US2878273A - Quaternary ammonium salts - Google Patents
Quaternary ammonium salts Download PDFInfo
- Publication number
- US2878273A US2878273A US608187A US60818756A US2878273A US 2878273 A US2878273 A US 2878273A US 608187 A US608187 A US 608187A US 60818756 A US60818756 A US 60818756A US 2878273 A US2878273 A US 2878273A
- Authority
- US
- United States
- Prior art keywords
- tetrakis
- hydroxyethyl
- ethylenediamine
- dimethyl sulfate
- ammonium salt
- 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
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 27
- -1 fatty acid esters Chemical class 0.000 description 25
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 22
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 22
- 150000003863 ammonium salts Chemical group 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 19
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000001993 wax Substances 0.000 description 14
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 12
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004753 textile Substances 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229940012017 ethylenediamine Drugs 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229940102396 methyl bromide Drugs 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- ULBTUVJTXULMLP-UHFFFAOYSA-N butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCC ULBTUVJTXULMLP-UHFFFAOYSA-N 0.000 description 2
- XGGKPIDDGLLMFG-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC.COS(=O)(=O)OC XGGKPIDDGLLMFG-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])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 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- NDKYEUQMPZIGFN-UHFFFAOYSA-N Butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 229940063013 borate ion Drugs 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- BSVOVKZEVXWQPJ-UHFFFAOYSA-N butyl dimethyl phosphate Chemical compound CCCCOP(=O)(OC)OC BSVOVKZEVXWQPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- JYCKNDWZDXGNBW-UHFFFAOYSA-N dipropyl sulfate Chemical compound CCCOS(=O)(=O)OCCC JYCKNDWZDXGNBW-UHFFFAOYSA-N 0.000 description 1
- ARLPTABUWXZQCY-UHFFFAOYSA-N ethane-1,2-diamine octadecanoic acid Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCCCC)(=O)O.C(CN)N ARLPTABUWXZQCY-UHFFFAOYSA-N 0.000 description 1
- AGZWCTVHYPLFHY-UHFFFAOYSA-N ethane-1,2-diamine;octadecanoic acid Chemical compound NCCN.CCCCCCCCCCCCCCCCCC(O)=O AGZWCTVHYPLFHY-UHFFFAOYSA-N 0.000 description 1
- KCWGHIAGIBAKFB-UHFFFAOYSA-N ethane-1,2-diamine;octadecanoic acid Chemical compound NCCN.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O KCWGHIAGIBAKFB-UHFFFAOYSA-N 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])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
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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
- 125000001312 palmitoyl group Chemical group O=C([*])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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- DJZKNOVUNYPPEE-UHFFFAOYSA-N tetradecane-1,4,11,14-tetracarboxamide Chemical compound NC(=O)CCCC(C(N)=O)CCCCCCC(C(N)=O)CCCC(N)=O DJZKNOVUNYPPEE-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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
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
- D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
Definitions
- the present invention relates to novel quaternary ammonium compounds and methods of preparing the same.
- An object of the invention is to provide novel quaternary ammonium salts of fatty acid esters of a polyhydroxypolyamine.
- An additional object is to prepare novel compounds useful to impart softening and lubricating characteristics to textiles.
- a further object is to prepare novel textile softeners having increased stability to heat. i,
- Yet another object is to prepare novel anti-static agents for textiles.
- R can be lauroyl, stearoyl, oleoyl, myristoyl, palmitoyl, ricinoleoyl, etc.
- M can be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl.
- X can be a sulfate ion, a halide ion, e. g., chloride, bromide, iodide, benzene sulfonate ion, toluenesulfonate ion, borate ion, phosphate ion, etc.
- M groups When there are 2 M groups, they can be alike or different. Similarly, when more than one R is an acyl group, the acyl groups can be alike or different.
- the compounds of the present invention are valuable as softening and anti-static agents for textile fabrics such as cellulose acetate, nylon, vinyl resins, e. g., vinyl chloride resins, etc. I a I
- the compounds of the present invention lend valuable softening and lubricity to textile fabric and also prevent the undesirable physical manifestation of static electrical charges which tend to accumulate on many fibers.
- the compounds are water dispersible which results in easy and low cost application.
- the compounds also are unique "ice in that they afford a means of binding three or four long fatty acid chains, which when quaternized possess unexpected solubility and compatability in conventional aqueous textile resin treating baths with internal pH buifering. Such buffering is necessary for urea and melamine formaldehyde resin bath stability.
- the present products also haveinherent stability to heat (non-scorching) which is superior to the nonquaternized acetate salts of the same starting compound, for example.
- the compounds of the present invention are made by reacting the appropriate tertiary amine with a quaternizing agent.
- quaternizing agents there can be employed alkyl halides, e. g., methyl bromide, methyl chloride, methyl iodide, ethyl bromide, propyl chloride, n-butyl chloride, dimethyl sulfate, diethyl.
- sulfate di-npropyl sulfate, di-n-butyl sulfate, methyl benzene sulfonate, methyl p-toluenesulfonate, ethyl p-toluenesulfonate, butyl p-toluenesulfonate, trimethyl phosphate, tributyl phosphate, dimethyl butyl phosphate, trimethyl borate, allyl chloride, allyl bromide, crotyl chloride, etc.
- Whether the mono or diquaternary ammonium salt is formed depends on the proportions of the tertiary amine and the quaternizing agent. Two equivalents of quaternizing agent are required to form the diquaternary compound and only one equivalent to form the monoquaternary compound.
- the monoquaternary ammonium salt prepared from N,N,N',N-tetrakis(Z-hydroxyethyl) ethylenedia-mine -monostearate and dimethyl sulfate, the corresponding salt from diethyl sulfate, the corresponding salt from methyl bromide, the corresponding salt from di-nbutylsulfate, the corresponding salt from di-n-propyl sulfate, the corresponding salt from metyl chloride, the corresponding salt from methyl bromide, the corresponding salt from methyl iodide, the corresponding salt from ethyl bromide, the corresponding salt from n-propyl bromide, the corresponding salt from n-butyl bromide, the corresponding salt from isobutyl chloride, the corresponding salt from tributyl phosphate, the corresponding salt from trimethyl phosphate, the corresponding salt from tri
- the corresponding diquaternary compound e. g., the diquaternary ammonium salt prepared from N,N,N',N'-tetrakis(2-hydroxyethyl) ethylenediamine monostearate and dimethyl sulfate.
- the monoquaternary ammonium salt prepared from N,N,N,N-tetrakis(2-hydroxyethyl)ethylenediamine distearate and. dimethyl sulfate, as well as of the other quaternizing agents set forth supra.
- the diquaternary salt of this compound e. g., with dimethyl sulfate, also can be made.
- the diquaternary salt of this compound, e. g., with dimethyl sulfate also can be made.
- stearate compounds In place of the stearate compounds, compounds containing any of the acyl groups previously set forth can be made. Additionally, mixed acyl group containing compounds can be prepared.
- amine fatty acid ester products are oils or waxes. Increas ing the number of acyl'groups in the molecule gives a harder wax.
- N ,N ,N ',N '-letrakis(Z-Izydroxyethyl ethylenediam ine monostearate A mixture of 472 g. of N,N,N',N-tetrakis(2-hydroxy ethyl)ethylenediamine, 680 g. n-butyl stearate and 2.9 g. sodium hydroxide was stirred and heated to 110 C. at 70 mm. pressure. n-Butyl alcohol began to distill from the reaction mixture. The temperature was raised to 140 C. during an hour. The pressure was then reduced to 17 mm. and the charge stirred at 140/ 17 mm.
- N,N,N,N'-tetrakis(ZrhydrOxyethyZ) ethylenediamine tristearate A stirred mixture-of .236 g.” N,N,N.',N'-tetrakis::(2-hydroxyethyl)ethylenediamine; 1020 g. of n-butyl stearate and 3.1 g; of sodium hydroxide was heated at 70 mm.
- N,N,N,N-tetral is(2-hydroxyethyl) ethylenediamine dioleate as a dark viscous liquid.
- N ,N ,N 'N -tetrakis Z-hydroxyethyl ethylenediamine dilaurate-
- 236 g. of N,N,N',N- tetrakis(2-hydroxyethyl)ethylenediamine was treated with 512g. n-butyl laurate and 1.9 g. of sodium hydroxide to. yield N,N,N',N-tetrakis,(2-hydroxyethyl) ethylenediamine dilaurate as a low melting wax.
- the compounds ofthe present invention are. prepared as follows:
- N ,N -tetrakis( Z-hydroxyethyl ethylenediamine monostearate and dimethyl sulfate N,N,N',N' tetrakis(2 hydroxyethyl)ethylenediamine monostearate (150.6 g.) was heated to C. and 37.8 g. of dimethyl sulfate added slowly with stirring. The temperature was maintained between 100 C. and C. and held there for two hours. A soft wax, easily dispersible in water, was obtained.
- N ,N -tetrakis(Z-hydroxyethyl) ethylenediamine monostearate and dimethyl sulfate in aqueous solution A stirred mixture of 72 g. of N,N,N,N'-tetrakis(2- hydroxyethyl)ethylenediamine monostearate and 150 ml. of water was heated to 100 C. and 18 g.'of dimethyl sulfate was slowly added. The mixture was heated at 100 C. forfive hours and then cooled to room temperature to yield a water dispersible product.
- N,N,N,N' tetrakis(2 hydroxyethyl)ethylenediamine monostearate (150.6 g.) was heated to 110 C. and 55.8 g. of methyl toluenesulfonatewas slowly added with stirring. The temperature was increased to and maintained at C. for four hours, A water dispersible product was. obtained.
- N,N'-tetrakis(2 hydroxyethyl)ethylenediamine distearate and dimethyl sulfate N,N,N',N"- tetrakis(2 hydroxyethyl) ethylenediamine distearate (153.6 g.) was heated to 130 C. and 25.2 g. ofdimethyl'sulfate was slowly added. After the addition was complete, the whole was maintained at 130 C. for an additional hour anda half. The product was a water dispersible wax.
- Dimethyl sulfate (50.4 g.) was added slowly with stirring to 153.6 g. of N,N,N,N'-tetrakis(2-hydroxyethyl) ethylenediamine distearate at 130 C. The. heating was continued after the addition-was complete for an additional-:two hours.
- The-product was a hard wax and may be dispersed in water.
- EXAMPLE 12 M onoquaternary ammonium salt prepared from .N,N.
- N,N-tetrakis(2 hydroxyethyl)ethylenediamine distearate and methyl bromide Monoquaternary ammonium salt prepared from N,N,
- N ',N-tetrakis(2 hydroxyethyl)ethylenediamine dilaurate and dimethyl sulfate 120 g. of N,N,N,N'-tetrakis(2-hydroxyethyl)ethylenediamine dilaurate was heated to 65 C. and 25.2 g. of dimethyl sulfate was slowly added with stirring. After all of the dimethyl sulfate had been added, the mixture was heated to 130 C. for three hours. The product was a low melting wax that formed a dispersion with water.
- EXAMPLE 16 Monoquaternary ammonium salt prepared from N,N, N ,N -tetrakis(Z-hydroxyethyl )ethylenediamine dioleate and dimethyl sulfate 152.8 g. of N,N,N',N-tetrakis(2-hydroxyethyl)ethylenediamine dioleate was heated to 65 C., and 25.2 g. of dimethyl sulfate slowly added with stirring. After the addition was complete, the temperature was increased to and maintained at 130 C. for three hours. The product was a viscous liquid that formed a dispersion in water.
- EXAMPLE 18 Monoquaternary ammonium salt prepared from nbutyl bromide and N,N,N,N'-tetraki (Z-hydroxyethyl) ethylenediamine distearate n-Butyl bromide (27.4 g.) was "added slowly to a stirred melt of 153 g. of N,N,N,N'-tetrakis (Z-hydroxyethyl)ethylenediamine distearate at 100 C. When the addition was complete, the reaction mixture was stirred and heated at 120 C. for an additional three hours and thirty minutes. The product was a water dispersible wax.
- Dimethyl sulfate (6.3 g.) was slowly added to 65 g. of N,N,N,N' tetrakis(2-hydroxyethyl)ethylenediamine tetrastearate at C. After the addition was complete, the whole was stirred and heated at 100 C. for one hour to yield a water dispersible wax.
- the quaternary ammonium salts of the present invention are water dispersible and possess surface active properties. They are easily applied to fabrics by the usual padding methods from aqueous dispersions. A typical example illustrating this use is as follows:
- EXAMPLE 20 A 0.30% dispersion of the monoquaternary ammonium salt prepared from N,N,N,N-tetrakis(2-hydroxyethyl)ethylenediamine distearate and dimethyl sulfate was applied to Nylon 200 taffeta by standard padding techniques, i. e., a conventional padding machine, at F. in such a manner as to result in 50% pickup of the dispersion by the fabric. The fabric was dried at 225 F. Nylon 200 taffeta treated in this manner possessed improved softness to the hand, increased lubricity, and superior anti-scorch and anti-static properties. Nylon 200 is a synthetic linear superpolyamide of the hexamethyleneadipamide type.
- a compound selected from the group consisting of ROCHzCHr CHzCHzOR Z where R is selected from the group consisting of aliphatic acyl radicals containing from 12 to 18 carbon atoms and hydrogen, at least one R being said aliphatic acyl radical, M is a monovalent hydrocarbon group containing l to 4 carbon atoms, X is an anion and Z is the valence of X.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL98011D NL98011C (enrdf_load_stackoverflow) | 1956-09-06 | ||
| BE560506D BE560506A (enrdf_load_stackoverflow) | 1956-09-06 | ||
| US608187A US2878273A (en) | 1956-09-06 | 1956-09-06 | Quaternary ammonium salts |
| CH5017457A CH363351A (de) | 1956-09-06 | 1957-09-05 | Verfahren zur Herstellung von quaternären Ammoniumsalzen |
| FR1182114D FR1182114A (fr) | 1956-09-06 | 1957-09-06 | Sels d'ammonium quaternaire |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US608187A US2878273A (en) | 1956-09-06 | 1956-09-06 | Quaternary ammonium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2878273A true US2878273A (en) | 1959-03-17 |
Family
ID=24435439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US608187A Expired - Lifetime US2878273A (en) | 1956-09-06 | 1956-09-06 | Quaternary ammonium salts |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2878273A (enrdf_load_stackoverflow) |
| BE (1) | BE560506A (enrdf_load_stackoverflow) |
| CH (1) | CH363351A (enrdf_load_stackoverflow) |
| FR (1) | FR1182114A (enrdf_load_stackoverflow) |
| NL (1) | NL98011C (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072690A (en) * | 1961-02-01 | 1963-01-08 | Nalco Chemical Co | Water-dispersible amido-quaternary ammonium salts |
| US3168416A (en) * | 1957-04-23 | 1965-02-02 | Atlas Chem Ind | Textile yarn coated with cationic surfactant |
| US3342630A (en) * | 1963-09-13 | 1967-09-19 | Colgate Palmolive Co | Silicate and titanate orthoesters and soil-proofed textile materials |
| US3350218A (en) * | 1963-09-13 | 1967-10-31 | Colgate Palmolive Co | Soilproofing with quaternary ammonium derivatives of highly fluorinated carboxylic acids |
| US4812263A (en) * | 1986-08-22 | 1989-03-14 | Ppg Industries, Inc. | Bis-quaternary ammonium compounds |
| EP0643038A3 (en) * | 1993-07-15 | 1995-05-31 | Aranor Sa | Polyfunctional cationic surfactants, their compositions, processes for their preparation and uses. |
| US20110203975A1 (en) * | 2008-11-07 | 2011-08-25 | Clariant Finance (Bvi) Limited | Mixture of an Amine Alkoxylate Ester and a Quaternary Ammonium Compound as a Collector for Minerals Containing Silicate |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3135014A1 (de) * | 1981-09-04 | 1983-03-24 | Hoechst Ag, 6000 Frankfurt | Waescheweichspuelmittel |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB678604A (en) * | 1950-11-20 | 1952-09-03 | Lankro Chem Ltd | New fatty acid amido-alkyl-amino ester salts and process for the production thereof |
| US2719156A (en) * | 1953-12-04 | 1955-09-27 | Rohm & Haas | Methylolated quaternary ammonium compounds |
-
0
- NL NL98011D patent/NL98011C/xx active
- BE BE560506D patent/BE560506A/xx unknown
-
1956
- 1956-09-06 US US608187A patent/US2878273A/en not_active Expired - Lifetime
-
1957
- 1957-09-05 CH CH5017457A patent/CH363351A/de unknown
- 1957-09-06 FR FR1182114D patent/FR1182114A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB678604A (en) * | 1950-11-20 | 1952-09-03 | Lankro Chem Ltd | New fatty acid amido-alkyl-amino ester salts and process for the production thereof |
| US2719156A (en) * | 1953-12-04 | 1955-09-27 | Rohm & Haas | Methylolated quaternary ammonium compounds |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168416A (en) * | 1957-04-23 | 1965-02-02 | Atlas Chem Ind | Textile yarn coated with cationic surfactant |
| US3072690A (en) * | 1961-02-01 | 1963-01-08 | Nalco Chemical Co | Water-dispersible amido-quaternary ammonium salts |
| US3342630A (en) * | 1963-09-13 | 1967-09-19 | Colgate Palmolive Co | Silicate and titanate orthoesters and soil-proofed textile materials |
| US3350218A (en) * | 1963-09-13 | 1967-10-31 | Colgate Palmolive Co | Soilproofing with quaternary ammonium derivatives of highly fluorinated carboxylic acids |
| US4812263A (en) * | 1986-08-22 | 1989-03-14 | Ppg Industries, Inc. | Bis-quaternary ammonium compounds |
| EP0643038A3 (en) * | 1993-07-15 | 1995-05-31 | Aranor Sa | Polyfunctional cationic surfactants, their compositions, processes for their preparation and uses. |
| ES2080655A1 (es) * | 1993-07-15 | 1996-02-01 | Lorente Hidalgo Antonio | Nuevos tensioactivos cationicos polifuncionales, composiciones a base de los mismos, procedimiento para su preparacion y aplicaciones. |
| US20110203975A1 (en) * | 2008-11-07 | 2011-08-25 | Clariant Finance (Bvi) Limited | Mixture of an Amine Alkoxylate Ester and a Quaternary Ammonium Compound as a Collector for Minerals Containing Silicate |
| US9027757B2 (en) * | 2008-11-07 | 2015-05-12 | Clariant Finance (Bvi) Limited | Mixture of an amine alkoxylate ester and a quaternary ammonium compound as a collector for minerals containing silicate |
Also Published As
| Publication number | Publication date |
|---|---|
| NL98011C (enrdf_load_stackoverflow) | |
| CH363351A (de) | 1962-07-31 |
| BE560506A (enrdf_load_stackoverflow) | |
| FR1182114A (fr) | 1959-06-23 |
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