DE2310135C3 - 4-Phenylbenzylidenmalonsäurederivate und ihre Verwendung zur Stabilisierung von Polymeren gegen UV-Strahlung - Google Patents
4-Phenylbenzylidenmalonsäurederivate und ihre Verwendung zur Stabilisierung von Polymeren gegen UV-StrahlungInfo
- Publication number
- DE2310135C3 DE2310135C3 DE2310135A DE2310135A DE2310135C3 DE 2310135 C3 DE2310135 C3 DE 2310135C3 DE 2310135 A DE2310135 A DE 2310135A DE 2310135 A DE2310135 A DE 2310135A DE 2310135 C3 DE2310135 C3 DE 2310135C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- compounds
- ester
- absorber
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- VUKIGYZXHRSZFY-UHFFFAOYSA-N 2-[(4-phenylphenyl)methylidene]propanedioic acid Chemical class C1=CC(C=C(C(=O)O)C(O)=O)=CC=C1C1=CC=CC=C1 VUKIGYZXHRSZFY-UHFFFAOYSA-N 0.000 title claims description 3
- 229920000642 polymer Polymers 0.000 title description 19
- 230000000087 stabilizing effect Effects 0.000 title description 4
- 230000005855 radiation Effects 0.000 title description 3
- 239000006096 absorbing agent Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000004417 polycarbonate Substances 0.000 description 12
- 229920000515 polycarbonate Polymers 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000012760 heat stabilizer Substances 0.000 description 9
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- -1 polypropylene Polymers 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 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 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- SIQFBETXJAVNCI-UHFFFAOYSA-N diethyl 2-[(4-phenylphenyl)methylidene]propanedioate Chemical compound C1=CC(C=C(C(=O)OCC)C(=O)OCC)=CC=C1C1=CC=CC=C1 SIQFBETXJAVNCI-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- WDFCIMPKVFWSRF-UHFFFAOYSA-N (2,3-didecylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCCC1=CC=CC(OP(O)O)=C1CCCCCCCCCC WDFCIMPKVFWSRF-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 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
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- DMDDCFWIEQFNIE-UHFFFAOYSA-N dimethyl 2-[(4-phenylphenyl)methylidene]propanedioate Chemical compound C1=CC(C=C(C(=O)OC)C(=O)OC)=CC=C1C1=CC=CC=C1 DMDDCFWIEQFNIE-UHFFFAOYSA-N 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000005496 tempering Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- QLAFGHVZDNLIDW-UHFFFAOYSA-N 1-[3-(benzotriazol-2-yl)-5-(3-methylbutyl)phenyl]-3-methylbutan-2-ol Chemical compound CC(C)CCC1=CC(CC(O)C(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1 QLAFGHVZDNLIDW-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- QYXHQRJWUMDWGJ-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methylidene]propanedioic acid Chemical compound COC1=CC=C(C=C(C(O)=O)C(O)=O)C=C1 QYXHQRJWUMDWGJ-UHFFFAOYSA-N 0.000 description 1
- HIXTWHOXALRTPU-UHFFFAOYSA-N 2-cyano-n-cyclohexyl-3-(4-phenylphenyl)prop-2-enamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C=C(C#N)C(=O)NC1CCCCC1 HIXTWHOXALRTPU-UHFFFAOYSA-N 0.000 description 1
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical class OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- FXZJKVODWNYPKK-UHFFFAOYSA-N 3-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-1h-quinazoline-2,4-dione Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(C4=CC=CC=C4NC3=O)=O)CC2)=C1 FXZJKVODWNYPKK-UHFFFAOYSA-N 0.000 description 1
- XZDOHAPZTSLVFF-UHFFFAOYSA-N C(CCCCCCC)OC(C(=CC1=CC=C(C=C1)C1=CC=CC=C1)C#N)=O Chemical compound C(CCCCCCC)OC(C(=CC1=CC=C(C=C1)C1=CC=CC=C1)C#N)=O XZDOHAPZTSLVFF-UHFFFAOYSA-N 0.000 description 1
- XBLRPWWTIKQRQI-UHFFFAOYSA-N CCCCCCCCCCC1=CC=CC(P(O)(O)O)=C1CCCCCCCCCC Chemical compound CCCCCCCCCCC1=CC=CC(P(O)(O)O)=C1CCCCCCCCCC XBLRPWWTIKQRQI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- ITDASHAOHZCLPP-UHFFFAOYSA-N dioctyl 2-[(4-phenylphenyl)methylidene]propanedioate Chemical compound C1=CC(C=C(C(=O)OCCCCCCCC)C(=O)OCCCCCCCC)=CC=C1C1=CC=CC=C1 ITDASHAOHZCLPP-UHFFFAOYSA-N 0.000 description 1
- DTVMXQFQTCJMOR-UHFFFAOYSA-N dioctyl propanedioate Chemical compound CCCCCCCCOC(=O)CC(=O)OCCCCCCCC DTVMXQFQTCJMOR-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical class CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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)
- Macromonomer-Based Addition Polymer (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2310135A DE2310135C3 (de) | 1973-03-01 | 1973-03-01 | 4-Phenylbenzylidenmalonsäurederivate und ihre Verwendung zur Stabilisierung von Polymeren gegen UV-Strahlung |
| IT48759/74A IT1015822B (it) | 1973-03-01 | 1974-02-26 | Assorbitori di ultravioletto e procedimento per stabilizzare polimeri con essi |
| BE141429A BE811621A (fr) | 1973-03-01 | 1974-02-27 | Agents de protection contre la lumiere et procede de leur utilisation |
| CA193,658A CA1029389A (en) | 1973-03-01 | 1974-02-27 | 4-phenylbenzylidenemalonic acid derivatives as light-protective agents |
| JP49022435A JPS5945687B2 (ja) | 1973-03-01 | 1974-02-27 | 光安定剤 |
| NLAANVRAGE7402753,A NL170530C (nl) | 1973-03-01 | 1974-02-28 | Werkwijze voor de bereiding van 4-fenyl-benzylideenderivaten, werkwijze voor het stabiliseren van een polymeer tegen ultraviolette straling, alsmede gevormd voortbrengsel, dat geheel of ten dele daaruit bestaat. |
| GB908674A GB1416415A (en) | 1973-03-01 | 1974-02-28 | Biphenyl compounds and their use as light protective agents |
| FR7407113A FR2219930B1 (enExample) | 1973-03-01 | 1974-03-01 | |
| US06/002,882 US4228067A (en) | 1973-03-01 | 1979-01-12 | UV Light stabilized polycarbonate composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2310135A DE2310135C3 (de) | 1973-03-01 | 1973-03-01 | 4-Phenylbenzylidenmalonsäurederivate und ihre Verwendung zur Stabilisierung von Polymeren gegen UV-Strahlung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2310135A1 DE2310135A1 (de) | 1974-09-05 |
| DE2310135B2 DE2310135B2 (de) | 1981-07-23 |
| DE2310135C3 true DE2310135C3 (de) | 1982-05-06 |
Family
ID=5873451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2310135A Expired DE2310135C3 (de) | 1973-03-01 | 1973-03-01 | 4-Phenylbenzylidenmalonsäurederivate und ihre Verwendung zur Stabilisierung von Polymeren gegen UV-Strahlung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4228067A (enExample) |
| JP (1) | JPS5945687B2 (enExample) |
| BE (1) | BE811621A (enExample) |
| CA (1) | CA1029389A (enExample) |
| DE (1) | DE2310135C3 (enExample) |
| FR (1) | FR2219930B1 (enExample) |
| GB (1) | GB1416415A (enExample) |
| IT (1) | IT1015822B (enExample) |
| NL (1) | NL170530C (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5699250A (en) * | 1980-01-14 | 1981-08-10 | Toyobo Co Ltd | Modified polyester composition |
| US4496757A (en) * | 1981-11-05 | 1985-01-29 | Ciba-Geigy Corporation | Ultraviolet-absorbing stabilizers substituted an aliphatic hydroxyl group |
| DE100651T1 (de) * | 1982-08-03 | 1984-07-19 | Van Dyk & Co. Inc., Belleville, N.J. | Dialkylmalonate als organische hilfsmittel fuer sonnenschutzmittel. |
| DE3409921A1 (de) * | 1983-10-26 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Neue benzyliden- oder vinyloge benzylidenmalonsaeurepolyester, ihre herstellung und ihre verwendung zur uv-stabilisierung von thermoplastischen kunststoffen |
| US6207740B1 (en) | 1999-07-27 | 2001-03-27 | Milliken & Company | Polymeric methine ultraviolet absorbers |
| GB2361005B (en) | 2000-04-04 | 2002-08-14 | Ciba Sc Holding Ag | Synergistic mixtures of uv-absorbers in polyolefins |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL262168A (enExample) * | 1960-03-09 | |||
| DE1238469B (de) * | 1960-03-09 | 1967-04-13 | Gen Aniline & Film Corp | Ultraviolett-Absorptionsmittel fuer organische Stoffe |
| US3278448A (en) * | 1960-05-17 | 1966-10-11 | Bayer Ag | Ultra-violet protective light filter |
| GB1037169A (en) * | 1964-04-23 | 1966-07-27 | American Cyanamid Co | Stabilization of polymers |
| US3644466A (en) * | 1966-05-06 | 1972-02-22 | Gaf Corp | Alpha-cyano-beta beta-diphenylacrylic acid esters |
-
1973
- 1973-03-01 DE DE2310135A patent/DE2310135C3/de not_active Expired
-
1974
- 1974-02-26 IT IT48759/74A patent/IT1015822B/it active
- 1974-02-27 JP JP49022435A patent/JPS5945687B2/ja not_active Expired
- 1974-02-27 BE BE141429A patent/BE811621A/xx not_active IP Right Cessation
- 1974-02-27 CA CA193,658A patent/CA1029389A/en not_active Expired
- 1974-02-28 NL NLAANVRAGE7402753,A patent/NL170530C/xx not_active IP Right Cessation
- 1974-02-28 GB GB908674A patent/GB1416415A/en not_active Expired
- 1974-03-01 FR FR7407113A patent/FR2219930B1/fr not_active Expired
-
1979
- 1979-01-12 US US06/002,882 patent/US4228067A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2219930B1 (enExample) | 1978-01-06 |
| BE811621A (fr) | 1974-08-27 |
| DE2310135B2 (de) | 1981-07-23 |
| US4228067A (en) | 1980-10-14 |
| DE2310135A1 (de) | 1974-09-05 |
| NL170530B (nl) | 1982-06-16 |
| JPS5945687B2 (ja) | 1984-11-08 |
| GB1416415A (en) | 1975-12-03 |
| NL170530C (nl) | 1982-11-16 |
| JPS508844A (enExample) | 1975-01-29 |
| NL7402753A (enExample) | 1974-09-03 |
| IT1015822B (it) | 1977-05-20 |
| FR2219930A1 (enExample) | 1974-09-27 |
| CA1029389A (en) | 1978-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |