 6
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
229920000058 polyacrylate Polymers 0.000 description 6
229920001228 polyisocyanate Polymers 0.000 description 6
239000005056 polyisocyanate Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000005855 radiation Effects 0.000 description 6
239000000758 substrate Substances 0.000 description 6
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
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230000015572 biosynthetic process Effects 0.000 description 5
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TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
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235000011181 potassium carbonates Nutrition 0.000 description 1
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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
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