US3454625A - Novel quaternary ammonium carbamate antistatic agents - Google Patents
Novel quaternary ammonium carbamate antistatic agents Download PDFInfo
- Publication number
- US3454625A US3454625A US627859A US3454625DA US3454625A US 3454625 A US3454625 A US 3454625A US 627859 A US627859 A US 627859A US 3454625D A US3454625D A US 3454625DA US 3454625 A US3454625 A US 3454625A
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- US
- United States
- Prior art keywords
- gms
- antistatic agents
- antistatic
- alkyl
- swatches
- 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 - Lifetime
Links
- 239000002216 antistatic agent Substances 0.000 title description 21
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 title 1
- -1 alkaryl radical Chemical group 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 13
- 239000000835 fiber Substances 0.000 description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 229920004934 Dacron® Polymers 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000005020 polyethylene terephthalate Substances 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
- 239000004677 Nylon Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229920001778 nylon Polymers 0.000 description 8
- 229920002994 synthetic fiber Polymers 0.000 description 8
- 239000012209 synthetic fiber Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000001143 conditioned effect Effects 0.000 description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920002972 Acrylic fiber Polymers 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 238000007655 standard test method Methods 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- WNLWBCIUNCAMPH-UHFFFAOYSA-N 2-n,2-n-dimethylpropane-1,2-diamine Chemical compound NCC(C)N(C)C WNLWBCIUNCAMPH-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- DTDMYWXTWWFLGJ-JTQLQIEISA-N 4-Decanol Natural products CCCCCC[C@@H](O)CCC DTDMYWXTWWFLGJ-JTQLQIEISA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical group [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- KUKQTFWICPUJBP-UHFFFAOYSA-N cyclohexanamine;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.NC1CCCCC1 KUKQTFWICPUJBP-UHFFFAOYSA-N 0.000 description 1
- ICEQLCZWZXUUIJ-UHFFFAOYSA-N decan-3-ol Chemical compound CCCCCCCC(O)CC ICEQLCZWZXUUIJ-UHFFFAOYSA-N 0.000 description 1
- DTDMYWXTWWFLGJ-UHFFFAOYSA-N decan-4-ol Chemical compound CCCCCCC(O)CCC DTDMYWXTWWFLGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- OKDGZLITBCRLLJ-UHFFFAOYSA-N dodecan-3-ol Chemical compound CCCCCCCCCC(O)CC OKDGZLITBCRLLJ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 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
- 239000012530 fluid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 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 description 1
- 125000002460 pentacosyl 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])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 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/461—Quaternised amin-amides from polyamines or heterocyclic compounds or polyamino-acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05F—STATIC ELECTRICITY; NATURALLY-OCCURRING ELECTRICITY
- H05F1/00—Preventing the formation of electrostatic charges
- H05F1/02—Preventing the formation of electrostatic charges by surface treatment
Definitions
- R is an alkyl or alkaryl radical containing at least 7 carbon atoms
- X is hydrogen, methyl, or ethyl
- n is an integer from 1 to 10
- R and R are alkyl or hydroxy alkyl radicals of 1-3 carbon atoms
- R is a hydroxyalkyl radical of from 1-4 carbon atoms
- Y is an anion.
- antistatic agents are prepared by condensing an alkyl or aryl polyalkyleneoxy chlorocarbonate with a substituted alkyl diamine with subsequent acidification and alkoxylation to produce the quaternary compound, the chlorocarbonate being prepared by the reaction of the corresponding hydroxy compound with phosgene.
- the present invention relates to new and useful compositions of matter which function as antistatic agents when coated on synthetic and natural fibers, e.g., polyester fibers, acetate rayons, wool, polyolefins and the like, and to the method for their preparation. More particularly, the present invention relates to substituted carbamates exhibiting antistatic properties which are prepared by the condensation of alkyl and aryl polyalkyleneoxy chlorocarbonates with a substituted alkyl diamine followed by acidification and alkoxylation.
- antistatic agents function in two ways, both of which improve the electrical conductivity of the fiber surface.
- Such antistatic agents are either reasonably good conductors of electricity themselves, or they are hygroscopic and help concentrate atmospheric moisture on the fibers.
- antistatic agents fall into one of the following three categories: 1) polyhydroxy and polyethyleneoxy non-ionic compounds; (2) cationic, or neutral nitrogenous compounds with a hydrophobic moiety in their structure; (3) long-chain phosphates, phosphonates, or other oxygenated phosphorus derivatives. Additional types include sulfonated oils and ester emulsions, and other fiber lubricant emulsions which depend on the particular emulsifying agent used for their antistatic effect.
- Hygroscopic salts such as cyclohexylamine lactate
- polyethoxylated fatty acids and alcohols as antistatic agents for polypropylenes as well as fibers, is reported in U.S. 2,525,691.
- a further object of the present invention comprises antistatic agents of enhanced effectiveness, which antistatic agents contain an amide linkage and a polyalkoxylated hydrophobe.
- Yet a further object of the present invention comprises new and useful substituted carbamate antistatic agents derived from the chlorocarbonate of an alkoxylated primary or secondary alcohol or alkylphenol and a substituted alkyl diamine.
- Still a further object of the present invention comprises a process for preparing new and useful antistatic agents which process comprises condensing an alkyl or aryl polyalkylenoxy chlorocarbonate with an alkyl diamine followed by acidification and alkoxylation.
- the new and useful antistatic agents of the present invention correspond to the general formula:
- R is an alkyl or alkaryl radical containing at least 7 carbon atoms
- X is hydrogen, methyl, or ethyl
- n is an integer from 1 to 10;
- R and R are alkyl or hydroxyalkyl radicals of 1-3 carbon atoms
- R is a hydroxyalkyl radical of from 1-4 carbon atoms
- Y is an anion
- Exemplary alkyl or alkaryl radicals for R include: heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, hexadecyl, octadecly, nonadecyl, eicosyl, docosyl, pentacosyl, etc., methylphenyl, ethylphenyl, butylphenyl, hexylphenyl, octylphenyl, nonylphenyl, decylphenyl, dOdecylphenyl, petadecylphenyl, octadecylphenyl, nondecylphenyl, etc.
- Exemplary alkyl and hydroxyalkyl radicals for R and R include: methyl, ethyl, propyl, isopropyl, hydroxymethyl, hydroxyethyl, hydroxypropyl dihydroxypropyl, etc.
- Exemplary hydroxyalkyl radicals for R include; hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, dihydroxypropyl, dihydroxybutyl, etc.
- Exemplary anions for Y include: halides, chloride, bromide, iodide, phosphates, nitrates, sulfates, and the like.
- the new and useful antistatic agents of the present invention are prepared by condensing an alkyl or alkaryl polyalkylenoxy chlorocarbonate with a substituted alkyldiamine followed by acidification and alkoxylation.
- the alkyl or alkaryl polyalkylenoxy chlorocarbonate is prepared by reacting phosgene with a polyalkyleneoxylated aliphatic alcohol or alkylphenol under ambient conditions, in accordance with the following reaction:
- a substantially equivalent amount of the reactants is employed and the reaction is carried out by bubbling phosgene under the surface of the polyalkyleneoxylated aliphatic alcohol or alkylphenol until substantially all of the hydroxyl content of the reactants is converted into the chlorocarbonate as determined by infrared analysis or other suitable means.
- the polyalkyleneoxylated aliphatic alcohol or alkylphenol is prepared by any conventional procedure so as to incorporate 1 to moles of alkylene oxide, e.g., ethylene oxide, propylene oxide, or butylene oxide per mole of aliphatic alcohol or alkylphenol.
- alkyl or alkaryl polyalkyleneoxy chlorocarbonate prepared in Reaction I is further reacted with a substantialy equivalent amount of gamma dialkyl or dialkanol aminopropylamine to produce a substituted amide in accordance with the following reaction:
- the substituted amide produced in Reaction II is quaternized by reaction with an alkylene oxide or hydroxysubstituted alkylene oxide in the presence of an inorganic acid.
- Such a reaction is represented as follows:
- a commercial straight chain aliphatic alcohol admixture comprising approximately 5% C11, C12, C13, C14 and C15 is reacted with an alkylene oxide using an alkaline catalyst at C. and 13O p.s.i.g. until one to ten moles of the oxide is added.
- an alkaline catalyst In place of the alkaline catalyst, acidic catalysts such as BF H PO and the like can be used.
- Secondary alcohols such as Z-decanol, 3-decanol, 4-decanol, 3-dodecanol, -4-tetradecanol, fi-hexadecanol, and the like, or their admixtures as well as alkylphenols such as octylphenol, linear decyl phenol, branched dodecylphenol, etc., can be substituted for the primary aliphatic alcohol.
- alkyl or alkylarylpolyalkyleneoxyalkanol is then reacted with phosgene to form the corresponding alkyl or alkylarylpolyalkyleneoxy chlorocarbonate, and the latter compound converted to its carbamate by reaction with gamma dialkylaminopropylamine.
- This latter derivative is acidified and reacted with an alkylene oxide to form its quaternary ammonium salt.
- the new and useful antistatic agents of the present invention have been found to have unexpectedly advantageous antistatic properties, particularly when applied to synthetic fibers, such as polyesters, acrylics, polyolefins, polyamides, etc. Such antistatic agents have been found to reduce and maintain the electrostatic charges for extended periods of time below a potential of 3 kilovolts.
- EXAMPLE I (a) To a round bottom flask was charged a total of 288 parts by weight of an ethoxylate (av. app. 2.0 moles E0) of a C -C straight chain primary alcohol admixture calculated as a 209 mw. average and having the composition 5% C11, C12, C13, C14 and C15. The ethoxylate was agitated at ambient temperature (2030 C.) while phosgene was bubbled in under the surface over about 1.5 to 2.0 hours. Addition of phosgene was continued until examination of sample on IR showed essentially all absorption due to the hydroxyl group was eliminated. A total of 109 gms. phosgene (1.1 mole) were required.
- the swatches were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured. Results were as follows:
- the products correspond, in general, to the formula -(d)
- the quaternary formed above was applied from MeOH/CCI (520 mls./ 1000 mls.) solvent mixture to Dacron and to cotton swatches at 1.25% application rate according to AATCC Standard Test Method 76-1959.
- the swatcthes were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured. Results were as follows:
- the product was stripped to C. pot temperature under line vacuum and then filtered.
- the weight of the final product was 147 gms.
- the swatches were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured. Results were as follows:
- EXAMPLE IV (a) To a round bottom flask was charged a total of 174 parts by weight of an ethoxylate (1.0 mole E0.) of octyl alcohol. The ethoxylate was agitated at ambient temperature (2030 C.) while phosgene was bubbled in under the surface over about 1.5 to 2.0 hours. Addition of phosgene was continued until examination of sample on IR showed essentially all absorption due to the hydroxyl group was eliminated. A total of 107 gms. phosgene (1.08 mole) were required.
- the product was stripped to 110 C. pot temperature under line vacuum and then filtered.
- the weight of the final product was gms.
- the product corresponded, in general, to the formula
- the swatches were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured.
- Theoretical yield was mixture (520 mls. methanol/ 1000 mls. carbon tetrachloride) was then added by volume, i.e., 99 mls. and 97 mls., respectively, to produce soluble, fluid, clear solutions in each case.
- Preweighed and conditioned swatches (11x12 cms.). were immersed in the appropriate baths for one hour with good agitation. This agitation consisted of light shaking and swirling by hand. The swatches all appeared to wet nicely and uniformly. Removed swatches and allowed to drain back into bottle for about ten seconds, then hung under balance on a hook and adjusted to 100% pickup by lightly blotting with paper towels. All swatches were relatively easy to adjust to 100% pickup.
- R is a hydroxyalkyl radical having from 1 to 4 carbon
- Samples of the product of Example III were submitted Y riltoms; i for resistivity measurements.
- the first sample was ap- IS an q proximately 60% active in the mixture of isopropanol Anantlstatlc compound of the formula and water in which it was prepared while solvents had CH3 the SBCOI'ld sample, and ll.
- R is a radical selected from alkyl and alkyaryl radicals 117 138.8, 139.5; 260-75, 93.7, 94.9
- X is selected from hydrogen, methyl or ethyl
- n is a number from 1 to 10;
- R and R are selected from alkyl and hydroxyl alkyl radicals having from 1 to 3 carbon atoms;
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62785967A | 1967-04-03 | 1967-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3454625A true US3454625A (en) | 1969-07-08 |
Family
ID=24516446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US627859A Expired - Lifetime US3454625A (en) | 1967-04-03 | 1967-04-03 | Novel quaternary ammonium carbamate antistatic agents |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3454625A (en:Method) |
| BE (1) | BE713109A (en:Method) |
| CH (3) | CH1232369A4 (en:Method) |
| DE (1) | DE1768060A1 (en:Method) |
| FR (1) | FR1561574A (en:Method) |
| GB (1) | GB1219931A (en:Method) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035341A (en) * | 1971-05-24 | 1977-07-12 | Rhone-Poulenc-Textile | Polyester compositions with good dyeing affinity and a process for obtaining same |
| US4160648A (en) * | 1976-06-21 | 1979-07-10 | Chevron Research Company | Fuel compositions containing deposit control additives |
| US4191537A (en) * | 1976-06-21 | 1980-03-04 | Chevron Research Company | Fuel compositions of poly(oxyalkylene) aminocarbamate |
| US4198306A (en) * | 1978-07-03 | 1980-04-15 | Chevron Research Company | Deposit control and dispersant additives |
| US4233168A (en) * | 1978-06-19 | 1980-11-11 | Chevron Research Company | Lubricant compositions containing dispersant additives |
| US4236020A (en) * | 1976-06-21 | 1980-11-25 | Chevron Research Company | Carbamate deposit control additives |
| US4245110A (en) * | 1974-03-14 | 1981-01-13 | Bayer Aktiengesellschaft | Polyalkylene oxide-containing urethane polyols with sulphonic acid groups |
| US4288612A (en) * | 1976-06-21 | 1981-09-08 | Chevron Research Company | Deposit control additives |
| WO1985000620A1 (en) * | 1983-07-29 | 1985-02-14 | Chevron Research Company | Quaternary deposit control additives |
| US4521610A (en) * | 1982-09-30 | 1985-06-04 | Chevron Research Company | Poly(oxyalkylene) aminoether carbamates as deposit control additives |
| US4564372A (en) * | 1983-07-29 | 1986-01-14 | Chevron Research Company | Quaternary deposit control additives |
| US4600409A (en) * | 1983-07-29 | 1986-07-15 | Chevron Research Company | Quaternary deposit control additives |
| US4695291A (en) * | 1982-09-30 | 1987-09-22 | Chevron Research Company | Poly(oxyalkylene) aminoether carbamates as deposit control additives |
| US4728451A (en) * | 1982-09-30 | 1988-03-01 | Chevron Research Company | Lubricating oil compositions containing poly(oxyalkylene) aminoether carbamates as dispersing agents |
| US4956270A (en) * | 1986-05-06 | 1990-09-11 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic material having improved antistatic and antiblocking properties |
| RU2216535C1 (ru) * | 2002-04-08 | 2003-11-20 | Всероссийский научно-исследовательский ветеринарный институт | N-[алкоксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие фунгистатической и бактерицидной активностью, и способ их получения |
| RU2221776C2 (ru) * | 2002-04-08 | 2004-01-20 | Институт органической и физической химии им. А.Е.Арбузова КНЦ РАН | N, n-диметил-n-алкил-n-[алкоксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие фунгистатической и бактерицидной активностью, а также свойствами присадок, регулирующих вязкоупругие свойства ассоциированных мультикомпонентных нефтяных систем, и способ их получения |
| RU2221775C2 (ru) * | 2002-04-08 | 2004-01-20 | Институт органической и физической химии им. А.Е.Арбузова КНЦ РАН | N-[алкоксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие свойствами присадок, регулирующих вязкоупругие свойства ассоциированных мультикомпонентных нефтяных систем, способ их получения и применения |
| RU2221777C2 (ru) * | 2002-04-08 | 2004-01-20 | Институт органической и физической химии им. А.Е.Арбузова КНЦ РАН | N-[алкилфеноксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие свойствами присадок, регулирующих вязкоупругие свойства ассоциированных мультикомпонентных нефтяных систем, и способ их получения |
| RU2284317C1 (ru) * | 2005-07-06 | 2006-09-27 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | 1,2,3-трис{[аминополи(этиленамино)этиламмонио]-метилкарбонилоксиполи(алкиленокси)}пропан трихлориды, обладающие фунгицидной активностью, свойствами эмульгаторов катионных битумных эмульсий, способностью повышать адгезию битумов к минеральным материалам, и способ их получения |
| RU2294337C1 (ru) * | 2005-07-06 | 2007-02-27 | Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра РАН (ИОФХ им. А.Е. Арбузова КазНЦ РАН) | Трис[(аммонио)метилкарбонилоксиполи(2-метилэтиленокси)]пропан трихлориды, обладающие свойствами эмульгаторов водобитумных эмульсий, и способ их получения |
| RU2308468C2 (ru) * | 2005-07-06 | 2007-10-20 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | 1,2,3-трис[(аммонио)метилкарбонилоксиполи(алкиленокси)]пропан трихлориды, обладающие бактерицидной и фунгицидной активностью, и способ их получения |
| RU2308467C2 (ru) * | 2005-07-06 | 2007-10-20 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | [(аммонио)метилкарбонилоксиполи(алкиленокси)]пропан хлориды, обладающие бактерицидной активностью, и способ их получения |
| RU2308466C2 (ru) * | 2005-07-06 | 2007-10-20 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | [(гетерилонио)(аммонио)метилкарбонилоксиполи(алкиленокси)] пропан хлориды, обладающие фунгицидной активностью, и способ их получения |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626876A (en) * | 1951-08-17 | 1953-01-27 | American Cyanamid Co | Antistatic treatment of articles comprising a vinyl resin and treated articles |
| US2721208A (en) * | 1951-11-30 | 1955-10-18 | Olin Mathieson | Quaternary-ammonium-salt of n-beta-aminoethyl carbamates |
| US2998445A (en) * | 1959-06-22 | 1961-08-29 | California Research Corp | Polyglycol carbamates |
| US3359303A (en) * | 1964-01-31 | 1967-12-19 | Dow Chemical Co | Reaction products of poly (alkylenoxy) alkyl 1-aziridinecarboxylates with polyamines |
-
1967
- 1967-04-03 US US627859A patent/US3454625A/en not_active Expired - Lifetime
-
1968
- 1968-03-26 CH CH1232369D patent/CH1232369A4/xx unknown
- 1968-03-26 CH CH452368A patent/CH483400A/de not_active IP Right Cessation
- 1968-03-26 CH CH1232369A patent/CH511972A/de not_active IP Right Cessation
- 1968-03-27 DE DE19681768060 patent/DE1768060A1/de active Pending
- 1968-03-29 GB GB05358/68A patent/GB1219931A/en not_active Expired
- 1968-03-29 FR FR1561574D patent/FR1561574A/fr not_active Expired
- 1968-04-02 BE BE713109D patent/BE713109A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626876A (en) * | 1951-08-17 | 1953-01-27 | American Cyanamid Co | Antistatic treatment of articles comprising a vinyl resin and treated articles |
| US2721208A (en) * | 1951-11-30 | 1955-10-18 | Olin Mathieson | Quaternary-ammonium-salt of n-beta-aminoethyl carbamates |
| US2998445A (en) * | 1959-06-22 | 1961-08-29 | California Research Corp | Polyglycol carbamates |
| US3359303A (en) * | 1964-01-31 | 1967-12-19 | Dow Chemical Co | Reaction products of poly (alkylenoxy) alkyl 1-aziridinecarboxylates with polyamines |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035341A (en) * | 1971-05-24 | 1977-07-12 | Rhone-Poulenc-Textile | Polyester compositions with good dyeing affinity and a process for obtaining same |
| US4245110A (en) * | 1974-03-14 | 1981-01-13 | Bayer Aktiengesellschaft | Polyalkylene oxide-containing urethane polyols with sulphonic acid groups |
| US4160648A (en) * | 1976-06-21 | 1979-07-10 | Chevron Research Company | Fuel compositions containing deposit control additives |
| US4191537A (en) * | 1976-06-21 | 1980-03-04 | Chevron Research Company | Fuel compositions of poly(oxyalkylene) aminocarbamate |
| US4236020A (en) * | 1976-06-21 | 1980-11-25 | Chevron Research Company | Carbamate deposit control additives |
| US4288612A (en) * | 1976-06-21 | 1981-09-08 | Chevron Research Company | Deposit control additives |
| US4233168A (en) * | 1978-06-19 | 1980-11-11 | Chevron Research Company | Lubricant compositions containing dispersant additives |
| US4198306A (en) * | 1978-07-03 | 1980-04-15 | Chevron Research Company | Deposit control and dispersant additives |
| US4695291A (en) * | 1982-09-30 | 1987-09-22 | Chevron Research Company | Poly(oxyalkylene) aminoether carbamates as deposit control additives |
| US4521610A (en) * | 1982-09-30 | 1985-06-04 | Chevron Research Company | Poly(oxyalkylene) aminoether carbamates as deposit control additives |
| US4728451A (en) * | 1982-09-30 | 1988-03-01 | Chevron Research Company | Lubricating oil compositions containing poly(oxyalkylene) aminoether carbamates as dispersing agents |
| US4564372A (en) * | 1983-07-29 | 1986-01-14 | Chevron Research Company | Quaternary deposit control additives |
| US4600409A (en) * | 1983-07-29 | 1986-07-15 | Chevron Research Company | Quaternary deposit control additives |
| WO1985000620A1 (en) * | 1983-07-29 | 1985-02-14 | Chevron Research Company | Quaternary deposit control additives |
| US4956270A (en) * | 1986-05-06 | 1990-09-11 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic material having improved antistatic and antiblocking properties |
| RU2216535C1 (ru) * | 2002-04-08 | 2003-11-20 | Всероссийский научно-исследовательский ветеринарный институт | N-[алкоксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие фунгистатической и бактерицидной активностью, и способ их получения |
| RU2221776C2 (ru) * | 2002-04-08 | 2004-01-20 | Институт органической и физической химии им. А.Е.Арбузова КНЦ РАН | N, n-диметил-n-алкил-n-[алкоксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие фунгистатической и бактерицидной активностью, а также свойствами присадок, регулирующих вязкоупругие свойства ассоциированных мультикомпонентных нефтяных систем, и способ их получения |
| RU2221775C2 (ru) * | 2002-04-08 | 2004-01-20 | Институт органической и физической химии им. А.Е.Арбузова КНЦ РАН | N-[алкоксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие свойствами присадок, регулирующих вязкоупругие свойства ассоциированных мультикомпонентных нефтяных систем, способ их получения и применения |
| RU2221777C2 (ru) * | 2002-04-08 | 2004-01-20 | Институт органической и физической химии им. А.Е.Арбузова КНЦ РАН | N-[алкилфеноксиполи(этиленокси)карбонилметил]аммоний хлориды, обладающие свойствами присадок, регулирующих вязкоупругие свойства ассоциированных мультикомпонентных нефтяных систем, и способ их получения |
| RU2284317C1 (ru) * | 2005-07-06 | 2006-09-27 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | 1,2,3-трис{[аминополи(этиленамино)этиламмонио]-метилкарбонилоксиполи(алкиленокси)}пропан трихлориды, обладающие фунгицидной активностью, свойствами эмульгаторов катионных битумных эмульсий, способностью повышать адгезию битумов к минеральным материалам, и способ их получения |
| RU2294337C1 (ru) * | 2005-07-06 | 2007-02-27 | Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра РАН (ИОФХ им. А.Е. Арбузова КазНЦ РАН) | Трис[(аммонио)метилкарбонилоксиполи(2-метилэтиленокси)]пропан трихлориды, обладающие свойствами эмульгаторов водобитумных эмульсий, и способ их получения |
| RU2308468C2 (ru) * | 2005-07-06 | 2007-10-20 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | 1,2,3-трис[(аммонио)метилкарбонилоксиполи(алкиленокси)]пропан трихлориды, обладающие бактерицидной и фунгицидной активностью, и способ их получения |
| RU2308467C2 (ru) * | 2005-07-06 | 2007-10-20 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | [(аммонио)метилкарбонилоксиполи(алкиленокси)]пропан хлориды, обладающие бактерицидной активностью, и способ их получения |
| RU2308466C2 (ru) * | 2005-07-06 | 2007-10-20 | Всероссийский научный исследовательский ветеринарный институт (ВНИВИ) | [(гетерилонио)(аммонио)метилкарбонилоксиполи(алкиленокси)] пропан хлориды, обладающие фунгицидной активностью, и способ их получения |
Also Published As
| Publication number | Publication date |
|---|---|
| CH511972A (de) | 1971-08-31 |
| CH483400A (de) | 1969-12-31 |
| DE1768060A1 (de) | 1971-09-16 |
| FR1561574A (en:Method) | 1969-03-28 |
| GB1219931A (en) | 1971-01-20 |
| CH1232369A4 (en:Method) | 1971-05-14 |
| BE713109A (en:Method) | 1968-08-16 |
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