CA2068497C - Hydroxy-functional polyesters as thermoplastic barrier resins - Google Patents
Hydroxy-functional polyesters as thermoplastic barrier resins Download PDFInfo
- Publication number
- CA2068497C CA2068497C CA002068497A CA2068497A CA2068497C CA 2068497 C CA2068497 C CA 2068497C CA 002068497 A CA002068497 A CA 002068497A CA 2068497 A CA2068497 A CA 2068497A CA 2068497 C CA2068497 C CA 2068497C
- Authority
- CA
- Canada
- Prior art keywords
- phenylene
- polyester
- polymer
- individually
- isopropylidene
- 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 43
- 230000004888 barrier function Effects 0.000 title claims abstract description 18
- 229920001169 thermoplastic Polymers 0.000 title claims description 16
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 12
- 229920005989 resin Polymers 0.000 title description 4
- 239000011347 resin Substances 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 methylol moieties Chemical group 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 2
- GRZXREUFTYRRJH-UHFFFAOYSA-N 10-oxatetracyclo[6.5.0.02,7.09,11]trideca-1,3,5,7,12-pentaene Chemical compound C12=CC=CC=C2C2=C1C1OC1C=C2 GRZXREUFTYRRJH-UHFFFAOYSA-N 0.000 claims 1
- HXROKIMWMCMCOF-UHFFFAOYSA-N 10-thiatetracyclo[6.5.0.02,7.09,11]trideca-1,3,5,7,12-pentaene Chemical compound C12=CC=CC=C2C2=C1C1SC1C=C2 HXROKIMWMCMCOF-UHFFFAOYSA-N 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 11
- 239000001301 oxygen Substances 0.000 abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 abstract description 11
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- 150000002989 phenols Chemical class 0.000 abstract description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract description 3
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 239000008896 Opium Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229960001027 opium Drugs 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DJCYQEDZXFZHRL-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)peroxyphenol Chemical compound OC1=CC=CC=C1OOOC1=CC=CC=C1O DJCYQEDZXFZHRL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000010102 injection blow moulding Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003442 suberic acids Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920006230 thermoplastic polyester resin Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy 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)
- Containers Having Bodies Formed In One Piece (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/699,046 US5171820A (en) | 1991-05-13 | 1991-05-13 | Hydroxy-functional polyesters as thermoplastic barrier resins |
| US699,046 | 1991-05-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2068497A1 CA2068497A1 (en) | 1992-11-14 |
| CA2068497C true CA2068497C (en) | 2003-11-18 |
Family
ID=24807712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002068497A Expired - Fee Related CA2068497C (en) | 1991-05-13 | 1992-05-12 | Hydroxy-functional polyesters as thermoplastic barrier resins |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5171820A (enExample) |
| EP (1) | EP0513679B1 (enExample) |
| JP (1) | JP3207921B2 (enExample) |
| KR (1) | KR100208921B1 (enExample) |
| AU (1) | AU643173B2 (enExample) |
| CA (1) | CA2068497C (enExample) |
| DE (1) | DE69231139T2 (enExample) |
| ES (1) | ES2147179T3 (enExample) |
| TW (1) | TW206974B (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5814373A (en) * | 1991-11-26 | 1998-09-29 | Dow Chemical Company | Heat-resistant hydroxy-functional polyethers as thermoplastic barrier resins |
| US5458258A (en) * | 1993-09-02 | 1995-10-17 | The Dow Chemical Company | Storage tanks for compressed natural gas with a hydroxy-phenoxyether polymer barrier liner |
| US5386002A (en) * | 1993-12-03 | 1995-01-31 | The Dow Chemical Company | Fluorene based bisimides and thermoplastic polymers thereof |
| US5686551A (en) * | 1994-01-07 | 1997-11-11 | The Dow Chemical Company | Hydroxy ether polymers as thermoplastic barrier resins |
| US5496910A (en) * | 1994-07-21 | 1996-03-05 | The Dow Chemical Company | Hydroxyfunctional thermoplastic polyesters |
| US5574076A (en) * | 1995-05-03 | 1996-11-12 | National Starch And Chemical Investment Holding Corporation | Sucrose benzoate as a tackifier for water sensitive or biodegradable hot melt adhesives |
| US5583187A (en) * | 1995-05-03 | 1996-12-10 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives based on hydroxy-functional polyesters |
| CN1207755A (zh) * | 1995-12-21 | 1999-02-10 | 陶氏化学公司 | 含有羟基官能聚合物的组合物 |
| US5861216A (en) * | 1996-06-28 | 1999-01-19 | The United States Of America As Represented By The Secretary Of Agriculture | Biodegradable polyester and natural polymer laminates |
| US5852078A (en) * | 1996-02-28 | 1998-12-22 | The United States Of America As Represented By The Secretary Of Agriculture | Biodegradable polyester compositions with natural polymers and articles thereof |
| US5665786A (en) * | 1996-05-24 | 1997-09-09 | Bradley University | Biodegradable polyester and natural polymer compositions and expanded articles therefrom |
| US6025417A (en) * | 1996-02-28 | 2000-02-15 | Biotechnology Research & Development Corp. | Biodegradable polyester compositions with natural polymers and articles thereof |
| US5821286A (en) * | 1996-05-24 | 1998-10-13 | The United States Of America As Represented By The Secretary Of The Agriculture | Biodegradable polyester and natural polymer compositions and films therefrom |
| US6893527B1 (en) | 1996-06-28 | 2005-05-17 | William M. Doane | Biodegradable polyester and natural polymer laminates |
| CA2246269A1 (en) * | 1996-12-31 | 1998-07-09 | Jerry E. White | Polymer-organoclay-composites and their preparation |
| US5780582A (en) * | 1996-12-31 | 1998-07-14 | The Dow Chemical Company | Hydroxy-functionalized polyester and poly(ester ether) oligomers |
| CN1108333C (zh) * | 1997-09-05 | 2003-05-14 | 陶氏化学公司 | 含羟基官能团聚合物的高内相比乳液和稳定水分散体 |
| US5852163A (en) * | 1997-09-10 | 1998-12-22 | The Dow Chemical Company | Process for preparing hydroxy-functionalized polyesters |
| US6352426B1 (en) | 1998-03-19 | 2002-03-05 | Advanced Plastics Technologies, Ltd. | Mold for injection molding multilayer preforms |
| WO1999048962A1 (en) * | 1998-03-20 | 1999-09-30 | The Dow Chemical Company | Polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler and method for preparing the same |
| US5962621A (en) * | 1998-04-28 | 1999-10-05 | The Dow Chemical Company | Process for preparing hydroxy-functionalized polyesters |
| US6630543B1 (en) | 1998-08-21 | 2003-10-07 | Biotechnology Research And Development Corporation | Method of making biodegradable polymer compositions |
| WO2000055250A1 (en) | 1999-03-12 | 2000-09-21 | The Dow Chemical Company | Process for preparing starch and epoxy-based thermoplastic polymer compositions |
| US6632862B2 (en) | 1999-04-12 | 2003-10-14 | The United States Of America As Represented By The Secretary Of Agriculture | Biodegradable polymer compositions, methods for making same, and articles therefrom |
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| US3477990A (en) * | 1967-12-07 | 1969-11-11 | Shell Oil Co | Process for reacting a phenol with an epoxy compound and resulting products |
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| DE3409188A1 (de) * | 1984-03-14 | 1985-09-19 | Basf Farben + Fasern Ag, 2000 Hamburg | Mit alkoholen modifizierte polyepoxide, ihre herstellung und verwendung in haertbaren mischungen |
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1991
- 1991-05-13 US US07/699,046 patent/US5171820A/en not_active Expired - Lifetime
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1992
- 1992-05-08 EP EP92107770A patent/EP0513679B1/en not_active Expired - Lifetime
- 1992-05-08 DE DE69231139T patent/DE69231139T2/de not_active Expired - Fee Related
- 1992-05-08 ES ES92107770T patent/ES2147179T3/es not_active Expired - Lifetime
- 1992-05-12 JP JP11859292A patent/JP3207921B2/ja not_active Expired - Fee Related
- 1992-05-12 KR KR1019920007967A patent/KR100208921B1/ko not_active Expired - Fee Related
- 1992-05-12 AU AU16181/92A patent/AU643173B2/en not_active Ceased
- 1992-05-12 CA CA002068497A patent/CA2068497C/en not_active Expired - Fee Related
- 1992-05-12 TW TW081103677A patent/TW206974B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0513679B1 (en) | 2000-06-07 |
| KR100208921B1 (ko) | 1999-07-15 |
| US5171820A (en) | 1992-12-15 |
| JPH05306332A (ja) | 1993-11-19 |
| ES2147179T3 (es) | 2000-09-01 |
| JP3207921B2 (ja) | 2001-09-10 |
| AU643173B2 (en) | 1993-11-04 |
| DE69231139T2 (de) | 2000-12-14 |
| CA2068497A1 (en) | 1992-11-14 |
| AU1618192A (en) | 1992-11-19 |
| TW206974B (enExample) | 1993-06-01 |
| KR920021619A (ko) | 1992-12-18 |
| EP0513679A3 (en) | 1994-10-26 |
| DE69231139D1 (de) | 2000-07-13 |
| EP0513679A2 (en) | 1992-11-19 |
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