NZ208496A - Preparation of wholly aromatic polyesters having reproducible melting and crystallisation tempratures - Google Patents

Preparation of wholly aromatic polyesters having reproducible melting and crystallisation tempratures

Info

Publication number: NZ208496A
Authority: NZ; New Zealand
Prior art keywords: polyester; wholly aromatic; precursors; metal salt; acid
Prior art date: 1983-11-30

Application number

NZ208496A

Other languages

English (en)

Inventor

A B Finestone

Original Assignee

Dart Ind Inc

Priority date (The priority date 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 date listed.)

1983-11-30

Filing date

1984-06-13

Publication date

1987-04-30

1984-06-13 Application filed by Dart Ind Inc filed Critical Dart Ind Inc

1987-04-30 Publication of NZ208496A publication Critical patent/NZ208496A/en

Links

229920000728 polyester Polymers 0.000 title claims description 46
125000003118 aryl group Chemical group 0.000 title claims description 16
238000002844 melting Methods 0.000 title claims description 8
230000008018 melting Effects 0.000 title claims description 8
238000002425 crystallisation Methods 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 2
238000000034 method Methods 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 27
230000008569 process Effects 0.000 claims description 26
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
229910052939 potassium sulfate Inorganic materials 0.000 claims description 10
229920000642 polymer Polymers 0.000 claims description 9
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical group [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 9
235000011151 potassium sulphates Nutrition 0.000 claims description 9
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 7
-1 alkaline earth metal salt Chemical class 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
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 4
238000012662 bulk polymerization Methods 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
238000006116 polymerization reaction Methods 0.000 claims description 4
230000008025 crystallization Effects 0.000 claims description 3
IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
150000008065 acid anhydrides Chemical class 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
238000000375 direct analysis in real time Methods 0.000 claims description 2
238000012063 dual-affinity re-targeting Methods 0.000 claims description 2
229910017053 inorganic salt Inorganic materials 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000002243 precursor Substances 0.000 claims 6
238000001746 injection moulding Methods 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
238000002347 injection Methods 0.000 claims 1
239000007924 injection Substances 0.000 claims 1
229910052749 magnesium Inorganic materials 0.000 claims 1
239000011777 magnesium Substances 0.000 claims 1
238000010128 melt processing Methods 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
238000004519 manufacturing process Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
230000014759 maintenance of location Effects 0.000 description 8
230000007704 transition Effects 0.000 description 7
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
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
229940090248 4-hydroxybenzoic acid Drugs 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
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
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 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
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
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 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
230000015572 biosynthetic process Effects 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
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
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000010348 incorporation Methods 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
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
235000011285 magnesium acetate Nutrition 0.000 description 2
239000011654 magnesium acetate Substances 0.000 description 2
229940069446 magnesium acetate Drugs 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
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 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
239000000376 reactant Substances 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
238000003786 synthesis reaction Methods 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
GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-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
150000005168 4-hydroxybenzoic acids Chemical class 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
ZSJQOUZCZSWXAM-UHFFFAOYSA-N 7,9-dihydro-3h-purine-2,6,8-trione;hydrochloride Chemical compound Cl.N1C(=O)NC(=O)C2=C1NC(=O)N2 ZSJQOUZCZSWXAM-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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
235000006629 Prosopis spicigera Nutrition 0.000 description 1
240000000037 Prosopis spicigera Species 0.000 description 1
HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 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
125000003545 alkoxy group Chemical group 0.000 description 1
229940009827 aluminum acetate Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
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
150000001875 compounds Chemical class 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
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
150000002148 esters Chemical class 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
150000002431 hydrogen Chemical group 0.000 description 1
238000007689 inspection Methods 0.000 description 1
230000002452 interceptive effect Effects 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
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
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 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
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 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
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 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
238000010557 suspension polymerization 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)

NZ208496A 1983-11-30 1984-06-13 Preparation of wholly aromatic polyesters having reproducible melting and crystallisation tempratures NZ208496A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US55648583A	1983-11-30	1983-11-30

Publications (1)

Publication Number	Publication Date
NZ208496A true NZ208496A (en)	1987-04-30

Family

ID=24221522

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ208496A NZ208496A (en)	1983-11-30	1984-06-13	Preparation of wholly aromatic polyesters having reproducible melting and crystallisation tempratures

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)

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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

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* Cited by examiner, † Cited by third party
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

Also Published As

Publication number	Publication date
GB2150580A (en)	1985-07-03
MA20146A1 (fr)	1984-12-31
FR2555592B1 (fr)	1988-10-07
BE899785A (fr)	1984-09-17
SE8406043L (sv)	1985-05-31
CH664365A5 (de)	1988-02-29
FI842150A (fi)	1985-05-31
SE8406043D0 (sv)	1984-11-29
ZA845247B (en)	1985-02-27
BR8403550A (pt)	1985-07-02
DE3443219A1 (de)	1985-10-24
IT1176953B (it)	1987-08-26
AU2894784A (en)	1985-06-06
PT79392A (en)	1984-11-01
KR850004967A (ko)	1985-08-19
PT79392B (en)	1986-09-08
CA1251879A (en)	1989-03-28
JPH0532415B2 (fi)	1993-05-17
NO842580L (no)	1985-05-31
FR2555592A1 (fr)	1985-05-31
AU572151B2 (en)	1988-05-05
NO164420C (no)	1990-10-03
JPS60120719A (ja)	1985-06-28
DK565784A (da)	1985-05-31
PL250636A1 (en)	1985-07-30
NO164420B (no)	1990-06-25
GB2150580B (en)	1987-10-21
GR82172B (fi)	1984-12-13
ES8505705A1 (es)	1985-06-01
DK565784D0 (da)	1984-11-29
MX163260B (es)	1992-03-26
NL8403066A (nl)	1985-06-17
PH21225A (en)	1987-08-21
ES534769A0 (es)	1985-06-01
IT8423133A0 (it)	1984-10-12
GB8416337D0 (en)	1984-08-01
FI842150A0 (fi)	1984-05-29

Publication	Publication Date	Title
US4742149A (en)	1988-05-03	Production of melt consistent aromatic polyesters
EP0286444A2 (en)	1988-10-12	Process for producing a liquid crystalline polyester of a cyclohexanedicarboxylic acid and an aromatic diol
US4849499A (en)	1989-07-18	Melt processable, liquid crystalline polyesters
US4639504A (en)	1987-01-27	Production of thermally stabilized aromatic polyesters
JPS6357633A (ja)	1988-03-12	全芳香族熱互変性ポリエステル
NZ208496A (en)	1987-04-30	Preparation of wholly aromatic polyesters having reproducible melting and crystallisation tempratures
CA1096995A (en)	1981-03-03	Thermoplastic copolyesters
JPH04494B2 (fi)	1992-01-07
JPH02226A (ja)	1990-01-05	サーモトロピック液晶芳香族エステル類
JPS62132923A (ja)	1987-06-16	新規な全芳香族ポリエステルカルバミド及びその製法
CA1220889A (en)	1987-04-21	Process for the production of aromatic polyesters
EP0376380A1 (en)	1990-07-04	Polymer processeable from the melt
US4746566A (en)	1988-05-24	Optically anisotropic melt forming aromatic copolyesters based on t-butyl-4-hydroxybenzoic acid
Hussain et al.	2019	Single-step solution polymerization and thermal properties of copolyesters based on high trans-1, 4-cyclohexanedimethanol, terephthaloyl dichloride, and 2, 6-naphthalene dicarboxylic chloride
CA2159404A1 (en)	1996-12-06	Process for producing liquid crystal polymer
CA1101596A (en)	1981-05-19	Thermoplastic polyesters
JPS62135523A (ja)	1987-06-18	液晶質の完全芳香族重縮合体及びその製法
JP3077854B2 (ja)	2000-08-21	芳香族コポリエステル
JP3077852B2 (ja)	2000-08-21	芳香族コポリエステル
JP3077833B2 (ja)	2000-08-21	芳香族コポリエステル
JPH07188403A (ja)	1995-07-25	液晶性ポリエステル
JPH02629A (ja)	1990-01-05	スピロビインダンポリアリーレートーポリエステルコポリマー，製造方法
JP2565792B2 (ja)	1996-12-18	芳香族コポリエステル
JP3227856B2 (ja)	2001-11-12	芳香族コポリエステルアミド
JPH07304862A (ja)	1995-11-21	液晶性ポリエステルの製造方法