CA2723884C - Poly(meth)acrylimide having improved optical and color properties, particularly under thermal load - Google Patents
Poly(meth)acrylimide having improved optical and color properties, particularly under thermal load Download PDFInfo
- Publication number
- CA2723884C CA2723884C CA2723884A CA2723884A CA2723884C CA 2723884 C CA2723884 C CA 2723884C CA 2723884 A CA2723884 A CA 2723884A CA 2723884 A CA2723884 A CA 2723884A CA 2723884 C CA2723884 C CA 2723884C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- alkyl
- phosphorus compound
- optionally substituted
- hydrogen
- 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.)
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- 230000003287 optical effect Effects 0.000 title abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 238000000465 moulding Methods 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000002903 organophosphorus compounds Chemical class 0.000 claims abstract description 34
- 230000008569 process Effects 0.000 claims abstract description 29
- 238000006358 imidation reaction Methods 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- -1 C5-C8-cycloalkyl Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 230000006641 stabilisation Effects 0.000 claims abstract description 9
- 238000011105 stabilization Methods 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 14
- 239000011574 phosphorus Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- KNQVWTDLQQGKSV-UHFFFAOYSA-O hydroxy-oxo-phenylphosphanium Chemical compound O[P+](=O)C1=CC=CC=C1 KNQVWTDLQQGKSV-UHFFFAOYSA-O 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- HHJJPFYGIRKQOM-UHFFFAOYSA-N sodium;oxido-oxo-phenylphosphanium Chemical compound [Na+].[O-][P+](=O)C1=CC=CC=C1 HHJJPFYGIRKQOM-UHFFFAOYSA-N 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000012778 molding material Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005461 organic phosphorous group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 32
- 230000008646 thermal stress Effects 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 150000003018 phosphorus compounds Chemical class 0.000 abstract description 13
- 238000004383 yellowing Methods 0.000 abstract description 5
- 239000003381 stabilizer Substances 0.000 description 31
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000005022 packaging material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000012545 processing Methods 0.000 description 11
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 11
- 238000003860 storage Methods 0.000 description 9
- 239000008187 granular material Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 6
- 229910001376 inorganic hypophosphite Inorganic materials 0.000 description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- IHFQGEDFEXGPFR-UHFFFAOYSA-N 5-[4-(4-heptylbenzoyl)phenyl]pentanoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)C1=CC=C(CCCCC(O)=O)C=C1 IHFQGEDFEXGPFR-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 239000004411 aluminium Chemical group 0.000 description 2
- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical class C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001125 extrusion Methods 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
- 239000000178 monomer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FMGADNVMWHSJDJ-UHFFFAOYSA-N 1,4,4-trimethylpiperidine-2,6-dione Chemical group CN1C(=O)CC(C)(C)CC1=O FMGADNVMWHSJDJ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910001382 calcium hypophosphite Inorganic materials 0.000 description 1
- 229940064002 calcium hypophosphite Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006258 high performance thermoplastic Polymers 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical group O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- SIGUVTURIMRFDD-UHFFFAOYSA-M sodium dioxidophosphanium Chemical compound [Na+].[O-][PH2]=O SIGUVTURIMRFDD-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008001695.0 | 2008-05-09 | ||
| DE102008001695A DE102008001695A1 (de) | 2008-05-09 | 2008-05-09 | Poly(meth)acrylimide mit verbesserten optischen und Farbeigenschaften, insbesondere bei thermischer Belastung |
| PCT/EP2009/052380 WO2009135703A1 (de) | 2008-05-09 | 2009-02-27 | Poly(meth)acrylimide mit verbesserten optischen und farbeigenschaften, insbesondere bei thermischer belastung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2723884A1 CA2723884A1 (en) | 2009-11-12 |
| CA2723884C true CA2723884C (en) | 2016-01-05 |
Family
ID=40578091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2723884A Active CA2723884C (en) | 2008-05-09 | 2009-02-27 | Poly(meth)acrylimide having improved optical and color properties, particularly under thermal load |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8598280B2 (enExample) |
| EP (1) | EP2274371B1 (enExample) |
| JP (1) | JP5713890B2 (enExample) |
| KR (1) | KR101572292B1 (enExample) |
| CN (1) | CN102007174B (enExample) |
| AT (1) | ATE555155T1 (enExample) |
| BR (1) | BRPI0911435B1 (enExample) |
| CA (1) | CA2723884C (enExample) |
| DE (1) | DE102008001695A1 (enExample) |
| MX (1) | MX2010012177A (enExample) |
| MY (1) | MY148738A (enExample) |
| PL (1) | PL2274371T3 (enExample) |
| RU (1) | RU2499805C2 (enExample) |
| SI (1) | SI2274371T1 (enExample) |
| TW (1) | TWI450924B (enExample) |
| WO (1) | WO2009135703A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10345045A1 (de) * | 2003-09-26 | 2005-04-14 | Röhm GmbH & Co. KG | Verfahren zur Oberflächenvergütung von Werkstoffen durch Aufbringen insbesondere transparenter Schichten auf Basis von Polymethacrylaten |
| DE102004022540A1 (de) | 2004-05-05 | 2005-12-08 | Röhm GmbH & Co. KG | Formmasse für Formkörper mit hoher Witterungsbeständigkeit |
| DE102005055793A1 (de) | 2005-11-21 | 2007-05-24 | Röhm Gmbh | Transparente TPU (thermoplastische Polyurethane)/ PMMA (Polymethyl(meth)acrylat) Abmischungen mit verbesserter Kältesschlagzähigkeit |
| DE102007029263A1 (de) * | 2007-06-22 | 2008-12-24 | Evonik Röhm Gmbh | PMMA/PVDF-Folie mit besonders hoher Witterungsbeständigkeit und hoher UV-Schutzwirkung |
| DE102008042755A1 (de) | 2008-10-10 | 2010-04-22 | Evonik Röhm Gmbh | Poly(meth)acrylimide mit verbesserten optischen und Farbeigenschaften |
| KR102203605B1 (ko) | 2013-07-10 | 2021-01-14 | 리껭테크노스 가부시키가이샤 | 폴리(메트)아크릴이미드 필름, 그 접착 용이성 필름 및 그들의 제조 방법 |
| JP5999818B2 (ja) * | 2013-07-10 | 2016-09-28 | リケンテクノス株式会社 | 易接着性ポリ（メタ）アクリルイミドフィルムの製造方法 |
| CN105555534B (zh) | 2013-09-20 | 2017-12-08 | 理研科技株式会社 | 含聚(甲基)丙烯酰亚胺系树脂层的透明多层膜及其制造方法 |
| JP6538347B2 (ja) | 2014-03-21 | 2019-07-03 | リケンテクノス株式会社 | 多層コートフィルムの製造方法 |
| US10173392B2 (en) | 2014-03-24 | 2019-01-08 | Riken Technos Corporation | Process for producing article from layered hardcoat object, and article formed from layered hardcoat object including poly(meth)acrylimide-based resin layer |
| JP6276211B2 (ja) | 2014-05-30 | 2018-02-07 | リケンテクノス株式会社 | 透明樹脂積層体 |
| JP6153977B2 (ja) | 2014-10-02 | 2017-06-28 | リケンテクノス株式会社 | 粘着フィルム |
| KR101970093B1 (ko) | 2015-03-18 | 2019-04-17 | 리껭테크노스 가부시키가이샤 | 방현성 하드 코트 적층 필름 |
| EP3663089B1 (en) | 2015-03-18 | 2024-07-10 | Riken Technos Corporation | Molded body |
| PH12017501311B1 (en) | 2015-03-18 | 2024-07-03 | Riken Technos Corp | Hard coat laminate film and method for producing same |
| WO2018033502A1 (en) * | 2016-08-15 | 2018-02-22 | Evonik Röhm Gmbh | Acrylic materials for use in an ultraviolet light engine |
| CN111448251B (zh) * | 2017-12-19 | 2023-05-16 | 巴斯夫欧洲公司 | 稳定剂组合物、其用途和包含其的塑料组合物 |
| EP3640287A1 (de) | 2018-10-16 | 2020-04-22 | Röhm GmbH | Polyetherblockamid-poly(meth)acrylat-schäume |
| WO2023139195A1 (en) | 2022-01-24 | 2023-07-27 | Röhm Gmbh | Polymer foams based on poly(meth)acrylimide |
| EP4469507A1 (en) | 2022-01-24 | 2024-12-04 | Röhm GmbH | Polymer foams based on blends of poly(vinylidene fluoride) and poly(meth)acrylimide |
| WO2025061516A1 (en) | 2023-09-20 | 2025-03-27 | Röhm Gmbh | Copolymer based on methyl methacrylate and optical grade moulding composition comprising it |
Family Cites Families (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3246374A (en) | 1964-06-11 | 1966-04-19 | Union Carbide Corp | Process for casting metals into asbestoscontaining mold coating |
| US4246374A (en) | 1979-04-23 | 1981-01-20 | Rohm And Haas Company | Imidized acrylic polymers |
| JPS60120735A (ja) | 1983-12-02 | 1985-06-28 | Asahi Chem Ind Co Ltd | 無色透明な樹脂組成物 |
| JPH0699610B2 (ja) | 1983-12-07 | 1994-12-07 | 株式会社クラレ | 熱安定化されたメタクリル共重合体組成物 |
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| DE102008043719A1 (de) | 2008-11-13 | 2010-05-20 | Evonik Röhm Gmbh | Formmassen zur Herstellung von Solarzellenmodulen |
| DE102008043713A1 (de) | 2008-11-13 | 2010-05-20 | Evonik Röhm Gmbh | Herstellung von Solarzellenmodulen |
-
2008
- 2008-05-09 DE DE102008001695A patent/DE102008001695A1/de not_active Withdrawn
-
2009
- 2009-02-27 US US12/922,627 patent/US8598280B2/en active Active
- 2009-02-27 MX MX2010012177A patent/MX2010012177A/es active IP Right Grant
- 2009-02-27 KR KR1020107025007A patent/KR101572292B1/ko active Active
- 2009-02-27 BR BRPI0911435-1A patent/BRPI0911435B1/pt not_active IP Right Cessation
- 2009-02-27 RU RU2010150254/05A patent/RU2499805C2/ru active
- 2009-02-27 JP JP2011507847A patent/JP5713890B2/ja active Active
- 2009-02-27 EP EP09741921A patent/EP2274371B1/de active Active
- 2009-02-27 WO PCT/EP2009/052380 patent/WO2009135703A1/de not_active Ceased
- 2009-02-27 SI SI200930282T patent/SI2274371T1/sl unknown
- 2009-02-27 AT AT09741921T patent/ATE555155T1/de active
- 2009-02-27 MY MYPI2010004283A patent/MY148738A/en unknown
- 2009-02-27 CA CA2723884A patent/CA2723884C/en active Active
- 2009-02-27 CN CN2009801132679A patent/CN102007174B/zh active Active
- 2009-02-27 PL PL09741921T patent/PL2274371T3/pl unknown
- 2009-05-06 TW TW098114987A patent/TWI450924B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR101572292B1 (ko) | 2015-11-26 |
| CN102007174B (zh) | 2013-11-06 |
| US20110015317A1 (en) | 2011-01-20 |
| DE102008001695A1 (de) | 2009-11-12 |
| JP5713890B2 (ja) | 2015-05-07 |
| CA2723884A1 (en) | 2009-11-12 |
| JP2011519999A (ja) | 2011-07-14 |
| RU2499805C2 (ru) | 2013-11-27 |
| KR20110008213A (ko) | 2011-01-26 |
| RU2010150254A (ru) | 2012-06-20 |
| CN102007174A (zh) | 2011-04-06 |
| HK1153215A1 (en) | 2012-03-23 |
| BRPI0911435B1 (pt) | 2019-04-16 |
| MY148738A (en) | 2013-05-31 |
| PL2274371T3 (pl) | 2012-09-28 |
| TW201000548A (en) | 2010-01-01 |
| BRPI0911435A2 (pt) | 2015-10-06 |
| US8598280B2 (en) | 2013-12-03 |
| EP2274371A1 (de) | 2011-01-19 |
| MX2010012177A (es) | 2010-12-07 |
| WO2009135703A1 (de) | 2009-11-12 |
| ATE555155T1 (de) | 2012-05-15 |
| TWI450924B (zh) | 2014-09-01 |
| SI2274371T1 (sl) | 2012-08-31 |
| EP2274371B1 (de) | 2012-04-25 |
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