WO1992018684A1 - Verwendung von estern als textilweichmachender wirkstoff - Google Patents
Verwendung von estern als textilweichmachender wirkstoff Download PDFInfo
- Publication number
- WO1992018684A1 WO1992018684A1 PCT/EP1992/000743 EP9200743W WO9218684A1 WO 1992018684 A1 WO1992018684 A1 WO 1992018684A1 EP 9200743 W EP9200743 W EP 9200743W WO 9218684 A1 WO9218684 A1 WO 9218684A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- esters
- use according
- acid
- alkanolamines
- derived
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 31
- 239000004902 Softening Agent Substances 0.000 title claims description 5
- 239000004753 textile Substances 0.000 title abstract description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 13
- 229930195729 fatty acid Natural products 0.000 claims abstract description 13
- 239000000194 fatty acid Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 239000004310 lactic acid Substances 0.000 claims description 9
- 235000014655 lactic acid Nutrition 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000004744 fabric Substances 0.000 claims description 6
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical class C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- -1 Fatty acid esters Chemical class 0.000 abstract description 7
- 235000005985 organic acids Nutrition 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000021357 Behenic acid Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229940116226 behenic acid Drugs 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 229940031098 ethanolamine Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RRBXHIYJTGFUDF-UHFFFAOYSA-N 1-amino-2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(O)CN RRBXHIYJTGFUDF-UHFFFAOYSA-N 0.000 description 1
- QZXIXSZVEYUCGM-UHFFFAOYSA-N 2-aminopropan-2-ol Chemical compound CC(C)(N)O QZXIXSZVEYUCGM-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 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
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- 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
- D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
Definitions
- Textiles which come into contact with human skin are often treated with active ingredients which soften the textile and which give the textiles a pleasantly soft feel.
- active ingredients which soften the textile and which give the textiles a pleasantly soft feel.
- Numerous textile-softening active substances are known, of which quaternary ammonium compounds with two or three long residues are used very frequently and on a large scale because of their good activity.
- Such quaternary ammonium compounds are more readily degradable than the conventional quaternary ammonium compounds with fatty alkyl residues. Nevertheless, some of these more readily degradable quaternary ammonium compounds do not meet all the requirements for an ideal compound, since the degradation occasionally takes place via intermediate stages which are not entirely ecologically harmless. They can be produced in different ways, but it is generally difficult to obtain light-colored products that are accepted by the consumer. Additional operations are therefore often required to separate dark-colored products from light-colored ones, which increases the manufacturing costs for light-colored products. In addition, reagents are required for the quaternization reaction, the handling of which often requires additional safety measures. other. There is therefore still a need for textile-softening active ingredients which are readily biodegradable and which are degraded without the formation of ecologically unobjectionable intermediates and which can be easily prepared from conveniently handled starting materials.
- esters of alkanolamines can be used as fabric softening agents.
- the esters are derived from fatty acids, which can be natural or synthetic and accordingly can be straight-chain or branched, saturated or unsaturated and contain 6 to 24 carbon atoms per fatty acid residue.
- Esters preferred for the use according to the invention are derived from fatty acids which contain 8 to 24 carbon atoms and which are easily and inexpensively obtained from natural fats.
- Vegetable and animal fats come into question as sources of natural fats, for example coconut oil, palm kernel oil, sunflower oil, turnip oil, beef tallow, fish oil, sperm oil and the narrower or further fatty acid cuts produced therefrom.
- esters of alkanolamines which are derived from pure or technical fatty acids, for example from lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, behenic acid, acids which are derived from Guerbet alcohols and substituted acids, for example hydroxycarboxylic acids, are also very suitable.
- esters of alkanolamines are alkanolamines with 1, 2 or 3 alkanol residues.
- Esters which are particularly suitable for the use according to the invention are derived from alkanolamines whose alkanol groups contain 2 to 4, in particular 2 or 3, carbon atoms. These are, for example, ethanolamine, propanolamine and butanolamine, of which the ethanolamines and the propanolamines are particularly preferred.
- Alkanolamines with 3 carbon atoms are derived from n-propanolamine or i-propanolamine.
- Typical alkanolamines whose esters are suitable for the use according to the invention are, for example, dimethylethanolamine, ethyldiethanolamine, triethanolamine, diethylethanolamine, ethyldiethanolamine, dimethyl-n-propanolamine, methyldi-n-propanolamine, dimethyl-i-propanolamine, methyl-ii -propanolamine and the higher n-propyl or i-propyl homologues of mentioned connections.
- esters derived from alkanolamines, the alkyl or alkanol residues of which are different in the molecule in the event that the molecule contains several alkyl or alkanol groups examples of such compounds are methyl ethyl ethanol amine, methyl i-propyl ethanolamine, methyl ethyl i-propanolamine or methyl ethyl n-butanolamine.
- esters of alkanolamines mentioned are known compounds which are used as precursors to the quaternary ammonium compounds described in the abovementioned references. They can be produced by esterification of the alkanolamines with fatty acids, fatty acid halides and fatty acid esters, for example fatty acid ethyl ester or also with trifatty acid glycerides, the so-called triglycerides.
- Esters highly suitable for the use according to the invention are derived from alkanolamines which are in salt form.
- the salts of the alkanolamine esters are obtained by simply neutralizing the alkanolamine esters with acids. Salts of the esterified alkanolamines which have been obtained by neutralization with short-chain organic or inorganic acids are preferably used.
- Short-chain organic acids are taken to mean mono- or polybasic acids, for example formic acid, acetic acid, oxalic acid, succinic acid, malonic acid, fumaric acid, but also substituted acids, such as citric acid, tartaric acid, glycolic acid, lactic acid, tartronic acid or gluconic acid.
- Inorganic acids suitable for salt formation are, for example, hydrochloric acid, sulfuric acid, phosphoric acid or phosphorous acid.
- the esters are 100 mol% in salt form.
- it is advantageous that the alkanolamine esters are only in salt form at 30 to 90 mol.
- Alkanolamine esters exist as salts of lactic acid or phosphorous acid.
- a preferred use of the alkanolamine esters according to the invention takes place in aqueous treatment compositions which contain 0.5 to 20% by weight of the compounds mentioned as fabric softening active ingredients.
- the esters mentioned are present in dissolved or dispersed form in aqueous treatment agents. Such treatment agents are used to treat freshly washed textiles.
- Another possible use for the alkanolamine esters mentioned is their addition to detergents or wash liquors.
- the textiles to be washed accumulate the alkanolamine esters on their surface during the washing process, which leads to an improvement in handle after rinsing and drying the textiles.
- the inventive alkanolamine ester is also used as a fabric softening agent in tumble auxiliaries in which the fabric softener is applied to a substrate that transfers the active ingredients to the textiles in an automatic tumble dryer during the drying process.
- the aqueous treatment agents preferably have a pH in the range from 2 to 7.
- the treatment agents contain more or less different additives.
- Aqueous treatment agents contain, for example, preservatives, opacifiers, viscosity regulators, fragrances, dyes, emulsifiers or dispersants.
- the alkanolamine esters can also be used in combination with other textile-softening active ingredients. In some cases it may be expedient to add surface-active substances, optical brighteners or solubilizers. Examples
- the end product contained 2.12% titratable nitrogen.
- reaction product from Example 2 100 g of the reaction product from Example 2 were neutralized with 9.2 g of acetic acid and the hot melt at 80 ° C. was stirred into 436.8 g of water at 85 ° C.
- the finely divided dispersion obtained after cooling contained 20% by weight of active ingredient.
- the final product contained 2.14% titratable nitrogen.
- reaction product 100 g of the reaction product were neutralized with 17 g of lactic acid, 80% strength, and the melt at 80 ° C. was stirred into 554.4 g of water at 85 ° C.
- the finely divided dispersion obtained after cooling contained 20% by weight of active ingredient.
- the final product contained 1.7% titratable nitrogen. 67.6 g of the end product were made up with 10.2 g of lactic acid, 80% strength and 422.2 g of water as in Example 3 to form a viscous, finely divided dispersion with 15% by weight of active ingredient.
- Example 4 Analogously to Example 1, 677 g (2 mol) of the behenic acid used in Example 4 were reacted with 118.9 g (1 mol) of methyldiethanolamine.
- the final product contained 1.79% titratable nitrogen.
- Example 3 67.2 g of the end product, 10.7 g of lactic acid, 80% strength and 421.1 g of water were made up as in Example 3 to form a viscous, finely divided dispersion with 15% by weight of active ingredient.
- the end product contained 1.66% titratable nitrogen.
- Example 3 67.6 g of the end product, 10.2 g of lactic acid, 80%, and 422.2 g of water were made up as in Example 3 to form a viscous, finely divided dispersion with 15% by weight of active ingredient.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4507127A JPH06506730A (ja) | 1991-04-12 | 1992-04-03 | 繊維製品用柔軟剤としてのエステルの使用 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4111966.5 | 1991-04-12 | ||
DE19914111966 DE4111966A1 (de) | 1991-04-12 | 1991-04-12 | Verwendung von estern als textilweichmachender wirkstoff |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992018684A1 true WO1992018684A1 (de) | 1992-10-29 |
Family
ID=6429452
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1992/000743 WO1992018684A1 (de) | 1991-04-12 | 1992-04-03 | Verwendung von estern als textilweichmachender wirkstoff |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0579649A1 (de) |
JP (1) | JPH06506730A (de) |
CA (1) | CA2108287A1 (de) |
DE (1) | DE4111966A1 (de) |
WO (1) | WO1992018684A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994004641A1 (en) * | 1992-08-21 | 1994-03-03 | Colgate-Palmolive Company | Fabric conditioning composition |
WO1994004642A2 (en) * | 1992-08-21 | 1994-03-03 | Colgate-Palmolive Company | Fabric conditioning composition |
WO1997029171A1 (en) * | 1996-02-09 | 1997-08-14 | Unilever Plc | Fabric softening composition |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5288847A (en) * | 1992-08-21 | 1994-02-22 | Colgate-Palmolive Company | Fabric conditioning composition containing alkanol amine ester and acid |
DE19642038C1 (de) * | 1996-10-11 | 1997-12-11 | Henkel Kgaa | Esterquats |
DE102010029610B4 (de) | 2010-06-02 | 2013-02-21 | Evonik Goldschmidt Gmbh | Quartäre Dialkanolaminester |
DE102010029606B4 (de) | 2010-06-02 | 2013-02-21 | Evonik Goldschmidt Gmbh | Quartäre Dialkanolaminester |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2525771A (en) * | 1947-05-12 | 1950-10-17 | Arkansas Company Inc | Fatty acid-aliphatic amine polyglycol combinations useful as textile assistants and process of producing the same |
FR1281984A (fr) * | 1959-11-25 | 1962-01-19 | Bayer Ag | Perfectionnements aux moyens pour empêcher le chargement électrostatique des hauts polymères synthétiques |
DE2258564A1 (de) * | 1971-12-06 | 1973-06-14 | Colgate Palmolive Co | Verbindungen mit tensid- und weichspueleigenschaften und deren verwendung |
GB2052583A (en) * | 1979-06-20 | 1981-01-28 | Ceskoslovenska Akademie Ved | Agent for textile livening having an antistatic effect and favourable dermatological properties |
GB2160522A (en) * | 1984-06-22 | 1985-12-24 | Sandoz Ltd | Sulphomethylated amino-esters |
DE3437321A1 (de) * | 1984-10-11 | 1986-04-24 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | Umsetzungsprodukte von hoeheren fettsaeuren mit dialkanolaminen, deren herstellung und verwendung |
-
1991
- 1991-04-12 DE DE19914111966 patent/DE4111966A1/de not_active Withdrawn
-
1992
- 1992-04-03 WO PCT/EP1992/000743 patent/WO1992018684A1/de not_active Application Discontinuation
- 1992-04-03 CA CA002108287A patent/CA2108287A1/en not_active Abandoned
- 1992-04-03 JP JP4507127A patent/JPH06506730A/ja active Pending
- 1992-04-03 EP EP19920907697 patent/EP0579649A1/de not_active Withdrawn
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2525771A (en) * | 1947-05-12 | 1950-10-17 | Arkansas Company Inc | Fatty acid-aliphatic amine polyglycol combinations useful as textile assistants and process of producing the same |
FR1281984A (fr) * | 1959-11-25 | 1962-01-19 | Bayer Ag | Perfectionnements aux moyens pour empêcher le chargement électrostatique des hauts polymères synthétiques |
DE2258564A1 (de) * | 1971-12-06 | 1973-06-14 | Colgate Palmolive Co | Verbindungen mit tensid- und weichspueleigenschaften und deren verwendung |
GB2052583A (en) * | 1979-06-20 | 1981-01-28 | Ceskoslovenska Akademie Ved | Agent for textile livening having an antistatic effect and favourable dermatological properties |
GB2160522A (en) * | 1984-06-22 | 1985-12-24 | Sandoz Ltd | Sulphomethylated amino-esters |
DE3437321A1 (de) * | 1984-10-11 | 1986-04-24 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | Umsetzungsprodukte von hoeheren fettsaeuren mit dialkanolaminen, deren herstellung und verwendung |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994004641A1 (en) * | 1992-08-21 | 1994-03-03 | Colgate-Palmolive Company | Fabric conditioning composition |
WO1994004642A2 (en) * | 1992-08-21 | 1994-03-03 | Colgate-Palmolive Company | Fabric conditioning composition |
WO1994004642A3 (en) * | 1992-08-21 | 1994-03-31 | Colgate Palmolive Co | Fabric conditioning composition |
WO1997029171A1 (en) * | 1996-02-09 | 1997-08-14 | Unilever Plc | Fabric softening composition |
Also Published As
Publication number | Publication date |
---|---|
EP0579649A1 (de) | 1994-01-26 |
CA2108287A1 (en) | 1992-10-13 |
JPH06506730A (ja) | 1994-07-28 |
DE4111966A1 (de) | 1992-10-15 |
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