AU731977B2 - Hydroxyphenyltriazines - Google Patents

Hydroxyphenyltriazines Download PDF

Info

Publication number: AU731977B2
Authority: AU; Australia
Prior art keywords: alkyl; phenyl; formula; alkoxy; alkenyl
Prior art date: 1996-03-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

AU16441/97A

Other languages

English (en)

Other versions

AU1644197A (en

Inventor

Jean-Luc Birbaum

Roger Meuwly

Vien Van Toan

Andreas Valet

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Spezialitaetenchemie Holding AG

Ciba SC Holding AG

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.)

1996-03-26

Filing date

1997-03-20

Publication date

2001-04-12

1997-03-20 Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG

1997-10-02 Publication of AU1644197A publication Critical patent/AU1644197A/en

2001-04-12 Application granted granted Critical

2001-04-12 Publication of AU731977B2 publication Critical patent/AU731977B2/en

2017-03-20 Anticipated expiration legal-status Critical

Status Expired legal-status Critical Current

Links

VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims description 130
150000001875 compounds Chemical class 0.000 claims description 117
-1 phenyloxy Chemical group 0.000 claims description 116
239000000203 mixture Substances 0.000 claims description 80
125000001309 chloro group Chemical group Cl* 0.000 claims description 76
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
229910052739 hydrogen Inorganic materials 0.000 claims description 59
239000003381 stabilizer Substances 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 30
238000000034 method Methods 0.000 claims description 28
238000000576 coating method Methods 0.000 claims description 24
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 23
239000011230 binding agent Substances 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 21
125000003884 phenylalkyl group Chemical group 0.000 claims description 19
125000002947 alkylene group Chemical group 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
239000004611 light stabiliser Substances 0.000 claims description 10
229920005613 synthetic organic polymer Polymers 0.000 claims description 10
229920001169 thermoplastic Polymers 0.000 claims description 9
125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
150000001602 bicycloalkyls Chemical group 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 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
125000002071 phenylalkoxy group Chemical group 0.000 claims description 5
230000000087 stabilizing effect Effects 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
125000005293 bicycloalkoxy group Chemical group 0.000 claims description 4
125000003547 cyclohexylalkoxy group Chemical group 0.000 claims description 4
230000000254 damaging effect Effects 0.000 claims description 4
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
125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 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 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
229920001577 copolymer Polymers 0.000 description 35
229920000642 polymer Polymers 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
238000012512 characterization method Methods 0.000 description 22
239000008199 coating composition Substances 0.000 description 21
239000003054 catalyst Substances 0.000 description 20
239000003973 paint Substances 0.000 description 18
229920005989 resin Polymers 0.000 description 18
239000011347 resin Substances 0.000 description 18
239000007858 starting material Substances 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
150000003254 radicals Chemical class 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000000463 material Substances 0.000 description 16
229910052751 metal Inorganic materials 0.000 description 16
239000002184 metal Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000011248 coating agent Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
150000002148 esters Chemical group 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000004952 Polyamide Substances 0.000 description 11
238000005336 cracking Methods 0.000 description 11
229920002647 polyamide Polymers 0.000 description 11
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
239000005977 Ethylene Substances 0.000 description 10
150000001252 acrylic acid derivatives Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
229920000877 Melamine resin Polymers 0.000 description 9
239000004743 Polypropylene Substances 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000003795 chemical substances by application 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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229920002857 polybutadiene Polymers 0.000 description 9
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
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
238000001035 drying Methods 0.000 description 8
229920001971 elastomer Polymers 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
239000008096 xylene Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
239000012964 benzotriazole Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
238000001723 curing Methods 0.000 description 7
150000001993 dienes Chemical class 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
239000000758 substrate 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
239000004721 Polyphenylene oxide Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
229910052782 aluminium Inorganic materials 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
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
229920001903 high density polyethylene Polymers 0.000 description 6
229920000058 polyacrylate Polymers 0.000 description 6
229920000647 polyepoxide Polymers 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
239000005056 polyisocyanate Substances 0.000 description 6
229920001228 polyisocyanate Polymers 0.000 description 6
239000004814 polyurethane Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
229920002554 vinyl polymer Polymers 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
239000004698 Polyethylene Substances 0.000 description 5
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
239000004411 aluminium 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
238000009835 boiling Methods 0.000 description 5
239000010408 film Substances 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002739 metals Chemical class 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
239000000049 pigment Substances 0.000 description 5
239000004417 polycarbonate Substances 0.000 description 5
229920000573 polyethylene Polymers 0.000 description 5
229920006380 polyphenylene oxide Polymers 0.000 description 5
229920001155 polypropylene Polymers 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000000746 purification Methods 0.000 description 5
230000005855 radiation Effects 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000005060 rubber Substances 0.000 description 5
239000004416 thermosoftening plastic Substances 0.000 description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
239000006096 absorbing agent Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
229920000180 alkyd Polymers 0.000 description 4
230000008901 benefit Effects 0.000 description 4
FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
238000004061 bleaching Methods 0.000 description 4
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
150000002366 halogen compounds Chemical class 0.000 description 4
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
229910052748 manganese Inorganic materials 0.000 description 4
239000011572 manganese Substances 0.000 description 4
239000000178 monomer Substances 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
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229920000570 polyether Polymers 0.000 description 4
229920002635 polyurethane Polymers 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
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125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
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YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
UTPYJWDGMYOGGT-UHFFFAOYSA-N 5-(3-butoxy-2-hydroxypropoxy)-2-[4-[4-(3-butoxy-2-hydroxypropoxy)-2-hydroxyphenyl]-6-phenyl-1,3,5-triazin-2-yl]phenol Chemical compound CCCCOCC(O)COc1ccc(c(O)c1)-c1nc(nc(n1)-c1ccc(OCC(O)COCCCC)cc1O)-c1ccccc1 UTPYJWDGMYOGGT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
235000006708 antioxidants Nutrition 0.000 description 3
XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 3
229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
239000005038 ethylene vinyl acetate Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229920000554 ionomer Polymers 0.000 description 3
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
239000003446 ligand Substances 0.000 description 3
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150000002816 nickel compounds Chemical class 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
239000002667 nucleating agent Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
IXVLEAZXSJJKFR-UHFFFAOYSA-N octadecyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CSCC1=CC(C)=C(O)C(C)=C1 IXVLEAZXSJJKFR-UHFFFAOYSA-N 0.000 description 1
SFTYZRBELKLCCU-UHFFFAOYSA-N octadecyl 2-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1CCCC SFTYZRBELKLCCU-UHFFFAOYSA-N 0.000 description 1
125000005474 octanoate group Chemical group 0.000 description 1
DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl n-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
229960000969 phenyl salicylate Drugs 0.000 description 1
ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
239000012994 photoredox catalyst Substances 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
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
229920002401 polyacrylamide Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002312 polyamide-imide Polymers 0.000 description 1
229920002480 polybenzimidazole Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920006393 polyether sulfone Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000069 polyphenylene sulfide Polymers 0.000 description 1
229920005606 polypropylene copolymer Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920005749 polyurethane resin 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
229920002620 polyvinyl fluoride Polymers 0.000 description 1
239000005033 polyvinylidene chloride Substances 0.000 description 1
229920002981 polyvinylidene fluoride 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
KZNICNPSHKQLFF-HOSYLAQJSA-N pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)[15NH]1 KZNICNPSHKQLFF-HOSYLAQJSA-N 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 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
IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 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
239000011877 solvent mixture Substances 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
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229920000638 styrene acrylonitrile Polymers 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 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
239000010409 thin film Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 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
229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
239000003981 vehicle Substances 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
239000001993 wax Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 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
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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

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
- 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
- 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)
Compositions Of Macromolecular Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Paints Or Removers (AREA)
Printing Methods (AREA)

AU16441/97A 1996-03-26 1997-03-20 Hydroxyphenyltriazines Expired AU731977B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH78396		1996-03-26
CH783/96		1996-03-26

Publications (2)

Publication Number	Publication Date
AU1644197A AU1644197A (en)	1997-10-02
AU731977B2 true AU731977B2 (en)	2001-04-12

Family

ID=4195088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU16441/97A Expired AU731977B2 (en)	1996-03-26	1997-03-20	Hydroxyphenyltriazines

Country Status (18)

Country	Link
US (1)	US5959008A (2)
JP (1)	JP4332819B2 (2)
KR (1)	KR100448332B1 (2)
CN (1)	CN1104476C (2)
AU (1)	AU731977B2 (2)
BE (1)	BE1012428A3 (2)
BR (1)	BR9701462B1 (2)
CA (1)	CA2200807C (2)
CH (1)	CH692739A5 (2)
DE (1)	DE19712277B4 (2)
ES (1)	ES2130985B1 (2)
FR (1)	FR2747122B1 (2)
GB (1)	GB2312210B (2)
IT (1)	IT1290823B1 (2)
NL (1)	NL1005651C2 (2)
SE (1)	SE523139C2 (2)
TW (1)	TW449610B (2)
ZA (1)	ZA975233B (2)

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US20020165298A1 (en)	1996-04-02	2002-11-07	Dieter Reinehr	Amino- and hydroxysubstituted triphenyl-s-triazines as stabilizers
US6117997A (en) *	1997-11-19	2000-09-12	Ciba Specialty Chemicals Corporation	Hydroxyphenyltriazines
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JP2000026435A (ja) *	1998-05-07	2000-01-25	Ciba Specialty Chem Holding Inc	トリスレゾリシニルトリアジン
AU4425599A (en) *	1998-06-22	2000-01-10	Ciba Specialty Chemicals Holding Inc.	Trisaryl-1,3,5-triazine ultraviolet light absorbers containing hindered phenols
CO5231248A1 (es) *	2000-07-26	2002-12-27	Ciba Sc Holding Ag	Articulos transparentes de polimero de baja consistencia
TWI318208B (en) *	2001-07-02	2009-12-11	Ciba Sc Holding Ag	Highly compatible hydroxyphenyltriazine uv-absorbers
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US6893722B2 (en)	2002-04-29	2005-05-17	Exxonmobil Oil Corporation	Cationic, amino-functional, adhesion-promoting polymer for curable inks and other plastic film coatings, and plastic film comprising such polymer
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EP2912017A4 (en)	2012-10-23	2016-07-20	Basf Se	ETHYLENICALLY UNSATURATED OLIGOMERS WITH POLYMER STABILIZATION GROUPS
WO2015044785A2 (en)	2013-09-27	2015-04-02	Basf Se	Polyolefin compositions for building materials
WO2015077635A2 (en)	2013-11-22	2015-05-28	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
ES2632783T3 (es)	2014-12-19	2017-09-15	Evonik Degussa Gmbh	Sistemas de redes de cubierta para láminas de encapsulación que comprenden compuestos de bis-(alquenilamidas)
KR102580043B1 (ko)	2015-07-20	2023-09-20	바스프 에스이	난연성 폴리올레핀 물품
CN105693641A (zh) *	2015-12-29	2016-06-22	新秀化学（烟台）有限公司	一种三嗪紫外线吸收剂的制备方法
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CN107805224A (zh) *	2017-11-15	2018-03-16	利安隆（中卫）新材料有限公司	制备含有醚键的混合长碳链三嗪紫外线吸收剂的方法
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1997
- 1997-03-17 CH CH00638/97A patent/CH692739A5/de not_active IP Right Cessation
- 1997-03-19 SE SE9701012A patent/SE523139C2/sv not_active IP Right Cessation
- 1997-03-20 AU AU16441/97A patent/AU731977B2/en not_active Expired
- 1997-03-21 BE BE9700253A patent/BE1012428A3/fr active
- 1997-03-21 GB GB9705854A patent/GB2312210B/en not_active Expired - Lifetime
- 1997-03-21 US US08/828,200 patent/US5959008A/en not_active Expired - Lifetime
- 1997-03-24 CA CA002200807A patent/CA2200807C/en not_active Expired - Lifetime
- 1997-03-24 DE DE19712277.9A patent/DE19712277B4/de not_active Expired - Lifetime
- 1997-03-25 BR BRPI9701462-1A patent/BR9701462B1/pt not_active IP Right Cessation
- 1997-03-25 ES ES009700638A patent/ES2130985B1/es not_active Expired - Fee Related
- 1997-03-25 ZA ZA9702533A patent/ZA975233B/xx unknown
- 1997-03-25 IT IT97MI000689A patent/IT1290823B1/it active IP Right Grant
- 1997-03-25 TW TW086103743A patent/TW449610B/zh not_active IP Right Cessation
- 1997-03-25 CN CN97109694A patent/CN1104476C/zh not_active Expired - Lifetime
- 1997-03-25 FR FR9703596A patent/FR2747122B1/fr not_active Expired - Lifetime
- 1997-03-26 NL NL1005651A patent/NL1005651C2/nl not_active IP Right Cessation
- 1997-03-26 JP JP11329997A patent/JP4332819B2/ja not_active Expired - Lifetime
- 1997-03-26 KR KR1019970010541A patent/KR100448332B1/ko not_active Expired - Lifetime

Also Published As

Publication number	Publication date
BR9701462B1 (pt)	2008-11-18
GB2312210A (en)	1997-10-22
FR2747122A1 (fr)	1997-10-10
DE19712277A1 (de)	1997-10-30
ES2130985B1 (es)	2000-03-01
FR2747122B1 (fr)	2003-01-17
KR100448332B1 (ko)	2004-12-04
CN1104476C (zh)	2003-04-02
ITMI970689A1 (it)	1998-09-25
BE1012428A3 (fr)	2000-11-07
ZA975233B (en)	1997-09-26
BR9701462A (pt)	1998-08-25
SE9701012L (sv)	1997-11-04
DE19712277B4 (de)	2014-11-06
CA2200807C (en)	2007-04-17
NL1005651A1 (nl)	1997-09-30
NL1005651C2 (nl)	2000-06-19
US5959008A (en)	1999-09-28
TW449610B (en)	2001-08-11
KR970065611A (ko)	1997-10-13
SE523139C2 (sv)	2004-03-30
CH692739A5 (de)	2002-10-15
IT1290823B1 (it)	1998-12-11
ES2130985A1 (es)	1999-07-01
AU1644197A (en)	1997-10-02
JP4332819B2 (ja)	2009-09-16
CA2200807A1 (en)	1997-09-26
GB2312210B (en)	1998-08-19
MX9702211A (es)	1998-05-31
SE9701012D0 (sv)	1997-03-19
CN1171422A (zh)	1998-01-28
GB9705854D0 (en)	1997-05-07
JPH1045729A (ja)	1998-02-17

Legal Events

Date	Code	Title	Description
2001-08-09	FGA	Letters patent sealed or granted (standard patent)

Publication	Publication Date	Title
AU731977B2 (en)	2001-04-12	Hydroxyphenyltriazines
US6060543A (en)	2000-05-09	Stabilizer combination
US5668200A (en)	1997-09-16	Stabilizer combination
US6117995A (en)	2000-09-12	Preparation of sterically hindered amine ethers
EP0912531B1 (en)	2003-03-19	Polyoxyalkylene substituted and bridged benzophenone derivatives as uv absorbers
JP4114176B2 (ja)	2008-07-09	光安定剤としてのビフェニル基で置換されたトリアジン
KR100525173B1 (ko)	2006-05-16	히드록시페닐트리아진
US20010039341A1 (en)	2001-11-08	Biphenyl-Substituted Triazines
JP5497077B2 (ja)	2014-05-21	トリスレゾリシニルトリアジン
AU724746B2 (en)	2000-09-28	Mixtures of polyalkylpiperidin-4-yl dicarboxylic acid esters as stabilizers for organic materials
US20030096993A1 (en)	2003-05-22	Stabilizer mixture
US5962683A (en)	1999-10-05	Oxazoline compounds as stabilizers
US6117997A (en)	2000-09-12	Hydroxyphenyltriazines
US6762226B2 (en)	2004-07-13	Compositions stabilized by dioxopiperazinyl derivatives
GB2371543A (en)	2002-07-31	3,3,5,5-Tetraalkyl-piperazine-2,6-dione stabilizers
MXPA97002211A (en)	1998-10-23	Hidroxifenil triazi
MXPA99004239A (en)	2000-02-02	Trisresorciniltriazi