CA1251879A - Production of melt consistent aromatic polyester - Google Patents
Production of melt consistent aromatic polyesterInfo
- Publication number
- CA1251879A CA1251879A CA000455438A CA455438A CA1251879A CA 1251879 A CA1251879 A CA 1251879A CA 000455438 A CA000455438 A CA 000455438A CA 455438 A CA455438 A CA 455438A CA 1251879 A CA1251879 A CA 1251879A
- Authority
- CA
- Canada
- Prior art keywords
- polyester
- moiety
- precursors
- metal salt
- formula vii
- 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
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 91
- 125000003118 aryl group Chemical group 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 21
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 13
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims abstract description 11
- 229910052939 potassium sulfate Inorganic materials 0.000 claims abstract description 11
- 235000011151 potassium sulphates Nutrition 0.000 claims abstract description 10
- 239000002243 precursor Substances 0.000 claims description 29
- 238000002844 melting Methods 0.000 claims description 24
- 230000008018 melting Effects 0.000 claims description 24
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkaline earth metal salt Chemical class 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 8
- 230000000306 recurrent effect Effects 0.000 claims description 8
- 238000012662 bulk polymerization Methods 0.000 claims description 7
- 238000010128 melt processing Methods 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 238000001746 injection moulding Methods 0.000 claims description 4
- IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 238000010348 incorporation Methods 0.000 abstract description 3
- 235000013350 formula milk Nutrition 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 230000014759 maintenance of location Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 230000007704 transition Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920001634 Copolyester Polymers 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- LUYZTDPLLWFWQU-UHFFFAOYSA-L magnesium;terephthalate Chemical compound [Mg+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 LUYZTDPLLWFWQU-UHFFFAOYSA-L 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JTUIDPCUTRXCPW-UHFFFAOYSA-N (6-acetyloxynaphthalen-2-yl) acetate Chemical compound C1=C(OC(C)=O)C=CC2=CC(OC(=O)C)=CC=C21 JTUIDPCUTRXCPW-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- NALNZSALNRPKIG-UHFFFAOYSA-N 2-methylpropyl 4-acetyloxybenzoate Chemical compound CC(C)COC(=O)C1=CC=C(OC(C)=O)C=C1 NALNZSALNRPKIG-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 1
- SGPZSOQUJLFTMQ-UHFFFAOYSA-N 4-o-ethyl 1-o-methyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OC)C=C1 SGPZSOQUJLFTMQ-UHFFFAOYSA-N 0.000 description 1
- WDCVVRPXMOAZLY-UHFFFAOYSA-N 5-acetyloxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(OC(=O)C)=CC=CC2=C1C(O)=O WDCVVRPXMOAZLY-UHFFFAOYSA-N 0.000 description 1
- JCJUKCIXTRWAQY-UHFFFAOYSA-N 6-hydroxynaphthalene-1-carboxylic acid Chemical compound OC1=CC=C2C(C(=O)O)=CC=CC2=C1 JCJUKCIXTRWAQY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000003332 Ilex aquifolium Nutrition 0.000 description 1
- 235000002296 Ilex sandwicensis Nutrition 0.000 description 1
- 235000002294 Ilex volkensiana Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- GUWYYXPNUUACGW-UHFFFAOYSA-N phenyl 5-hydroxynaphthalene-1-carboxylate Chemical compound C1=CC=C2C(O)=CC=CC2=C1C(=O)OC1=CC=CC=C1 GUWYYXPNUUACGW-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- C08G63/605—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds the hydroxy and carboxylic groups being bound to aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
- C08K3/105—Compounds containing metals of Groups 1 to 3 or of Groups 11 to 13 of the Periodic Table
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
-
- 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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55648583A | 1983-11-30 | 1983-11-30 | |
| US556,485 | 1983-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1251879A true CA1251879A (en) | 1989-03-28 |
Family
ID=24221522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000455438A Expired CA1251879A (en) | 1983-11-30 | 1984-05-30 | Production of melt consistent aromatic polyester |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS60120719A (fi) |
| KR (1) | KR850004967A (fi) |
| AU (1) | AU572151B2 (fi) |
| BE (1) | BE899785A (fi) |
| BR (1) | BR8403550A (fi) |
| CA (1) | CA1251879A (fi) |
| CH (1) | CH664365A5 (fi) |
| DE (1) | DE3443219A1 (fi) |
| DK (1) | DK565784A (fi) |
| ES (1) | ES534769A0 (fi) |
| FI (1) | FI842150A (fi) |
| FR (1) | FR2555592B1 (fi) |
| GB (1) | GB2150580B (fi) |
| GR (1) | GR82172B (fi) |
| IT (1) | IT1176953B (fi) |
| MA (1) | MA20146A1 (fi) |
| MX (1) | MX163260B (fi) |
| NL (1) | NL8403066A (fi) |
| NO (1) | NO164420C (fi) |
| NZ (1) | NZ208496A (fi) |
| PH (1) | PH21225A (fi) |
| PL (1) | PL250636A1 (fi) |
| PT (1) | PT79392B (fi) |
| SE (1) | SE8406043L (fi) |
| ZA (1) | ZA845247B (fi) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0311287B1 (en) * | 1987-10-05 | 1993-03-03 | Polyplastics Co. Ltd. | Resin having excellent heat resistance and exhibiting anisotropy in molten state |
| US4952663A (en) * | 1988-06-17 | 1990-08-28 | Amoco Corporation | Wholly aromatic polyesters with reduced char content |
| EP0356343A1 (en) * | 1988-07-25 | 1990-02-28 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Copolymers of poly(ethylene terephthalate) having rapid crystallization rate from the glassy state |
| IT1227902B (it) * | 1988-12-23 | 1991-05-14 | Enichem Spa | Copolimeri termotropici liquido-cristallini aromatici |
| US5397502A (en) * | 1993-06-10 | 1995-03-14 | E. I. Du Pont De Nemours And Company | Heat resistant liquid crsytalline polymers |
| DE4401055A1 (de) * | 1994-01-15 | 1995-07-20 | Basf Ag | Verfahren zur Herstellung von thermoplastischen Polyestern mit niedrigem Carboxylendgruppengehalt |
| CN1060185C (zh) * | 1995-02-21 | 2001-01-03 | Basf公司 | 低端羧基含量的热塑性聚酯的制备 |
| WO2001004196A1 (en) * | 1999-07-12 | 2001-01-18 | E.I. Du Pont De Nemours And Company | Heat resistant liquid crystalline polymer parts |
| US20040135118A1 (en) * | 2002-12-18 | 2004-07-15 | Waggoner Marion G. | Process for producing a liquid crystalline polymer |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2038287C3 (de) * | 1970-08-01 | 1974-05-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zum Herstellen von Halogen enthaltenden Polyarylestern |
| JPS4929394A (fi) * | 1972-07-19 | 1974-03-15 | ||
| US3824213A (en) * | 1973-04-16 | 1974-07-16 | Celanese Corp | Acid-interchange reaction for forming halogenated aromatic polyesters |
| DE2544069B2 (de) * | 1974-10-04 | 1979-11-15 | Teijin Ltd., Osaka (Japan) | Verfahren zur Herstellung von Polyestern |
| DE2549528A1 (de) * | 1975-11-05 | 1977-05-18 | Basf Ag | Verfahren zur herstellung sulfongruppenhaltiger polyarylate |
| JPS5935921B2 (ja) * | 1976-04-07 | 1984-08-31 | 帝人株式会社 | 芳香族ポリエステルの製造方法 |
| US4101517A (en) * | 1977-02-22 | 1978-07-18 | Monsanto Company | Preparation of polyesters of 1,2-bis(hydroxyphenyl)ethanes and aromatic dicarboxylic acids |
| JPS6050821B2 (ja) * | 1977-05-04 | 1985-11-11 | 帝人株式会社 | 共重合ポリエステル |
| US4127560A (en) * | 1977-08-08 | 1978-11-28 | Celanese Corporation | Melt polymerization process for preparing a melt processable resorcinol phthalate polyester utilizing a metal acetate catalyst |
| JPS55161821A (en) * | 1979-06-04 | 1980-12-16 | Teijin Ltd | Production of polyester having high polymerization degree |
| US4256624A (en) * | 1979-07-02 | 1981-03-17 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, aromatic diol, and aromatic diacid capable of undergoing melt processing |
| US4296232A (en) * | 1979-08-27 | 1981-10-20 | Union Carbide Corporation | Process for preparing polyarylates in the presence of a diphenyl ether compound and a catalyst |
| JPS5690829A (en) * | 1979-12-25 | 1981-07-23 | Teijin Ltd | Production of polyester |
| CA1193390A (en) * | 1980-03-10 | 1985-09-10 | Jerold C. Rosenfeld | Catalytic process for preparation of polyester of bisphenol and dicarboxylic acid by transesterification polymerization and product thereof |
| JPS5761046A (en) * | 1980-09-30 | 1982-04-13 | Asahi Chem Ind Co Ltd | Aromatic polyamide-polyester resin composition |
| US4436894A (en) * | 1980-07-31 | 1984-03-13 | Teijin Limited | Novel wholly aromatic copolyester, process for production thereof, and film melt-shaped therefrom |
| US4321355A (en) * | 1980-09-23 | 1982-03-23 | Union Carbide Corporation | Process for preparing polyarylates |
| US4318841A (en) * | 1980-10-06 | 1982-03-09 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, para-hydroxy benzoic acid, terephthalic acid, and resorcinol capable of readily undergoing melt processing to form shaped articles having increased impact strength |
| GB2085458A (en) * | 1980-10-21 | 1982-04-28 | Hooker Chemicals Plastics Corp | Production of linear aromatic polyester |
| US4355133A (en) * | 1981-07-27 | 1982-10-19 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, 4-hydroxy benzoic acid, 1,4-cyclohexanedicarboxylic acid, and aromatic diol capable of readily undergoing melt processing to form articles possessing high impact properties |
| DE3365960D1 (en) * | 1982-03-04 | 1986-10-16 | Monsanto Co | Liquid crystal copolyesters |
| CA1220889A (en) * | 1982-06-08 | 1987-04-21 | Dart Industries Inc. | Process for the production of aromatic polyesters |
-
1984
- 1984-05-29 FI FI842150A patent/FI842150A/fi not_active Application Discontinuation
- 1984-05-29 BE BE0/213032A patent/BE899785A/fr not_active IP Right Cessation
- 1984-05-30 CA CA000455438A patent/CA1251879A/en not_active Expired
- 1984-06-01 AU AU28947/84A patent/AU572151B2/en not_active Ceased
- 1984-06-11 MA MA20370A patent/MA20146A1/fr unknown
- 1984-06-13 NZ NZ208496A patent/NZ208496A/en unknown
- 1984-06-15 KR KR1019840003360A patent/KR850004967A/ko not_active Application Discontinuation
- 1984-06-18 MX MX201701A patent/MX163260B/es unknown
- 1984-06-22 GR GR75091A patent/GR82172B/el unknown
- 1984-06-26 NO NO842580A patent/NO164420C/no unknown
- 1984-06-27 GB GB08416337A patent/GB2150580B/en not_active Expired
- 1984-07-06 ZA ZA845247A patent/ZA845247B/xx unknown
- 1984-07-16 PH PH30990A patent/PH21225A/en unknown
- 1984-07-17 BR BR8403550A patent/BR8403550A/pt unknown
- 1984-07-31 ES ES534769A patent/ES534769A0/es active Granted
- 1984-07-31 JP JP59159449A patent/JPS60120719A/ja active Granted
- 1984-10-09 NL NL8403066A patent/NL8403066A/nl not_active Application Discontinuation
- 1984-10-12 IT IT23133/84A patent/IT1176953B/it active
- 1984-10-23 PT PT79392A patent/PT79392B/pt unknown
- 1984-11-27 DE DE19843443219 patent/DE3443219A1/de not_active Ceased
- 1984-11-28 CH CH5682/84A patent/CH664365A5/de not_active IP Right Cessation
- 1984-11-29 DK DK565784A patent/DK565784A/da not_active Application Discontinuation
- 1984-11-29 SE SE8406043A patent/SE8406043L/xx not_active Application Discontinuation
- 1984-11-29 FR FR8418200A patent/FR2555592B1/fr not_active Expired
- 1984-11-29 PL PL25063684A patent/PL250636A1/xx unknown
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