EP2566914A1 - Mousses polyméthacrylimide présentant une inflammabilité réduite ainsi que procédé pour la fabrication desdites mousses polyméthacrylimide - Google Patents
Mousses polyméthacrylimide présentant une inflammabilité réduite ainsi que procédé pour la fabrication desdites mousses polyméthacrylimideInfo
- Publication number
- EP2566914A1 EP2566914A1 EP11706249A EP11706249A EP2566914A1 EP 2566914 A1 EP2566914 A1 EP 2566914A1 EP 11706249 A EP11706249 A EP 11706249A EP 11706249 A EP11706249 A EP 11706249A EP 2566914 A1 EP2566914 A1 EP 2566914A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- meth
- poly
- foam
- acrylimide foam
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000006261 foam material Substances 0.000 title abstract 2
- 229920007790 polymethacrylimide foam Polymers 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims abstract description 22
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000006260 foam Substances 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 15
- 238000005187 foaming Methods 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 8
- 239000004604 Blowing Agent Substances 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 claims description 6
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- YWDFOLFVOVCBIU-UHFFFAOYSA-N 1-dimethoxyphosphorylpropane Chemical compound CCCP(=O)(OC)OC YWDFOLFVOVCBIU-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 12
- 239000003063 flame retardant Substances 0.000 description 21
- 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 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000003999 initiator Substances 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CQCXMYUCNSJSKG-UHFFFAOYSA-N 1-dimethoxyphosphorylethene Chemical compound COP(=O)(OC)C=C CQCXMYUCNSJSKG-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- -1 di-tert-butycarbonat Chemical compound 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 230000003505 mutagenic effect Effects 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KYEAGAAZBYGBRM-UHFFFAOYSA-N C(O)(O)=O.C(#N)O.CC(=O)C Chemical compound C(O)(O)=O.C(#N)O.CC(=O)C KYEAGAAZBYGBRM-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- GCNKJQRMNYNDBI-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(2-methylprop-2-enoyloxymethyl)butyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CC)COC(=O)C(C)=C GCNKJQRMNYNDBI-UHFFFAOYSA-N 0.000 description 1
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 description 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 239000000011 acetone peroxide Substances 0.000 description 1
- 235000019401 acetone peroxide Nutrition 0.000 description 1
- CGBYBGVMDAPUIH-UHFFFAOYSA-N acide dimethylmaleique Natural products OC(=O)C(C)=C(C)C(O)=O CGBYBGVMDAPUIH-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- WSYCKBNUJPXUDK-UHFFFAOYSA-N di(pentan-2-yl)diazene Chemical compound CCCC(C)N=NC(C)CCC WSYCKBNUJPXUDK-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- CGBYBGVMDAPUIH-ARJAWSKDSA-N dimethylmaleic acid Chemical compound OC(=O)C(/C)=C(/C)C(O)=O CGBYBGVMDAPUIH-ARJAWSKDSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
- CUICPJOPYVMUPK-UHFFFAOYSA-N ethyl n-tert-butylcarbamate Chemical compound CCOC(=O)NC(C)(C)C CUICPJOPYVMUPK-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant 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
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- NKVMCSDLYHGDMD-UHFFFAOYSA-N methanetetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)(C(O)=O)C(O)=O NKVMCSDLYHGDMD-UHFFFAOYSA-N 0.000 description 1
- DUVTXUGBACWHBP-UHFFFAOYSA-N methyl 2-(1h-benzimidazol-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1=NC2=CC=CC=C2N1 DUVTXUGBACWHBP-UHFFFAOYSA-N 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- MAIURHHAZPZPGJ-UHFFFAOYSA-N n'-butyloxamide Chemical compound CCCCNC(=O)C(N)=O MAIURHHAZPZPGJ-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
- BNOIMFITGLLJTH-UHFFFAOYSA-N trimethyl methanetricarboxylate Chemical compound COC(=O)C(C(=O)OC)C(=O)OC BNOIMFITGLLJTH-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0038—Use of organic additives containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/18—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/24—Homopolymers or copolymers of amides or imides
-
- 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
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
Definitions
- the invention relates to compositions for the preparation of polymethacrylimide foams with particular
- the present invention relates to the process for their preparation, processing and use.
- PMI foams Polymethacrylimide foams
- ROHACELL ® Polymethacrylimide foams
- applications include processing
- Laminates composites, foam composites,
- Coating materials are shaped bodies which consist of an outer covering layer and an inner layer
- Core material are constructed.
- the cover layers used are materials that can absorb uniaxial or multiaxial extremely high tensile forces. Examples are glass and glass
- Adhesive resins are fixed on the core material.
- the core materials used are preferably materials with low densities, typically in the range of 30 kg / m 3 and 200 kg / m 3 . Special significance of such materials in lightweight construction, especially in aircraft or vehicle construction. In addition, the flame retardance of the materials is also of great importance in these fields of application. State of the art
- PMI Polymethacrylimide
- DMMP Dimethylmethanphosphonaten
- EP 0 146 892 in which DMMP and functionalized DMMP are disclosed as flame retardants for polymethacrylimide. Meanwhile, however, DMMP has been identified as a mutagen, so there is a great need for DMMP as a
- polymethacrylimide foams represent sensitive systems and are difficult to optimize in terms of the foaming behavior.
- flame retardant stabilizers in such foam formulations reduce or prevent the foamability.
- Flame retardants some of which contain antimony oxides, can also be used phosphorus-containing compounds. Phosphorus compounds are preferred because of lower smoke toxicity in case of fire.
- Phosphorus compounds include phosphines
- Phosphine oxides Phosphine oxides, phosphonium compounds, phosphonates,
- Phosphites and / or phosphates may be organic and / or inorganic in nature. To date, however, no flame retardant is described in the prior art, with respect to comparable
- methacrylic acrylonitrile foams can be stabilized according to CN 101 544 720 with chlorinated flame retardants.
- chlorinated systems are not preferred for various reasons, especially in connection with flame retardancy or for reasons of health protection.
- EP 1 501 891 phosphorus compounds are generally described for the flameproofing of polyurethane foams.
- EP 2 152 834 Alkyldimethylphosphonate to
- DMPP Dimehtylpropylphosphonat
- PAI Polyacrylimide
- the object was to provide a flame-retardant PMI foams, the at least the same flame retardancy, comparable
- the object was that the foams have at least the same good thermomechanical properties and a similar good processability as the known PMI foams.
- novel PMI foams should be just as easy to produce as the PMI foams according to the prior art.
- DMPP Dimethylpropylphosphonate
- the notation poly (meth) acrylimide is in the following also for polymethacrylimide (PMI) and polyacrylimide (PAI).
- Methacrylic acid or acrylic acid is methacrylic acid or acrylic acid
- the poly (meth) acrylimide foam is usually obtained by foaming and crosslinking this mixture.
- the poly (meth) acrylimide foam is polymerized in bulk to a plate which
- Examples of the other vinylically unsaturated monomers mentioned under (A) are: esters of acrylic or
- the proportion of comonomers which can not or only with great difficulty be cyclized to anhydride or imide should not exceed 30% by weight, preferably 20% by weight and more preferably 10% by weight, based on the weight of the monomers.
- blowing agent (C) the following compounds or
- N-butyl oxamide trimethyl methane tricarboxylate, triethyl methane tricarboxylate, and monohydric alcohols of 3-8 carbon atoms such as propanol-1, propanol-2, butanol-1, butanol-2, tert-butanol and iso-butanol.
- crosslinking agents (D) are used for easy crosslinking, which stabilizes the foam during the foaming process and thus enables the production of homogeneous foams.
- crosslinkers can be divided into two groups: covalent crosslinkers (Dl), ie
- dimethacrylate 1,3-butanediol diacrylate or dimethacrylate, 1,4-butanediol diacrylate or dimethacrylate,
- ionic crosslinkers D2
- D2 ionic crosslinkers
- Examples include the acrylates or methacrylates the alkaline earth metals or the zinc. Zn and Mg (meth) acrylates are preferred.
- the (meth) acrylate salts can also be prepared by dissolving, for example, ZnO or MgO in the monomer batch.
- the foam may also be uncrosslinked.
- Initiators (E) are compounds and
- Classes of compounds are peroxides, hydroperoxides, and
- Peroxodisulfates percarbonates, perketals, peroxyesters, hydrogen peroxide and azo compounds.
- Initiators are hydrogen peroxide, dibenzoyl peroxide, dicyclohexyl peroxodicarbonate, dilauryl peroxide,
- the initiators are preferred (E) in amounts of from 0.01 to 2% by weight, more preferably from 0.15 to 1.5% by weight, based on the total weight of
- additives can be added to the mixtures.
- additives include, but are not limited to, antistatic agents, antioxidants, mold release agents, lubricants,
- Coating materials can be produced from the poly (meth) acrylimide foams produced according to the invention. Coating materials include one-sided with a solid
- Sandwich materials in which the foam is surrounded on both sides by solid material may be films or plates. These can be made of metal, wood or preferably other polymers
- Consist of materials The connection can be made by gluing, melting or sewing.
- the poly (meth) acrylimide foams according to the invention or the layer materials produced therefrom have a broad field of application. They can be used in motor vehicles, rail vehicles, aircraft, watercraft, Spacecraft, machine parts, antennas, X-ray tables, speakers and pipes are used.
- the density or density was determined according to ISO 845.
- Methacrylonitrile and 5.9 g of allyl methacrylate were added as blowing agents 66 g of water and 69 g of formamide. Furthermore, 2.0 g of tert. Butyl perpivalate, 1.5 g tert. Butyl per-2-ethyl hexanoate, 4.9 g tert-butyl perbenzoate, 4.9 g cumyl perneodecanoate, 35 g zinc oxide and 9.8 g release agent (Moldwiz INT 20E). As a flame retardant 491 g of DMMP were used.
- This mixture was for 68 h at 39 ° C and in one of two glass plates of size 50x50 cm and 28 mm thick
- the subsequent foaming in the hot air process was carried out at 201 ° C for 2 h.
- the resulting foam had a density of 118 kg / m 3 .
- Another sample was foamed for 2 hours at 219 ° C.
- the resulting foam had a density of 76 kg / m 3 .
- the foams have a homogeneous foaming pattern and fully meet the requirements of the fire test.
- This mixture was for 72 h at 40 ° C and in one of two glass plates of size 50x50 cm and 28 mm thick
- the subsequent foaming in the hot air process was 2h at 203 ° C.
- the resulting foam had a
- Example 1 The foams of Example 1 have a homogeneous
- Foaming can be distinguished from Comparative Example 1. Both foams fully met the requirements of the fire test.
- Methacrylonitrile and 590 mg of allyl methacrylate were added as blowing agents 6, 6 g of water and 6, 9 g of formamide. Furthermore, the mixture was 200 mg tert. Butyl perpivalate, 150 mg tert. Butyl per-2-ethyl hexanoate, 49 mg tert-butyl perbenzoate, 49 mg cumyl perneodecanoate, 3.5 g zinc oxide and 980 mg release agent (Moldwiz INT 20E). The flame retardant was 42.7 g of vinylphosphonic acid
- the subsequent foaming in the hot air process was 2h at 220 ° C.
- the resulting foam had a
- the subsequent foaming in the hot air process was 2 hours at 200 ° C.
- the resulting foam had a
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
L'invention concerne des compositions pour la fabrication de mousses poly (méth) acrylimide présentant une inflammabilité particulièrement réduite. La présente invention concerne en outre le procédé de fabrication, de traitement et d'utilisation desdites mousses polyméthacrylimide.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102010028695A DE102010028695A1 (de) | 2010-05-06 | 2010-05-06 | Polymethacrylimid-Schaumstoffe mit verminderter Entflammbarkeit sowie Verfahren zur Herstellung dieser |
PCT/EP2011/053138 WO2011138060A1 (fr) | 2010-05-06 | 2011-03-03 | Mousses polyméthacrylimide présentant une inflammabilité réduite ainsi que procédé pour la fabrication desdites mousses polyméthacrylimide |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2566914A1 true EP2566914A1 (fr) | 2013-03-13 |
Family
ID=43982282
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP11706249A Withdrawn EP2566914A1 (fr) | 2010-05-06 | 2011-03-03 | Mousses polyméthacrylimide présentant une inflammabilité réduite ainsi que procédé pour la fabrication desdites mousses polyméthacrylimide |
Country Status (10)
Country | Link |
---|---|
US (1) | US20130041056A1 (fr) |
EP (1) | EP2566914A1 (fr) |
JP (1) | JP2013525580A (fr) |
KR (1) | KR20130084226A (fr) |
DE (1) | DE102010028695A1 (fr) |
RU (1) | RU2012152234A (fr) |
SG (1) | SG184531A1 (fr) |
TW (1) | TW201213419A (fr) |
WO (1) | WO2011138060A1 (fr) |
ZA (1) | ZA201208301B (fr) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102011085026A1 (de) * | 2011-10-21 | 2013-04-25 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Korngrenzenhaftung von expandierten Copolymeren auf Basis von Methacryl- und Acrylverbindungen und Anhaftung diverser Deckschichten auf dem Schaumkern |
DE102012208428A1 (de) | 2012-05-21 | 2013-11-21 | Evonik Industries Ag | Pul-Core-Verfahren mit PMI-Schaumkern |
CN104619484A (zh) | 2012-07-24 | 2015-05-13 | 赢创工业集团股份有限公司 | Pmi泡沫材料的新成型方法和/或由其制备的复合组件 |
JP6077905B2 (ja) * | 2013-03-28 | 2017-02-08 | 積水化成品工業株式会社 | アクリル系重合成形体の製造方法及び発泡成形体の製造方法 |
DE102013205963A1 (de) | 2013-04-04 | 2014-10-09 | Evonik Industries Ag | Verfahren zur kontinuierlichen PMI-Schaumfertigung |
PL3062994T3 (pl) | 2013-10-30 | 2021-07-12 | Evonik Operations Gmbh | Ciągłe wytwarzanie profili w konstrukcji typu sandwich z profilem wypełnionym rdzeniami piankowymi i sztywną pianką |
DE102013223353A1 (de) | 2013-11-15 | 2015-05-21 | Evonik Industries Ag | One-shot Herstellung von Composites |
DE102013223347A1 (de) | 2013-11-15 | 2015-05-21 | Evonik Industries Ag | Mit Poly(meth)acrylimid-Schaum gefüllte Wabenstrukturen |
DE102013225132A1 (de) | 2013-12-06 | 2015-06-11 | Evonik Industries Ag | Vorschäumung von Poly(meth)acrylimid-Partikeln für das anschließende Formschäumen in geschlossenen Werkzeugen |
DE102014209425A1 (de) | 2014-05-19 | 2015-11-19 | Evonik Röhm Gmbh | Formschäumen von Poly(meth)acrylimid-Partikeln in geschlossenen Werkzeugen zur Herstellung von Hartschaumkernen |
CN104017127B (zh) * | 2014-06-20 | 2016-08-17 | 江苏兆鋆新材料股份有限公司 | 一种耐高温无卤阻燃树脂添加型an/maa共聚物泡沫及其制备方法 |
CN104045764B (zh) * | 2014-06-23 | 2016-04-13 | 浙江理工大学 | 一种聚甲基丙烯酰亚胺泡沫塑料的制备方法 |
DE102014009338A1 (de) | 2014-06-27 | 2015-12-31 | Evonik Röhm Gmbh | Druckabhängiges Formschäumen von Poly(meth)acrylimid-Partikeln in geschlossenen Werkzeugen zur Herstellung von Hartschaumstoffkernen |
DE102014009584A1 (de) | 2014-07-01 | 2016-01-07 | Evonik Röhm Gmbh | One-shot HD-RTM-Verfahren |
EP2982503A1 (fr) | 2014-08-07 | 2016-02-10 | Evonik Röhm GmbH | Composants sandwich en corps de mousse à base de poly(méth)acrylate et composites réticulés réversibles |
EP3015256A1 (fr) | 2014-10-27 | 2016-05-04 | Evonik Röhm GmbH | Fabrication de plusieurs composants composites en fibres différents pour une production en grande série dans un processus continu |
EP3015255A1 (fr) | 2014-10-27 | 2016-05-04 | Evonik Röhm GmbH | Fabrication d'éléments composites en fibres renforcés à certains endroits pour la production en grande série dans un processus continu et profilé creux rempli de mousse |
EP3159129A1 (fr) | 2015-10-22 | 2017-04-26 | Evonik Röhm GmbH | Fabrication de structures complexes creuses en sandwich ou en mousse a l'aide d'un noyau de moule |
EP3225654A1 (fr) | 2016-03-30 | 2017-10-04 | Evonik Röhm GmbH | Reduction de la phase de refroidissement lors du moussage de particules par des additifs augmentant la conduction thermique |
CN107417846A (zh) * | 2017-08-31 | 2017-12-01 | 湖南和铸新材料科技有限公司 | 聚甲基丙烯酰亚胺泡沫塑料及其制备方法 |
CN107629162B (zh) * | 2017-10-31 | 2020-04-14 | 浙江中科恒泰新材料科技有限公司 | 一步投料凝胶法制备聚(甲基)丙烯酰亚胺泡沫的方法 |
CN109280306B (zh) * | 2018-08-25 | 2021-04-13 | 浙江中科恒泰新材料科技有限公司 | 一种聚甲基丙烯酰亚胺复合泡沫导电吸波材料的制备方法 |
RU2707601C1 (ru) * | 2019-02-05 | 2019-11-28 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный технологический институт (технический университет)" | Способ получения газонаполненных полиакрилимидов |
CN111040230B (zh) * | 2019-12-12 | 2022-05-27 | 浙江中科恒泰新材料科技有限公司 | 一种高断裂伸长率pmi泡沫及其制备方法 |
EP3978215A1 (fr) | 2020-09-30 | 2022-04-06 | Evonik Operations GmbH | Fabrication de moules à noyau en mousse complexes pourvus de surfaces de classe a |
CA3196473A1 (fr) | 2020-10-29 | 2022-05-05 | Felix GOLDMANN | Procede de fabrication de panneaux en mousse pour la production de films en mousse |
CN112708258B (zh) * | 2021-01-12 | 2022-08-05 | 北京九天行歌航天科技有限公司 | 一种聚甲基丙烯酰亚胺泡沫、其制备方法及应用 |
CN113831442B (zh) * | 2021-09-24 | 2023-07-07 | 湖南兆恒材料科技有限公司 | 一种高性价比的阻燃聚甲基丙烯酰亚胺泡沫及其制备方法 |
WO2023232614A1 (fr) | 2022-06-03 | 2023-12-07 | Evonik Operations Gmbh | Procédé de production de pièces en mousse rigides multidimensionnelles au moyen d'une liaison pièces de puzzle |
CN114874481A (zh) * | 2022-06-24 | 2022-08-09 | 湖南博翔新材料有限公司 | 一种带有多层吸波结构的聚甲基丙烯酰亚胺泡沫及其制备方法 |
CN115895016A (zh) * | 2022-12-21 | 2023-04-04 | 湖南博翔新材料有限公司 | 一种聚甲基丙烯酰亚胺吸波泡沫及其制备方法 |
WO2024153615A1 (fr) | 2023-01-20 | 2024-07-25 | Evonik Operations Gmbh | Procédé de traitement automatisé de mousses dures rigides, à pores fermés, stables aux hautes températures |
CN118005987B (zh) * | 2024-02-01 | 2024-09-10 | 山东天集新材料有限公司 | 聚甲基丙烯酰亚胺泡沫及其制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3346060A1 (de) | 1983-12-21 | 1985-07-04 | Röhm GmbH, 6100 Darmstadt | Flammgeschuetzter polyacryl- oder polymethacrylimidschaumstoff und verfahren zu seiner herstellung |
DE4418307A1 (de) | 1994-05-26 | 1995-11-30 | Bayer Ag | Verwendung von Dimethylpropanphosphonat (DMPP) als Flammschutzmittel bei der Herstellung von Kunststoffen auf Isocyanatbasis |
DE19606530C2 (de) * | 1996-02-22 | 1998-04-02 | Roehm Gmbh | Verfahren zur Herstellung von Polymethacrylimid-Schaumstoffen mit flammhemmenden Zusätzen und danach hergestellte Schaumstoffe |
DE10052239A1 (de) * | 2000-10-21 | 2002-05-02 | Roehm Gmbh | Zusammensetzungen zur Herstellung von Poly(meth)arylimid-Schaumstoffen mit verminderter Entflammbarkeit, Poly(meth)acrylimid-Formmassen, Poly(meth)acrylimid-Schaumstoffe sowie Verfahren zur Herstellung |
DE10135414C1 (de) * | 2001-07-25 | 2003-03-13 | Roehm Gmbh | Herstellung nicht-flacher Membranen für elektroakustische Wandler |
RU2004128950A (ru) * | 2002-02-28 | 2005-05-27 | РЕМ ГмбХ унд Ко. КГ (DE) | Полиметакрилимидные пенопласты с пониженной воспламеняемостью и способ их получения |
ATE377626T1 (de) | 2002-05-06 | 2007-11-15 | Pabu Services Inc | Mischungen von tetrahalogenphthalaten und phosphorverbindungen als flammschutzmittel für polyurethane |
WO2004024806A2 (fr) * | 2002-09-09 | 2004-03-25 | Röhm GmbH & Co. KG | Mousses de polymethacrylimide peu inflammables et procedes de production associes |
TW200916561A (en) | 2007-05-07 | 2009-04-16 | Martinswerk Gmbh | Flame retarded thermosets |
CN101487299A (zh) | 2009-01-19 | 2009-07-22 | 夏良强 | 一种多功能硬泡聚氨酯复合保温板的制作方法 |
CN101544720B (zh) | 2009-05-07 | 2010-10-13 | 西北工业大学 | 阻燃maa/an共聚物泡沫塑料及其所用阻燃剂的制备方法 |
-
2010
- 2010-05-06 DE DE102010028695A patent/DE102010028695A1/de not_active Withdrawn
-
2011
- 2011-03-03 US US13/640,427 patent/US20130041056A1/en not_active Abandoned
- 2011-03-03 EP EP11706249A patent/EP2566914A1/fr not_active Withdrawn
- 2011-03-03 JP JP2013508404A patent/JP2013525580A/ja not_active Withdrawn
- 2011-03-03 KR KR1020127028954A patent/KR20130084226A/ko not_active Application Discontinuation
- 2011-03-03 RU RU2012152234/05A patent/RU2012152234A/ru unknown
- 2011-03-03 SG SG2012075123A patent/SG184531A1/en unknown
- 2011-03-03 WO PCT/EP2011/053138 patent/WO2011138060A1/fr active Application Filing
- 2011-05-03 TW TW100115465A patent/TW201213419A/zh unknown
-
2012
- 2012-11-05 ZA ZA2012/08301A patent/ZA201208301B/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO2011138060A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2011138060A1 (fr) | 2011-11-10 |
RU2012152234A (ru) | 2014-06-20 |
SG184531A1 (en) | 2012-11-29 |
JP2013525580A (ja) | 2013-06-20 |
DE102010028695A1 (de) | 2011-11-10 |
TW201213419A (en) | 2012-04-01 |
KR20130084226A (ko) | 2013-07-24 |
US20130041056A1 (en) | 2013-02-14 |
ZA201208301B (en) | 2013-07-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2566914A1 (fr) | Mousses polyméthacrylimide présentant une inflammabilité réduite ainsi que procédé pour la fabrication desdites mousses polyméthacrylimide | |
EP1678244B1 (fr) | Mousses de polymethacrylimide a stabilite dimensionnelle a chaud et a pores fins | |
EP2611857B1 (fr) | Mousses de pmi présentant de meilleures propriétés mécaniques en particulier une meilleure élongation à la rupture | |
EP1478690A1 (fr) | Mousses polymethacrylimides presentant une inflammabilite reduite et procede de fabrication | |
EP0400402B1 (fr) | Matériaux protecteurs contre l'incendie | |
EP2768892B1 (fr) | Procédé de production de copolymères expansés à base de poly(méth)acrylimide contenant un agent adhésif | |
EP1137699A2 (fr) | Mousses de polystyrene ignifugees | |
EP0146892B1 (fr) | Mousse plastique ignefugeante à base de polyacryl ou polymethacrylimide et procédé pour sa préparation | |
EP3350252B1 (fr) | Alcools multifonctionnels comme agents de réticulation pour pmi expansé | |
DE2202791A1 (de) | Schwerbrennbares acrylglas | |
DE112007003711T5 (de) | Expandierbares Polystyrolkügelchen und Verfahren um dieses herzustellen | |
US8722751B2 (en) | Thermostable microporous polymethacrylimide foams | |
WO2010149441A1 (fr) | Procédé de fabrication d'une pièce en mousse à partir de poly(méth)acrylates réticulés ainsi que ladite mousse et ses utilisations | |
DE10217005A1 (de) | Polymethacrylimid-Schaumstoffe mit verminderter Entflammbarkeit sowie Verfahren zur Herstellung | |
DE10052239A1 (de) | Zusammensetzungen zur Herstellung von Poly(meth)arylimid-Schaumstoffen mit verminderter Entflammbarkeit, Poly(meth)acrylimid-Formmassen, Poly(meth)acrylimid-Schaumstoffe sowie Verfahren zur Herstellung | |
DE10212235A1 (de) | Polymethacrylimid-Schaumstoffe mit verringerter Porengröße | |
WO2004024806A2 (fr) | Mousses de polymethacrylimide peu inflammables et procedes de production associes | |
WO2009077473A1 (fr) | Plastisols ignifugés contenant du graphite expansible | |
DE10256816A1 (de) | Neue, schwer brennbare Polymethacrylimid-Schaumstoffe sowie Verfahren zu deren Herstellung | |
WO2004056920A2 (fr) | Nouvelles mousses synthetiques peu inflammables grace au sulfate d'ammonium et a d'autres agents ignifuges | |
DE102007061509A1 (de) | Flammfeste Plastisole | |
DD160561A1 (de) | Verfahren zur herstellung von flammgeschuetzten thermoplastischen polyurethanen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20121011 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
DAX | Request for extension of the european patent (deleted) | ||
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
INTG | Intention to grant announced |
Effective date: 20130920 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20140131 |