EP1268670A1 - Reduction de particules carbonisees dans une composition de polyarylene ether polyamide - Google Patents
Reduction de particules carbonisees dans une composition de polyarylene ether polyamideInfo
- Publication number
- EP1268670A1 EP1268670A1 EP01901996A EP01901996A EP1268670A1 EP 1268670 A1 EP1268670 A1 EP 1268670A1 EP 01901996 A EP01901996 A EP 01901996A EP 01901996 A EP01901996 A EP 01901996A EP 1268670 A1 EP1268670 A1 EP 1268670A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- poly
- arylene ether
- polyamide
- produce
- polyamide composition
- 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- Withdrawn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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 154
- 239000000203 mixture Substances 0.000 title claims abstract description 146
- 229920002647 polyamide Polymers 0.000 title claims abstract description 120
- 239000004952 Polyamide Substances 0.000 title claims abstract description 118
- 239000002245 particle Substances 0.000 title claims description 20
- 230000009467 reduction Effects 0.000 title description 11
- -1 poly(arylene ether Chemical compound 0.000 claims abstract description 173
- 238000000034 method Methods 0.000 claims abstract description 68
- 230000008569 process Effects 0.000 claims abstract description 51
- 239000003607 modifier Substances 0.000 claims abstract description 41
- 229920005989 resin Polymers 0.000 claims abstract description 30
- 239000011347 resin Substances 0.000 claims abstract description 30
- 239000012298 atmosphere Substances 0.000 claims abstract description 25
- 238000013329 compounding Methods 0.000 claims abstract description 24
- 239000000654 additive Substances 0.000 claims abstract description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 239000011261 inert gas Substances 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 17
- 229920006122 polyamide resin Polymers 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 238000011010 flushing procedure Methods 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 150000004053 quinones Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229920001778 nylon Polymers 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 239000004609 Impact Modifier Substances 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 229910052734 helium Inorganic materials 0.000 claims description 6
- 239000001307 helium Substances 0.000 claims description 6
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052754 neon Inorganic materials 0.000 claims description 6
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims description 6
- 238000005453 pelletization Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229920000578 graft copolymer Polymers 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 239000012963 UV stabilizer Substances 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 239000002216 antistatic agent Substances 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 239000006258 conductive agent Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000003063 flame retardant Substances 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000012766 organic filler Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000004677 Nylon Substances 0.000 claims description 3
- 229920003189 Nylon 4,6 Polymers 0.000 claims description 3
- 229920002292 Nylon 6 Polymers 0.000 claims description 3
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 3
- 229920000554 ionomer Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 2
- 229920000299 Nylon 12 Polymers 0.000 claims description 2
- 229920001007 Nylon 4 Polymers 0.000 claims description 2
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000005826 halohydrocarbons Chemical class 0.000 claims 1
- 239000001301 oxygen Substances 0.000 abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 17
- 238000001746 injection moulding Methods 0.000 abstract description 8
- 238000002844 melting Methods 0.000 abstract description 4
- 230000008018 melting Effects 0.000 abstract description 4
- 230000007812 deficiency Effects 0.000 abstract description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 238000000465 moulding Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000013400 design of experiment Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- VCLWNCAUAKTVII-UHFFFAOYSA-N C=C.CC=C.C=CC1=CC=CC=C1 Chemical group C=C.CC=C.C=CC1=CC=CC=C1 VCLWNCAUAKTVII-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000002905 orthoesters Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 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 2
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 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 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000004615 ingredient Substances 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
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- CPEMSVQIDGEZCG-AATRIKPKSA-N (e)-2,5-dimethylhex-3-ene-2,5-diol Chemical compound CC(C)(O)\C=C\C(C)(C)O CPEMSVQIDGEZCG-AATRIKPKSA-N 0.000 description 1
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- OJMZQYGIPTULAQ-UHFFFAOYSA-N 2,5-dioxooxolane-3-carbonyl chloride Chemical compound ClC(=O)C1CC(=O)OC1=O OJMZQYGIPTULAQ-UHFFFAOYSA-N 0.000 description 1
- ICMZFZGUTLNLAJ-UHFFFAOYSA-N 2,6-dimethyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical group CC1=CC=CC2(C)OC12 ICMZFZGUTLNLAJ-UHFFFAOYSA-N 0.000 description 1
- SENUUPBBLQWHMF-UHFFFAOYSA-N 2,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=C(C)C1=O SENUUPBBLQWHMF-UHFFFAOYSA-N 0.000 description 1
- FVNJVBDCJZYQEV-UHFFFAOYSA-N 2,6-dioxooxane-3-carbonyl chloride Chemical compound ClC(=O)C1CCC(=O)OC1=O FVNJVBDCJZYQEV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- PEGWVOACELENRK-UHFFFAOYSA-N 2-(2-amino-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound NC(=O)CC(O)(C(O)=O)CC(O)=O PEGWVOACELENRK-UHFFFAOYSA-N 0.000 description 1
- MZJKINAHEDNRTM-UHFFFAOYSA-N 2-(2-anilino-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(=O)NC1=CC=CC=C1 MZJKINAHEDNRTM-UHFFFAOYSA-N 0.000 description 1
- IQSXMSIFHUYYAC-UHFFFAOYSA-N 2-(2-chloroacetyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)C(=O)CCl IQSXMSIFHUYYAC-UHFFFAOYSA-N 0.000 description 1
- GBFMDWWQSKICTH-UHFFFAOYSA-N 2-(2-chloroacetyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(=O)CCl GBFMDWWQSKICTH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ABGBGJXCHTWNJK-UHFFFAOYSA-N 2-[2-(dodecylamino)-2-oxoethyl]-2-hydroxybutanedioic acid Chemical compound CCCCCCCCCCCCNC(=O)CC(O)(C(O)=O)CC(O)=O ABGBGJXCHTWNJK-UHFFFAOYSA-N 0.000 description 1
- WSUBIRCPENZBDS-UHFFFAOYSA-N 2-carbonochloridoylpentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(Cl)=O WSUBIRCPENZBDS-UHFFFAOYSA-N 0.000 description 1
- SMVYBGQWEPTNQG-UHFFFAOYSA-N 2-chloro-2-formylbutanedioic acid Chemical compound OC(=O)CC(Cl)(C=O)C(O)=O SMVYBGQWEPTNQG-UHFFFAOYSA-N 0.000 description 1
- WOGWYSWDBYCVDY-UHFFFAOYSA-N 2-chlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C=CC1=O WOGWYSWDBYCVDY-UHFFFAOYSA-N 0.000 description 1
- WKGCZVNVRCDJPF-UHFFFAOYSA-N 2-cyclohexylethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCC1CCCCC1 WKGCZVNVRCDJPF-UHFFFAOYSA-N 0.000 description 1
- IMQYZLJIDNYQLX-UHFFFAOYSA-N 2-hydroxy-4-octadecoxy-2-(2-octadecoxy-2-oxoethyl)-4-oxobutanoic acid Chemical class CCCCCCCCCCCCCCCCCCOC(=O)CC(O)(C(O)=O)CC(=O)OCCCCCCCCCCCCCCCCCC IMQYZLJIDNYQLX-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 1
- FNEKYGYYCSEBNI-UHFFFAOYSA-N 3-(2-chloroacetyl)oxolane-2,5-dione Chemical compound ClCC(=O)C1CC(=O)OC1=O FNEKYGYYCSEBNI-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- WWXUGNUFCNYMFK-UHFFFAOYSA-N Acetyl citrate Chemical compound CC(=O)OC(=O)CC(O)(C(O)=O)CC(O)=O WWXUGNUFCNYMFK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910014571 C—O—Si Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004957 Zytel Substances 0.000 description 1
- 229920006102 Zytel® Polymers 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CJPIDIRJSIUWRJ-UHFFFAOYSA-N benzene-1,2,4-tricarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C(C(Cl)=O)=C1 CJPIDIRJSIUWRJ-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 229960004256 calcium citrate Drugs 0.000 description 1
- 239000001362 calcium malate Substances 0.000 description 1
- OLOZVPHKXALCRI-UHFFFAOYSA-L calcium malate Chemical compound [Ca+2].[O-]C(=O)C(O)CC([O-])=O OLOZVPHKXALCRI-UHFFFAOYSA-L 0.000 description 1
- 229940016114 calcium malate Drugs 0.000 description 1
- 235000011038 calcium malates Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000002134 carbon nanofiber Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- SLBHRPOLVUEFSG-UHFFFAOYSA-N naphthalene-2,6-dione Chemical compound O=C1C=CC2=CC(=O)C=CC2=C1 SLBHRPOLVUEFSG-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- SVICABYXKQIXBM-UHFFFAOYSA-L potassium malate Chemical compound [K+].[K+].[O-]C(=O)C(O)CC([O-])=O SVICABYXKQIXBM-UHFFFAOYSA-L 0.000 description 1
- 239000001415 potassium malate Substances 0.000 description 1
- 235000011033 potassium malate Nutrition 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000011179 visual inspection Methods 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
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/25—Component parts, details or accessories; Auxiliary operations
- B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
- B29C48/50—Details of extruders
- B29C48/76—Venting, drying means; Degassing means
- B29C48/762—Vapour stripping
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/04—Particle-shaped
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/07—Flat, e.g. panels
- B29C48/08—Flat, e.g. panels flexible, e.g. films
-
- 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
- the present invention relates to a method for making poly(arylene ether)- polyamide compositions.
- Poly(arylene ether) resins are characterized by a unique combination of chemical, physical and electrical properties over a broad temperature range. This combination of properties renders poly(arylene ether)s suitable for a wide range of applications.
- the usefulness of poly(arylene ether) resins is limited as a consequence of their poor processability, impact resistance and chemical resistance.
- Poly(arylene ether)-polyamide compositions as disclosed by Finholt (U.S. Pat. No. 3,379,792), overcame processability issues.
- the advantages of the Finholt invention are limited by the fact that when the concentration of the polyamide exceeds 20 weight percent (wt%), appreciable losses in other physical properties result. Specifically, there is no, or at best poor, compatibility between the poly(arylene ether) and tht polyamide such that phase separation of the resin occurs on molding or the molded article is inferior in mechanical properties.
- Compatibilized poly(arylene ether)-polyamide compositions have been produced utilizing a variety of base resins and compatibilizing systems. These thermoplastic products offer a wide range of beneficial properties which take advantage of the strengths of the basic resins while improving upon the weaknesses of each. Among the most useful properties of compatibilized poly(arylene ether)- polyamide compositions are excellent heat resistance, chemical resistance, impact strength, hydrolytic stability and dimensional stability. Such compatibilized poly(arylene ether)-polyamide compositions have found great utility in exterior automotive applications such as body panels. Examples of compatibilized poly(arylene ether)-polyamide compositions can be found in U.S. Pat. No. 4,315,086.
- Polyfunctional compatibility modifiers can facilitate formation of a copolymer of the poly(arylene ether) and polyamide components. Such a reaction has been readily shown to take place under the time, temperature and shear conditions of typical thermoplastic extrusion processes. Copolymer produced in this fashion may serve as a melt surfactant which stabilizes the morphology of the resinous components of the system. Compatibility may also be achieved by improved interfacial adhesion of the resinous components.
- Poly(arylene ether)-polyamide compositions are usually amenable to many different types of processing operations, such as extrusion, compression molding and injection molding. However under certain conditions, final products resulting from the operations exhibit some imperfections. These imperfections fall into two classes, solid particles visible on the surface and flow disturbance artifacts such as pinholes, "V" shape imperfections, and sinkmarks visible as dents in the surface. These imperfections, which often become magnified when painted, are caused by carbonized particles (also known as pits) which are formed during processing operations such as extrusion and injection molding. Articles formed from poly(arylene ether)-polyamide compositions with surface imperfections are typically rejected, thereby increasing the manufacturing cost.
- a process to produce a poly(arylene ether)-polyamide composition comprising creating and maintaining a substantially inert atmosphere in an extruder; combining poly(arylene ether) resin and an optional compatibility modifier in said extruder to form a mixture; compounding said mixture; and adding polyaniide to said mixture and further compounding to form the poly(arylene ether)-polyamide composition.
- the process for producing a poly(arylene ether)-polyamide composition comprises creating and maintaining a substantially inert atmosphere in an extruder; combining poly(arylene ether) resin, an optional compatibility modifier, and up to about 20 wt% polyamide resin in said extruder to form a mixture; compounding said mixture; and adding additional polyamide resin to said compounded mixture and further compounding to form the poly(arylene ether)- polyamide composition.
- Also part of the invention is a process for forming an article from a poly(arylene ether)-polyamide composition, comprising creating and maintaining an inert atmosphere in a molding device; adding the poly(arylene ether)-polyamide composition to the molding device; melting the poly(arylene ether)-polyamide composition; forcing said molten composition into a mold; and cooling said mold and releasing the resulting article.
- the Figure is meant to illustrate, not limit, the present invention.
- the Figure is a cube plot of the number of pits per plaque for the Design of Experiments set up described in Example 11 and Table 5, based upon the use of the atmospheric vent, a nitrogen purge, and/or the introduction of polyamide upstream.
- poly(arylene ether)-polyamide compositions which utilize about 10 weight percent (wt%) to about 90 wt% poly(arylene ether), about 90 wt% to about 10 wt% polyamide, optionally about 0.01 wt% to about 15 wt% compatibility modifier, and other additives known in the art, based on the total weight of the composition.
- the process comprises several components which can be employed singly or in combination, namely: utilizing resins- and additives that are substantially free of gaseous oxygen (air-free, e.g.
- the process comprises: flushing the poly(arylene ether) resin with an inert gas to obtain a resin which is air-free or alternately, employing a poly(arylene ether) resin which is already air-free; adding the poly(arylene ether), optionally a compatibility modifier, and/or other additives ..nd up to about 20 wt% of polyamide based on the total weight of the composition to an extruder under an inert atmosphere; melting and compounding the above components; adding the remaining polyamide; and further compounding.
- the resulting polymer can be pelletized or otherwise processed by any method known in the art, with underwater pelletization preferred.
- the whole process from production of raw materials to compounding, extruding, pelletization and molding is performed under a substantially inert atmosphere.
- poly(arylene ether)s can be employed with the present invention.
- the term includes poly(arylene ether) and copolymers, graft copolymers, and ionomers thereof; block copolymers of alkenyl aromatic compounds, vinyl aromatic compounds and poly(arylene ether); and combinations comprising at least one of the foregoing.
- Poly(arylene ether)s per se are known polymers comprising a plurality of structural units of the formula (I):
- each Q 1 is independently hydrogen, halogen, primary or secondary lower alkyl (e.g., alkyl containing up to 7 carbon atoms), phenyl, haloalkyl, aminoalkyl, hydrocarbonoxy, or halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each Q 2 is independently hydrogen, halogen, primary or secondary lower alkyl, phenyl, haloalkyl, hydrocarbonoxy or halohydrocarbonoxy as defined for Q 1 .
- each Q 1 is alkyl or phenyl, especially C alkyl
- each Q 2 is hycrogen.
- Both homopolymer and copolymer poly(arylene ether) are included.
- the preferred homopolymers are those containing 2,6-dimethylphenylene ether units.
- Suitable copolymers include random copolymers containing, for example, such units in combination with 2,3,6-trimethyl-l,4-phenylene ether units or copolymers derived from copolymerization of 2,6-dimethylphenol with 2,3,6-trimethylphenol.
- poly(arylene ether) containing moieties prepared by grafting vinyl monomers or polymers such as polystyrenes, as well as coupled poly(arylene ether) in which coupling agents such as low molecular weight polycarbonates, quinones, heterocycles and formals undergo reaction in known manner with the hydroxy groups of two poly(arylene ether) chains to produce a higher molecular weight polymer.
- the poly(arylene ether)s further include combinations comprising at least one of the above.
- poly(arylene ether) contemplated for use in the present invention include all those presently known, irrespective of variations in structural units or ancillary chemical features.
- Examples of poly(arylene ether)s and methods for their production are disclosed in U.S. Pat. Nos. 3,306,874; 3,306,875; 3,257,357; 3,257,358; 3,337,501 and 3,787,361.
- the amount of poly(arylene ether) used in the composition can be about 10 to about 90 wt%, with about 20 to about 80 wt% preferred, and about 30 to about 60 wt% especially preferred.
- the polyamide resins include a generic family of resins known as nylons, characterized by the presence of an amide group (-C(O)NH-).
- Nylon-6 and nylon-6,6 are the generally preferred polyamides and are available from a variety of commercial sources.
- Other polyamides such as nylon-4, nylon-4,6, nylon- 12, nylon- 6,10, nylon 6,9, and others such as the amorphous nylons, may be useful for particular poly(arylene ether)-polyamide applications.
- Mixtures of various polyamides, as well as various polyamide copolymers, are also useful, with nylo ⁇ -6,6, especially preferred.
- polyamides can be obtained by a number of well known processes such as those described in U.S. Patent Nos. 2,071,250; 2,071,251; 2,130,523; 2,130,948; 2,241,322; 2,312,966; and 2,512,606.
- Nylon-6 for example, is a polymerization product of caprolactam.
- Nylon-6,6 is a condensation product of adipic acid and 1,6- diaminohexane.
- nylon 4,6 is a condensation product between adipic acid and 1,4-diaminobutane.
- adipic acid other useful diacids for the preparation of nylons include azelaic acid, sebacic acid, dodecane diacid, as well as terephthalic and isophthalic acids, and the like.
- Other useful diamines include m-xylyene diamine, di-(4-aminophenyl)methane, di-(4-aminocyclohexyl)methane; 2,2-di-(4- aminophenyl)propane, 2,2-di-(4-aminocyclohexyl)propane, among others. Copolymers of caprolactam with diacids and diamines are also useful.
- polyamides herein and in the appended claims is intended to include the toughened or super tough polyamides.
- Super tough polyamides, or super tough nylons as they are more commonly known, such as those available commercially, e.g. from E.I. duPont under the trade name Zytel ST, or those prepared in accordance with U.S. Pat. No. 4,174,358 to Epstein; U.S. Pat. No. 4,474,927 to Novak; U.S. Pat. No. 4,346,194 to Roura; and U.S. Pat. No. 4,251,644 to Jeffrion, among others and combinations comprising at least one of the foregoing, can be employed.
- these super tough nylons are prepared by blending one or more polyamides with one or more polymeric or copolymeric elastomeric toughening agents.
- Suitable toughening agents are disclosed in the above-identified U.S. Patents as well as in U.S. Pat. No. 3,884,882 to Caywood, Jr., U.S. Pat. No. 4,147,740 to Swiger, and Gallucci et al., "Preparation and Reactions of Epoxy-Modified Polyethylene", J. Appl. Poly. Sci., V 27, pp. 425-437 (1982) (which are herein incorporated by reference).
- these elastomeric polymers and copolymers may be straight chain or branched as well as graft polymers and copolymers, including core-shell graft copolymers, and are characterized as having incorporated therein either by copolymerization or by grafting on the preformed polymer, a monomer having functional and/or active or highly polar groupings capable of interacting with or adhering to the polyamide matrix so as to enhance the toughness of the polyamide polymer.
- the amount of polyamide utilized in the composition can be about 10 to about 90 wt%, with about 20 to about 80 wt% preferred, and about 30 to about 60 wt% especially preferred.
- Compatibility Modifier The two fold purpose for using compatibility modifiers is to improve the physical properties of the poly(arylene ether)-polyamide resin, as well as to enable the use of a greater proportion of the polyamide component.
- a compatibility modifier may not be necessary when all of a portion of the poly(arylene ether) is an ionomer.
- the expression "compatibility modifier” refers to those polyfunctional compounds which interact with the poly(arylene ether), the polyamide, or both. This interaction may be chemical (e.g. grafting) or physical (e.g. affecting the surface characteristics of the dispersed phases).
- the resulting poly(arylene ether)-polyamide composition appears to exhibit improved compatibility, particularly as evidenced by enhanced impact strength, mold knit line strength and/or elongation.
- the expression "compatibilized poly(arylene ether)-poly amide resin” refers to those compositions which have been physically or chemically compatibilized with a modifier as discussed above, as well as those compositions which are physically compatible without such agents, as taught in U.S. Patent No. 3,379,792.
- compatibilizing modifiers examples include: a) liquid diene polymers, b) epoxy compounds, c) oxidized polyolefin wax, d) quinones, e) organosilane compounds, and f) polyfunctional compounds.
- Functionalized poly(arylene ether), as described, are obtained by reacting one or more of the previously mentioned compatibility modifiers with poly(arylene ether).
- Liquid diene polymers include homopolymers of a conjugated diene with at least one monomer selected from other conjugated dienes; vinyl monomer, e.g. styrene and alphamethyl styrene; olefins, e.g. ethylene, propylene, butene-1, isobutylene, hexene-1, octene-1 and dodecene-1, and mixtures thereof, having a number average molecular weight of about 150 to about 10,000, preferably about 150 to about 5,000.
- These homopolymers and copolymers can be produced by the methods described in, for example, U.S. Pat. Nos.
- 4,054,612; 3,876,721 and 3,428,699 and include, among others, polybutadiene, polyisoprene, poly(l,3- pentadiene), poly(butadiene-isoprene), poly(styrene-butadiene), polychloroprene, poly(butadiene-alpha methylstyrene), poly(butadiene-styrene-isoprene), poly(butylene-butadiene), and combinations comprising at least one of the foregoing.
- Epoxy compounds (b) include: (1) epoxy resins produced by condensing polyhydric phenols (e.g. bisphenol-A, tetrabromobisphenol-A, resorcinol and hydroquinone) and epichlorohydrin; (2) epoxy resins produced by condensing polyhydric alcohols (e.g., ethylene glycol, propylene glycol, butylene glycol, polyethylene glycol, polypropylene glycol, pentaerythritol and trimethylolethane, and the like) and epichlorohydrin; (3) glycidyletherified products of monohydric alcohols and monohydric phenols including phenyl glycidylether, butyl glycidyl ether and cresyl glycidylether; (4) glycidyl derivates of amino compounds, for example, the diglycidyl derivate of aniline; (5) epoxidized products of higher olefinic or cycl
- Oxidized polyolefin waxes (c) are well known and an illustrative description thereof and processes for the production of the same are found in U.S : Pat. Nos. 3,822,227 and 3,756,999. Generally, these are prepared by an oxidation or suspension oxidation of polyolefin.
- Quinone compounds (d) are characterized as having in the molecule of the unsubstituted derivative at least one six-membered carbon ring; at least two carbonyl groups in the ring structure, both of which may be in the same or, if more than one ring, different rings, provided that they occupy positions corresponding to the 1 ,2- or 1 ,4-orientation of the monocyclic quinone; and at least two carbon-carbon double bonds in the ring structure, said carbon-carbon double bounds and carbonyl carbon- oxygen double bonds in the ring structure, said carbon-carbon double bonds and carbonyl carbon-oxygen double bonds being conjugated with respect to each other.
- Substituted quinones may also be used.
- the degree of substitution, where substitution is desired, may be from one to the maximum number of replaceable hydrogen atoms.
- Exemplary of the various substituents that may be present on the unsubstituted quinone structures include halogen (e.g.
- hydrocarbon radicals including branched and unbranched, saturated and unsaturated alkyl, aryl, alkyl aryl and cycloalkyl radicals and halogenated derivatives thereof; and similar hydrocarbons having hetero atoms therein, particularly oxygen, sulfur, or phosphorous and wherein the same connects the radical to the quinone ring (e.g. oxygen link).
- Suitable quinones include 1,2- and 1 ,4-benzoquinone; 2,6- diphenyl quinone; tetramethyldiquinone; 2,2'- and 4,4'-diphenoquinone; 1,2-, 1,4- and 2,6-naphthoquinone; tetrachlorobenzoquinone; 2-chloro- 1 ,4-benzoquinone; and 2,6- dimethyl benzoquinone.
- Organosilane compounds (e) suitable as compatibility modifiers are characterized as having in the molecule (1) at least one silicon atom bonded to a carbon through an oxygen link and (2) at least one carbon-carbon double bond or carbon-carbon triple bond and/or a functional group selected from an amine group or a mercapto group provided that the functional group is not directly bonded to the silicon atom.
- the C-O-Si component is generally present as an alkoxyl or acetoxy group bonded directly to the silicon atom, wherein the alkoxy or acetoxy group generally has less than 15 carbon atoms and may also contain hetero atoms.
- silicon atoms there may also be more than one silicon atom in the compound, such multiple silicon atoms, if present, being linked through an oxygen link (e.g. siloxanes), a silicon bond, or a bifunctional organic radical (e.g. methylene or phenylene groups), or the like.
- an oxygen link e.g. siloxanes
- a silicon bond e.g. a silicon bond
- a bifunctional organic radical e.g. methylene or phenylene groups
- organosilane compounds include: gamma amino propyltriethoxy silane, 2-(3-cyclohexanyl)ethyl trimethoxy silane; 1,3-divinyl tetraethoxy silane, vinyl tris-(2-methoxyethoxy)silane, 5-bicycloheptenyl triethoxy silane, and gamma mercapto propyl trimethoxy silane.
- Polyfunctional compounds (f) which may be employed as a compatibility modifier are of three types.
- the first type of polyfunctional compounds are those having in the molecule both (1) a carbon-carbon double bond or a carbon-carbon triple bond and (2) at least one carboxylic acid, anhydride, amide, ester, imide, amino, epoxy, orthoester, or hydroxy group.
- Examples of such polyfunctional compounds include maleic acid; maleic anhydride; fumaric acid; glycidyl acrylate, itaconic acid; aconitic acid; maleimide; maleic hydrazide; reaction products resulting from a diamine and maleic anhydride, maleic acid, fumaric acid, etc.; dichloro maleic anhydride; maleic acid amide; unsaturated dicarboxylic acids (e.g.
- esters e.g. alkyl alcohol, crotyl alcohol, methyl vinyl carbinol, 4-pentene-l-ol, l,4-hexadiene-3- ol, 3-butene- 1,4-diol, 2,5-dimethyl-3-hexene-2,5-diol and alcohols of the formula C n H n .
- unsaturated alcohols e.g. alkyl alcohol, crotyl alcohol, methyl vinyl carbinol, 4-pentene-l-ol, l,4-hexadiene-3- ol, 3-butene- 1,4-diol, 2,5-dimethyl-3-hexene-2,5-diol and alcohols of the formula C n H n .
- n is a positive integer up to 30
- unsaturated amines resulting from replacing from replacing the hydroxyl group(s) of the above unsaturated alcohols with NH groups
- functionalized diene polymers and copolymers and the like.
- Maleic anhydride and fumaric acid are preferred.
- the second group of polyfunctional compatibility modifiers suitable for use herein are characterized as having both (1) a group represented by the formula (OR) wherein R is hydrogen or an alkyl, aryl, acyl or carbonyl dioxy group and (2) at least two groups each of which may be the same or different selected from carboxylic acid, acid halide, anhydride, acid halide anhydride, ester, orthoester, amide, imido, amino, and various salts thereof.
- R is hydrogen or an alkyl, aryl, acyl or carbonyl dioxy group
- R is hydrogen or an alkyl, aryl, acyl or carbonyl dioxy group
- at least two groups each of which may be the same or different selected from carboxylic acid, acid halide, anhydride, acid halide anhydride, ester, orthoester, amide, imido, amino, and various salts thereof are the aliphatic polycarboxylic acids, acid esters and acid amides represented by the formula:
- R v is a linear or branched chain, saturated aliphatic hydrocarbon of from 2 to 20, preferably 2 to 10, carbon atoms;
- R 1 is hydrogen or an alkyl, aryl, acyl or carbonyl dioxy group of 1 to 10, preferably 1 to 6, most preferably 1 to 4, carbon atoms, preferably hydrogen;
- each R 11 is independently hydrogen or an alkyl or aryl group from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms;
- each R ⁇ and R IV are independently hydrogen or an alkyl or aryl group of from 1 to 10, preferably from 1 to 6, most preferably 1 to 4, carbon atoms;
- m is equal to 1 and (n + s) is greater than or equal to 2, preferably equal to 2 or 3, and n and s are each greater than or equal to zero and wherein (OR 1 ) is alpha or beta to a carbonyl group and at least two carbonyl groups are separated by 2 to 6 carbon atoms.
- Suitable polycarboxylic acids include, for example, citric acid, malic acid, agaricic acid, and the like; including the various commercial forms thereof, such as - for example, the anhydrous and hydrated acids. Of these, citric acid is another of the preferred compatibility- modifiers.
- esters useful herein include, for example, acetyl citrate and mono- and/or distearyl citrates and the like.
- Suitable amides useful herein include, for example, N,N'-diethyl citric acid amide; N-phenyl citric acid amide; N-dodecyl citric acid amide; N,N'-didodecyl citric acid amide and N-dodecyl malic acid.
- Especially preferred derivates are the salts thereof, including the salts with amines and/preferably, the alkali and alkaline metal salts.
- suitable salts include calcium malate, calcium citrate, potassium malate, and potassium citrate.
- the third group of polyfunctional compatibility modifiers suitable for use herein are characterized as having in the molecule both (1) an acid halide group, most preferably an acid chloride group and (2) at least one carboxylic acid, anhydride, ester, epoxy, orthoester, or amide group, preferably a carboxylic acid or anhydride group.
- compatibility modifiers within this group include trimellitic anhydride acid chloride, chloroformyl succinic anhydride, chloro formyl succinic acid, chloroformyl glutaric anhydride, chloroformyl glutaric acid, chloroacetyl succinic anhydride, chloroacetylsuccinic acid, trimellitic acid chloride, and chloroacetyl glutaric acid.
- trimellitic anhydride acid chloride is preferred. Furthermore, it is especially preferred that compatibility modifiers of this group be prereacted with at least a portion of the poly(arylene ether) whereby the compatibility modifier is a poly(arylene ether)-functionalized compound.
- the foregoing compatibility modifiers may be used alone or in various combinations comprising at least one of the above mentioned compatibility modifiers. Furthermore, they may be added directly to the melt blend or pre-reacted with either or both the poly(arylene ether) and polyamide, as well as with other resinous materials employed in the preparation of the compositions. With many of the foregoing compatibility modifiers, particularly the polyfunctional compounds, even greater improvement in compatibility is found where at least a portion of the compatibility modifier is pre-reacted, either in the melt or in a solution of a suitable solvent, with all or a part of the poly(arylene ether). It is believed that such pre- reacting may cause the compatibility modifier to react with the polymer and, consequently, functionalize the poly(arylene ether) as noted above.
- the poly(arylene ether) may be pre-reacted with maleic anhydride to form an anhydride functionalized poly(arylene ether) which has improved compatibility with the polyamiue compared to a non-functionalized poly(arylene ether).
- the initial amount used will be dependent upon the specific compatibility modifier chosen and the specific polymeric system to which it is added.
- the amount of compatibility modifier used should be sufficient to prevent phase separation of the poly(arylene ether) and polyamide.
- the typical amounts are up to about 10 wt%, with about 0.05 to about 5.0 wt% preferred, and about 0.1 to about 3 wt% especially preferred.
- the composition can also include effective amounts of at least one additive selected from impact modifiers, release agents, stabilizers, organic and/or inorganic fillers, conductive agents, UV stabilizers, anti-oxidants, flame retardants, drip retardants, dyes, pigments, colorants, stabilizers, small particle mineral (such as clay, mica, talc and the like), antistatic agents, plasticizers, lubricants, and mixtures comprising at least one of the above mentioned additives.
- additives are known in the art, as are their effective levels and methods of incorporation. Effective amounts of the additives vary widely, but they are usually present in an amount up to about 50 wt% or more, based on the weight of the entire composition.
- Especially preferred additives include hindered phenols, thio compounds and amides derived from various fatty acids. The preferred amounts of these additives generally ranges up to about 3 wt%.
- additives for conductivity carbon black, carbon fibrils, carbon fibers, carbon nanofibers, carbon nanotubes, carbon particles, and combinations comprising at least one of the above mentioned additives.
- the composition comprising the above mentioned components can be prepared in numerous fashions. As described earlier, the process comprises several components, which can be employed singly or in combination.
- the general procedure comprises: introducing the poly(arylene ether) resin, preferably air free, optionally up to 20 wt% polyamide resin, with up to about 15 wt% preferred, and about 5 to about 10 wt% especially preferred, and optionally a compatibility modifier and other additives, to an extruder or similar mixing device, preferably with an inert atmosphere, to form a mixture.
- the mixture is melted and compounded, preferably under an inert atmosphere, prior to adding the remaining polyamide.
- an extruder with an atmospheric vent as described below, it is preferable to operate with the atmospheric vent open.
- the remaining polyamide is added, preferably under an inert atmosphere, and the resulting mixture is then further melted, compounded, and finally palletized preferably by underwater pelletization, or otherwise finally processed by any method known in the art.
- Air free poly(arylene ether) can be obtained by flushing the poly(arylene ether) particles with an inert gas a sufficient number of times such that the resin is substantially free of gaseous oxygen.
- Inert gases include all gases which are unreactive towards poly(arylene ether), polyamide or other components of the composition. Possible inert gases include hydrogen, helium, neon, argon, nitrogen, carbon dioxide, and the like, and mixtures comprising at least one of the above mentioned gases, with nitrogen preferred.
- Poly(arylene ether) particles are porous and as a result gaseous oxygen can infiltrate the interior of the particles. Flushing the particles removes this oxygen which can cause oxidation of the poly(arylene ether) and therefore the formation of carbon particles. As stated earlier, carbon particles cause surface imperfections.
- the extruder preferably has an inert atmosphere obtained by flushing the extruder with an inert gas so as to substantially remove the gaseous oxygen contained within.
- the inert atmosphere is preferably maintained during addition of the above mentioned components by a continuing flow of inert gas.
- the flow rate can be up to or exceeding about 20 liters of inert gas per kilogram of poly(arylene ether) (1 N 2 kg PPE), with about 1 liter inert ga:> kg poly(arylene ether) to about 15 liters inert gas/kg poly(arylene ether) preferred, ar.d about 6 liters inert gas/kg poly(arylene ether) to about 13 liters inert gas/kg poly(arylene ether) especially preferred.
- the flow rates of the various components which is determined by the screw design and geometry of the extruder, can be determined by an artisan without undue experimentation.
- Possible extruders include all conventional devices capable of intimately mixing the components and maintaining the desired environment, for example single screw, twin screw or other multiple screw extruders, as well as other mixing devices such as kneaders and the like capable of effectively mixing the composition. Due to mixing requirements and environmental controls, an extruder having at least two feed ports with an atmospheric vent there between is preferred, with an extruder having at least two feedports, an atmospheric vent and at least one vacuum vent especially preferred.
- the resin(s), additives and optional modifiers are intimately mixed at a temperature sufficient to melt and compound the poly(arylene ether), e.g. typically about 250°C to about 320°C, and preferably about 275°C to about 305°C.
- the r maining polyamide is then added and the mixture is further mixed so as to obtain the desired product.
- the resulting polymer is then put through a die, roller, or other final processor, and formed into pellets, sheets, a web or the like, by any method known in the art, with underwater pelletization preferred.
- the various initial components e.g. the poly(arylene ether) resin, the portion of the polyamide resin, compatibility modifier, and optional impact modifier and other additives, can be premixed.
- This mixture can then be flushed with an inert gas so as to obtain a mixture which is substantially free of gaseous oxygen.
- the flushed mixture is then added to the extruder or other appropriate mixing device, with an inert atmosphere under the flow of an inert gas as described above. From the extruder the mixture is pelletized, formed into a sheet, or otherwise processed as is conventional.
- the processed mixture can be uti Sized to form various articles, such as automotive parts.
- One technique of forming these parts comprises injection molding; a method commonly utilized to form articles from polymer resins. This process involves adding the mixture to a feed hopper, heating the mixture to a temperature sufficient to melt the mixture and forming the mixture into the desired shape by forcing it into a mold. Again, to further prevent the formation of pits, it is preferable to use inert gas(es) to create and maintain an inert atmosphere over the mixture during this processing.
- the preferred inert atmosphere during article formation comprise the use of inert gas as described above, with the use of nitrogen and hydrogen more preferred.
- the nitrogen-hydrogen mixture can be about 90 volume percent (vol%) to about 99 vol% nitrogen, with about 93 vol% to about 98 vol% preferred.
- Other conventional further processing techniques can also be employed. All patents cited are incorporated herein by reference. The invention is further illustrated by the following non-limiting examples.
- a WP-28 Werner and Pfleiderer twin screw extruder was used with a main feeder disposed at the front-end of the extruder and a second feeder located approximately halfway down the extruder with an atmospheric vent located between the two feeders and a vacuum vent located between the downstream feeder and the die of the extruder.
- Nitrogen was introduced via a pipe at the bottom of the main feeder to flush the extruder and maintain the nitrogen atmosphere during the addition of ingredients.
- the nitrogen flow rate was monitored with a flow meter.
- the extruder was operated using the parameters defined in Table 1.
- Feeder % is the percentage of the total throughput of the extruder.
- the poly(arylene ether)-polyamide composition comprised about 50 wt% poly(arylene ether) and additives and about 50 wt% polyamide. Molding was done on a KM350, forming DIN A5 plaques for molding with inert atmosphere while for the standard molding conditions 4 cm x 4 cm plaques were used. The 4 cm x 4 cm plaques were formed by injection molding with a low injection speed and the plaque was not completely filled. Low injection speed is defined as the minimal speed of injection required to obtain a good quality plaque. The plaques were not completely filled in order to improve the visibility of the defect. Incomplete filling makes the carbonized particles surface at the flow end of the plaque.
- the plaques were evaluated for pits by two methods.
- the first method involved a visual inspection and quantification of the number of surface defects.
- the second method was a filtration test.
- the plaque was dissolved in a mixture of chloroform and trifluoroacetic acid. The solution was then filtered and the amount of insoluble was evaluated using automatic image analysis software. This method of evaluation is also known as the insolubles test.
- Examples 1-3 use the same procedure with varying nitrogen flow rates.
- No polyamide was introduced through the first feeder of the extruder.
- 3.67 kilograms (kg) of poly(arylene ether) and additives, 0.8 kg of styrene ethylene propylene, 0.7 kg of styrene ethylene butylene styrene, and 0.65 kg of citric acid were introduced to the main feeder with nitrogen flow.
- 4.8 kg of polyamide were introduced at the second feeder and processing continued.
- the resulting composition was then pelletized and formed into plaques.
- the plaques were evaluated for pits and insolubles as shown in Table 2.
- the nitrogen flow rates for Examples 1-3 were 1.2 liter per kg (1/kg), 5.5 1/kg, and 11.5 1/kg, respectively.
- the control material was made without nitrogen flow.
- Examples 12 - 13 A molding trial was done on a KM350 with a compatibilized poly(arylene ether)-polyamide composition molding DIN A5 plaques using the conditions shown in Table 6.
- the feed hopper of the molding machine was flushed with an inert gas. A slight over pressure was maintained to ensure an oxygen level below 1 vol% in feed hopper (oxygen level of about 0.02 vol% or less typically achieved).
- Example 12 In the control no inert gas was used; in Example 12 the inert gas was nitrogen; and in Example 13 the inert gas was a mixture of nitrogen and hydrogen gas (97 vol% N / 3 vol% H 2 ). The plaques were evaluated for pits and insolubles. Results are shown in Table 7.
- the present invention reduces pits by namely compounding under an inert atmosphere, flushing the poly(arylene ether) with an inert gas, operating the extruder with the atmospheric vent open, and or adding up to 20 wt% of polyamide in the first compounding step.
- the beneficial effect of compounding under an inert atmosphere is clearly seen in Examples 1-3 where the number of pits per plaque was reduced from 20 in the control to 2.3 in Example 3. The number of insolubles showed a similar drop from 3294 in the control to 637 in Example 3.
- a comparison of Examples 4 and 5 clearly shows the benefit of flushing the poly(arylene ether) resin with nitrogen.
- Examples 4 and 5 are both compounded under an inert atmosphere but in Example 5 the poly(arylene ether) resin is flushed with nitrogen.
- Example 5 The number of pits per plaque was further reduced by 1 in Example 5 when compared to Example 4 and the number of insolubles is reduced from 1 151 in Example 4 to 500 in Example 5.
- the advantage of operating with the atmospheric vent is clearly seen in Example 1 1.
- Examples 6 through 9 demonstrate the utility of adding a portion of the polyamide at the main feeder as evidenced by a dramatic drop in the number of pits per plaque from the Control (20) to Example 8 (4.2). A similar trend is seen in the insolubles data.
- each improvement to the process results in a decrease in the number of pits/insolubles and the combination of improvements results in a greater decrease in pits/insolubles.
- the improvements to the injection molding process may be used in combination with improvements to the process of making poly(arylene ether)- polyamide compositions or separately.
- the amount of carbonized particles formed during injection molding of poly(arylene ether)-polyamide polymer compositions was distinctly reduced when the feed hopper was flushed with an inert gas or mixture of gases and a slight over pressure of inert gas was maintained.
- poly(arylene ether)- polyamide compositions can be produced having a significantly reduced number of carbon particles and/or insolubles.
- the poly(arylene ether)-polyamide composition comprises an about 50% or greater reduction of carbon particles, with about 75% or greater reduction preferred, about 85% or greater more preferred and about 90% or greater reduction especially preferred. Additionally, an about 50% or greater reduction in insolubles has been achieved with an about 70% or greater reduction preferred, about 80%) or greater reduction more preferred, and an about 85% or greater reduction especially preferred.
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Abstract
Applications Claiming Priority (3)
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US09/516,830 US6365677B1 (en) | 2000-03-01 | 2000-03-01 | Reduction of carbonized particles |
US516830 | 2000-03-06 | ||
PCT/US2001/000949 WO2001064790A1 (fr) | 2000-03-01 | 2001-01-11 | Reduction de particules carbonisees dans une composition de polyarylene ether polyamide |
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EP (1) | EP1268670A1 (fr) |
JP (1) | JP2003525336A (fr) |
AU (1) | AU2001227846A1 (fr) |
WO (1) | WO2001064790A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4190941B2 (ja) * | 2002-08-22 | 2008-12-03 | 旭化成ケミカルズ株式会社 | 製造方法及びその樹脂組成物 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04250005A (ja) | 1991-01-17 | 1992-09-04 | Asahi Chem Ind Co Ltd | 樹脂組成物の製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3379792A (en) * | 1965-08-12 | 1968-04-23 | Gen Electric | Polymer blend of a polyphenylene oxide and a polyamide |
US5000897A (en) * | 1986-03-20 | 1991-03-19 | General Electric Company | Polyphenylene ether-polyamide compositions and methods for preparation |
JPH0753713A (ja) * | 1993-08-18 | 1995-02-28 | Asahi Chem Ind Co Ltd | 変成ポリフェニレンエーテル樹脂の製造方法 |
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2001
- 2001-01-11 JP JP2001564281A patent/JP2003525336A/ja active Pending
- 2001-01-11 WO PCT/US2001/000949 patent/WO2001064790A1/fr active Application Filing
- 2001-01-11 AU AU2001227846A patent/AU2001227846A1/en not_active Abandoned
- 2001-01-11 EP EP01901996A patent/EP1268670A1/fr not_active Withdrawn
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04250005A (ja) | 1991-01-17 | 1992-09-04 | Asahi Chem Ind Co Ltd | 樹脂組成物の製造方法 |
Non-Patent Citations (1)
Title |
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See also references of WO0164790A1 |
Also Published As
Publication number | Publication date |
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WO2001064790A1 (fr) | 2001-09-07 |
JP2003525336A (ja) | 2003-08-26 |
AU2001227846A1 (en) | 2001-09-12 |
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