MXPA98009672A - Compositions of compatibilized mixtures of polyphenylene-polyamide ether resins improved with impa modifier - Google Patents
Compositions of compatibilized mixtures of polyphenylene-polyamide ether resins improved with impa modifierInfo
- Publication number
- MXPA98009672A MXPA98009672A MXPA/A/1998/009672A MX9809672A MXPA98009672A MX PA98009672 A MXPA98009672 A MX PA98009672A MX 9809672 A MX9809672 A MX 9809672A MX PA98009672 A MXPA98009672 A MX PA98009672A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- acid
- composition according
- copolymer
- alkylene
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 239000004952 Polyamide Substances 0.000 title claims abstract description 35
- 229920002647 polyamide Polymers 0.000 title claims abstract description 35
- 239000011528 polyamide (building material) Substances 0.000 title claims abstract description 30
- 229920005989 resin Polymers 0.000 title claims abstract description 23
- 239000011347 resin Substances 0.000 title claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 10
- 239000003607 modifier Substances 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims abstract description 38
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 13
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 13
- 150000002905 orthoesters Chemical class 0.000 claims abstract description 10
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 6
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 6
- -1 polyphenylene Polymers 0.000 claims description 25
- 229920001955 polyphenylene ether Polymers 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- FPYJFEHAWHCUMM-UHFFFAOYSA-N Maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 229920001400 block copolymer Polymers 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 241000424123 Trachinotus baillonii Species 0.000 claims description 5
- 229920000359 diblock copolymer Polymers 0.000 claims description 5
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 5
- 229920000428 triblock copolymer Polymers 0.000 claims description 5
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N Malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N Trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 229940099690 malic acid Drugs 0.000 claims description 3
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- 239000003738 black carbon Substances 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 230000000996 additive Effects 0.000 claims 1
- 230000003014 reinforcing Effects 0.000 claims 1
- 239000004609 Impact Modifier Substances 0.000 abstract description 12
- 230000000704 physical effect Effects 0.000 abstract description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 17
- 101700033949 RPE Proteins 0.000 description 17
- 101700049344 rpe1 Proteins 0.000 description 17
- 239000002253 acid Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 125000004432 carbon atoms Chemical group C* 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 150000004053 quinones Chemical class 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 229920002302 Nylon 6,6 Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- LCJRHAPPMIUHLH-UHFFFAOYSA-N 1-$l^{1}-azanylhexan-1-one Chemical compound [CH]CCCCC([N])=O LCJRHAPPMIUHLH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Xylenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 229920003189 Nylon 4,6 Polymers 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
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000002092 orthoester group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-Aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 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
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-Octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 1
- CPEMSVQIDGEZCG-UHFFFAOYSA-N 2,5-dimethylhex-3-ene-2,5-diol Chemical compound CC(C)(O)C=CC(C)(C)O CPEMSVQIDGEZCG-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
- 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
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- FYDMBFIJIQPURU-UHFFFAOYSA-N 2-[2-(2-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC=C(N)C=1C(C)(C)C1=CC=CC=C1N FYDMBFIJIQPURU-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
- 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-M 2-hydroxy-4-octadecoxy-2-(2-octadecoxy-2-oxoethyl)-4-oxobutanoate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)CC(O)(C([O-])=O)CC(=O)OCCCCCCCCCCCCCCCCCC IMQYZLJIDNYQLX-UHFFFAOYSA-M 0.000 description 1
- 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 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
- MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical group CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-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
- 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
- WWXUGNUFCNYMFK-UHFFFAOYSA-L Acetyl citrate Chemical compound CC(=O)OC(=O)CC(O)(C([O-])=O)CC([O-])=O WWXUGNUFCNYMFK-UHFFFAOYSA-L 0.000 description 1
- 229940091181 Aconitic Acid Drugs 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N Aconitic acid Chemical compound OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N Butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229960004256 Calcium Citrate Drugs 0.000 description 1
- 229940016114 Calcium Malate Drugs 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
- OLOZVPHKXALCRI-UHFFFAOYSA-L Calcium malate Chemical compound [Ca+2].[O-]C(=O)C(O)CC([O-])=O OLOZVPHKXALCRI-UHFFFAOYSA-L 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N Crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N Crotyl alcohol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007842 Glycine max Species 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 235000005058 Madhuca longifolia Nutrition 0.000 description 1
- 240000004212 Madhuca longifolia Species 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
- 239000004677 Nylon Substances 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 210000003800 Pharynx Anatomy 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 241001582367 Polia Species 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene (PE) Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001451 Polypropylene glycol Polymers 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K Potassium citrate Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 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
- KIDHWZJUCRJVML-UHFFFAOYSA-N Putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 229920002725 Thermoplastic elastomer Polymers 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N Trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 229940040563 agaric acid Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000001588 bifunctional Effects 0.000 description 1
- 229940106691 bisphenol A Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N butylene glycol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 239000001362 calcium malate Substances 0.000 description 1
- 235000013962 calcium malate Nutrition 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 229960004106 citric acid Drugs 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
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WCJAFRYVCLHKTK-UHFFFAOYSA-N hexa-1,4-dien-3-ol Chemical compound CC=CC(O)C=C WCJAFRYVCLHKTK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 238000005691 oxidative coupling reaction Methods 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
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- 239000001415 potassium malate Substances 0.000 description 1
- 235000011033 potassium malate Nutrition 0.000 description 1
- ZUZSFMQBICMDEZ-UHFFFAOYSA-N prop-1-enylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CC=CC1=CC=CC=C1 ZUZSFMQBICMDEZ-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 239000011791 tripotassium citrate Substances 0.000 description 1
- 235000015870 tripotassium citrate Nutrition 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention relates to thermoplastic compositions comprising a compatibilized blend of polyphenylene-polyamide terephthalate that is modified with an impact modifier that contains at least portions that are reactive with the polyamide resin. The preferred impact modifier is an alkylene-alkyl methacrylate copolymer comprising at least two portions selected from the group consisting of carboxylic acid, anhydride, epoxy, oxazoline and orthoester. The compositions of the invention show improved physical properties, especially energy to rupture and deformation when measured at low temperatures.
Description
COMPOSITIONS PE MIXES CQMPftTIBILIZftPflS OF POLYPHENYLENE-POLYAMINE ETHER RESINS IMPROVED WITH IMPACT MODIFIER
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
The invention relates to a thermoplastic composition of a compatibilized mixture of polyphenylene-polyalphaide ether resin that is modified with an impact modifier containing at least two portions that are reactive with the polyamide resin. The invention also relates to articles formed by compositions of the invention.
BRIEF DESCRIPTION OF RELATED TECHNIQUE
Polyphenylene ether resins (hereinafter referred to as "PPE") are commercially attractive materials because of their unique combination of physical, chemical and electrical properties. In addition, the combination of such resins with the polyamide resins in compatibilized mixtures results in additional total properties such as chemical resistance, high voltage and high flux. Examples of such compatibilized mixtures can be found in U.S. Patents. 4,315,086 (Ueno, et al.); 4,659,760 (Van der Mee);
and 4,732,938 (Grant et al.). The properties of such mixtures can be further improved by the addition of various additives such as impact modifiers, flame retardants, light stabilizers, processing stabilizers, heat stabilizers, antioxidants and fillers. The physical properties of the PPE / polia ida blends make them attractive for a variety of end-use items in the automotive market, especially for engine components and various exterior components. Many such components are subject to a variety of abuses, such as impacts, and as such, require extraordinary resistance and ductility to impact. These same items are also subject to wide variation in temperature in end-use applications due to the temperature extremes found in various parts of the world. Accordingly, there is a need to co-adapt the PPE-poliated compositions having improved strength and ductility to impact over a wide range of temperatures, especially at low temperatures.
BRIEF DESCRIPTION OF I TO TNVFNCTON
The needs discussed above have generally been satisfied by the discovery of an improved thermoplastic composition comprising: a) a co-tailored mixture of polyphenylene ether-polyamide resin, and b) an alkylene-alkyl (meth) acrylate copolymer comprising minus two portions selected from the group consisting of carboxylic acid, anhydride, epoxy, oxasoline, and orthoester. The following description provides more details in regard to the present invention.
DETAILED DESCRIPTION OF THE INVENTION
Polyphenylene ether resins are a well-known class of compounds sometimes referred to as polyphenylene oxide resins. Examples of suitable PPE and methods for their preparation can be found, for example, in U.S. Patents. with us
3,306,874; 3,306,875; 3,257,357; and 3,257,358. The compositions
• of the present invention will include homopolymers, copolymers and grafts of copolymers obtained by the oxidative coupling of the phenolic compounds. Preferred PPEs used as base resins in compositions of the present invention will be comprised of ml / g derived from 2,6-dimethylphenol. Also contemplated are the copolymers of PPE derived from 2,6-dimethylphenol and 2,3,6-trimethylphenol. Particularly useful PPE's are the poly (2,6-dimethyl-1,4-phenylene) esters, which have an intrinsic viscosity ( VI) of between about 0.30 and about 0.60 dl / g as measured in toluene at 25 ° C and at a concentration of 0.6 grams per 100 ml. The polyamide resins useful in the practice of the present invention are a generic family of known resins. like nylon, characterized by the presence of an amide group (-C (O) NH-). Nylon-6 and nylon-6,6 are the most preferred polyamides and are available from a variety of commercial sources. However, other polyamides, such as nylon-4,6, nylo-12, nylon-6,10, nylon-6,9, nylon-6 / 6T and nylon 6,6 / 61 with triamine contents below about 0.5% by weight as well as others, such as amorphous nylons, can be useful for particular applications of PPE-polyamide. Mixtures of various polyamides as well as various polyamide copolymers are also useful. The most preferred polyamide for the blends of the present invention is polyamide-6,6. The polyamides can be obtained by a number of well-known procedures, such as those described in US Pat. 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 caprolacta. Nylon-6,6 is a condensation product of adipic acid and 1,6-diaminohexane. Similarly, nylon 4,6 is a condensation product between adipic acid and 1,4-diaminobutane. In addition to adipic acid, other diacids useful for the preparation of nylons include acelaic acid, cebasic acid, dodecanoic diacid, as well as terephthalic and isophthalic acids. Other useful diamines include diaminylxylene, di- (4-aminopheni) methane, di- (4-aminociclohexyl) methane; 2,2-di- (aminophenyl) propane, and 2,2-di- (4-aminociclohexyl) propane. Copolymers of caprolactam with diacids and diamines are also useful. Polyamides having a viscosity number of about 90 to about 350 ml / g, preferably between about 110 and about 240 ml / g are preferred as measured in a solution of 0.5 wt% in 96 wt% sulfuric acid of according to ISO 307. In the mixtures of the present invention, a compatibilizing agent must be used in the preparation of the composition. The dual purpose for using the compatibilizing agents is to improve, in general, the physical properties of the PPE-polyamide resin mixture, as well as to allow the use of a greater proportion of the polyamide component. When used herein, the term "compatibilizing agent" refers to those polyfunctional compounds that interact with the PPE, the polyamide resin, or both. Such reaction can be chemical (ie insert) or physical (ie it affects the surface characteristics of the dispersed phases). In any case, the resulting PPE-polyamide composition appears to show improved compatibility, particularly as evidenced by improved impact strength, in-line bond strength and / or elongation. As used herein, the term "compatibilized polyphenylene ether-polyamide ether base resin" refers to compositions that have been physically or chemically compacted with an agent as discussed above, as well as those compositions that are physically compatible without such agents, as taught in the US patent No. 3,379,792. Examples of various compatibilizing agents that can be employed in the practice of the present invention include: a) liquid diene polymers, b) epoxy compounds, c) oxidized polyolefin wax, d) quinones, e) organosilane compounds, f) compounds polyfunctional and functionalized PPE, which as described above, were obtained by the reaction of one or more of the aforementioned compatibilizing agents with PPE in the following. The diene liquid polymers (a) suitable for use herein include homopolymers of a conjugated diene with at least one monomer selected from the group consisting of other conjugated dienes; vinyl monomer, ie styrene and alphamethylstyrene; olefins, ie, ethylene, propylene, butene-1, isobutylene, hexene-1, octene-1 and dodecene-1 and mixtures thereof, having an average molecular weight number between 150 to 10,000, preferably 150 to 5000
Such homopolymers and copolymers can be produced by the methods described, for example, in U.S. Pat. Nos. 4,054,612; 3,876,721 and 3,428,699 and include, among others, polybutadiene, polysiprene, poly (l, 3-pentadiene), poly (butadiene-isoprene), poly (styrene-butadiene), polychloroprene, poly (butadiene-alphamethylstyrene), poly ( butadiene-styrene-isoprene), poly (butylene-butadiene) and the like. The epoxy compounds (b) suitable for use in the practice of the present invention include: (1) epoxy resins produced by the condensation polyhydric phenols (ie, bisphenol-A, tet rab romobisf enol-A, resor hydroquinone) and epichlorohydrin; (2) epoxy resins produced by polyhydric condensation alcohols (i.e., 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 glycidyl ether , butyl glycidyl ether and crecilyglycidyl ether; (4) glycidyl derivatives of amino compounds for example, the diglycidyl derivative of aniline, and (5) epoxidized products of higher olefinic oils or of cycloalkene, or natural unsaturated oils (ie of soybean) as well as the above liquid diene polymers .
The oxidized polyolefin waxes (c) are well known and a description thereof and the processes for the production thereof are found in US Patents. Nos. 3,822,227 and 3,756,999. Generally, such waxes are prepared by an oxidation or suspension of polyolefin oxidation. A particularly preferred polyolefin wax is "Hoechst achs". The quinone compounds (d) suitable for use herein are characterized by having at least one six-membered carbon ring on the unsubstituted derivative molecule; at least two carbonyl groups in the ring structure, which may be in the same or, if there is more than one ring, different rings, since they occupy positions corresponding to the orientation 1, 2 or 1,4- of the monocyclic quinone; and at least two carbon-carbon double bonds in the ring structure, such carbon-carbon double bonds and carbon-oxygen carbonyl double bonds in the ring structure, such carbon-carbon double bonds and carbon double bonds -oxigen carbonyl conjugate with each other. The rings can be fused, not fused or both, where more than one ring is present in the unsubstituted quinone: the unfused rings can be linked by means of a direct carbon-carbon double bond or by means of a hydrocarbon radical that it has a conjugated unsaturation such as -C = CC = C-.
Unsubstituted quinones are also within the scope of the present invention. The degree of substitution; where the substitution is desired, it can be from 1 to the maximum number of replaceable hydrogen atoms. Examples of various substituents that may be present in the unsubstituted quinone structures include halogen (ie, chloride, bromide, fluoride, etc.), hydrocarbon radicals including branched, unbranched, branched, unsaturated alkyl, aryl, alkylaryl, and cycloalkyl radicals and unsaturated and halogenated derivatives thereof; and similar hydrocarbons having other atoms in them, particularly oxygen, sulfur or phosphorus and wherein the same hydrocarbon connects the radical to the quinone ring (ie, oxygen bond). Examples of various quinones 1,2- and 1,4-benzoquinone; 2,6-d-phenylquinone; tetramethyldi-quinone; 2,2'- and
4,4'-diphenoquinone; 1,2-, 1,4- and 2,6-naphthoquinone; chloranyls;
2-chloro-1,4-benzoquinone; 2,6-dimethylbenzoquinone and the like. The organosilane compounds (e) suitable as compatibilizing agents are characterized by having in the molecule (a) at least one silicon atom bonded to the carbon through an oxygen bond and (b) at least one carbon-carbon double bond or carbon-carbon triple bond and / or a functional group selected from the group consisting of an amine group or a mercapto group in order that the functional group is not directly linked to the silicon atom.
In such compounds, the CO-Si component is generally present as an alkoxy or acetoxy group directly linked to the silicon atom, wherein the alkoxy or acetoxy group generally has less than 15 carbon atoms and may also contain other atoms (i.e. oxygen). In addition, there can also be more than one silicon atom in the compound, if the multiple silicon atoms are present, being linked through the oxygen bond (ie, siloxanes), a silicon bond; or a bifunctional organic radical (ie, methylene or phenylene groups). Examples of suitable organosilane compounds include: aminopropyltriethoxysilane range, 2- (3-cyclohexanyl) ethyltrimethoxysilane; 1,3-divinyltetra-ethoxysilane; vinyl trs- (2-methoxyethoxy) silane; 5-bicycloheptenyltriethoxysilane and mercapto propyltrimethoxysilane range. The polyfunctional compounds (f) which can be used as compatibilizers in the practice of the present invention are of three types. The first type of polyfunctional compounds are those that have in the molecule (a) a carbon-carbon double bond or a carbon-carbon triple bond and b) 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 product resulting from a diamine and maleic anhydride, maleic acid, fumaric acid, etc; dichloromaléic anhydride; amide maleic acid; unsaturated dicarboxylic acids (ie, acrylic acid, butenoic acid, methacrylic acid, t-ethylacrylic acid, pentenoic acid); decaic acids, indecenic acids, dodecenic acids, linoleic acid, etc.); ethers, acid amines or anhydrides of the above unsaturated carboxylic acids; unsaturated alcohols (ie alkyl alcohol, crotyl alcohol, carbinolmethylvinyl, 4-pentene-1-ol, 1, 4-hexadiene-3-ol, 3-butene-1,4-diol, 2,5-dimethyl-3-hexene - 2,5-diol and alcohols of the formula nH2n-5 ° H, CnH2n-7? H and CnH2n-90H "where n is a positive integer of up to 30), the unsaturated amines are replaced by replacement of the -OH groups of the above unsaturated alcohols with NH2 groups; and functionalized diene polymers and copolymers. Of these, two of the preferred compatibilizing agents for the compositions of the present invention are maleic anhydride and fumaric acid. The second group of polyfunctional compatibilizing compounds suitable for use herein are characterized by having (a) a group represented by the formula (OR) wherein R is hydrogen or an alkyl, aryl, acyl or carbonyl dioxy group and (b) al minus two groups which may be the same or different groups selected from the carboxylic acid, acid halide, anhydride, acid halide anhydride, ester, orthoester, amide, imido, amino and various salts thereof. Typical of this group of compatibilizers are polycarboxylic aliphatic acids, acidic esters and acid amides represented by the formula: (Rl?) MR (COOR11) m (CONRIIIRIV) s wherein R is a straight or branched chain, saturated aliphatic hydrocarbon 2 to 20, preferably 2 to 10, carbon atoms; R * is selected from the group consisting of hydrogen or an alkyl, aryl, acyl or carbonyl dioxy group of 1 to 10, preferably 1 to 6, more preferably 1 to 4, carbon atoms, especially preferred is hydrogen; each R ^ is independently selected from the group consisting of hydrogen or an alkyl or aryl group from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms; each RIII RIV is independently selected from the group consisting essentially of hydrogen or an alkyl or aryl group from 1 to 10, preferably from 1 to 6, more 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 where (0R1) is alpha or beta to a carbonyl group and at minus two carbonyl groups are separated by 2 to 6 carbon atoms. Obviously, R1, R11, RIII and R * v can not be aryl when the respective substituent has less than 6 carbon atoms.
Suitable polycarboxylic acids include, for example, citric acid, malic acid, and agaric acid; including various commercial forms thereof, such as, for example, anhydrous and hydrated acids. Of these, citric acid is another of the preferred compatibilizing agents. Illustrations of the esters useful herein include, for example, acetyl citrate and mono- and / or distearyl citrates and the like. Suitable amides useful herein include, for example, citric acid amide N, N'-diethyl; N-phenyl citric acid amide; amide of citric acid
N-dodecyl; N, N'-didodecyl and malic acid citric acid amide
N-dodecyl of the present invention. Especially preferred derivatives are the salts thereof, including the salts with amines and / preferably, the alkali and alkali metal salts. Examples of suitable salts include calcium malate, calcium citrate, potassium malate, and potassium citrate. The third group of polyfunctional compatibilizing compounds suitable for use herein are characterized by having in the molecule (a) an acid halide group, more preferably an acid chloride group and (b) at least one carboxylic acid, anhydride, ester, epoxy , orthoester, or amide group, preferably a carboxylic acid or an anhydride group. Examples of compatibilizers within this group include trimellitic anhydride acid chloride, cyclo-formyl succinic anhydride, cyclo-formylglutaric anhydride, chloroformyl glutaric acid, cloacetylsuccinic anhydride, chloroacetyl succinic acid, tri-elytic acid chloride, and chloroacetylglutaric acid. Among these, trimellitic anhydride acid chloride is preferred. Furthermore, it is especially preferred that the compatibilizers of this group are pre-reacted with at least a portion of polyphenylene ether wherein the compatibilizing agent is a functionalized PPE-compound. The above compatibilizing agents are described in more detail in U.S. Pat. Nos. 4,315,086; 4,600,741; 4,642,358; 4,826,933; 4,927,894; 4,980,424; 5,041,504; and 5,115,042. The above compatibilizing agents can be used alone or in various combinations with each other. In addition, they can be added directly to the melt or prereaction mixture with any of the PPE or polyamide or both, as well as with other resinous materials used in the preparation of the compositions of the present invention. With several of the above compatibilizing agents, particularly the polyfusional compounds, even greater compatibility improvement is discovered wherein at least a portion of the co-stabilization agent is prereacted, either in the melt or in a solution of a suitable solvent, with all or part of the PPE. It is believed that such pre-reaction can cause the compatibilizing agent to react with the polymer and, consequently, functionalize the PPE as mentioned above. For example, PPE can be prereacted with maleic anhydride to form a functionalized PPE anhydride having improved compatibility with the polyamide compared to a non-functionalized PPE. Where the compatibilizing agent is employed in the preparation of the compositions of the present invention, the initial amount used will depend on the specific compatibilizing agent selected and the specific polymer system to which it is added. It is possible to use any other known compatibilization system in the composition according to the invention. Other systems have been described, for example, in U.S. Pat. No. 4,866,114. The present compositions also contain an alkylene-vinyl methacrylate copolymer comprising at least two portions selected from the group consisting of carboxylic acid, anhydride, epoxy, oxazoline, and orthoester. The alkylene groups preferably have from 2 to about 6 carbon atoms and the alkyl group of the alkyl methacrylate generally has from about 1 to about 8 carbon atoms. This type of polymers can be prepared by copolymerizing an olefin, for example, of ethylene and propylene, with several methacrylate monomers and / or several maleic monomers of base. The term (meth) acrylate refers to the acrylate as well as to the corresponding analog methacrylate. The term "methacrylate monomers" includes alkyl (et) acrylate monomers as well as various (meth) acrylate monomers containing at least one of the reactive portions mentioned above. In a preferred embodiment, the copolymer is derived from ethylene, propylene, or mixtures of ethylene and propylene, such as the alkylene component; butylacrylate, exillacrylate, or propyl acrylate as well as the alkyl (methyl) acrylate, for the alkyl (et) acrylate monomer component, with acrylic acid and maleic anhydride as monomers that provide the two reactive portions (i.e., acid and carboxylic anhydride). The olefin content in the copolymer can be from about 40 to about 90% by weight, preferably from about 50 to about 70% by weight, based on the weight of the copolymer. The content of (et) acrylate monomer in the copolymer can be from about 10 to about 60% by weight, preferably from about 30 to about
50% by weight based on the weight of the copolymer. The (meth) acrylate monomers containing the reactive portions are generally present in the copolymer from about 0.1 to about 15% by weight, preferably from about 0.5 to about
% by weight, and more preferably from about 1.0 to about 8% by weight, based on the weight of the copolymer.
The amount of the aforementioned alkyl alkylene- (meth) acrylate copolymer can vary widely in the compositions of the present invention; however, the scale is generally from about 1 to about 15% by weight, preferably from up to about 2 to about 8% by weight based on the weight of the total composition. A preferred composition is one that results in compositions that show a deformation of more than 10 mm, preferably more than 12 mm, when a plate is hit at -30 ° C by dropping a dart in accordance with ISO 6603-2. It is also preferred that the amount of the aforementioned alkyl alkyl methacrylate copolymer is that which results in the compatibilized PPE-polyamide compositions having an energy in a break greater than 40 J, preferably greater than 50 J and even more preferably higher of approximately 60 J, when a plate is hit at -30 ° C when dropping a dart in accordance with ISO 6603-2. In an especially preferred embodiment, the compositions of the present invention will have a breaking energy greater than 40 J with a deformation of more than 10 mm, more preferably have a breaking energy greater than 50 J with a deformation of more than 12 mm, and more preferably have a breaking energy greater than 60 J with a deformation of more than 12 mm, when a plate is hit at -30 ° C when dropping a dart in accordance with ISO 6603-2.
In a preferred embodiment, the alkylene-alkyl methacrylate copolymer is derived from ethylene, butylacrylate, acrylic acid, and maleic anhydride wherein the ethylene content is from about 55 to about 65%, butyl acrylate is from about 30 to about about 40%, the acrylic acid is from about 3 to about 7%, and the maleic anhydride is from about 0.08 to about 0.5% by weight, wherein all the weights are based on the weight of the copolymer. In an especially preferred embodiment, the alkylene-alkyl methacrylate copolymer is derived from ethylene, butyl acrylate, acrylic acid, and maleic anhydride, wherein the butyl acrylate is between about 32-36, acrylic acid is between about 4.8-5.8%, and the maleic anhydride is between about 0.55-0.75% by weight, with the residue derived from ethylene, and wherein all the weights are based on the weight of the copolymer. It is possible to incorporate in the composition according to the invention one or more additional impact modifiers. All impact modifiers generally used for compositions comprising a polyphenylene ether, a polyamide or a combination of polyphenylene ether and a polyamide can be used. The so-called block copolymers are particularly suitable, that is, the triblock copolymers and the diblock copolymers. The diblock and triblock copolymer rubber additives that can be used are thermoplastic rubbers comprising one or two aromatic alkenyl blocks, which are typically styrene blocks and a rubber block, i.e., a butadiene block that can be hydrogenated. partially. Mixtures of such triblock copolymers and diblock copolymers are especially useful in the present compositions. When a combination of at least one block copolymer and the alkylene alkyl methacrylate copolymer comprising at least two portions selected from the group consisting of carboxylic acid is used, anhydride, epoxy, ixazoline, and orthoester, it is believed that dual phase impact modification is possible. By dual phase impact modification it is meant that the PPE phase and the polyamide resin phase contain an impact modifier. It is believed that the alkyl alkylene methacrylate copolymer portions react with the polyamide resin in a manner similar to that previously described for compatibilizing agents to provide a copolymer between the alkylene alkyl methacrylate copolymer and the polyamide resin. A variety of useful compatibilized PPE-polyamide compositions can be provided, which includes varying the amount of various impact modifiers (i.e., the alkyl methacrylate copolymer comprises at least two reactive portions selected from the group consisting of carboxylic acid, anhydride, epoxy, oxazoline, and orthoester; in addition to the block copolymer or copolymers). Typically, the combined level of impact modifiers will be made from about 1 to about 30% by weight, preferably from about 2 to about 18% by weight based on the weight of the total composition with the amount of the methacrylate copolymer as previously described . The thermoplastic composition of the invention may comprise any of the following additives: reinforcement fibers, filler pieces, conductive black carbon, carbon fibers and carbon fibrils, stabilizers, dyes, pigments, polyolefins, and flame retardants. All of the cited patents and patent applications are incorporated herein by reference. The invention will also be illustrated with the following examples.
EXPERIMENTAL SECTION The following materials have been used in the examples: PPE: a poly (2,6-dimethyl-1,4-phenylene ether) with an intrinsic viscosity of 45 ml / g as measured in toluene at 25 ° C and a concentration of 0.6 grams per 100 ml;
PA: a polyamide -6.6 with a reduced viscosity of 145 ml / g as measured in sulfuric acid according to ISO 307; CA: citric acid; SEBS: polystyrene block copolymer reno-poly (ethylene-butylene) -polystyrene; SEP: block copolymer of polystyrene ren-poly (ethylene-propylene); EPDM-MAH: ethylene-propylene-diene rubber copolymer containing 0.6% by weight of grafted maleic anhydride; EBA-AA-MAH: copolymer of ethylene, butyl acrylate, acrylic acid, and maleic anhydride in a weight ratio of 60: 35: 4: 8.02. The ingredients were compounded in the weight ratios, as indicated in the following table, in a two screw extruder with temperatures throughout the extruder between about 280 and about 310 ° C. The screw speed was 300 rpm, the production amount was 10 kg per hour. All the ingredients except the polyamide were introduced through the throat of the extruder; the polyamide was supplied downstream about half the extruder. The strings exiting the extruder were interlaced in laboratory equipment and dried for about 3 hours at about 110PC. The dried granules were molded by injection into the specimens of the normal ISO test for the measurement of physical properties.
2. 3
As can be seen from the results of the table, compositions containing an alkylene alkyl methacrylate copolymer comprising less two portions selected from the group consisting of carboxylic acid, anhydride, epoxy, oxazoline, and orthoester, markedly exhibit a improved energy in breaking and deformation, especially at low temperature, than compositions containing an impact modifier containing only a single reactive group. For example, the comparison of sample 6 with sample 1 shows that the breaking energy for sample 6 is surprisingly 1.7 times that of sample 1 when measured at -30"^ The deformation for sample 6 is also surprisingly more of 1.4 times the deformation of sample 1 when measured at -30 ° C. Similar unexpected results were obtained for compositions containing up to about 8% by weight of the alkylene-alkyl copolymer comprising at least two portions selected from the group it consists of carboxylic acid, anhydride, epoxy, oxazoline, and orthoester when compared to an impact modifier that contains only a single reactive portion.
Claims (11)
1. - A thermoplastic composition comprising: (a) a compatibilized mixture of polyphenyl ether-polyamide resin, and (b) an alkylene-alkyl methacrylate copolymer comprising at least two portions selected from the group consisting of carboxylic acid, anhydride , epoxy, oxazoline, and orthoester; characterized in that the alkylene alkyl methacrylate copolymer is present from about 1 to about 15% by weight based on the weight of the total composition.
2. A composition according to claim 1, further characterized in that the alkylene-alkyl methacrylate copolymer is a copolymer of ethylene, butyl acrylate, acrylic acid and maleic anhydride monomers.
3. A composition according to claim 1, further characterized in that the alkylene-alkyl methacrylate copolymer is present from about 2 to about 8% by weight based on the weight of the total composition.
4. The composition according to claim 1, further characterized in that it comprises minus one block copolymer of the group consisting of triblock copolymers and diblock copolymers.
5. The composition according to claim 1, characterized in that it has a breaking energy greater than 40 J when a plate is hit at -30 ° C by a falling dart in accordance with ISO 6603-2.
6. The composition according to claim 1, characterized in that it has a deformation of more than 10 mm when a plate is hit at -30 ° C by a falling dart in accordance with ISO 6603-2.
7. The composition according to claim 1, further characterized in that the compatibilized mixture of polyphenylene ether-polyamide resin is compatibilized with a compatibilizing agent selected from the group consisting of maleic anhydride, fumaric acid, citric acid, malic acid and reaction products of a polyphenylene ether and trimellitic anhydride acid chloride.
8. The composition according to claim 1, further characterized in that it comprises an additive selected from the group consisting of reinforcing fiber, filler pieces, conductive black carbon, carbon fibers and carbon fibrils, stabilizers, dyes, pigments. , polyolefins, flame retardants, and mixtures thereof.
9. Articles formed by the composition according to claim 1. 26
10. - A thermoplastic composition consisting essentially of: (a) a compatibilized mixture of polyphenylene ether-polyamide resin, and (b) an alkylene-alkyl methacrylate copolymer comprising at least two portions selected from the group consisting of carboxylic acid , anhydride, epoxy, oxazoline, and orthoester; further characterized in that the alkylene alkyl methacrylate copolymer is present from about 1 to about 15% by weight, based on the weight of the total composition.
11. The composition according to claim 10, further characterized in that it consists essentially of at least one block copolymer of the group consisting of triblock copolymer and diblock copolymer.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US974940 | 1997-11-20 |
Publications (1)
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MXPA98009672A true MXPA98009672A (en) | 2000-01-01 |
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