CA2179697A1

CA2179697A1 - Polysiloxane light stabilizers

Polysiloxane light stabilizers

Info

Publication number: CA2179697A1
Authority: CA; Canada
Prior art keywords: formula; compound; tert; hydrogen; range
Prior art date: 1995-06-23
Legal status : Abandoned

Application number

CA002179697A

Other languages

English (en)

French (fr)

Inventor

Roger Meuwly

Andreas Valet

Current Assignee

BASF Schweiz AG

Original Assignee

Individual

Priority date

1995-06-23

Filing date

1996-06-21

Publication date

1996-12-24

1996-06-21 Application filed by Individual filed Critical Individual

1996-12-24 Publication of CA2179697A1 publication Critical patent/CA2179697A1/en

Status Abandoned legal-status Critical Current

Links

-1 Polysiloxane Polymers 0.000 title claims abstract description 81
239000004611 light stabiliser Substances 0.000 title claims description 9
229920001296 polysiloxane Polymers 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 113
238000000576 coating method Methods 0.000 claims abstract description 38
239000011248 coating agent Substances 0.000 claims abstract description 22
239000003381 stabilizer Substances 0.000 claims abstract description 15
239000000463 material Substances 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
239000011368 organic material Substances 0.000 claims abstract description 8
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 29
229920000642 polymer Polymers 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
239000011230 binding agent Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
229920000620 organic polymer Polymers 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000004956 cyclohexylene group Chemical group 0.000 claims description 2
230000000087 stabilizing effect Effects 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
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229910052757 nitrogen Inorganic materials 0.000 description 31
150000003254 radicals Chemical class 0.000 description 28
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 20
229910052751 metal Inorganic materials 0.000 description 19
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239000003054 catalyst Substances 0.000 description 17
239000011572 manganese Substances 0.000 description 17
239000000243 solution Substances 0.000 description 17
238000005481 NMR spectroscopy Methods 0.000 description 16
238000001816 cooling Methods 0.000 description 14
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239000008199 coating composition Substances 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
239000004952 Polyamide Substances 0.000 description 11
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150000001252 acrylic acid derivatives Chemical class 0.000 description 11
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239000000741 silica gel Substances 0.000 description 11
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NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
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150000002148 esters Chemical class 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
229910019032 PtCl2 Inorganic materials 0.000 description 9
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 9
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238000004587 chromatography analysis Methods 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
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229920001903 high density polyethylene Polymers 0.000 description 7
239000004700 high-density polyethylene Substances 0.000 description 7
150000002739 metals Chemical class 0.000 description 7
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239000000758 substrate Substances 0.000 description 7
229920001169 thermoplastic Polymers 0.000 description 7
239000008096 xylene Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000005062 Polybutadiene Substances 0.000 description 6
239000004698 Polyethylene Substances 0.000 description 6
239000004721 Polyphenylene oxide Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
229920001971 elastomer Polymers 0.000 description 6
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229920002857 polybutadiene Polymers 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
229920000573 polyethylene Polymers 0.000 description 6
229920001155 polypropylene Polymers 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
229910052710 silicon Inorganic materials 0.000 description 6
239000004416 thermosoftening plastic Substances 0.000 description 6
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
239000004925 Acrylic resin Substances 0.000 description 5
229920002943 EPDM rubber Polymers 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
239000000178 monomer Substances 0.000 description 5
239000000049 pigment Substances 0.000 description 5
239000004417 polycarbonate Substances 0.000 description 5
229920000647 polyepoxide Polymers 0.000 description 5
229920000570 polyether Polymers 0.000 description 5
239000005056 polyisocyanate Substances 0.000 description 5
229920001228 polyisocyanate Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
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
FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-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
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
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
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
229910052748 manganese Inorganic materials 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
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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239000007787 solid Substances 0.000 description 4
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150000008064 anhydrides Chemical class 0.000 description 3
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GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
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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
ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 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
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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
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FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 2
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FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 description 2
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KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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239000005977 Ethylene Substances 0.000 description 2
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