WO1980000971A1 - Process for rendering aromatic polymers resistant to discoloration - Google Patents
Process for rendering aromatic polymers resistant to discoloration Download PDFInfo
- Publication number
- WO1980000971A1 WO1980000971A1 PCT/US1979/000914 US7900914W WO8000971A1 WO 1980000971 A1 WO1980000971 A1 WO 1980000971A1 US 7900914 W US7900914 W US 7900914W WO 8000971 A1 WO8000971 A1 WO 8000971A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tert
- resin
- ultraviolet light
- antioxidant
- butyl
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 13
- 238000002845 discoloration Methods 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 16
- 229920000642 polymer Polymers 0.000 title description 7
- 238000009877 rendering Methods 0.000 title description 3
- 239000011347 resin Substances 0.000 claims abstract description 39
- 229920005989 resin Polymers 0.000 claims abstract description 39
- 239000003381 stabilizer Substances 0.000 claims abstract description 19
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 17
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 12
- -1 poly(phenylene oxide) Polymers 0.000 claims description 10
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 7
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical group CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical group CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 3
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical group C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 2
- 230000000593 degrading effect Effects 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N para-hydroxystyrene Natural products OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims 1
- 229920006380 polyphenylene oxide Polymers 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 abstract description 7
- 238000004381 surface treatment Methods 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- MJFOVRMNLQNDDS-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MJFOVRMNLQNDDS-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 1
- DNCLEPRFPJLBTQ-UHFFFAOYSA-N 2-cyclohexyl-4-[1-(3-cyclohexyl-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound OC1=CC=C(C2(CCCCC2)C=2C=C(C(O)=CC=2)C2CCCCC2)C=C1C1CCCCC1 DNCLEPRFPJLBTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- GXUYCJJDHBJKHA-UHFFFAOYSA-N 4-methyl-2,6-di(octadecan-2-yl)phenol Chemical compound CCCCCCCCCCCCCCCCC(C)C1=CC(C)=CC(C(C)CCCCCCCCCCCCCCCC)=C1O GXUYCJJDHBJKHA-UHFFFAOYSA-N 0.000 description 1
- IEMHIOUNBGZEAG-UHFFFAOYSA-N 4-tert-butyl-2-(5-chlorobenzotriazol-2-yl)phenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=C(Cl)C=CC3=N2)=C1 IEMHIOUNBGZEAG-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- MJVGBKJNTFCUJM-UHFFFAOYSA-N mexenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 MJVGBKJNTFCUJM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- 150000002989 phenols Chemical class 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002863 poly(1,4-phenylene oxide) polymer Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 101150011213 uvs-1 gene Proteins 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- 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
Definitions
- This invention relates to aromatic resins and more particularly to a process for rendering aromatic resins resistant to discoloration by surface treatment with a synergistic stabilizer combination of an antioxidant and an ultraviolet light, absorber.
- Aromatic polymers such as bisphenol-A polycarbonates, polystyrene, ABS and the like are particularly subject to degradation by exposure to ultraviolet light. Not generally known, however, is the fact that these resins are also subject to discoloration by photooxidation. Thus, the incorporation of both an antioxidant and an ultraviolet light absorber would be beneficial in inhibiting discoloration of these resins.
- the combination is found to be synergistic when the resin is given a surface treatment of the combination in a suitable solvent.
- a solvent in which the resin is only partly soluble whereby it can diffuse into the surface of the resin without substantially degrading it enables one to use far less stabilizer than would be required if directly incorporated into the resin precursors as there is no substantial amount bound into the center of the resin and consequently unavailable for protecting the resin.
- by treating the surface of the resin in accordance with the invention there is no degradation or impairment of the desirable resin properties caused by incorporation of the stabilizers. While surface treatment of aromatic resins with protective ultraviolet light stabilizers has previously been accomplished, to applicant's knowledge it has not been previously suggested to combine an antioxidant and an ultraviolet light absorber to coat an aromatic resin and it is the provision of such a system to which this invention is directed.
- Aromatic resins which can be employed in the invention are those which are normally degraded by exposure to ultraviolet light.
- Typical resins include polycarbonate resins prepared by reacting a dihydric phenol such as bisphenol-A (BPA) with a carbonate precursor such as phosgene which are disclosed in U.S. Patent No. 3,309,220.
- BPA bisphenol-A
- phosgene phosgene which are disclosed in U.S. Patent No. 3,309,220.
- These polycarbonate resins which may be formed from mononuclear or polynuclear aromatic compounds can also be formed from halo substituted dihydric phenols such as 1,1-dichloro2,2-bis(4-hydroxyphenyl)ethylene (BPC) .
- styrene polymers such as polystyrene and ABS
- polymers containing ether linkages such as poly(2,6-dimethylphenylene oxide)
- polymer blends such as formed of 20 to 99% by weight of a polyphenylene ether which can be substituted with alkyl groups of from 1 to 4 carbon atoms, e.g., poly(2,6-dimethylphenylene)oxide, and 1 to 80% of a styrene polymer such as polystyrene.
- the particular resin employed is not critical as the stabilizer combination is effective in protecting conventional aromatic resins.
- Any ultraviolet absorber can be used, such as, for example, benzophenone derivatives, such as 2-hydroxy-4-methoxy-benzophenone , 2,4-dihydroxy-benzophenone, 2,2'-dihydroxy-4-methoxy-benzo ⁇ henone , 2-hydroxy-4-n-octoxybenzophenone , 2,2' -dihydroxy-4,4'-dimethoxy-benzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone , benzotriazole derivatives, such as 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-tert butylphenyl)-benzotriazole.
- benzophenone derivatives such as 2-hydroxy-4-methoxy-benzophenone , 2,4-dihydroxy-benzophenone, 2,2'-dihydroxy-4-methoxy-benzo ⁇ henone , 2-hydroxy-4-n-octoxybenzophenone , 2,
- Any antioxidant can be used, such as, for example,2, 6-di-tert-butyl-p-cresol , 2,2'-methylene bis(4-methyl-6-tert-butyl-phenol) , 4,4'-butylidene bis (6-tert-butyl-m-cresol) , 1,1,3-tris (2' -methyl-4'-hydroxy-5'-tert-butyl-phenyl) butane, 4,4'-methylene bis (2 , 6-di-tert-butyl ⁇ henol), octadecyl 3-(3' , 5 ' -di-tert-butyl-4'-hydroxy-phenyl)propionate, 2,6-di-(1-methylheptadecyl)p-cresol, 1,3,5-trimethyl-2,4,6-tris (3', 5'-di-tert-butyl-4'-hydroxybenzyl)benzene, tetrakis [methylene 3-(
- ultraviolet light absorber and antioxidant employed will depend upon the particular stabilizer, the resin,. and solvent employed but generally an absorber concentration in the solvent from about 0.5% to about 20% and an antioxidant from about 0.1% to about 5% by weight is sufficient.
- Solvents which can be employed are those which will not decompose either the stabilizers or the resin but which will diffuse into at least the surface of the polymer so as to deposit the stabilizers.
- Typical solvents include aromatic, chloroaromatic and chloroaliphatic solvents.
- the particular solvent will depend upon the resin but exemplary of suitable solvents are methylene chloride, chloroform, toluene, benzene, tetrahydrofuran, chlorobenzene , and dichlorobenzene.
- the solvent is employed in an amount sufficient to contain the stabilizers and provide a vehicle for submerging or coating the resin.
- an immersion time of no more than about 5 to 15 seconds is sufficient to impregnate the resin and the solvent can be easily evaporated at room temperature in a period of between about 1/2 hour and about 24 hours .
- Molded chips (2" x 2" x 1/8") of the copolycarbonate of BPC (85 pts) and BPA (15 pts) of the type described in Polish Patent 48,893 containing a mold stabilizer and formed by injection molding were dipped for 10 seconds in ethylene dichloride containing a stabilizer in the amount indicated (infra) and tested under accelerated weather conditions with a QUV cyclic ultraviolet weather tester (Q-Panel Co.) maintained on a 4 hr light/dark cycle at full humidity. After exposure, the weathered chips were assessed for discoloration by measuring their yellowness index, YI, according to ASTM method D1925.
- A' is 2(2'-hydroxy-5'-methylphenyl)benzotriazole
- B 2 is 2(2'-hydroxy-5'-tert-octylphenyl)benzotriazole
- C 3 is 3,5-di-tert-butyl-4-hydroxyhydrocinnamic acid triester of is 1,3,5-tris(2-hydroxyethyl-s-triazine-2,4,6-(1H,3H,5H)- trione
- D 4 is octadecyl 3-(3',5'-di-tert-butyl-4'-hydroxy-phenyl)propionate
- Molded stabilized chips (2" x 2" x 1/8") of Lexan polycarbonate containing 0.3% of 2(2' -hydroxy-5'-methylphenyl) benzotriazole as a bulk stabilizer plus a mold stabilizer were dipped for 10 seconds in ethylene dichloride containing stabilizer in the amount indicated (infra) and exposed to a 400 watt clear mercury lamp and rotated in an exposure chamber so as to maintain a surface temperature for the chips of 110oC.
- EDC is Ethylene Dichloride .
- UVS-1 is 2(2'-hydroxy-5'-methylphenyl)benzotriazole
- AO-1 is 3 , 5-di-tert-butyl-4-hydroxyhydrocinnamic acid triester of 1,3,5-tris (2-hydroxyethyl)s-triazine-2,4,6 1H, 3H, 5H) -trione
- AO-2 is tris (2', 5' - di-tert-butyl-4'-hydroxylbenzyl) isocyanurate
- AO-3 is 2 , 6-di-tert-butyl-4-tert-nonylphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR7908893A BR7908893A (pt) | 1978-11-13 | 1979-10-29 | Processo para tratamento de uma resina aromatica normalmente sujeita a descoloracao quando exposta ao ar e a luz ultravioleta |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95959678A | 1978-11-13 | 1978-11-13 | |
| US959596 | 1978-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1980000971A1 true WO1980000971A1 (en) | 1980-05-15 |
Family
ID=25502196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1979/000914 WO1980000971A1 (en) | 1978-11-13 | 1979-10-29 | Process for rendering aromatic polymers resistant to discoloration |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0020595A4 (enrdf_load_stackoverflow) |
| JP (1) | JPS55500905A (enrdf_load_stackoverflow) |
| WO (1) | WO1980000971A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0152012A3 (en) * | 1984-02-10 | 1986-03-12 | General Electric Company | Method for enhancing ionizing radiation resistance of polymer compositions |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2906055B2 (ja) * | 1988-03-10 | 1999-06-14 | セイコーエプソン株式会社 | 合成樹脂製レンズ |
| JP2744262B2 (ja) * | 1988-11-25 | 1998-04-28 | 株式会社クラレ | 樹脂組成物 |
| US7887882B2 (en) * | 2005-02-09 | 2011-02-15 | Essilor International (Compagnie Generale D'optique) | Stabilized ultra-violet absorbers |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2919259A (en) * | 1956-08-22 | 1959-12-29 | Ralph A Naylor | Light stabilized polyvinyl chloride compositions |
| US3035020A (en) * | 1959-04-06 | 1962-05-15 | Union Carbide Corp | Process for preparing polycarbonate resins |
| US3134748A (en) * | 1961-12-21 | 1964-05-26 | American Cyanamid Co | Polystyrene color stabilized with trialkyl phenol and a benzotriazole |
| US3330859A (en) * | 1961-10-30 | 1967-07-11 | Geigy Chem Corp | Alkyl esters of carboxylic acids containing an alkylhydroxyphenyl group |
| US3368997A (en) * | 1965-11-15 | 1968-02-13 | Geigy Chem Corp | Composition and method for the stabilization of organic material |
| US3531483A (en) * | 1968-10-25 | 1970-09-29 | Goodrich Co B F | Hydroxyphenylalkyleneyl isocyanurates |
| US3617330A (en) * | 1967-03-09 | 1971-11-02 | Bayer Ag | Mouldings of polycarbonates with improved surfaces and process for their production |
| US3676531A (en) * | 1969-05-19 | 1972-07-11 | Ciba Geigy Corp | Bis-(hindered phenol)-alkane phosphonates |
| US3707542A (en) * | 1971-02-25 | 1972-12-26 | Ciba Geigy Corp | Dialkyl-4-hydroxyphenylcarboxylates of tris(hydroxy-alkyl) isocyanurate |
| US3892889A (en) * | 1972-03-10 | 1975-07-01 | Bayer Ag | Process for stabilizing moldings of high molecular weight thermo-plastic polycarbonates |
| US3959207A (en) * | 1971-01-18 | 1976-05-25 | The Goodyear Tire & Rubber Company | Latex viscosity depressants |
| US3987001A (en) * | 1975-02-03 | 1976-10-19 | Chevron Research Company | Ultraviolet protectorant composition |
| US4124652A (en) * | 1976-12-14 | 1978-11-07 | General Electric Company | Thermoplastic molding composition |
| US4146658A (en) * | 1978-04-12 | 1979-03-27 | General Electric Company | Process for producing an ultraviolet light stabilized polycarbonate article |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6597174A (en) * | 1973-04-04 | 1975-08-28 | Gen Electric | Photooxidatively stable polycarbonate composition |
| JPS5021067A (enrdf_load_stackoverflow) * | 1973-06-25 | 1975-03-06 |
-
1979
- 1979-10-29 WO PCT/US1979/000914 patent/WO1980000971A1/en unknown
- 1979-10-29 JP JP50198079A patent/JPS55500905A/ja active Pending
-
1980
- 1980-05-20 EP EP19790901564 patent/EP0020595A4/en not_active Withdrawn
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2919259A (en) * | 1956-08-22 | 1959-12-29 | Ralph A Naylor | Light stabilized polyvinyl chloride compositions |
| US3035020A (en) * | 1959-04-06 | 1962-05-15 | Union Carbide Corp | Process for preparing polycarbonate resins |
| US3330859A (en) * | 1961-10-30 | 1967-07-11 | Geigy Chem Corp | Alkyl esters of carboxylic acids containing an alkylhydroxyphenyl group |
| US3134748A (en) * | 1961-12-21 | 1964-05-26 | American Cyanamid Co | Polystyrene color stabilized with trialkyl phenol and a benzotriazole |
| US3134752A (en) * | 1961-12-21 | 1964-05-26 | American Cyanamid Co | Polystyrene color stabilized with trialkyl phenol and a benzophenone |
| US3368997A (en) * | 1965-11-15 | 1968-02-13 | Geigy Chem Corp | Composition and method for the stabilization of organic material |
| US3617330A (en) * | 1967-03-09 | 1971-11-02 | Bayer Ag | Mouldings of polycarbonates with improved surfaces and process for their production |
| US3531483A (en) * | 1968-10-25 | 1970-09-29 | Goodrich Co B F | Hydroxyphenylalkyleneyl isocyanurates |
| US3676531A (en) * | 1969-05-19 | 1972-07-11 | Ciba Geigy Corp | Bis-(hindered phenol)-alkane phosphonates |
| US3959207A (en) * | 1971-01-18 | 1976-05-25 | The Goodyear Tire & Rubber Company | Latex viscosity depressants |
| US3707542A (en) * | 1971-02-25 | 1972-12-26 | Ciba Geigy Corp | Dialkyl-4-hydroxyphenylcarboxylates of tris(hydroxy-alkyl) isocyanurate |
| US3892889A (en) * | 1972-03-10 | 1975-07-01 | Bayer Ag | Process for stabilizing moldings of high molecular weight thermo-plastic polycarbonates |
| US3987001A (en) * | 1975-02-03 | 1976-10-19 | Chevron Research Company | Ultraviolet protectorant composition |
| US4124652A (en) * | 1976-12-14 | 1978-11-07 | General Electric Company | Thermoplastic molding composition |
| US4146658A (en) * | 1978-04-12 | 1979-03-27 | General Electric Company | Process for producing an ultraviolet light stabilized polycarbonate article |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP0020595A4 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0152012A3 (en) * | 1984-02-10 | 1986-03-12 | General Electric Company | Method for enhancing ionizing radiation resistance of polymer compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0020595A1 (en) | 1981-01-07 |
| JPS55500905A (enrdf_load_stackoverflow) | 1980-11-06 |
| EP0020595A4 (en) | 1981-06-17 |
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