PL93248B1 - - Google Patents
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- Publication number
- PL93248B1 PL93248B1 PL18010475A PL18010475A PL93248B1 PL 93248 B1 PL93248 B1 PL 93248B1 PL 18010475 A PL18010475 A PL 18010475A PL 18010475 A PL18010475 A PL 18010475A PL 93248 B1 PL93248 B1 PL 93248B1
- Authority
- PL
- Poland
- Prior art keywords
- koh
- acids
- weight
- alcohols
- mixture
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- -1 aliphatic dicarboxylic acids Chemical class 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000000137 annealing Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 229920002601 oligoester Polymers 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 150000001261 hydroxy acids Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical class CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL18010475A PL93248B1 (enExample) | 1975-05-02 | 1975-05-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL18010475A PL93248B1 (enExample) | 1975-05-02 | 1975-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL93248B1 true PL93248B1 (enExample) | 1977-05-30 |
Family
ID=19971940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL18010475A PL93248B1 (enExample) | 1975-05-02 | 1975-05-02 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL93248B1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130042659A1 (en) * | 2011-06-13 | 2013-02-21 | Invista North America S.A R.L | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
| US9982089B2 (en) | 2014-04-01 | 2018-05-29 | Chemenergia Korzeniowski Waclaw | Method of manufacturing polyester resins |
| PL423453A1 (pl) * | 2017-11-15 | 2019-05-20 | Pcc Mcaa Spolka Z Ograniczona Odpowiedzialnoscia | Sposób otrzymywania nisko- i/lub średniocząsteczkowych polimerowych związków powierzchniowo-czynnych o określonej równowadze hydrofilowo-lipofilowej |
-
1975
- 1975-05-02 PL PL18010475A patent/PL93248B1/pl unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130042659A1 (en) * | 2011-06-13 | 2013-02-21 | Invista North America S.A R.L | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
| US9056940B2 (en) * | 2011-06-13 | 2015-06-16 | Invista North America S.A R. L. | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
| US9982089B2 (en) | 2014-04-01 | 2018-05-29 | Chemenergia Korzeniowski Waclaw | Method of manufacturing polyester resins |
| PL423453A1 (pl) * | 2017-11-15 | 2019-05-20 | Pcc Mcaa Spolka Z Ograniczona Odpowiedzialnoscia | Sposób otrzymywania nisko- i/lub średniocząsteczkowych polimerowych związków powierzchniowo-czynnych o określonej równowadze hydrofilowo-lipofilowej |
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