IL126237A - Synergistic stabilizer composition comprising a photoreactive polyalkylpiperidine and a non-photoreactive polyalkylpiperidine or polyalkyl-piperazine and a process for stabilizing a natural or synthetic polymeric or prepolymeric substrate against the damage effected by light, heat and/or oxidation using this composition - Google Patents

Synergistic stabilizer composition comprising a photoreactive polyalkylpiperidine and a non-photoreactive polyalkylpiperidine or polyalkyl-piperazine and a process for stabilizing a natural or synthetic polymeric or prepolymeric substrate against the damage effected by light, heat and/or oxidation using this composition

Info

Publication number: IL126237A
Authority: IL; Israel
Prior art keywords: defined above; alkyl; tert; signifies; butyl
Prior art date: 1996-04-12

Application number

IL12623797A

Other languages

English (en)

Other versions

IL126237A0 (en

Inventor

Karl Bechtold

Original Assignee

Clariant Finance Bvi Ltd

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.)

1996-04-12

Filing date

1997-04-10

Publication date

2004-03-28

1997-04-10 Application filed by Clariant Finance Bvi Ltd filed Critical Clariant Finance Bvi Ltd

1999-05-09 Publication of IL126237A0 publication Critical patent/IL126237A0/xx

2004-03-28 Publication of IL126237A publication Critical patent/IL126237A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 59
239000003381 stabilizer Substances 0.000 title claims abstract description 14
230000002195 synergetic effect Effects 0.000 title claims abstract description 7
239000000758 substrate Substances 0.000 title claims description 19
238000000034 method Methods 0.000 title claims description 9
230000000087 stabilizing effect Effects 0.000 title claims description 8
230000003647 oxidation Effects 0.000 title claims description 4
238000007254 oxidation reaction Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 28
239000001257 hydrogen Substances 0.000 claims abstract description 27
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000004122 cyclic group Chemical group 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 2
-1 coatings Substances 0.000 claims description 54
150000002431 hydrogen Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000004594 Masterbatch (MB) Substances 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
239000011368 organic material Substances 0.000 claims description 6
238000000576 coating method Methods 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
239000000463 material Substances 0.000 claims description 3
238000000465 moulding Methods 0.000 claims description 3
229920003023 plastic Polymers 0.000 claims description 3
239000004033 plastic Substances 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000000853 adhesive Substances 0.000 claims description 2
230000001070 adhesive effect Effects 0.000 claims description 2
239000004744 fabric Substances 0.000 claims description 2
239000000835 fiber Substances 0.000 claims description 2
239000004922 lacquer Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000002966 varnish Substances 0.000 claims description 2
125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 7
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
229910003849 O-Si Inorganic materials 0.000 abstract 1
229910003872 O—Si Inorganic materials 0.000 abstract 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 45
229920001577 copolymer Polymers 0.000 description 32
229920000642 polymer Polymers 0.000 description 22
CMXLJKWFEJEFJE-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical compound C1=CC(OC)=CC=C1C=C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 CMXLJKWFEJEFJE-UHFFFAOYSA-N 0.000 description 20
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
239000004743 Polypropylene Substances 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000004952 Polyamide Substances 0.000 description 11
229920002647 polyamide Polymers 0.000 description 11
229920001155 polypropylene Polymers 0.000 description 10
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
239000005977 Ethylene Substances 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
229920002857 polybutadiene Polymers 0.000 description 9
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 7
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 7
150000001993 dienes Chemical class 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
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
239000004800 polyvinyl chloride Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
239000004698 Polyethylene Substances 0.000 description 5
239000004721 Polyphenylene oxide Substances 0.000 description 5
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical group 0.000 description 5
239000012964 benzotriazole Substances 0.000 description 5
BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 5
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 5
239000003054 catalyst Substances 0.000 description 5
229920001903 high density polyethylene Polymers 0.000 description 5
239000004700 high-density polyethylene Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
229920000573 polyethylene Polymers 0.000 description 5
229920006380 polyphenylene oxide Polymers 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
229920002554 vinyl polymer Polymers 0.000 description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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 4
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-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
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
229920000877 Melamine resin Polymers 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
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
229920001971 elastomer Polymers 0.000 description 4
229940093476 ethylene glycol Drugs 0.000 description 4
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
239000004611 light stabiliser Substances 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
229940117969 neopentyl glycol Drugs 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
239000004417 polycarbonate Substances 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000004814 polyurethane Substances 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
229960004063 propylene glycol Drugs 0.000 description 4
235000013772 propylene glycol Nutrition 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
229920001897 terpolymer Polymers 0.000 description 4
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
229940113165 trimethylolpropane Drugs 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
229920002943 EPDM rubber Polymers 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
229920002396 Polyurea Polymers 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
239000005038 ethylene vinyl acetate Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000003446 ligand Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
150000005673 monoalkenes Chemical class 0.000 description 3
239000000178 monomer Substances 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
229920000647 polyepoxide Polymers 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 2
HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 2
WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 description 2
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
229920002292 Nylon 6 Polymers 0.000 description 2
229920002367 Polyisobutene Polymers 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229920000800 acrylic rubber Polymers 0.000 description 2
229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 2
239000012190 activator Substances 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
125000005250 alkyl acrylate group Chemical group 0.000 description 2
IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000002542 deteriorative effect Effects 0.000 description 2
125000003438 dodecyl group Chemical group [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])* 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000003822 epoxy resin Substances 0.000 description 2
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
229920000554 ionomer Polymers 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
229920000092 linear low density polyethylene Polymers 0.000 description 2
239000004707 linear low-density polyethylene Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
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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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
- 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
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring

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)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Processes Of Treating Macromolecular Substances (AREA)

IL12623797A 1996-04-12 1997-04-10 Synergistic stabilizer composition comprising a photoreactive polyalkylpiperidine and a non-photoreactive polyalkylpiperidine or polyalkyl-piperazine and a process for stabilizing a natural or synthetic polymeric or prepolymeric substrate against the damage effected by light, heat and/or oxidation using this composition IL126237A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9607565.0A GB9607565D0 (en)	1996-04-12	1996-04-12	Stabilizer composition
PCT/IB1997/000388 WO1997039051A1 (en)	1996-04-12	1997-04-10	Stabilizer composition

Publications (2)

Publication Number	Publication Date
IL126237A0 IL126237A0 (en)	1999-05-09
IL126237A true IL126237A (en)	2004-03-28

Family

ID=10791925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12623797A IL126237A (en)	1996-04-12	1997-04-10	Synergistic stabilizer composition comprising a photoreactive polyalkylpiperidine and a non-photoreactive polyalkylpiperidine or polyalkyl-piperazine and a process for stabilizing a natural or synthetic polymeric or prepolymeric substrate against the damage effected by light, heat and/or oxidation using this composition

Country Status (17)

Country	Link
US (1)	US6126861A (de)
EP (1)	EP0892827B1 (de)
JP (1)	JP2000509083A (de)
CN (1)	CN1082519C (de)
AT (1)	ATE270691T1 (de)
AU (1)	AU725011B2 (de)
BR (1)	BR9708639A (de)
CA (1)	CA2251315A1 (de)
CZ (1)	CZ294846B6 (de)
DE (1)	DE69729793T2 (de)
ES (1)	ES2224227T3 (de)
GB (1)	GB9607565D0 (de)
HU (1)	HUP9902407A3 (de)
IL (1)	IL126237A (de)
SK (1)	SK285113B6 (de)
TR (1)	TR199802046T2 (de)
WO (1)	WO1997039051A1 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0709426B2 (de) †	1994-10-28	2005-01-05	Ciba SC Holding AG	Synergistisches Stabilisatorgemisch
TW401437B (en) *	1995-02-10	2000-08-11	Ciba Sc Holding Ag	Synergistic stabilizer mixture
GB9800935D0 (en)	1998-01-17	1998-03-11	Clariant Int Ltd	Improvements in or relating to organic compounds
US6559207B1 (en) *	2000-03-14	2003-05-06	Si Corporation	Flame resistant polymer composition and method for rendering polymers flame resistant
GB0009965D0 (en) *	2000-04-25	2000-06-14	Clariant Int Ltd	Synergistic stabilizer compositions comprising copolymers of ethylene with hin dered amine moieties containing acrylate or methacrylate comonomers
DE10196267T1 (de)	2000-05-31	2003-05-15	Ciba Sc Holding Ag	Stabilisatorgemische
CN1235958C (zh)	2000-05-31	2006-01-11	西巴特殊化学品控股有限公司	稳定剂混合物
TWI226351B (en) *	2000-07-14	2005-01-11	Clariant Int Ltd	Synergistic mixtures of phosphorus-containing compounds for stabilizing polymers
GB0019465D0 (en) *	2000-08-09	2000-09-27	Clariant Int Ltd	Synergistic stabilizer for color stable pigmented thermoplastic polyners in prolonged contact with water
KR20030060903A (ko) *	2000-10-03	2003-07-16	앤더슨 디벨롭먼트 캄파니	아크릴계 수지의 탈휘발 방법, 코팅용 분말 조성물의 제조방법 및 코팅용 분말 조성물을 형성할 수 있는 조성물
GB0104371D0 (en) *	2001-02-22	2001-04-11	Clariant Int Ltd	Color improving stabilizing compositions comprising leucine
AU2003243282B2 (en)	2002-05-17	2008-05-01	Othera Holding, Inc.	Amelioration of the development of cataracts and other opthalmic diseases
US7825134B2 (en)	2003-05-19	2010-11-02	Othera Holding, Inc.	Amelioration of cataracts, macular degeneration and other ophthalmic diseases
US20050050793A1 (en) *	2003-09-08	2005-03-10	Randy Johnson	Weed barrier and artificial mulch with degradable portion and related method
US20050282943A1 (en) *	2004-06-22	2005-12-22	Invista North America S.A R.L.	Solubilized additive composition comprising acidic and basic constituents
ES2593089T3 (es)	2007-05-25	2016-12-05	Clariant International Ltd	Estabilización de policarbonatos y combinaciones de policarbonatos
KR20190090415A (ko) *	2018-01-24	2019-08-02	삼성디스플레이 주식회사	전자 장치 및 이의 제조방법
US11417857B2 (en)	2018-01-24	2022-08-16	Samsung Display Co., Ltd.	Heterocyclic compound and electronic apparatus

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0052579B1 (de) *	1980-11-17	1984-11-14	Ciba-Geigy Ag	Neue Lichtschutzmittel
DE3412227A1 (de) *	1983-04-11	1984-10-11	Sandoz-Patent-GmbH, 7850 Lörrach	Neue piperidinverbindungen
GB8608315D0 (en) *	1986-04-04	1986-05-08	Sandoz Ltd	Organic compounds
US4863981A (en) *	1986-06-30	1989-09-05	Ciba-Geigy Corporation	Synergistic mixture of stabilizers
EP0389427B1 (de) *	1989-03-21	1994-04-27	Ciba-Geigy Ag	Verbindungen mit sowohl UV absorbierenden als auch eine gehinderte 1-Hydrocarbyloxy-Aminogruppe enthaltenden Resten und damit stabilisierte Mischungen
GB9211602D0 (en) *	1992-06-02	1992-07-15	Sandoz Ltd	Improvements in or relating to organic compounds
DE4327297B4 (de) *	1992-08-17	2007-05-24	Clariant Finance (Bvi) Ltd.	Verwendung von Piperidinverbindungen
DE4327247A1 (de) *	1993-08-13	1995-02-16	Hoechst Ag	Thermoreversible Acrylsäureamid-Polymere und ihre Verwendung
DE19530468A1 (de) *	1995-08-18	1997-02-20	Sandoz Ag	Verwendung von Piperidinverbindungen
DE69705040T2 (de) *	1996-04-12	2001-09-20	Clariant Finance (Bvi) Ltd., Road Town	Stabilisation von polyolefinen

1996
- 1996-04-12 GB GBGB9607565.0A patent/GB9607565D0/en active Pending
1997
- 1997-04-10 AT AT97914516T patent/ATE270691T1/de not_active IP Right Cessation
- 1997-04-10 US US09/171,115 patent/US6126861A/en not_active Expired - Fee Related
- 1997-04-10 TR TR1998/02046T patent/TR199802046T2/xx unknown
- 1997-04-10 CA CA002251315A patent/CA2251315A1/en not_active Abandoned
- 1997-04-10 CZ CZ19983277A patent/CZ294846B6/cs not_active IP Right Cessation
- 1997-04-10 ES ES97914516T patent/ES2224227T3/es not_active Expired - Lifetime
- 1997-04-10 CN CN97195235A patent/CN1082519C/zh not_active Expired - Fee Related
- 1997-04-10 WO PCT/IB1997/000388 patent/WO1997039051A1/en not_active Ceased
- 1997-04-10 SK SK1338-98A patent/SK285113B6/sk not_active IP Right Cessation
- 1997-04-10 HU HU9902407A patent/HUP9902407A3/hu unknown
- 1997-04-10 BR BR9708639A patent/BR9708639A/pt not_active IP Right Cessation
- 1997-04-10 AU AU21746/97A patent/AU725011B2/en not_active Ceased
- 1997-04-10 IL IL12623797A patent/IL126237A/en not_active IP Right Cessation
- 1997-04-10 JP JP9536906A patent/JP2000509083A/ja not_active Ceased
- 1997-04-10 DE DE69729793T patent/DE69729793T2/de not_active Expired - Fee Related
- 1997-04-10 EP EP97914516A patent/EP0892827B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO1997039051A1 (en)	1997-10-23
CN1082519C (zh)	2002-04-10
HK1019885A1 (en)	2000-03-03
GB9607565D0 (en)	1996-06-12
CN1221438A (zh)	1999-06-30
US6126861A (en)	2000-10-03
AU725011B2 (en)	2000-10-05
AU2174697A (en)	1997-11-07
ATE270691T1 (de)	2004-07-15
HUP9902407A3 (en)	1999-12-28
EP0892827B1 (de)	2004-07-07
SK133898A3 (en)	1999-06-11
ES2224227T3 (es)	2005-03-01
SK285113B6 (sk)	2006-06-01
CZ294846B6 (cs)	2005-03-16
HUP9902407A2 (hu)	1999-11-29
CZ327798A3 (cs)	1999-01-13
IL126237A0 (en)	1999-05-09
JP2000509083A (ja)	2000-07-18
EP0892827A1 (de)	1999-01-27
DE69729793T2 (de)	2005-07-14
CA2251315A1 (en)	1997-10-23
TR199802046T2 (xx)	1998-12-21
DE69729793D1 (de)	2004-08-12
BR9708639A (pt)	1999-04-13

Legal Events

Date	Code	Title
2004-09-27	KB	Patent renewed
2007-07-24	KB	Patent renewed
2011-12-29	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5980783A (en)	1999-11-09	Synergistic stabilizer mixture
AU780925B2 (en)	2005-04-28	Synergistic mixtures of UV-absorbers in polyolefins
US6020406A (en)	2000-02-01	Synergistic stabilizer mixture
AU725011B2 (en)	2000-10-05	Stabilizer composition
US5965643A (en)	1999-10-12	Synergistic stabilizer mixture
US5719217A (en)	1998-02-17	Synergistic stabiliser mixture
US6015849A (en)	2000-01-18	Synergistic stabilizer mixture
US5977221A (en)	1999-11-02	Synergistic stabilizer mixture
US5496875A (en)	1996-03-05	Derivatives of 2,2,6,6-tetramethyl-4-piperidinol for use as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials
CA2408651C (en)	2012-10-16	Stabilizer mixtures
EP0665233A2 (de)	1995-08-02	Silangruppen enthaltende 1-Hydrocarbyloxy-Piperidin-Verbindungen als Stabilisatoren für organisches Material
CA2196266C (en)	2006-03-14	Synergistic mixture consisting of a 2,4-dimethyl-6-s-alkylphenol and a sterically hindered phenol
AU2001262311A1 (en)	2002-02-28	Stabilizer mixtures
US5610211A (en)	1997-03-11	2,2,6,6-tetramethylpiperidine derivatives for use as stabilizing agents for organic materials
EP0636610A1 (de)	1995-02-01	Neue 2, 2, 6, 6-Tetramethyl-4-piperidinol Derivate als Stabilisatoren für organische Materialien
EP0634412A1 (de)	1995-01-18	Piperdinverbindungen als Stabilisatoren für organische Stoffe
KR100496096B1 (ko)	2005-09-27	안정화제조성물
HK1019885B (en)	2002-08-16	Stabilizer composition and a process for stabilizing a natural or synthetic polymeric or prepolymeric substrate
GB2377703A (en)	2003-01-22	Sterically hindered amine compounds
GB2390608A (en)	2004-01-14	Mixtures of UV absorbers in polyolefins