CA1077196A - Polymers and copolymers based on acrylates and their use as flameproofing agents - Google Patents
Polymers and copolymers based on acrylates and their use as flameproofing agentsInfo
- Publication number
- CA1077196A CA1077196A CA255,002A CA255002A CA1077196A CA 1077196 A CA1077196 A CA 1077196A CA 255002 A CA255002 A CA 255002A CA 1077196 A CA1077196 A CA 1077196A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- thermoplasts
- polymer
- acrylate
- bis
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 41
- 229920001577 copolymer Polymers 0.000 title claims abstract description 40
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 29
- 239000004033 plastic Substances 0.000 claims abstract description 22
- 229920003023 plastic Polymers 0.000 claims abstract description 21
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 10
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 6
- UJJSQULCWJOFRO-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(chloromethyl)benzene Chemical class ClCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br UJJSQULCWJOFRO-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 1
- 150000001639 boron compounds Chemical class 0.000 claims 1
- BZYFSQTXMFJOEB-UHFFFAOYSA-N buta-2,3-dienoic acid Chemical group OC(=O)C=C=C BZYFSQTXMFJOEB-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 59
- 239000011347 resin Substances 0.000 description 33
- 229920005989 resin Polymers 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- GRKDVZMVHOLESV-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl)methyl prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(COC(=O)C=C)C(Br)=C1Br GRKDVZMVHOLESV-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 238000007792 addition Methods 0.000 description 19
- 238000007334 copolymerization reaction Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 16
- -1 pentabromobenzyl esters Chemical class 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000000875 corresponding effect Effects 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 241000428199 Mustelinae Species 0.000 description 10
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 8
- QJCKBPDVTNESEF-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br QJCKBPDVTNESEF-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000007373 indentation Methods 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 125000006839 xylylene group Chemical group 0.000 description 4
- NDRKXFLZSRHAJE-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4-tribromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=CC=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br NDRKXFLZSRHAJE-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CAUZPKXGWLCQJX-UHFFFAOYSA-N C(C(=C)C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C(=C)C)=O)(Cl)Cl Chemical compound C(C(=C)C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C(=C)C)=O)(Cl)Cl CAUZPKXGWLCQJX-UHFFFAOYSA-N 0.000 description 2
- 241000543381 Cliftonia monophylla Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
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- 238000001125 extrusion Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
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- 239000003999 initiator Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
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- AQPHBYQUCKHJLT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br AQPHBYQUCKHJLT-UHFFFAOYSA-N 0.000 description 1
- ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- HKYOKVYTJWJHJS-UHFFFAOYSA-N 4-[2-(3-carboxy-2,3-dichloroprop-2-enyl)phenyl]-2,3-dichlorobut-2-enoic acid Chemical compound C1=CC=C(C(=C1)CC(=C(C(=O)O)Cl)Cl)CC(=C(C(=O)O)Cl)Cl HKYOKVYTJWJHJS-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- GSJJGQZEFCJFPH-UHFFFAOYSA-N C(C=C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C=C)=O)(Cl)Cl Chemical compound C(C=C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C=C)=O)(Cl)Cl GSJJGQZEFCJFPH-UHFFFAOYSA-N 0.000 description 1
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- 101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/24—Flameproof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752527803 DE2527803C2 (de) | 1975-06-21 | Brandgeschützte Kunststoffe | |
| DE2527802A DE2527802C3 (de) | 1975-06-21 | 1975-06-21 | Verfahren zur Herstellung von Homopolymerisaten und Copolymerisaten aus Pentabrombenzylestern oder Tetrabromxylylendiestern |
| DE19752543746 DE2543746C2 (de) | 1975-10-01 | 1975-10-01 | Verfahren zur Herstellung von Polymerisaten und Copolymerisaten auf der Basis von Tetrabromxylylendiacrylat sowie substituierter Acrylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077196A true CA1077196A (en) | 1980-05-06 |
Family
ID=27186426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,002A Expired CA1077196A (en) | 1975-06-21 | 1976-06-16 | Polymers and copolymers based on acrylates and their use as flameproofing agents |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4128709A (enEXAMPLES) |
| JP (1) | JPS605608B2 (enEXAMPLES) |
| AT (1) | AT356890B (enEXAMPLES) |
| CA (1) | CA1077196A (enEXAMPLES) |
| CH (1) | CH637660A5 (enEXAMPLES) |
| DK (1) | DK144918C (enEXAMPLES) |
| ES (1) | ES449056A1 (enEXAMPLES) |
| FR (1) | FR2316254A1 (enEXAMPLES) |
| GB (1) | GB1547839A (enEXAMPLES) |
| IT (1) | IT1061590B (enEXAMPLES) |
| NL (1) | NL173412C (enEXAMPLES) |
| NO (1) | NO150441C (enEXAMPLES) |
| SE (2) | SE421072B (enEXAMPLES) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2048044B1 (enEXAMPLES) * | 1969-06-30 | 1973-01-12 | Fmc Corp | |
| US4211730A (en) * | 1975-06-21 | 1980-07-08 | Dynamit Nobel Aktiengesellschaft | Acrylate-based polymers and copolymers and their use as flameproofing agents |
| US4282138A (en) * | 1976-12-07 | 1981-08-04 | Ici Americas Inc. | Esters of tetracarboxylic acids and resins derived therefrom |
| JPS6025054B2 (ja) * | 1981-09-09 | 1985-06-15 | 三菱化学株式会社 | ポリエステル樹脂組成物 |
| DE3223104A1 (de) * | 1982-06-21 | 1983-12-22 | Hoechst Ag, 6230 Frankfurt | Photopolymerisierbares gemisch und damit hergestelltes photopolymerisierbares kopiermaterial |
| JPS596248A (ja) * | 1982-07-02 | 1984-01-13 | Mitsubishi Chem Ind Ltd | ポリエステル樹脂組成物 |
| JPS5920351A (ja) * | 1982-07-27 | 1984-02-02 | Mitsubishi Chem Ind Ltd | ポリエステル樹脂組成物 |
| JPS5920350A (ja) * | 1982-07-27 | 1984-02-02 | Mitsubishi Chem Ind Ltd | ポリエステル樹脂組成物 |
| US4525513A (en) * | 1982-12-27 | 1985-06-25 | Allied Corporation | Flame retardant polyamide composition |
| US4564650A (en) * | 1983-12-22 | 1986-01-14 | Allied Corporation | Flame retardant amine terminated polyamide composition |
| JPS60252652A (ja) * | 1984-05-30 | 1985-12-13 | Toray Ind Inc | 難燃化ポリエステル組成物 |
| IL86605A (en) * | 1988-06-02 | 1992-02-16 | Bromine Compounds Ltd | Process for the polymerization of pentabromobenzylester monoacrylate |
| IL89791A0 (en) * | 1989-03-29 | 1989-09-28 | Bromine Compounds Ltd | Process for the preparation of bromo-substituted aromatic esters of alpha,beta-unsaturated acids |
| EP0421610B1 (en) * | 1989-09-28 | 2003-05-14 | Bromine Compounds Ltd. | Flame retardant compositions |
| CA2030145A1 (en) * | 1989-11-20 | 1991-05-21 | Thomas E. Dueber | Flame retardant adhesive composition and laminates |
| DE4003088A1 (de) * | 1990-02-02 | 1991-08-08 | Roehm Gmbh | Vertraegliche polymermischungen |
| IL100540A (en) * | 1991-12-27 | 1995-12-08 | Bromine Compounds Ltd | Flame retarded poly (methylmethacrylates) |
| US6028156A (en) * | 1996-01-16 | 2000-02-22 | Bromine Compounds, Ltd. | Process for the preparation of poly-(halobenzyl acrylate) |
| US6342572B1 (en) | 1999-12-28 | 2002-01-29 | Honeywell International Inc. | Flame retardant benzocyclobutene resin with reduced brittleness |
| IL136725A (en) * | 2000-06-12 | 2007-08-19 | Bromine Compounds Ltd | Aqueous suspensions of pentabromobenzyl acrylate, their use and process for preparing them |
| CA2502520A1 (en) * | 2002-10-18 | 2004-04-29 | Surface Specialties, S.A. | Flame retardant composition |
| JP4851346B2 (ja) * | 2004-01-27 | 2012-01-11 | ビー．ジー．・ポリマーズ・エー．・シー．・エー．・リミテッド | 臭素化ポリマーおよびそれらを含む難燃製品 |
| WO2011077439A1 (en) | 2009-12-24 | 2011-06-30 | Bromine Compounds Ltd. | Flame retarted compositions |
| FR2966464B1 (fr) | 2010-10-26 | 2012-11-02 | Arkema France | Compositions thermoplastiques a haute tenue thermomecanique et ignifugees, en particulier pour les cables electriques |
| CN103608367B (zh) * | 2011-04-14 | 2016-02-10 | 溴化合物有限公司 | 制备丙烯酸五溴苄酯单体的方法及其聚合 |
| KR101301464B1 (ko) * | 2011-04-26 | 2013-08-29 | 금호석유화학 주식회사 | 유기반사방지막용 공중합체, 단량체 및 그 공중합체를 포함하는 조성물 |
| CN104903367B (zh) * | 2012-10-17 | 2018-11-27 | 溴化合物有限公司 | (甲基)丙烯酸五溴苄基酯的聚合方法、获得的聚合物及其用途 |
| WO2017043334A1 (ja) | 2015-09-11 | 2017-03-16 | 三菱エンジニアリングプラスチックス株式会社 | ポリエステル系樹脂組成物及びその製造方法 |
| JP6890388B2 (ja) * | 2015-09-11 | 2021-06-18 | 三菱エンジニアリングプラスチックス株式会社 | ポリエステル系樹脂組成物 |
| US20190249004A1 (en) | 2016-10-18 | 2019-08-15 | Bromine Compounds Ltd. | Flame-retarded polyester compositions |
| WO2018073819A1 (en) | 2016-10-18 | 2018-04-26 | Bromine Compounds Ltd. | Flame-retarded polyester formulations |
| JP7144924B2 (ja) * | 2017-08-22 | 2022-09-30 | ポリプラスチックス株式会社 | 難燃性ポリブチレンテレフタレート樹脂組成物 |
| CN111868172B (zh) * | 2018-03-22 | 2022-04-15 | 宝理塑料株式会社 | 阻燃性聚对苯二甲酸丁二醇酯树脂组合物 |
| JP7256822B2 (ja) * | 2018-11-13 | 2023-04-12 | ポリプラスチックス株式会社 | 難燃性ポリブチレンテレフタレート樹脂組成物 |
| CN113174000B (zh) * | 2021-03-31 | 2022-07-26 | 潍坊鑫洋化工有限公司 | 一种可控分子量聚丙烯酸五溴苄基酯的制备方法 |
| US20240026050A1 (en) * | 2022-07-08 | 2024-01-25 | B/E Aerospace, Inc. | Fire resistant copolymer matrix composite |
| WO2024038431A1 (en) | 2022-08-18 | 2024-02-22 | Bromine Compounds Ltd. | Flame-retarded polyamide compositions with good electrical performance |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2855434A (en) * | 1956-01-05 | 1958-10-07 | Pittsburgh Plate Glass Co | Method for preparing unsaturated aromatic compounds |
| US2891092A (en) * | 1957-01-28 | 1959-06-16 | Us Rubber Co | Neutral diesters of 2, 2'-[isopropylidenebis (2, 6-dichloro-p-phenyleneoxy)]-diethanol |
| BE624340A (enEXAMPLES) * | 1961-11-02 | |||
| US3207721A (en) * | 1963-06-05 | 1965-09-21 | Gen Electric | Polyvinyl chloride compositions cured with a cobalt halide |
| US3538149A (en) * | 1966-09-28 | 1970-11-03 | American Cyanamid Co | Poly(alpha,beta-unsaturated benzyl esters) |
| GB1186109A (en) * | 1967-08-08 | 1970-04-02 | Monsanto Chemicals | Flame-Retardant Synthetic Resin Materials and Flame-Retardant Agents; Foamable Resin Materials |
| US3629197A (en) * | 1969-04-01 | 1971-12-21 | Du Pont | Monomers and polymers of acryloyloxyphenol and derivatives thereof |
| US3649668A (en) * | 1970-06-15 | 1972-03-14 | Dow Chemical Co | Halogen containing esters of vinyl arylene acetic acid |
| US3891695A (en) * | 1971-08-04 | 1975-06-24 | Nat Starch Chem Corp | Bromine-containing esters |
| DE2202791A1 (de) * | 1972-01-21 | 1973-08-02 | Roehm Gmbh | Schwerbrennbares acrylglas |
| US3932321A (en) * | 1973-06-18 | 1976-01-13 | Japan Synthetic Rubber Company Limited | Flame-retardant polymer composition |
-
1976
- 1976-02-19 SE SE7601949A patent/SE421072B/xx not_active IP Right Cessation
- 1976-03-30 DK DK143276A patent/DK144918C/da not_active IP Right Cessation
- 1976-04-28 NO NO761466A patent/NO150441C/no unknown
- 1976-06-16 CH CH771376A patent/CH637660A5/de not_active IP Right Cessation
- 1976-06-16 CA CA255,002A patent/CA1077196A/en not_active Expired
- 1976-06-17 GB GB25005/76A patent/GB1547839A/en not_active Expired
- 1976-06-17 US US05/697,190 patent/US4128709A/en not_active Expired - Lifetime
- 1976-06-18 IT IT50012/76A patent/IT1061590B/it active
- 1976-06-18 FR FR7618613A patent/FR2316254A1/fr active Granted
- 1976-06-18 NL NLAANVRAGE7606647,A patent/NL173412C/xx not_active IP Right Cessation
- 1976-06-19 ES ES449056A patent/ES449056A1/es not_active Expired
- 1976-06-21 JP JP51073080A patent/JPS605608B2/ja not_active Expired
- 1976-06-21 AT AT449676A patent/AT356890B/de not_active IP Right Cessation
-
1980
- 1980-01-23 SE SE8000541A patent/SE429557B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK144918C (da) | 1982-11-29 |
| NO761466L (enEXAMPLES) | 1976-12-22 |
| ATA449676A (de) | 1979-10-15 |
| NO150441B (no) | 1984-07-09 |
| FR2316254A1 (fr) | 1977-01-28 |
| SE7601949L (sv) | 1976-12-22 |
| SE429557B (sv) | 1983-09-12 |
| NO150441C (no) | 1984-10-17 |
| NL173412B (nl) | 1983-08-16 |
| ES449056A1 (es) | 1977-12-01 |
| US4128709A (en) | 1978-12-05 |
| FR2316254B1 (enEXAMPLES) | 1980-09-05 |
| CH637660A5 (de) | 1983-08-15 |
| DK144918B (da) | 1982-07-05 |
| JPS605608B2 (ja) | 1985-02-13 |
| AT356890B (de) | 1980-05-27 |
| JPS523682A (en) | 1977-01-12 |
| GB1547839A (en) | 1979-06-27 |
| SE421072B (sv) | 1981-11-23 |
| SE8000541L (sv) | 1980-01-23 |
| NL7606647A (nl) | 1976-12-23 |
| IT1061590B (it) | 1983-04-30 |
| NL173412C (nl) | 1984-01-16 |
| DK143276A (da) | 1976-12-22 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |