AU2011284866A1

AU2011284866A1 - Phosphinic acid hydrazide flame retardant compositions

Phosphinic acid hydrazide flame retardant compositions Download PDF

Info

Publication number: AU2011284866A1
Authority: AU; Australia
Prior art keywords: alkyl; group; cycloalkyl; aryl; hydroxy
Prior art date: 2010-07-28
Legal status : Abandoned

Application number

AU2011284866A

Other languages

English (en)

Inventor

Simon Kniesel

Rainer Xalter

Current Assignee

BASF SE

Original Assignee

BASF SE

Priority date

2010-07-28

Filing date

2011-07-26

Publication date

2013-02-21

2011-07-26 Application filed by BASF SE filed Critical BASF SE

2013-02-21 Publication of AU2011284866A1 publication Critical patent/AU2011284866A1/en

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 79
239000003063 flame retardant Substances 0.000 title claims abstract description 42
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 title abstract description 20
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title abstract description 7
229920000307 polymer substrate Polymers 0.000 claims abstract description 19
-1 nitrogen containing compound Chemical class 0.000 claims description 134
125000000217 alkyl group Chemical group 0.000 claims description 122
150000001875 compounds Chemical class 0.000 claims description 70
229910052739 hydrogen Inorganic materials 0.000 claims description 66
239000001257 hydrogen Substances 0.000 claims description 65
125000003118 aryl group Chemical group 0.000 claims description 50
125000000753 cycloalkyl group Chemical group 0.000 claims description 46
230000036961 partial effect Effects 0.000 claims description 41
125000002619 bicyclic group Chemical group 0.000 claims description 40
229920000642 polymer Polymers 0.000 claims description 39
125000002950 monocyclic group Chemical group 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 27
239000000654 additive Substances 0.000 claims description 26
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 26
125000003342 alkenyl group Chemical group 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
238000000034 method Methods 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
239000003381 stabilizer Substances 0.000 claims description 15
230000008569 process Effects 0.000 claims description 10
229920001169 thermoplastic Polymers 0.000 claims description 10
229920000877 Melamine resin Polymers 0.000 claims description 8
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 5
239000000758 substrate Substances 0.000 claims description 5
AYJOUNOHHNLBJP-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]-1,3,5-triazine-2,4-diamine Chemical compound C1C(C)(C)N(OC2CCCCC2)C(C)(C)CC1CCCCNC(N=1)=NC(Cl)=NC=1NCCCCC(CC1(C)C)CC(C)(C)N1OC1CCCCC1 AYJOUNOHHNLBJP-UHFFFAOYSA-N 0.000 claims description 4
239000004114 Ammonium polyphosphate Substances 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
235000019826 ammonium polyphosphate Nutrition 0.000 claims description 4
229920001276 ammonium polyphosphate Polymers 0.000 claims description 4
239000007859 condensation product Substances 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 3
229920000388 Polyphosphate Polymers 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
COAPBYURHXLGMG-UHFFFAOYSA-N azane;1,3,5-triazine-2,4,6-triamine Chemical compound N.NC1=NC(N)=NC(N)=N1 COAPBYURHXLGMG-UHFFFAOYSA-N 0.000 claims description 3
239000001205 polyphosphate Substances 0.000 claims description 3
235000011176 polyphosphates Nutrition 0.000 claims description 3
FYQOHJWNKFULEZ-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC(C)(O)CON1C(C)(C)CC(O)CC1(C)C FYQOHJWNKFULEZ-UHFFFAOYSA-N 0.000 claims description 2
FUVBNYKKKZSBCG-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC(C)(O)CON1C(C)(C)CC(=O)CC1(C)C FUVBNYKKKZSBCG-UHFFFAOYSA-N 0.000 claims description 2
OKELZJLBUAZSCL-UHFFFAOYSA-N 1-cyclohexyloxy-2,2,6,6-tetramethyl-n-octadecylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCCCCCCCCCCCCCCCC)CC(C)(C)N1OC1CCCCC1 OKELZJLBUAZSCL-UHFFFAOYSA-N 0.000 claims description 2
VVISQEKWYPFFLK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetrabutyl-6-chloro-1,3,5-triazine-2,4-diamine Chemical compound CCCCN(CCCC)C1=NC(Cl)=NC(N(CCCC)CCCC)=N1 VVISQEKWYPFFLK-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
KGUHWHHMNQPSRV-UHFFFAOYSA-N [1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 KGUHWHHMNQPSRV-UHFFFAOYSA-N 0.000 claims description 2
JLOAPAGFWFMZLD-UHFFFAOYSA-N bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) hexanedioate Chemical compound CC1(C)CC(OC(=O)CCCCC(=O)OC2CC(C)(C)N(OC3CCCCC3)C(C)(C)C2)CC(C)(C)N1OC1CCCCC1 JLOAPAGFWFMZLD-UHFFFAOYSA-N 0.000 claims description 2
OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 claims description 2
DVXRGUXKOSSOHV-UHFFFAOYSA-N bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] decanedioate Chemical compound C1C(C)(C)N(OCC(C)(O)C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 DVXRGUXKOSSOHV-UHFFFAOYSA-N 0.000 claims description 2
WUXGYZUOHKJTEY-UHFFFAOYSA-N bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] hexanedioate Chemical compound C1C(C)(C)N(OCC(C)(O)C)C(C)(C)CC1OC(=O)CCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 WUXGYZUOHKJTEY-UHFFFAOYSA-N 0.000 claims description 2
125000006309 butyl amino group Chemical group 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
AVIZTSRRMBGYCJ-UHFFFAOYSA-N tetraazanium phosphonato phosphate 1,3,5-triazine-2,4,6-triamine Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].NC1=NC(N)=NC(N)=N1.[O-]P([O-])(=O)OP([O-])([O-])=O AVIZTSRRMBGYCJ-UHFFFAOYSA-N 0.000 claims description 2
125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 3
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 0.000 claims 1
150000004885 piperazines Chemical class 0.000 claims 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 51
229920001577 copolymer Polymers 0.000 description 48
239000000306 component Substances 0.000 description 31
229920003319 Araldite® Polymers 0.000 description 30
229940044603 styrene Drugs 0.000 description 28
125000004432 carbon atom Chemical group C* 0.000 description 21
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 20
239000005977 Ethylene Substances 0.000 description 20
125000002947 alkylene group Chemical group 0.000 description 20
229940093470 ethylene Drugs 0.000 description 20
239000002253 acid Substances 0.000 description 18
239000004952 Polyamide Substances 0.000 description 16
229920002647 polyamide Polymers 0.000 description 16
239000004417 polycarbonate Substances 0.000 description 16
125000001931 aliphatic group Chemical group 0.000 description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
239000004743 Polypropylene Substances 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
229920000515 polycarbonate Polymers 0.000 description 13
229920001155 polypropylene Polymers 0.000 description 13
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
230000000996 additive effect Effects 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
150000002170 ethers Chemical class 0.000 description 9
239000007788 liquid Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
229920002554 vinyl polymer Polymers 0.000 description 9
KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
229920001684 low density polyethylene Polymers 0.000 description 8
239000004702 low-density polyethylene Substances 0.000 description 8
239000000178 monomer Substances 0.000 description 8
229920002857 polybutadiene Polymers 0.000 description 8
229920006324 polyoxymethylene Polymers 0.000 description 8
238000012545 processing Methods 0.000 description 8
238000012360 testing method Methods 0.000 description 8
239000004698 Polyethylene Substances 0.000 description 7
239000004721 Polyphenylene oxide Substances 0.000 description 7
150000001993 dienes Chemical class 0.000 description 7
239000003822 epoxy resin Substances 0.000 description 7
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
229920000647 polyepoxide Polymers 0.000 description 7
229920000915 polyvinyl chloride Polymers 0.000 description 7
239000004800 polyvinyl chloride Substances 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
229920000570 polyether Polymers 0.000 description 6
229920000573 polyethylene Polymers 0.000 description 6
239000007787 solid Substances 0.000 description 6
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 5
239000004433 Thermoplastic polyurethane Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000000732 arylene group Chemical group 0.000 description 5
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
125000002993 cycloalkylene group Chemical group 0.000 description 5
229920001971 elastomer Polymers 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
239000004611 light stabiliser Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
BAQLUVXNKOTTHU-UHFFFAOYSA-N metofenazate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCN2CCN(CCCN3C4=CC(Cl)=CC=C4SC4=CC=CC=C43)CC2)=C1 BAQLUVXNKOTTHU-UHFFFAOYSA-N 0.000 description 5
229920003986 novolac Polymers 0.000 description 5
229920001707 polybutylene terephthalate Polymers 0.000 description 5
239000004848 polyfunctional curative Substances 0.000 description 5
229920000098 polyolefin Polymers 0.000 description 5
229920006380 polyphenylene oxide Polymers 0.000 description 5
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
229920002803 thermoplastic polyurethane Polymers 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
229920000092 linear low density polyethylene Polymers 0.000 description 4
239000004707 linear low-density polyethylene Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
229920002492 poly(sulfone) Polymers 0.000 description 4
229920000728 polyester Polymers 0.000 description 4
229920000139 polyethylene terephthalate Polymers 0.000 description 4
239000005020 polyethylene terephthalate Substances 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229920001897 terpolymer Polymers 0.000 description 4
OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 3
DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
229920002943 EPDM rubber Polymers 0.000 description 3
239000004593 Epoxy Substances 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
229920002396 Polyurea Polymers 0.000 description 3
BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
239000001361 adipic acid Substances 0.000 description 3
235000011037 adipic acid Nutrition 0.000 description 3
125000005250 alkyl acrylate group Chemical group 0.000 description 3
229920001585 atactic polymer Polymers 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
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