CA2695466C - Phosphite stabilizers for ionomeric polyester compounds - Google Patents
Phosphite stabilizers for ionomeric polyester compounds Download PDFInfo
- Publication number
- CA2695466C CA2695466C CA2695466A CA2695466A CA2695466C CA 2695466 C CA2695466 C CA 2695466C CA 2695466 A CA2695466 A CA 2695466A CA 2695466 A CA2695466 A CA 2695466A CA 2695466 C CA2695466 C CA 2695466C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- acid
- polyester
- polymer
- ionomeric
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 104
- 239000003381 stabilizer Substances 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 title description 18
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 47
- 239000011574 phosphorus Substances 0.000 claims abstract description 47
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims description 108
- 229910052751 metal Inorganic materials 0.000 claims description 79
- 239000002184 metal Substances 0.000 claims description 79
- -1 phosphorus compound Chemical class 0.000 claims description 58
- 239000004952 Polyamide Substances 0.000 claims description 42
- 229920002647 polyamide Polymers 0.000 claims description 42
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 38
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 32
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000011800 void material Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 5
- IWEATXLWFWACOA-UHFFFAOYSA-N 2,6-dimethylnaphthalene-1-carboxylic acid Chemical compound OC(=O)C1=C(C)C=CC2=CC(C)=CC=C21 IWEATXLWFWACOA-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 61
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 20
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 16
- YESSCOKKOLMTNS-UHFFFAOYSA-L dilithium;2-sulfobenzene-1,3-dicarboxylate Chemical group [Li+].[Li+].OS(=O)(=O)C1=C(C([O-])=O)C=CC=C1C([O-])=O YESSCOKKOLMTNS-UHFFFAOYSA-L 0.000 description 15
- 239000005020 polyethylene terephthalate Substances 0.000 description 15
- ZJSXTJPARZJENS-UHFFFAOYSA-N lithium;2-sulfobenzene-1,3-dicarboxylic acid Chemical compound [Li].OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O ZJSXTJPARZJENS-UHFFFAOYSA-N 0.000 description 14
- 229910052744 lithium Inorganic materials 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 9
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Chemical group 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 150000003018 phosphorus compounds Chemical class 0.000 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 description 4
- 239000011135 tin Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
- 229960002684 aminocaproic acid Drugs 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- YWJNJZBDYHRABW-UHFFFAOYSA-N 2,4-dihydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(O)C(C(O)=O)=C1O YWJNJZBDYHRABW-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940045996 isethionic acid Drugs 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- 150000002531 isophthalic acids Chemical class 0.000 description 2
- SOTMTGOXKALQPI-UHFFFAOYSA-N lithium;2-sulfobenzoic acid Chemical compound [Li].OC(=O)C1=CC=CC=C1S(O)(=O)=O SOTMTGOXKALQPI-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WRETZZGIXMFJOQ-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid;lithium Chemical compound [Li].OC1=CC=CC=C1S(O)(=O)=O WRETZZGIXMFJOQ-UHFFFAOYSA-N 0.000 description 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical class CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101000576320 Homo sapiens Max-binding protein MNT Proteins 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920000007 Nylon MXD6 Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920006121 Polyxylylene adipamide Polymers 0.000 description 1
- 229910006145 SO3Li Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OAOXPQKIXSVSRH-UHFFFAOYSA-N butanedioic acid;propanedioic acid Chemical compound OC(=O)CC(O)=O.OC(=O)CCC(O)=O OAOXPQKIXSVSRH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 150000001923 cyclic compounds Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- C08L69/005—Polyester-carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95770507P | 2007-08-23 | 2007-08-23 | |
| US60/957,705 | 2007-08-23 | ||
| US9074408P | 2008-08-21 | 2008-08-21 | |
| US9086408P | 2008-08-21 | 2008-08-21 | |
| US61/090,864 | 2008-08-21 | ||
| US61/090,744 | 2008-08-21 | ||
| PCT/US2008/074092 WO2009026555A1 (en) | 2007-08-23 | 2008-08-22 | Phosphite stabilizers for ionomeric polyester compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2695466A1 CA2695466A1 (en) | 2009-02-26 |
| CA2695466C true CA2695466C (en) | 2016-06-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2695466A Expired - Fee Related CA2695466C (en) | 2007-08-23 | 2008-08-22 | Phosphite stabilizers for ionomeric polyester compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US20090054567A1 (enExample) |
| EP (1) | EP2181152B1 (enExample) |
| JP (1) | JP5264909B2 (enExample) |
| KR (1) | KR101524118B1 (enExample) |
| CN (1) | CN101784598A (enExample) |
| AU (1) | AU2008288788B2 (enExample) |
| BR (1) | BRPI0815299B1 (enExample) |
| CA (1) | CA2695466C (enExample) |
| MX (1) | MX2010002103A (enExample) |
| RU (1) | RU2480493C2 (enExample) |
| WO (1) | WO2009026555A1 (enExample) |
| ZA (1) | ZA201000481B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090054567A1 (en) * | 2007-08-23 | 2009-02-26 | Heater Paul Lewis | Phosphite stabilizers for ionomeric polyester compounds |
| KR20120014889A (ko) * | 2009-03-13 | 2012-02-20 | 바스프 에스이 | 폴리에스테르 및 폴리아미드의 안정화된 블렌드 |
| CN102348761A (zh) * | 2009-03-13 | 2012-02-08 | 巴斯夫欧洲公司 | 聚酯和聚酰胺的稳定共混物 |
| WO2011049940A2 (en) | 2009-10-20 | 2011-04-28 | Futurefuel Chemical Company | Use of an acetic acid/water solvent mixture for the preparation of low-sulfate 5-sulfoisophthalic acid, mono-lithium salt from 5-sulfoisophthalic acid |
| EP2681225A4 (en) | 2011-03-02 | 2014-08-06 | Futurefuel Chemical Co | METALLIC SALTS OF SULFO-5-ISOPHTHALIC ACID DIALKYL ESTER AND PROCESS FOR PRODUCTION THEREOF |
| WO2013025784A2 (en) * | 2011-08-16 | 2013-02-21 | Oster Timothy | Salts of 5-sulfoisophthalic acid and method of making same |
| US8809565B2 (en) | 2011-08-29 | 2014-08-19 | Futurefuel Chemical Company | 5-sulfoisophthalic acid salts and process for the preparation thereof |
| AU2016205389B2 (en) | 2015-01-06 | 2019-09-12 | Lawter, Inc. | Polyamide resins for coating of sand or ceramic proppants used in hydraulic fracturing |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50105755A (enExample) * | 1974-01-28 | 1975-08-20 | ||
| US4680371A (en) * | 1986-02-25 | 1987-07-14 | Celanese Corporation | Preparation of aromatic polyester with improved stability by addition of phosphite during preparation |
| AU628651B2 (en) * | 1989-10-13 | 1992-09-17 | Idemitsu Kosan Co. Ltd | Styrene polymer composition |
| US5138024A (en) * | 1991-01-25 | 1992-08-11 | Eastman Kodak Company | Modified polyester useful as photographic roll film support |
| US5296550A (en) * | 1991-11-01 | 1994-03-22 | Enichem S.P.A. | Impact modified polyester blends with improved polymer compatibility |
| TW297822B (enExample) * | 1994-04-13 | 1997-02-11 | Ciba Geigy Ag | |
| US6066694A (en) * | 1998-03-04 | 2000-05-23 | General Electric Company | Polyester molding composition |
| US6300405B2 (en) * | 1998-06-30 | 2001-10-09 | General Electric Company | Polyester molding composition |
| US6437054B1 (en) * | 1999-02-17 | 2002-08-20 | General Electric Company | Composition of polyester sulfonate salt ionomer, polyamide and polyepoxide |
| US6001910A (en) * | 1999-04-09 | 1999-12-14 | National Starch And Chemical Investment Holding Corporation | Use of anionic or cationic plasticizers with sulfonated polyesters in hot melt formulations |
| US6500895B1 (en) * | 2000-10-13 | 2002-12-31 | General Electric Company | Thermoplastic blend comprising poly(arylene ether) and polyamide |
| JP2002294056A (ja) * | 2001-01-25 | 2002-10-09 | Mitsubishi Chemicals Corp | ポリエステル樹脂組成物及びそれからなる射出ブローボトル |
| US6908650B2 (en) * | 2001-03-02 | 2005-06-21 | Ciba Specialty Chemicals Corporation | Polyester and polyamide compositions of low residual aldehyde content |
| US6479619B1 (en) * | 2001-03-15 | 2002-11-12 | E. I. Du Pont De Nemours And Company | Sulfoisophthalic acid solution process therewith |
| US20020173591A1 (en) * | 2001-04-06 | 2002-11-21 | Chisholm Bert Ja | Polyester polyamide molding composition |
| WO2003080731A2 (en) | 2002-03-21 | 2003-10-02 | Advanced Plastics Technologies, Ltd. | Compatibilized polyester/polyamide blends |
| JP4256754B2 (ja) * | 2002-09-27 | 2009-04-22 | 富士フイルム株式会社 | ポリエステル樹脂組成物 |
| JP4677726B2 (ja) * | 2004-03-01 | 2011-04-27 | 東レ株式会社 | ポリエステル組成物及びそれからなる繊維 |
| CA2565922C (en) * | 2004-05-18 | 2013-02-19 | M & G Polimeri Italia S.P.A. | Compartmentalized resin pellets |
| US8465818B2 (en) * | 2005-10-07 | 2013-06-18 | M & G Usa Corporation | Polyamides and polyesters blended with a lithium salt interfacial tension reducing agent |
| WO2007049233A1 (en) * | 2005-10-25 | 2007-05-03 | M & G Polimeri Italia S.P.A. | Stable polyamides for simultaneous solid phase polymerization of polyesters and polyamides |
| US20070135586A1 (en) * | 2005-12-09 | 2007-06-14 | Shreyas Chakravarti | Polyamide blend compositions formed article and process thereof |
| US20080076841A1 (en) * | 2006-09-11 | 2008-03-27 | Graham Packaging Company, Lp | Phosphorous containing reprocessed polymer materials, articles formed thereof, and methods of forming such articles |
| US20090054567A1 (en) * | 2007-08-23 | 2009-02-26 | Heater Paul Lewis | Phosphite stabilizers for ionomeric polyester compounds |
-
2008
- 2008-08-22 US US12/196,499 patent/US20090054567A1/en not_active Abandoned
- 2008-08-22 JP JP2010522082A patent/JP5264909B2/ja not_active Expired - Fee Related
- 2008-08-22 AU AU2008288788A patent/AU2008288788B2/en not_active Ceased
- 2008-08-22 BR BRPI0815299-3A patent/BRPI0815299B1/pt not_active IP Right Cessation
- 2008-08-22 US US12/196,441 patent/US8436080B2/en active Active
- 2008-08-22 CA CA2695466A patent/CA2695466C/en not_active Expired - Fee Related
- 2008-08-22 MX MX2010002103A patent/MX2010002103A/es active IP Right Grant
- 2008-08-22 CN CN200880104049A patent/CN101784598A/zh active Pending
- 2008-08-22 WO PCT/US2008/074092 patent/WO2009026555A1/en not_active Ceased
- 2008-08-22 EP EP08798545.3A patent/EP2181152B1/en not_active Not-in-force
- 2008-08-22 KR KR1020107006328A patent/KR101524118B1/ko not_active Expired - Fee Related
- 2008-08-22 RU RU2010110807/05A patent/RU2480493C2/ru active
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2010
- 2010-01-21 ZA ZA2010/00481A patent/ZA201000481B/en unknown
- 2010-11-11 US US12/944,065 patent/US8063124B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20110057349A1 (en) | 2011-03-10 |
| KR20100080898A (ko) | 2010-07-13 |
| WO2009026555A1 (en) | 2009-02-26 |
| ZA201000481B (en) | 2011-03-30 |
| BRPI0815299A8 (pt) | 2017-10-10 |
| JP2010537007A (ja) | 2010-12-02 |
| AU2008288788A1 (en) | 2009-02-26 |
| KR101524118B1 (ko) | 2015-05-29 |
| US8063124B2 (en) | 2011-11-22 |
| JP5264909B2 (ja) | 2013-08-14 |
| CN101784598A (zh) | 2010-07-21 |
| RU2480493C2 (ru) | 2013-04-27 |
| CA2695466A1 (en) | 2009-02-26 |
| MX2010002103A (es) | 2010-03-26 |
| US20090054601A1 (en) | 2009-02-26 |
| US8436080B2 (en) | 2013-05-07 |
| EP2181152B1 (en) | 2013-10-30 |
| RU2010110807A (ru) | 2011-09-27 |
| AU2008288788B2 (en) | 2013-07-04 |
| US20090054567A1 (en) | 2009-02-26 |
| BRPI0815299B1 (pt) | 2019-07-09 |
| EP2181152A1 (en) | 2010-05-05 |
| BRPI0815299A2 (pt) | 2017-08-01 |
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