CA2449242A1

CA2449242A1 - Synergistic combinations of nano-scaled fillers and hindered amine light stabilizers

Synergistic combinations of nano-scaled fillers and hindered amine light stabilizers Download PDF

Info

Publication number: CA2449242A1
Authority: CA; Canada
Prior art keywords: tert; bis; butyl; hydroxy; stabilizers
Prior art date: 2001-06-29
Legal status : Abandoned

Application number

CA002449242A

Other languages

English (en)

French (fr)

Inventor

Hui Chin

Peter Shelsey Solera

Douglas Wayne Horsey

Nikolas Kaprinidis

Eugene Valentine Sitzmann

Current Assignee

BASF Schweiz AG

Original Assignee

Individual

Priority date

2001-06-29

Filing date

2002-06-20

Publication date

2003-01-09

2002-06-20 Application filed by Individual filed Critical Individual

2003-01-09 Publication of CA2449242A1 publication Critical patent/CA2449242A1/en

Status Abandoned legal-status Critical Current

Links

150000001412 amines Chemical class 0.000 title claims abstract description 92
239000000945 filler Substances 0.000 title claims abstract description 62
239000004611 light stabiliser Substances 0.000 title claims abstract description 22
239000011885 synergistic combination Substances 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 131
229920000642 polymer Polymers 0.000 claims abstract description 68
239000000654 additive Substances 0.000 claims abstract description 56
239000000758 substrate Substances 0.000 claims abstract description 24
230000000996 additive effect Effects 0.000 claims abstract description 22
230000015556 catabolic process Effects 0.000 claims abstract description 11
238000006731 degradation reaction Methods 0.000 claims abstract description 11
230000001590 oxidative effect Effects 0.000 claims abstract description 10
230000002939 deleterious effect Effects 0.000 claims abstract description 8
230000000087 stabilizing effect Effects 0.000 claims abstract description 7
239000003381 stabilizer Substances 0.000 claims description 61
239000000306 component Substances 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 44
239000003063 flame retardant Substances 0.000 claims description 36
238000006068 polycondensation reaction Methods 0.000 claims description 28
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
238000000034 method Methods 0.000 claims description 15
YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 14
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 claims description 11
229910052615 phyllosilicate Inorganic materials 0.000 claims description 11
229920000307 polymer substrate Polymers 0.000 claims description 10
239000003963 antioxidant agent Substances 0.000 claims description 8
125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
239000002530 phenolic antioxidant Substances 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 7
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
229940124543 ultraviolet light absorber Drugs 0.000 claims description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
230000005855 radiation Effects 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000012796 inorganic flame retardant Substances 0.000 claims description 2
230000001678 irradiating effect Effects 0.000 claims description 2
230000002195 synergetic effect Effects 0.000 abstract description 8
-1 ammonium cations Chemical class 0.000 description 84
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
229920001577 copolymer Polymers 0.000 description 49
239000000047 product Substances 0.000 description 29
239000004952 Polyamide Substances 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
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238000009472 formulation Methods 0.000 description 20
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229910052757 nitrogen Inorganic materials 0.000 description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
239000005977 Ethylene Substances 0.000 description 15
239000002245 particle Substances 0.000 description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
229920001155 polypropylene Polymers 0.000 description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
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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
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
230000006641 stabilisation Effects 0.000 description 12
238000011105 stabilization Methods 0.000 description 12
239000006096 absorbing agent Substances 0.000 description 11
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229910052751 metal Inorganic materials 0.000 description 11
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229920002397 thermoplastic olefin Polymers 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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VVISQEKWYPFFLK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetrabutyl-6-chloro-1,3,5-triazine-2,4-diamine Chemical compound CCCCN(CCCC)C1=NC(Cl)=NC(N(CCCC)CCCC)=N1 VVISQEKWYPFFLK-UHFFFAOYSA-N 0.000 description 9
229910019142 PO4 Inorganic materials 0.000 description 9
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150000001252 acrylic acid derivatives Chemical class 0.000 description 8
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
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239000002114 nanocomposite Substances 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
235000021317 phosphate Nutrition 0.000 description 8
229920002857 polybutadiene Polymers 0.000 description 8
229920005989 resin Polymers 0.000 description 8
239000011347 resin Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 7
UQAMDAUJTXFNAD-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1 UQAMDAUJTXFNAD-UHFFFAOYSA-N 0.000 description 7
STEYNUVPFMIUOY-UHFFFAOYSA-N 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 description 7
239000004698 Polyethylene Substances 0.000 description 7
239000007983 Tris buffer Substances 0.000 description 7
235000006708 antioxidants Nutrition 0.000 description 7
150000001993 dienes Chemical class 0.000 description 7
229920001971 elastomer Polymers 0.000 description 7
229920001684 low density polyethylene Polymers 0.000 description 7
239000004702 low-density polyethylene Substances 0.000 description 7
239000000178 monomer Substances 0.000 description 7
239000000049 pigment Substances 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
239000004416 thermosoftening plastic Substances 0.000 description 7
DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 6
229920000877 Melamine resin Polymers 0.000 description 6
239000004721 Polyphenylene oxide Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000004927 clay Substances 0.000 description 6
WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-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
239000006185 dispersion Substances 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
229940063583 high-density polyethylene Drugs 0.000 description 6
238000002156 mixing Methods 0.000 description 6
229910052901 montmorillonite Inorganic materials 0.000 description 6
239000008188 pellet Substances 0.000 description 6
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229920000098 polyolefin Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000001384 succinic acid Substances 0.000 description 6
229910052724 xenon Inorganic materials 0.000 description 6
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 6
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229940048053 acrylate Drugs 0.000 description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
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229920005669 high impact polystyrene Polymers 0.000 description 5
239000004797 high-impact polystyrene Substances 0.000 description 5
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230000007774 longterm Effects 0.000 description 5
238000000465 moulding Methods 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
239000004417 polycarbonate Substances 0.000 description 5
229920000647 polyepoxide Polymers 0.000 description 5
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DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
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RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
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CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
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239000004593 Epoxy Substances 0.000 description 4
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
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 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
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 4
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150000002170 ethers Chemical class 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens 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
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125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
150000002815 nickel Chemical class 0.000 description 4
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GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
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BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 4
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SCRNZBFVSFJGCI-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-3-amine Chemical compound CN1C(C)(C)CCC(N)C1(C)C SCRNZBFVSFJGCI-UHFFFAOYSA-N 0.000 description 3
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VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
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BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 description 3
VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 3
HMADMAFEFZHZLM-UHFFFAOYSA-N 2,4-dichloro-6-(2,4,4-trimethylpentan-2-yl)-2h-1,3,5-triazin-1-amine Chemical compound CC(C)(C)CC(C)(C)C1=NC(Cl)=NC(Cl)N1N HMADMAFEFZHZLM-UHFFFAOYSA-N 0.000 description 3
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MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
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