WO1980000028A1 - Compositions comprising polyphenylene ether and poly(vinyl chloride)resins - Google Patents
Compositions comprising polyphenylene ether and poly(vinyl chloride)resins Download PDFInfo
- Publication number
- WO1980000028A1 WO1980000028A1 PCT/US1979/000370 US7900370W WO8000028A1 WO 1980000028 A1 WO1980000028 A1 WO 1980000028A1 US 7900370 W US7900370 W US 7900370W WO 8000028 A1 WO8000028 A1 WO 8000028A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- plasticizer
- component
- poly
- polyphenylene ether
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 229920005989 resin Polymers 0.000 title claims abstract description 28
- 239000011347 resin Substances 0.000 title claims abstract description 28
- 229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 21
- 229920000915 polyvinyl chloride Polymers 0.000 title claims abstract description 15
- 239000004800 polyvinyl chloride Substances 0.000 title claims abstract description 15
- -1 poly(vinyl chloride) Polymers 0.000 title description 9
- 239000004014 plasticizer Substances 0.000 claims abstract description 29
- 230000015556 catabolic process Effects 0.000 claims abstract description 12
- 238000006731 degradation reaction Methods 0.000 claims abstract description 12
- 230000004927 fusion Effects 0.000 claims abstract description 12
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 description 7
- 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 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000012757 flame retardant agent Substances 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 239000004797 high-impact polystyrene Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000011115 styrene butadiene Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- RMCLVYNUTRHDDI-UHFFFAOYSA-N 1,1-dichloroethene;ethenyl acetate Chemical compound ClC(Cl)=C.CC(=O)OC=C RMCLVYNUTRHDDI-UHFFFAOYSA-N 0.000 description 1
- VNXBZAQCQINQQC-UHFFFAOYSA-N 1-o-benzyl 2-o-phenyl benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 VNXBZAQCQINQQC-UHFFFAOYSA-N 0.000 description 1
- BHKLONWXRPJNAE-UHFFFAOYSA-N 1-o-butyl 2-o-cyclohexyl benzene-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OC1CCCCC1 BHKLONWXRPJNAE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- RCRYBQKHEDNBDN-UHFFFAOYSA-N 6-methylheptyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCC(C)C)OC1=CC=CC=C1 RCRYBQKHEDNBDN-UHFFFAOYSA-N 0.000 description 1
- IACUZSWDFKEEMS-UHFFFAOYSA-N 8-methylnonyl bis(4-methylphenyl) phosphate Chemical compound C=1C=C(C)C=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=C(C)C=C1 IACUZSWDFKEEMS-UHFFFAOYSA-N 0.000 description 1
- RYUJRXVZSJCHDZ-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=CC=C1 RYUJRXVZSJCHDZ-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- MURWRBWZIMXKGC-UHFFFAOYSA-N Phthalsaeure-butylester-octylester Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC MURWRBWZIMXKGC-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- MTYUOIVEVPTXFX-UHFFFAOYSA-N bis(2-propylheptyl) benzene-1,2-dicarboxylate Chemical compound CCCCCC(CCC)COC(=O)C1=CC=CC=C1C(=O)OCC(CCC)CCCCC MTYUOIVEVPTXFX-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- UCVPKAZCQPRWAY-UHFFFAOYSA-N dibenzyl benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 UCVPKAZCQPRWAY-UHFFFAOYSA-N 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- GKZOUZJKVZPYPR-UHFFFAOYSA-N didecyl benzene-1,2-dicarboxylate;ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCC.CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC GKZOUZJKVZPYPR-UHFFFAOYSA-N 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- QHGRPTNUHWYCEN-UHFFFAOYSA-N dioctyl phenyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OC1=CC=CC=C1 QHGRPTNUHWYCEN-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920003047 styrene-styrene-butadiene-styrene Polymers 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 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
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
Definitions
- compositions Comprising Polyphenylene Ether and Poly (vinyl chloride) Resins
- the present invention relates to plasticized thermoplastic compositions of polyphenylene ether resins and poly (vinyl chloride) resins.
- the compositions of this invention possess good mechanical properties after molding, indicating an absence of significant degradation of the poly (vinylchloride) resin component during mixing.
- polyphenylene ether resins are well known in the art as a class of thermoplastics which posses a number of outstanding physical properties. They can be prepared, in general, by oxidative and non-oxidative methods, such as are disclosed, for example, in Hay, U.S. 3,306,874 and 3,306,875 and Stamatoff, U.S. 3,257,357 and 3,257,358, which are incorporated herein by reference.
- polystyrene resins such as crystal grade homopolystyrene or high impact rubber modified polystyrene
- these respective polymers are combinable in virtually all proportions, e.g., from 1 to 99 parts of polyphenylene ether to 99 to 1 parts of polystyrene.
- polyphenylene ether-polystyrene compositions are disclosed in Cizek, U.S. 3,383,435, which is incorporated herein by reference.
- polyphenylene ether is first combined with a plasticizer to reduce its fusion temperature to below that at which severe degradation of poly (vinyl chloride) takes place, and then to intimately admix the components, the poly (vinyl chloride) optionally containing a further amount of the same, or a different, plasticizer.
- compositions produced according to this invention are economically attractive, can have a wide degree of properties, and, depending in the amount of poly (vinyl chloride), they are quite resistant to open flames. They can be fabricated by any of the common techniques into various molded and shaped articles. They can also contain fillers, both reinforcing and non-reinforcing, and additional additives, such as flame retardants, colorants, pigments, stabilizers, impact improvers, e.g., acrylic-rubber graft copolymers, styrene-butadiene block copolymers, acrylonitrile-butadiene-styrene terpolymers, and the like. In preferred features, the compositions will also include polystyrene resins in combination with the polyphenylene ether resins, the former being of the type disclosed in above-mentioned U.S. 3,383,435. Description of the Invention
- thermoplastic compositions which comprise, in intimate admixture:
- component (a) a polyphenylene ether resin;
- a plasticizer for component (a) in an amount at least sufficient to reduce the fusion temperature of (a) to below that at which degradation of component (c) (i) or (ii) occurs;
- the term "reduce the fusion temperature” is used to describe compositions having a sufficient amount of a plasticizer which reduces the temperature required for extrusion of the polyphenylene ether per se by at least 50 to 100°F. as compared to the analagous unplasticized compositions.
- poly (2, 6-dimethy1-1,4-phenylene) ether has a fusion temperature of above about (500 o F.) 260 o C per se.
- Enough plasticizer should be added to reduce the fusion temperature to below about (300°F) 149 o C. Such a temperature is also below that at which severe degradation of poly (vinyl chloride) occurs, e.g., (350°F.) 177 o C.
- the polyphenylene ether resin (a) is preferably of the type having the structural formula:
- n is a positive integer and is at least 50
- each Q is a monovalent substituent selected from the group consisting of hydrogen, halo- gen, hydrocarbon radicals free of a tertiary alpha-carbon atom, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus, hydrocarbonoxy radicals and halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus.
- a more preferred class of polyphenylene ether resins for the compositions of this invention includes those of the above formula wherein each Q is alkyl, most preferably having from 1 to 4 carbon atoms.
- members of this class include poly (2, 6-dimethyl-l, 4-phenylene) ether; poly (2 , 6-diethyl-1,4-phenylene) ether; poly (2-methyl-6-ethyl-l,4- phenylene) ether; poly (2-methyl-6-propyl-l, 4-phenylene) ether; poly (2 , 6-dipropyl-l, 4-phenylene) ether; poly (2-ethyl-6-propyl-l,4-phenylene) ether; and the like.
- plasticizer component (b) is not critical and any of the conventional materials used for this purpose can be employed.
- component (b) will be selected from among phthalate and phosphate plasticizing materials, and especially phosphate plasticizers.
- the phosphate plasticizer is preferably a compound of the formula:
- R 1 , R 2 and R 3 are the same or different and are alkyl, cycloalkyl, aryl, alkyl substituted aryl, aryl substituted alkyl, hydroxyalkyl, hydroxyaryl, hydroxyalkaryl, halogen, haloaryl, and hydrogen.
- cresyl diphenyl phosphate examples include cresyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate, tricresyl phosphate, triisopropylphenyl phosphate, triphenyl phosphate, triethyl phosphate, dibutyl phenyl phosphate, diethyl phosphate, cresyl diphenyl phosphate, isooctyl diphenyl phosphate, tributyl phosphate, 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, isodecyl dicresyl phosphate, didecyl cresyl phosphate, tri-n- hexyl phosphate, di-n-octyl phenyl phosphate, di-2-ethyl-hexyl phenyl and tri-2-ethylhex
- phthalate plasticizers include dibenzyl phthalate, phenyl cresyl phthalate, diethyl phthalate, dimethyl phthalate, phenyl benzyl phthalate, butyl benzyl phthalate, butyl cyclohexyl phthalate, dibutyl phthalate, octyl cresyl phthalate, diphenyl phthalate, di-n-hexyl phthalate, disohexyl phthalate, butyl octyl phthalate, butyl decyl phthalate, diisooctyl phthalate, di-2-ethyl-hexyl phthalate, di-n-octyl phthalate, diisononyl phthalate, diisodecyl phthalate, di-2-propyl heptyl phthalate, di-n-nonyl phthalate, di-n-decyl phthal
- the plasticizer (b) is added in amounts which will be sufficient to provide a plasticized composition within the meaning of the term described above.
- the plasticizer is present in amounts ranging from about 15 to about 65 parts of plasticizer per 100 parts of total resin. Preferably from about 20 to about 45 parts of plasticizer per 100 parts of total resin are employed.
- the vinyl polymer component (c) of the present compositions will comprise poly (vinyl chloride) and its copolymers. They will have a molecular weight of about 25,000 to 150,000, Minor amounts of comonomers, e.g., vinylidene chloride vinyl acetate and the like can be present in polymerized form with vinyl chloride. All of the components (c) will be characteristically subject to high temperature degradation, releasing hydrogen chloride gas by various decomposition mechanisms.
- component (c) can further include (ii) a plasticizer.
- a plasticizer In general, any vinyl plasticizer can be employed, but those mentioned under (b) above are preferred. Especially preferred is tris (2-ethylhexyl) trimellitate.
- the amounts of components (c) (i) or (c) Cii) will vary between 1 and 99 parts by weight to 99 to 1 part by weight of components (a) and (b), combined.
- the amounts of (c) (i) or (c) (ii) will vary between 40 and 60 parts by weight per 60 to 40 parts by weight of components (a) and (b) combined.
- Conventional fillers e.g., clay, glass fibers, metal oxides, silica, and the like, can be used in conventional amounts, preferably from 2 to 50 parts by weight per 100 parts by weight of the composition.
- the present composition can also include impact modifiers, such as polystyrene resins which have been blended or co-polymerized with materials which are elastomeric at room temperature, e.g., 20 o to 25°C.
- the preferred styrene resins will be those having at least 25% by weight of repeating units derived from a vinyl aromatic compounds of the formula:
- R is hydrogen, (lower) alkyl or halogen
- Z is vinyl, halogen or (lower) alkyl
- p is 0 or an integer of from 1 to the number of replaceable hydrogen atoms on the benzene nucleus.
- (lower) alkyl means alkyl from 1 to 6 carbon atoms.
- the general formula above includes, by way. of illustration, homopolymers such as homopolystyrene and monochloropolystyrene, the modified polystyrenes, such as rubber modified high impact polystyrene, i.e., polystyrene which has been blended or grafted with natural or synthetic elastomers such as poly-butadiene, styrene-butadiene, EPDM rubber, and the like, and styrene containing copolymers such as the styrene acrylonitrile copolymers, styrene butadiene copolymers, styrene acrylonitrile-tf-alkyl styrene copolymers, styrene-acrylonitrile-butadiene copolymers, poly-A-methyl-styrene, copolymers of ethylvinylbenzene, divinylbenzene and s
- compositions can also include a flame retardant amount of a flame retardant agent.
- the flame retardant agent can comprise plasticizer component (b) if (b) itself is a flame retardant and is present in flame retardant amounts, e.g., triphenyl phosphate in at least 10 parts by weight per 100 parts by weight of the total composition.
- ingredients such as pigments, stabilizers, lubricants, and the like may be added for their conventional purposes.
- the manner in which the present compositions are prepared is not critical and conventional methods can be employed.
- each of the ingredients is added as part of a blend premix, and the latter is passed through an extruder at an extrusion temperature of from about 275 to about (340 o F.) 171 o C, dependent on the needs of the particular composition.
- the strands emerging from the extruder may be cooled, chopped into pellets, and molded or calendered to any desired shape. Description of the Preferred Embodiments
- Example 1 is illustrative of the composition of this invention. It is not intended to limit the invention in any manner.
- Example 2 is illustrative of the composition of this invention. It is not intended to limit the invention in any manner.
- compositions are prepared. All parts are by weight.
- the powdered polyphenylene ether is placed in a Henschel mixer vith the phosphate plasticizer and mixed until the powder temperature exceeds the phosphate melting temperature and the molten phosphate is absorbed by the polyphenylene ether.
- the resin is mixed with the plasticizer and filler in a Henschel mixer until the plasticizer is absorbed.
- One hundred parts of Composition I are dry mixed with 400 parts of Composition II and the blend is coextruded at (300°F.) 149 o C. in a
- the pellets are injection-molded in a 3 oz.
- the bars are tested for flame retardance properties by the UL-94 test.
- the UL-94 test is generally carried out by preparing a molded test piece of about 13 cm x 1.3cm x 0,16 cm (5" x 1/2" x 1/16"), supporting the sample vertically, and igniting it. If the sample does not form flowing droplets sufficient to ingite a piece of cotton held 30.5 cm (12 inches) beneath and extinguishes itself within an average of 5 seconds after each of two 10-seconds ignitions, the composition is deemed to be non-dripping and flame-retardant to the point where it satisfies the. V-0 requirements of the Underwriters' Laboratories. If the test sample extinguishes itself within 30 seconds, after two 10-second ignitions, the composition is deemed to be flame-retardant and non-dripping in satisfaction of the V-l requirements. Flame Out Times UL - 94 (seconds)
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91191978A | 1978-06-02 | 1978-06-02 | |
| US911919 | 1978-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1980000028A1 true WO1980000028A1 (en) | 1980-01-10 |
Family
ID=25431100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1979/000370 WO1980000028A1 (en) | 1978-06-02 | 1979-05-30 | Compositions comprising polyphenylene ether and poly(vinyl chloride)resins |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0016045A1 (enrdf_load_stackoverflow) |
| JP (1) | JPS55500472A (enrdf_load_stackoverflow) |
| WO (1) | WO1980000028A1 (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350804B2 (en) * | 1999-04-14 | 2002-02-26 | General Electric Co. | Compositions with enhanced ductility |
| US7271209B2 (en) | 2002-08-12 | 2007-09-18 | Exxonmobil Chemical Patents Inc. | Fibers and nonwovens from plasticized polyolefin compositions |
| US7619026B2 (en) | 2002-08-12 | 2009-11-17 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
| US7622523B2 (en) | 2002-08-12 | 2009-11-24 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3533978A (en) * | 1967-05-10 | 1970-10-13 | Union Carbide Corp | Vinyl chloride resin plastisols |
| US3639506A (en) * | 1969-05-21 | 1972-02-01 | Gen Electric | Flame retardant composition of polyphenylene ether styrene resin aromatic phosphate and aromatic halogen compound |
| US3652710A (en) * | 1969-07-01 | 1972-03-28 | Gen Electric | Curable polyaryleneoxide compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2441157C3 (de) * | 1974-08-28 | 1981-08-20 | Bayer Ag, 5090 Leverkusen | Formmassen auf Basis von Polyvinylchlorid |
| DE2751496C2 (de) * | 1976-12-21 | 1994-09-22 | Gen Electric | Flammhemmende, biegsam gemachte Polyphenylenäther-Zusammensetzungen |
-
1979
- 1979-05-30 JP JP50091979A patent/JPS55500472A/ja active Pending
- 1979-05-30 WO PCT/US1979/000370 patent/WO1980000028A1/en unknown
-
1980
- 1980-01-10 EP EP79900660A patent/EP0016045A1/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3533978A (en) * | 1967-05-10 | 1970-10-13 | Union Carbide Corp | Vinyl chloride resin plastisols |
| US3639506A (en) * | 1969-05-21 | 1972-02-01 | Gen Electric | Flame retardant composition of polyphenylene ether styrene resin aromatic phosphate and aromatic halogen compound |
| US3652710A (en) * | 1969-07-01 | 1972-03-28 | Gen Electric | Curable polyaryleneoxide compositions |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP0016045A4 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350804B2 (en) * | 1999-04-14 | 2002-02-26 | General Electric Co. | Compositions with enhanced ductility |
| US7271209B2 (en) | 2002-08-12 | 2007-09-18 | Exxonmobil Chemical Patents Inc. | Fibers and nonwovens from plasticized polyolefin compositions |
| US7619026B2 (en) | 2002-08-12 | 2009-11-17 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
| US7622523B2 (en) | 2002-08-12 | 2009-11-24 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
| US7632887B2 (en) | 2002-08-12 | 2009-12-15 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0016045A4 (en) | 1980-09-29 |
| JPS55500472A (enrdf_load_stackoverflow) | 1980-07-31 |
| EP0016045A1 (en) | 1980-10-01 |
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