CA1053694A - Polyesters soufres et leurs applications - Google Patents
Polyesters soufres et leurs applicationsInfo
- Publication number
- CA1053694A CA1053694A CA214,307A CA214307A CA1053694A CA 1053694 A CA1053694 A CA 1053694A CA 214307 A CA214307 A CA 214307A CA 1053694 A CA1053694 A CA 1053694A
- Authority
- CA
- Canada
- Prior art keywords
- polyester
- acid
- polyacid
- sulfur
- group
- 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 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000005864 Sulphur Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 229920001021 polysulfide Polymers 0.000 claims abstract description 27
- 229920006295 polythiol Polymers 0.000 claims abstract description 20
- 239000011593 sulfur Substances 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 27
- 239000010426 asphalt Substances 0.000 claims description 21
- 239000005077 polysulfide Substances 0.000 claims description 20
- 150000008117 polysulfides Polymers 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 150000002148 esters Chemical group 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000013638 trimer Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 238000005987 sulfurization reaction Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000011269 tar Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 239000011295 pitch Substances 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 150000005691 triesters Chemical class 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 4
- 239000000565 sealant Substances 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- -1 dithiol diesters Chemical class 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005213 imbibition Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 150000008116 organic polysulfides Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- HKNNAYPWWDWHFR-UHFFFAOYSA-N 1-sulfanylbutan-1-ol Chemical compound CCCC(O)S HKNNAYPWWDWHFR-UHFFFAOYSA-N 0.000 description 1
- ILWVAHWMSULXIG-UHFFFAOYSA-N 1-sulfanyloctan-1-ol Chemical class CCCCCCCC(O)S ILWVAHWMSULXIG-UHFFFAOYSA-N 0.000 description 1
- AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 description 1
- MEAHFJBYWLCGDM-UHFFFAOYSA-N 2-pentadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCC(C(O)=O)C(O)=O MEAHFJBYWLCGDM-UHFFFAOYSA-N 0.000 description 1
- KORUJGYFKIIFGA-UHFFFAOYSA-N 2-tricosylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C(O)=O)C(O)=O KORUJGYFKIIFGA-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- GXFFCJFXZPEAKI-UHFFFAOYSA-N decane-1,1,1-tricarboxylic acid Chemical compound CCCCCCCCCC(C(O)=O)(C(O)=O)C(O)=O GXFFCJFXZPEAKI-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical class CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/14—Polysulfides
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/26—Polythioesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/04—Polysulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7341558A FR2252363B1 (ja) | 1973-11-22 | 1973-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053694A true CA1053694A (fr) | 1979-05-01 |
Family
ID=9128095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA214,307A Expired CA1053694A (fr) | 1973-11-22 | 1974-11-21 | Polyesters soufres et leurs applications |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5093916A (ja) |
| BE (1) | BE822356A (ja) |
| CA (1) | CA1053694A (ja) |
| CH (1) | CH622539A5 (ja) |
| DE (1) | DE2455374A1 (ja) |
| DK (1) | DK607474A (ja) |
| FR (1) | FR2252363B1 (ja) |
| GB (1) | GB1482995A (ja) |
| IT (1) | IT1030819B (ja) |
| LU (1) | LU71328A1 (ja) |
| NL (1) | NL7415124A (ja) |
| PL (1) | PL97719B1 (ja) |
| SE (1) | SE418193B (ja) |
| SU (1) | SU1103798A3 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504651A (en) * | 1982-12-03 | 1985-03-12 | Hodogaya Chemical Co., Ltd. | Sulfur-containing polyester and process for its production |
-
1973
- 1973-11-22 FR FR7341558A patent/FR2252363B1/fr not_active Expired
-
1974
- 1974-11-13 CH CH1512674A patent/CH622539A5/fr not_active IP Right Cessation
- 1974-11-19 BE BE150647A patent/BE822356A/xx unknown
- 1974-11-20 NL NL7415124A patent/NL7415124A/xx not_active Application Discontinuation
- 1974-11-20 SE SE7414593A patent/SE418193B/xx unknown
- 1974-11-20 PL PL1974175806A patent/PL97719B1/pl unknown
- 1974-11-21 SU SU742078992A patent/SU1103798A3/ru active
- 1974-11-21 LU LU71328A patent/LU71328A1/xx unknown
- 1974-11-21 DK DK607474A patent/DK607474A/da unknown
- 1974-11-21 CA CA214,307A patent/CA1053694A/fr not_active Expired
- 1974-11-21 IT IT29671/74A patent/IT1030819B/it active
- 1974-11-22 JP JP49135026A patent/JPS5093916A/ja active Pending
- 1974-11-22 DE DE19742455374 patent/DE2455374A1/de not_active Ceased
- 1974-11-22 GB GB50767/74A patent/GB1482995A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK607474A (ja) | 1975-07-21 |
| PL97719B1 (pl) | 1978-03-30 |
| BE822356A (fr) | 1975-05-20 |
| CH622539A5 (en) | 1981-04-15 |
| LU71328A1 (ja) | 1975-08-20 |
| JPS5093916A (ja) | 1975-07-26 |
| IT1030819B (it) | 1979-04-10 |
| SU1103798A3 (ru) | 1984-07-15 |
| NL7415124A (nl) | 1975-05-26 |
| FR2252363B1 (ja) | 1976-11-19 |
| SE418193B (sv) | 1981-05-11 |
| GB1482995A (en) | 1977-08-17 |
| FR2252363A1 (ja) | 1975-06-20 |
| SE7414593L (ja) | 1975-05-23 |
| DE2455374A1 (de) | 1975-05-28 |
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