DE2504053C3 - N-23-Dihydroxypropyl-N-2'-hydroxyalkyl-amine sowie deren Säureadditionsbzw, quaternäre Ammoniumsalze, Verfahren zu deren Herstellung und ihre Verwendung als Antistatika für Kunststoffe - Google Patents
N-23-Dihydroxypropyl-N-2'-hydroxyalkyl-amine sowie deren Säureadditionsbzw, quaternäre Ammoniumsalze, Verfahren zu deren Herstellung und ihre Verwendung als Antistatika für KunststoffeInfo
- Publication number
- DE2504053C3 DE2504053C3 DE2504053A DE2504053A DE2504053C3 DE 2504053 C3 DE2504053 C3 DE 2504053C3 DE 2504053 A DE2504053 A DE 2504053A DE 2504053 A DE2504053 A DE 2504053A DE 2504053 C3 DE2504053 C3 DE 2504053C3
- Authority
- DE
- Germany
- Prior art keywords
- dihydroxypropyl
- antistatic
- weight
- amines
- amine
- 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
- 239000002253 acid Substances 0.000 title claims description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims description 3
- 239000002216 antistatic agent Substances 0.000 title description 19
- 229920003023 plastic Polymers 0.000 title description 9
- 239000004033 plastic Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 title description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 21
- -1 2-hydroxypropyl Chemical group 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 230000003750 conditioning effect Effects 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 11
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229920001169 thermoplastic Polymers 0.000 description 9
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000007524 organic acids Chemical group 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000004416 thermosoftening plastic Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- IPTLKMXBROVJJF-UHFFFAOYSA-N azanium;methyl sulfate Chemical compound N.COS(O)(=O)=O IPTLKMXBROVJJF-UHFFFAOYSA-N 0.000 description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MPGVRLGIUWFEPA-UHFFFAOYSA-N 1-aminooctan-2-ol Chemical compound CCCCCCC(O)CN MPGVRLGIUWFEPA-UHFFFAOYSA-N 0.000 description 2
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 2
- PFGDHGPYLSLZQD-UHFFFAOYSA-N 3-[2-hydroxydodecyl(methyl)amino]propane-1,2-diol Chemical compound CCCCCCCCCCC(O)CN(C)CC(O)CO PFGDHGPYLSLZQD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DDDWJBKYBSZILK-UHFFFAOYSA-N 1-(dimethylamino)dodecan-2-ol Chemical compound CCCCCCCCCCC(O)CN(C)C DDDWJBKYBSZILK-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 239000004930 VINNOL Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WDMPYXXSNYABKC-UHFFFAOYSA-N diazanium diperchlorate Chemical compound [NH4+].[NH4+].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O WDMPYXXSNYABKC-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- FUJXKFCTVKZXTJ-UHFFFAOYSA-N hexacosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCN FUJXKFCTVKZXTJ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- 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
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/91—Antistatic compositions
- Y10S524/912—Contains metal, boron, phosphorus, or silicon
-
- 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
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/91—Antistatic compositions
- Y10S524/913—Contains nitrogen nonreactant material
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2504053A DE2504053C3 (de) | 1975-01-31 | 1975-01-31 | N-23-Dihydroxypropyl-N-2'-hydroxyalkyl-amine sowie deren Säureadditionsbzw, quaternäre Ammoniumsalze, Verfahren zu deren Herstellung und ihre Verwendung als Antistatika für Kunststoffe |
| FR7602398A FR2299311A1 (fr) | 1975-01-31 | 1976-01-29 | N-2,3-dihydroxypropyl-n-2'-hydroxyalcoyl-amines et leurs sels |
| NL7600907A NL7600907A (en) | 1975-01-31 | 1976-01-29 | Hydroxylated fatty amine cpds - useful antistatic agents for thermoplastics (BE300776) |
| GB3503/76A GB1531522A (en) | 1975-01-31 | 1976-01-29 | N-2,3-dihydroxypropyl-n-2'-hydroxy-alkyl amines and their salts |
| IT47857/76A IT1061213B (it) | 1975-01-31 | 1976-01-29 | Composizioni n 2.3 diidrossipropil n 2 idrossialchilamminici e loro sali |
| JP51009923A JPS607655B2 (ja) | 1975-01-31 | 1976-01-30 | 熱可塑性プラスチックの帯電防止剤 |
| US05/653,835 US4083872A (en) | 1975-01-31 | 1976-01-30 | N-2,3-Dihydroxypropyl-N-2-hydroxyalkyl-amine and its salts |
| BE6045347A BE838146A (fr) | 1975-01-31 | 1976-01-30 | Composes convenant en particulier comme agents antistatiques destines notamment a des resines thermoplastiques |
| CA244,593A CA1092157A (en) | 1975-01-31 | 1976-01-30 | N-2,3-dihydroxy-propyl-n-2'-hydroxy-alkyl-amines and their salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2504053A DE2504053C3 (de) | 1975-01-31 | 1975-01-31 | N-23-Dihydroxypropyl-N-2'-hydroxyalkyl-amine sowie deren Säureadditionsbzw, quaternäre Ammoniumsalze, Verfahren zu deren Herstellung und ihre Verwendung als Antistatika für Kunststoffe |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2504053A1 DE2504053A1 (de) | 1976-08-05 |
| DE2504053B2 DE2504053B2 (de) | 1977-08-25 |
| DE2504053C3 true DE2504053C3 (de) | 1978-04-27 |
Family
ID=5937788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2504053A Expired DE2504053C3 (de) | 1975-01-31 | 1975-01-31 | N-23-Dihydroxypropyl-N-2'-hydroxyalkyl-amine sowie deren Säureadditionsbzw, quaternäre Ammoniumsalze, Verfahren zu deren Herstellung und ihre Verwendung als Antistatika für Kunststoffe |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4083872A (show.php) |
| JP (1) | JPS607655B2 (show.php) |
| BE (1) | BE838146A (show.php) |
| CA (1) | CA1092157A (show.php) |
| DE (1) | DE2504053C3 (show.php) |
| FR (1) | FR2299311A1 (show.php) |
| GB (1) | GB1531522A (show.php) |
| IT (1) | IT1061213B (show.php) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675443A (en) * | 1981-03-05 | 1987-06-23 | The Dow Chemical Company | Dihydroxypropoxy derivatives of hydroxybenzamides |
| JPS61106544A (ja) * | 1984-10-30 | 1986-05-24 | Kao Corp | 第四級アンモニウム塩の製造法 |
| US4696771A (en) * | 1985-12-03 | 1987-09-29 | Henkel Corporation | Aminopolyols and polyurethanes prepared therefrom |
| JPH053138U (ja) * | 1991-06-28 | 1993-01-19 | 株式会社コバヤシ | 断熱容器 |
| US5227091A (en) * | 1991-10-30 | 1993-07-13 | Ppg Industries, Inc. | Antistatic poly(vinyl chloride) composition |
| JP3615545B2 (ja) * | 1993-02-01 | 2005-02-02 | キアゲン・エヌ・ブイ | 第四級アンモニウム塩界面活性剤及びそのｒｎａの単離剤 |
| EP0691327B1 (en) * | 1993-03-17 | 1999-07-21 | Kao Corporation | Amine derivative and dermatologic preparation containing the same |
| DE19517048C1 (de) * | 1995-05-10 | 1996-10-02 | Henkel Kgaa | Verwendung von quartären Aminoglycerinverbindungen |
| CN103140469B (zh) * | 2010-09-30 | 2016-03-02 | 陶氏环球技术有限责任公司 | 季铵多羟基化合物及其在个人护理组合物中的用途 |
| KR101554410B1 (ko) * | 2011-06-20 | 2015-09-18 | 더 프록터 앤드 갬블 캄파니 | β-하이드록시아미노 화합물의 제조 방법 |
| JP6001070B2 (ja) * | 2011-07-28 | 2016-10-05 | アンガス ケミカル カンパニー | アミノアルコール化合物ならびに塗料およびコーティング用ゼロまたは低ｖｏｃ添加剤としてのそれらの使用 |
| US8496916B2 (en) * | 2011-11-22 | 2013-07-30 | Conopco, Inc. | Sunscreen composition with polyhydroxy quaternary ammonium salts |
| WO2013076148A2 (en) * | 2011-11-22 | 2013-05-30 | Unilever Plc | Personal care compositions with enhanced fragrance delivery via polyhydroxy quaternary ammonium salts |
| EP3954743A1 (de) | 2020-08-12 | 2022-02-16 | Evonik Operations GmbH | Verwendung von siliziumdioxid zur verbesserung der leitfähigkeit von beschichtungen |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR854314A (fr) * | 1938-05-13 | 1940-04-10 | Ig Farbenindustrie Ag | Procédé pour traiter des matières fibreuses |
| US2856363A (en) * | 1955-12-01 | 1958-10-14 | Pure Oil Co | Stable anti-rust lubricating oil |
| US2884459A (en) * | 1955-12-15 | 1959-04-28 | Visco Products Co | Diamine derivatives containing hydroxyalkyl groups |
| FR1146332A (fr) * | 1956-03-29 | 1957-11-08 | Produits de nettoyage de la chevelure et sels de diamines bitertiaires entrant dans la composition de ces produits | |
| US2891028A (en) * | 1956-03-30 | 1959-06-16 | Myron A Coler | Polymers of vinylidene monomers, destaticized with n, n, n', n' tetrakis (2-hydroxypropyl) ethylene diamine |
| US2944030A (en) * | 1957-05-31 | 1960-07-05 | Wyandotte Chemicals Corp | Binary emulsifiers |
| NL133294C (show.php) * | 1963-10-10 | |||
| US3365435A (en) * | 1963-12-26 | 1968-01-23 | American Cyanamid Co | Antistatics |
| DE1230210B (de) * | 1964-06-24 | 1966-12-08 | Huels Chemische Werke Ag | Thermoplastische Massen zur Herstellung antielektrostatischer Formkoerper aus Polyolefinen |
| DE1544887A1 (de) * | 1964-09-26 | 1969-06-26 | Hoechst Ag | Verfahren zur antistatischen Ausruestung hochmolekularer Verbindungen |
| DK133307A (show.php) * | 1968-06-12 | Colgate Palmolive Co | ||
| DE2404070A1 (de) * | 1974-01-29 | 1975-08-14 | Henkel & Cie Gmbh | Hautpflege- und hautschutzmittel mit einem gehalt an haut-feuchthaltemitteln |
-
1975
- 1975-01-31 DE DE2504053A patent/DE2504053C3/de not_active Expired
-
1976
- 1976-01-29 IT IT47857/76A patent/IT1061213B/it active
- 1976-01-29 FR FR7602398A patent/FR2299311A1/fr active Granted
- 1976-01-29 GB GB3503/76A patent/GB1531522A/en not_active Expired
- 1976-01-30 CA CA244,593A patent/CA1092157A/en not_active Expired
- 1976-01-30 US US05/653,835 patent/US4083872A/en not_active Expired - Lifetime
- 1976-01-30 JP JP51009923A patent/JPS607655B2/ja not_active Expired
- 1976-01-30 BE BE6045347A patent/BE838146A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2504053A1 (de) | 1976-08-05 |
| US4083872A (en) | 1978-04-11 |
| FR2299311A1 (fr) | 1976-08-27 |
| FR2299311B1 (show.php) | 1979-06-29 |
| JPS607655B2 (ja) | 1985-02-26 |
| CA1092157A (en) | 1980-12-23 |
| GB1531522A (en) | 1978-11-08 |
| IT1061213B (it) | 1983-02-28 |
| JPS51136609A (en) | 1976-11-26 |
| DE2504053B2 (de) | 1977-08-25 |
| BE838146A (fr) | 1976-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |