CA1089487A - Polyether urethanes, their production and their use as antistatic additives in polyamide compositions - Google Patents
Polyether urethanes, their production and their use as antistatic additives in polyamide compositionsInfo
- Publication number
- CA1089487A CA1089487A CA251,329A CA251329A CA1089487A CA 1089487 A CA1089487 A CA 1089487A CA 251329 A CA251329 A CA 251329A CA 1089487 A CA1089487 A CA 1089487A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- cyclic
- saturated
- branched
- carbon atoms
- 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
- 239000004952 Polyamide Substances 0.000 title claims abstract description 37
- 229920002647 polyamide Polymers 0.000 title claims abstract description 37
- 229920000570 polyether Polymers 0.000 title claims abstract description 28
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 27
- 150000003673 urethanes Chemical class 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 23
- 239000000654 additive Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 28
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 5
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 39
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 15
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 10
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 8
- 239000000155 melt Substances 0.000 abstract description 4
- 239000004745 nonwoven fabric Substances 0.000 abstract description 4
- 239000002759 woven fabric Substances 0.000 abstract description 4
- 230000000875 corresponding effect Effects 0.000 abstract 1
- 208000007106 menorrhagia Diseases 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000004953 Aliphatic polyamide Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 101100511454 Epichloe uncinata lolO1 gene Proteins 0.000 description 2
- 101100511455 Epichloe uncinata lolO2 gene Proteins 0.000 description 2
- 229920003231 aliphatic polyamide Polymers 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- HSUGDXPUFCVGES-UHFFFAOYSA-N n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCCCC HSUGDXPUFCVGES-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004381 surface treatment Methods 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/922—Static electricity metal bleed-off metallic stock
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)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2519260.3 | 1975-04-30 | ||
| DE19752519259 DE2519259A1 (de) | 1975-04-30 | 1975-04-30 | Antistatische polyamidmassen und verfahren zu ihrer herstellung |
| DE19752519260 DE2519260A1 (de) | 1975-04-30 | 1975-04-30 | Polyaetherurethane, deren herstellung und ihre verwendung als antistatisch wirksame zusaetze in polyamidmassen |
| DEP2519259.0 | 1975-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1089487A true CA1089487A (en) | 1980-11-11 |
Family
ID=25768826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,329A Expired CA1089487A (en) | 1975-04-30 | 1976-04-28 | Polyether urethanes, their production and their use as antistatic additives in polyamide compositions |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4111920A (en:Method) |
| JP (1) | JPS51133399A (en:Method) |
| AT (1) | AT351770B (en:Method) |
| CA (1) | CA1089487A (en:Method) |
| DD (2) | DD129126A5 (en:Method) |
| DK (1) | DK191876A (en:Method) |
| ES (1) | ES447449A1 (en:Method) |
| FR (1) | FR2309582A1 (en:Method) |
| GB (1) | GB1519912A (en:Method) |
| LU (1) | LU74844A1 (en:Method) |
| NL (1) | NL7604545A (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806410A (en) * | 1986-09-18 | 1989-02-21 | Ranpak Corp. | Processes for the production of antistatic or static dissipative paper, and the paper products thus produced, and apparatus utilized |
| DE3922300A1 (de) * | 1989-07-07 | 1991-01-17 | Kunststoffverarbeitung Wilhelm | Leitfaehige brandsohle fuer schuhe sowie verfahren zu deren herstellung |
| FR3152746B1 (fr) | 2023-09-12 | 2025-08-15 | Psa Automobiles Sa | Procédé de pilotage d'un blocage d'un differentiel de vitesse d'un train de roues arrière |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE498005A (en:Method) * | ||||
| US2998445A (en) * | 1959-06-22 | 1961-08-29 | California Research Corp | Polyglycol carbamates |
| DE1224031B (de) * | 1964-07-31 | 1966-09-01 | Basf Ag | Durch Polyaetheramide antistatische Polyamidformmassen |
| DE2409715C3 (de) * | 1974-03-01 | 1979-10-04 | Bayer Ag, 5090 Leverkusen | Antistatische Polyamidmassen, ihre Verwendung und Verfahren zu ihrer Herstellung |
| DE2457233A1 (de) * | 1974-12-04 | 1976-06-10 | Bayer Ag | Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppen |
-
1976
- 1976-04-27 US US05/680,668 patent/US4111920A/en not_active Expired - Lifetime
- 1976-04-28 DD DD7600192563A patent/DD129126A5/xx unknown
- 1976-04-28 DD DD7600199481A patent/DD129920A5/xx unknown
- 1976-04-28 LU LU74844A patent/LU74844A1/xx unknown
- 1976-04-28 NL NL7604545A patent/NL7604545A/xx unknown
- 1976-04-28 CA CA251,329A patent/CA1089487A/en not_active Expired
- 1976-04-28 JP JP51047948A patent/JPS51133399A/ja active Pending
- 1976-04-28 AT AT310876A patent/AT351770B/de not_active IP Right Cessation
- 1976-04-29 ES ES447449A patent/ES447449A1/es not_active Expired
- 1976-04-29 DK DK191876A patent/DK191876A/da unknown
- 1976-04-30 FR FR7613033A patent/FR2309582A1/fr active Granted
- 1976-04-30 GB GB17666/76A patent/GB1519912A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK191876A (da) | 1976-10-31 |
| FR2309582A1 (fr) | 1976-11-26 |
| ATA310876A (de) | 1979-01-15 |
| DD129126A5 (de) | 1977-12-28 |
| AT351770B (de) | 1979-08-10 |
| JPS51133399A (en) | 1976-11-19 |
| LU74844A1 (en:Method) | 1977-02-08 |
| US4111920A (en) | 1978-09-05 |
| FR2309582B1 (en:Method) | 1980-06-06 |
| GB1519912A (en) | 1978-08-02 |
| NL7604545A (nl) | 1976-11-02 |
| DD129920A5 (de) | 1978-02-15 |
| ES447449A1 (es) | 1977-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |