CA1053827A - Antistatic polyamide compositions, their use and processes for their production - Google Patents
Antistatic polyamide compositions, their use and processes for their productionInfo
- Publication number
- CA1053827A CA1053827A CA221,125A CA221125A CA1053827A CA 1053827 A CA1053827 A CA 1053827A CA 221125 A CA221125 A CA 221125A CA 1053827 A CA1053827 A CA 1053827A
- Authority
- CA
- Canada
- Prior art keywords
- antistatic
- group
- carbon atoms
- formula
- alkyl
- 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 84
- 229920002647 polyamide Polymers 0.000 title claims abstract description 81
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000004519 manufacturing process Methods 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 239000002216 antistatic agent Substances 0.000 claims abstract description 21
- 239000004744 fabric Substances 0.000 claims abstract description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- 239000000155 melt Substances 0.000 claims abstract description 8
- 239000002759 woven fabric Substances 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- -1 unsaturated alkyl radical Chemical class 0.000 claims description 32
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229920001281 polyalkylene Polymers 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000008187 granular material Substances 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 239000004745 nonwoven fabric Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 26
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 238000009827 uniform distribution Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 13
- 150000003673 urethanes Chemical group 0.000 abstract description 12
- 125000001033 ether group Chemical group 0.000 abstract description 7
- 239000004953 Aliphatic polyamide Substances 0.000 abstract description 4
- 229920003231 aliphatic polyamide Polymers 0.000 abstract description 4
- 239000000835 fiber Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- SUDHEDJJFGYYPL-UHFFFAOYSA-N ethyl n,n-dimethylcarbamate Chemical compound CCOC(=O)N(C)C SUDHEDJJFGYYPL-UHFFFAOYSA-N 0.000 description 12
- 229920002292 Nylon 6 Polymers 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229960002684 aminocaproic acid Drugs 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UZVAZDQMPUOHKP-UHFFFAOYSA-N 2-(7-methyloctyl)phenol Chemical class CC(C)CCCCCCC1=CC=CC=C1O UZVAZDQMPUOHKP-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 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 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Polymers CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Polymers NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Polymers CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical class CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004608 Heat Stabiliser Substances 0.000 description 1
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241001302210 Sida <water flea> Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- DSICTTBMRSZYJL-UHFFFAOYSA-N ethyl n,n-dibutylcarbamate Chemical class CCCCN(CCCC)C(=O)OCC DSICTTBMRSZYJL-UHFFFAOYSA-N 0.000 description 1
- 125000003916 ethylene diamine group Polymers 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229960005141 piperazine Drugs 0.000 description 1
- 229960003506 piperazine hexahydrate Drugs 0.000 description 1
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000009732 tufting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/324—Polymers modified by chemical after-treatment with inorganic compounds containing oxygen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742409715 DE2409715C3 (de) | 1974-03-01 | 1974-03-01 | Antistatische Polyamidmassen, ihre Verwendung und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053827A true CA1053827A (en) | 1979-05-01 |
Family
ID=5908740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,125A Expired CA1053827A (en) | 1974-03-01 | 1975-03-03 | Antistatic polyamide compositions, their use and processes for their production |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS50121355A (en, 2012) |
| AT (1) | AT340142B (en, 2012) |
| BE (1) | BE826059A (en, 2012) |
| CA (1) | CA1053827A (en, 2012) |
| CH (1) | CH611323A5 (en, 2012) |
| DD (1) | DD118665A5 (en, 2012) |
| DE (1) | DE2409715C3 (en, 2012) |
| DK (1) | DK81475A (en, 2012) |
| ES (1) | ES435201A1 (en, 2012) |
| FR (1) | FR2262684B1 (en, 2012) |
| GB (1) | GB1480298A (en, 2012) |
| IE (1) | IE40815B1 (en, 2012) |
| IT (1) | IT1033274B (en, 2012) |
| LU (1) | LU71932A1 (en, 2012) |
| NL (1) | NL7502424A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2457233A1 (de) * | 1974-12-04 | 1976-06-10 | Bayer Ag | Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppen |
| US4111920A (en) * | 1975-04-30 | 1978-09-05 | Bayer Aktiengesellschaft | Polyether urethanes as antistatic additives in polyamide compositions |
| IT1170091B (it) * | 1983-12-30 | 1987-06-03 | Snia Fibre | Procedimento per la filatura di materiali polimerici termoplastici per fusione di fibre sintetiche, fibre e manufatti relativi |
-
1974
- 1974-03-01 DE DE19742409715 patent/DE2409715C3/de not_active Expired
-
1975
- 1975-02-27 DD DD18446275A patent/DD118665A5/xx unknown
- 1975-02-27 BE BE153809A patent/BE826059A/xx unknown
- 1975-02-27 CH CH251775A patent/CH611323A5/xx not_active IP Right Cessation
- 1975-02-27 LU LU71932A patent/LU71932A1/xx unknown
- 1975-02-27 IT IT2074775A patent/IT1033274B/it active
- 1975-02-27 AT AT150375A patent/AT340142B/de not_active IP Right Cessation
- 1975-02-28 ES ES435201A patent/ES435201A1/es not_active Expired
- 1975-02-28 FR FR7506447A patent/FR2262684B1/fr not_active Expired
- 1975-02-28 JP JP2410075A patent/JPS50121355A/ja active Pending
- 1975-02-28 NL NL7502424A patent/NL7502424A/xx not_active Application Discontinuation
- 1975-02-28 DK DK81475A patent/DK81475A/da unknown
- 1975-02-28 GB GB842075A patent/GB1480298A/en not_active Expired
- 1975-02-28 IE IE43375A patent/IE40815B1/xx unknown
- 1975-03-03 CA CA221,125A patent/CA1053827A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE40815L (en) | 1975-09-01 |
| ATA150375A (de) | 1977-03-15 |
| DK81475A (en, 2012) | 1975-09-02 |
| BE826059A (fr) | 1975-08-27 |
| AT340142B (de) | 1977-11-25 |
| IE40815B1 (en) | 1979-08-29 |
| DE2409715A1 (de) | 1975-09-11 |
| DE2409715B2 (de) | 1979-02-01 |
| DE2409715C3 (de) | 1979-10-04 |
| GB1480298A (en) | 1977-07-20 |
| FR2262684A1 (en, 2012) | 1975-09-26 |
| NL7502424A (nl) | 1975-09-03 |
| DD118665A5 (en, 2012) | 1976-03-12 |
| FR2262684B1 (en, 2012) | 1979-02-09 |
| ES435201A1 (es) | 1977-03-01 |
| JPS50121355A (en, 2012) | 1975-09-23 |
| IT1033274B (it) | 1979-07-10 |
| CH611323A5 (en) | 1979-05-31 |
| LU71932A1 (en, 2012) | 1975-12-09 |
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| US3743685A (en) | Antistatic thermoplastic polyester composition containing sulfonated polyoxyalkylene | |
| US3928298A (en) | Polyethers containing hydantoin rings as antistatic agents for synthetic fibers and foils | |
| US3882190A (en) | Antistatic polyamide fiber | |
| US4035346A (en) | Conductive N-alkyl polyamide having units containing phosphonium sulfonate groups | |
| US5136016A (en) | Melt-processible aromatic polyamide from n,n'-isophthaloyl bis lactam | |
| US3160677A (en) | Polyamide-polyoxamide blends | |
| US3541053A (en) | Segmented polyurethanes containing monodisperse hard segments | |
| US3787524A (en) | Antistatic polyamide fiber containing sulfonic acid polyether reaction product | |
| US3966835A (en) | Permanently antistatic polyamide compositions | |
| US3741966A (en) | Antistatic fiber containing high molecular weight tris(b - hydroxyalkyl)-isocyanurate-alkylene oxide adducts | |
| US3962176A (en) | Antistatic polyamide compositions which are stabilized against yellowing | |
| US3860671A (en) | Polyamide fibers with improved antistatic effect and their preparation | |
| JPS6234848B2 (en, 2012) | ||
| US3485805A (en) | N-alkyl substituted polyamide elastomers | |
| US3825619A (en) | Antistatic fiber containing high molecular weight tris(b-hydroxyalkyl)-iso-cyanurate-alkylene oxide adducts | |
| USRE28212E (en) | Table iii |