GB808265A - Quaternary ammonium salts - Google Patents
Quaternary ammonium saltsInfo
- Publication number
- GB808265A GB808265A GB26663/57A GB2666357A GB808265A GB 808265 A GB808265 A GB 808265A GB 26663/57 A GB26663/57 A GB 26663/57A GB 2666357 A GB2666357 A GB 2666357A GB 808265 A GB808265 A GB 808265A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrakis
- hydroxyethyl
- ethylenediamine
- methyl
- sulphate
- 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 title 1
- 150000003863 ammonium salts Chemical group 0.000 abstract 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- 239000004677 Nylon Substances 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 2
- 150000002500 ions Chemical class 0.000 abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 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 abstract 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 2
- 229940102396 methyl bromide Drugs 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 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 abstract 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 229920001778 nylon Polymers 0.000 abstract 2
- 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 abstract 2
- 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 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 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 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 abstract 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- NDKYEUQMPZIGFN-UHFFFAOYSA-N Butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 abstract 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 abstract 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- JYCKNDWZDXGNBW-UHFFFAOYSA-N dipropyl sulfate Chemical compound CCCOS(=O)(=O)OCCC JYCKNDWZDXGNBW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 abstract 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 abstract 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 abstract 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention comprises compounds of the formul <FORM:0808265/IV (b)/1> <FORM:0808265/IV (b)/2> where R is hydrogen or a C12-18 aliphatic acyl radical, at least one R being said acyl radical, M is a C1-4 monovalent hydrocarbon group which may be saturated or ethylenically unsaturated, X is an anion and Z is the valence of X. The compounds are prepared by reacting a compound of the formula <FORM:0808265/IV (b)/3> with one or two equivalents of a quaternizing agent of the formula MzX. The R's may be lauroyl, stearoyl, oleoyl, myristoyl, palmitoyl and/or ricinoleoyl. X may be a chloride, bromide, iodide, sulphate, borate, phosphate, benzenesulphonate or toluenesulphonate ion. M may be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, allyl or crotyl. The examples describe the preparation of the monoquaternary ammonium salts of N : N : N1 : N1 - tetrakis-(2-hydroxyethyl) - ethylenediamine monostearate and methyl chloride, methyl bromide, methyl iodide, ethyl bromide, n-propyl bromide, n-butyl bromide, isobutyl chloride, trimethyl phosphate, tributyl phosphate, trimethyl borate, dimethyl sulphate, diethyl sulphate, di-n-propyl sulphate, di-n-butyl sulphate, methyl benzenesulphonate and methyl para-toluenesulphonate respectively; the monoquaternary ammonium salts of N : N : N1 : N1 - tetrakis (2 - hydroxyethyl) - ethylenediamine distearate and methyl bromide, n-butyl bromide, allyl chloride, dimethyl sulphate and methyl para-toluenesulphonate respectively, the monoquaternary ammonium salts of N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) - ethylenediamine dilaurate and dioleate and dimethyl sulphate, the diquaternary ammonium salts of N : N: N1 : N1 - tetrakis - (2 - hydroxyethyl - ethylenediamine mono- and di-stearates and dimethyl sulphate, and the mono- and diquaternary ammonium salts of N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) - ethylenediamine tri- and tetra-stearates and dimethyl sulphate. O-acylated N : N : N1 : N1-tetrakis-(2-hydroxyethyl)-ethylenediamine of the formula <FORM:0808265/IV (b)/4> where R is as above, are prepared by ester interchange between N : N : N1 : N1 - tetrakis - (2 - hydroxyethyl)-ethylenediamine and a C1-4 alkyl ester of a C12-18 fatty acid or fat acid. Mixed esters may be prepared by using a mixture of ester reactants, e.g. butyl stearate and butyl laurate, in the ester interchange. The interchange is catalysed by alkaline earth and alkali metal hydroxides and alkoxides, and also by aluminium isopropoxide. Toluene and xylene may be used as solvents. Examples are given of the preparation of N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) - ethylenediamine mono-, di-, tri- and tetra-stearates and corresponding dioleate and dilaurate compounds.ALSO:Quaternary O-acylated N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) ethylenediamines of the formul <FORM:0808265/IV (c)/1> and <FORM:0808265/IV (c)/2> where R is hydrogen or a C12-18 aliphatic acyl radical, at least one R being an acyl radical, M is a C1-4 monovalent hydrocarbon group which may be saturated or ethylenically unsaturated, X is an anion and Z is the valence of X, are applied as aqueous dispersions to textile fabrics prepared from cellulose acetate, nylon or vinyl chloride resins, to which they impart lubricity, softness of feel, anti-scorch properties and anti-static properties. The compounds may be applied in aqueous urea- or melamine-formaldehyde resin baths. In the above formul the R's may be lauroyl, stearoyl, oleoyl, myristoyl, palmitoyl and/or ricinoleyl; M may be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, allyl or crotyl; and X may be a chloride, bromide, iodide, sulphate, borate, phosphate, benzenesulphonate or toluenesulphonate ion. In an example, an aqueous-dispersion of the monoquaternary ammonium salt prepared from N : N : N1 : N1-tetrakis-(2-hydroxyethyl) ethylenediamine distearate and dimethyl sulphate is padded on to nylon taffeta at 120 DEG F. and the fabric dried at 225 DEG F.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US808265XA | 1956-09-06 | 1956-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808265A true GB808265A (en) | 1959-01-28 |
Family
ID=22159853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26663/57A Expired GB808265A (en) | 1956-09-06 | 1957-08-23 | Quaternary ammonium salts |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB808265A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055749A (en) * | 1959-04-16 | 1962-09-25 | Exxon Research Engineering Co | Additives for modifying the electrical properties of combustible organic liquids |
| US3954633A (en) * | 1973-07-13 | 1976-05-04 | Hoechst Aktiengesellschaft | Antistatic and lubricating agents for the processing of fibers |
| US3956143A (en) * | 1973-07-13 | 1976-05-11 | Hoechst Aktiengesellschaft | Preparation for the antistatic finishing of fibers |
| US4439331A (en) * | 1981-09-04 | 1984-03-27 | Hoechst Aktiengesellschaft | Textile softener |
| EP0803498A1 (en) * | 1996-04-26 | 1997-10-29 | Witco Corporation | Polyester, polyquaternary compounds, compositions containing them and their use as fabric softener |
| WO2006040332A1 (en) * | 2004-10-13 | 2006-04-20 | Clariant Finance (Bvi) Limited | Fatty acid esters of alkanolamines and their use as softening agents |
| WO2010150816A1 (en) * | 2009-06-24 | 2010-12-29 | 富士フイルム株式会社 | Composition, compound and membrane formation method |
| US9255058B2 (en) | 2009-09-28 | 2016-02-09 | Fujifilm Corporation | Complex alcohol ester composition, method for production same, and use of same |
| WO2016121370A1 (en) * | 2015-01-28 | 2016-08-04 | 川研ファインケミカル株式会社 | Tertiary amine compound and manufacturing method therefor, and liquid softening agent composition containing same |
| WO2025036787A1 (en) | 2023-08-17 | 2025-02-20 | Evonik Operations Gmbh | Active substances for cleaning compositions |
| WO2025036785A1 (en) | 2023-08-17 | 2025-02-20 | Evonik Operations Gmbh | Active substances for cleaning compositions |
-
1957
- 1957-08-23 GB GB26663/57A patent/GB808265A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055749A (en) * | 1959-04-16 | 1962-09-25 | Exxon Research Engineering Co | Additives for modifying the electrical properties of combustible organic liquids |
| US3954633A (en) * | 1973-07-13 | 1976-05-04 | Hoechst Aktiengesellschaft | Antistatic and lubricating agents for the processing of fibers |
| US3956143A (en) * | 1973-07-13 | 1976-05-11 | Hoechst Aktiengesellschaft | Preparation for the antistatic finishing of fibers |
| US4439331A (en) * | 1981-09-04 | 1984-03-27 | Hoechst Aktiengesellschaft | Textile softener |
| EP0803498A1 (en) * | 1996-04-26 | 1997-10-29 | Witco Corporation | Polyester, polyquaternary compounds, compositions containing them and their use as fabric softener |
| WO2006040332A1 (en) * | 2004-10-13 | 2006-04-20 | Clariant Finance (Bvi) Limited | Fatty acid esters of alkanolamines and their use as softening agents |
| WO2010150816A1 (en) * | 2009-06-24 | 2010-12-29 | 富士フイルム株式会社 | Composition, compound and membrane formation method |
| US9255058B2 (en) | 2009-09-28 | 2016-02-09 | Fujifilm Corporation | Complex alcohol ester composition, method for production same, and use of same |
| WO2016121370A1 (en) * | 2015-01-28 | 2016-08-04 | 川研ファインケミカル株式会社 | Tertiary amine compound and manufacturing method therefor, and liquid softening agent composition containing same |
| WO2025036787A1 (en) | 2023-08-17 | 2025-02-20 | Evonik Operations Gmbh | Active substances for cleaning compositions |
| WO2025036785A1 (en) | 2023-08-17 | 2025-02-20 | Evonik Operations Gmbh | Active substances for cleaning compositions |
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