NO135523B - - Google Patents
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- NO135523B NO135523B NO420672A NO420672A NO135523B NO 135523 B NO135523 B NO 135523B NO 420672 A NO420672 A NO 420672A NO 420672 A NO420672 A NO 420672A NO 135523 B NO135523 B NO 135523B
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- Norway
- Prior art keywords
- compounds
- alcohol
- mol
- methyl
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- Prior art date
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- 239000000463 material Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 238000007786 electrostatic charging Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- PWAJCNITSBZRBL-UHFFFAOYSA-N ketazolam Chemical compound O1C(C)=CC(=O)N2CC(=O)N(C)C3=CC=C(Cl)C=C3C21C1=CC=CC=C1 PWAJCNITSBZRBL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 39
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000004753 textile Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 amide compound Chemical group 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 150000002191 fatty alcohols Chemical class 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- 239000013065 commercial product Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- SZCFXFXQJBVCQI-UHFFFAOYSA-N 3-chloro-3-(1-chloro-2,3-dihydroxypropoxy)propane-1,2-diol Chemical compound OCC(O)C(Cl)OC(Cl)C(O)CO SZCFXFXQJBVCQI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 3
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000011490 mineral wool Substances 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 125000004079 stearyl 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])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- RHSBIGNQEIPSCT-UHFFFAOYSA-N stearonitrile Chemical compound CCCCCCCCCCCCCCCCCC#N RHSBIGNQEIPSCT-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010698 whale oil Substances 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
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- 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
- C11D1/62—Quaternary ammonium compounds
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Polyethers (AREA)
- Extraction Or Liquid Replacement (AREA)
Description
Foreliggende oppfinnelse vedrorer en kationisk overflateaktiv forbindelse som gir materiale, behandlet hermed, mindre til-bøyelighet til oppladning av statisk elektrisitet og/eller forbedrer dets mykhet. The present invention relates to a cationic surface-active compound which gives material, treated with it, less tendency to charge up static electricity and/or improves its softness.
Man har tidligere ved behandling av tekstilmateriale med kvartære forbindelser av typen (R") (R')2N+C1~, hvor R<1> betegner en methyl- eller ethylgruppe og R" en cetyl- eller stearylgruppe, sokt å gi tekstilmateriale et mykere grep og redusere materialets evne til å opplade statisk elektrisitet. En vesentlig ulempe med denne type forbindelser er at de på grunn av sin hydrofobe karakter sterkt forringer vannabsorpsjonsevnen hos tekstilmaterialet. Disse forbindelser fremstilles ved kvaternisering av f.eks. distearylamin med methylklorid eller dimethylsulfat. Distearylaminet erholdes ved i nærvær av ammoniakk å oppvarme tilsvarende fettsyre, som via sitt ammoniumsalt og amidforbindelse danner stearonnitril, som ved hydrer-ing overfores til stearylamin. Denne fremstillingsmåte har vist seg både besværlig og kostbar, og gir relativt dårlig utbytte. In the past, by treating textile material with quaternary compounds of the type (R") (R')2N+C1~, where R<1> denotes a methyl or ethyl group and R" a cetyl or stearyl group, it has been sought to give textile material a softer grip and reduce the material's ability to charge static electricity. A significant disadvantage of this type of compound is that, due to its hydrophobic nature, it greatly impairs the water absorption capacity of the textile material. These compounds are produced by quaternization of e.g. distearylamine with methyl chloride or dimethyl sulfate. The distearylamine is obtained by heating the corresponding fatty acid in the presence of ammonia, which via its ammonium salt and amide compound forms stearonitrile, which is converted to stearylamine by hydrogenation. This method of production has proven to be both difficult and expensive, and gives a relatively poor yield.
Det har nu overraskende vist seg at en ny gruppe kationaktive kvartære forbindelser gir meget god myknende og antistatisk effekt samtidig som de nye forbindelser er meget enkle og billige å fremstille. Videre oppviser tekstilmateriale som behandles med disse forbindelser betydelig bedre vannabsorpsjonsegenskaper enn de som behandles med de tidligere angitte kvartære alkylforbindelser. Den gruppe forbindelser som omfattes av foreliggende oppfinnelse kan sammenfattes i folgende generelle formel: It has now surprisingly been shown that a new group of cationically active quaternary compounds gives a very good softening and antistatic effect, while the new compounds are very simple and cheap to produce. Furthermore, textile material treated with these compounds exhibits significantly better water absorption properties than those treated with the previously mentioned quaternary alkyl compounds. The group of compounds covered by the present invention can be summarized in the following general formula:
—li^drocarbon-hvor R^ eller R^ uavhengig av hverandre betegner en alifatisk"-gruppe med 8-22 carbonatomer, X betegner hydrogen eller en methyl- eller ethylgruppe, R3 og R^ betegner en methyl- eller ethylgruppe, n1 og. n er heltallige og har en verdi på 0 til 5, og A^betegner et anion. Omfattende undersøkel-ser av disse forbindelsers virkning på forskjellig tekstilmateriale har-"vist at forbindelsene ifolge oppfinnelsen gjennomgående har avgjort bedre antistatiske egenskaper enn tidligere anvendte kvartære forbindelser. Spesielt bemerkelsesverdig er her det forhold at nærvær av glycerylgruppen samt av små mengder alkylenglycolenheter, .spesielt da ethylenglycolenheter, i forbindelsen markert forbedrer antistatiske ' verdier . Med hensyn til forbindelsenes mykgjbrende egenskaper påvirkes også disse av antallet alkylenglycolenheter i forbindelsen, og man har funnet at forbindelser med n^- og n2 verdier fra 0 —li^drocarbon-where R^ or R^ independently of each other denotes an aliphatic" group with 8-22 carbon atoms, X denotes hydrogen or a methyl or ethyl group, R3 and R^ denotes a methyl or ethyl group, n1 and. n are integers and have a value of 0 to 5, and A^ denotes an anion. Extensive investigations of the effect of these compounds on different textile materials have shown that the compounds according to the invention have consistently had better antistatic properties than previously used quaternary compounds. Particularly noteworthy here is the fact that the presence of the glyceryl group and of small amounts of alkylene glycol units, especially when ethylene glycol units, in the compound markedly improves antistatic values. With regard to the compounds' softening properties, these are also affected by the number of alkylene glycol units in the compound, and it has been found that compounds with n^ and n2 values from 0
til 2 har de avgjort beste egenskaper. På grunn av det ovenfor angitte foretrekkes forbindelser med den ovenfor angitte formel hvor X er hydrogen, og n^ og n^ gjennomsnittlig er et tall fra 0 til 2. Spesielt foretrukne forbindelser ifolge oppfinnelsen er de hvor R^ og R2 uavhengig av hverandre betegner en hydrocarbonkjede med 8-14 carbonatomer, fordi de er frysnings- og opptiningsstabile i 5 - 10 %'s vandige oppldsninger, dvs. de har ingen eller bare liten tendens til geldannelse og separasjon ved gjentatt frysning og opptining. Videre er de flytende i konsentrert form, hvilket letter produktenes tilbe-redning. to 2, they have decidedly the best qualities. Because of the above, compounds with the formula above are preferred where X is hydrogen, and n^ and n^ on average is a number from 0 to 2. Particularly preferred compounds according to the invention are those where R^ and R2 independently of each other denote a hydrocarbon chain with 8-14 carbon atoms, because they are freeze- and thaw-stable in 5-10% aqueous solutions, i.e. they have no or only a slight tendency to gel formation and separation upon repeated freezing and thawing. Furthermore, they are liquid in concentrated form, which facilitates the preparation of the products.
En vesentlig fordel med de nye kationaktive forbindelser er at de er lette å fremstille i industriell målestokk. Således kan de erholdes ved at en alkohol med 8-22 carbonatomer, til hvilken eventuelt O - 5 triol ethylen-, propylen- eller butylenoxyd tilleires på i og for seg kjent måte, omsettes med epiklorhydrin til tilsvarende klorglycerylether, som bringes til å reagere med et sekundært amin med den generelle formel: A significant advantage of the new cationically active compounds is that they are easy to produce on an industrial scale. Thus, they can be obtained by reacting an alcohol with 8-22 carbon atoms, to which optionally O-5 triol ethylene, propylene or butylene oxide is added in a manner known per se, with epichlorohydrin to the corresponding chloroglyceryl ether, which is brought to react with a secondary amine of the general formula:
hvor R3 og R4 uavhengig av hverandre betegner en methyl- eller ethylgruppe til en kvartær forbindelse i form av sitt kloridsalt. Om det ansees hensiktsmessig kan dette anion på i og for seg kjent måte ut-byttes med andre anioner, f.eks. ved tilsetning av et natriumsalt where R3 and R4 independently of each other denote a methyl or ethyl group of a quaternary compound in the form of its chloride salt. If it is considered appropriate, this anion can be replaced in a manner known per se with other anions, e.g. by adding a sodium salt
med hbyere oppldselighetskonstant enn natriumklorid eller ved ione-bytte i en anionbytter. Som anioner kan foruten kloridionene nevnes hydroxyl-, bromid-, methylsulfat-, acetat-, sulfat-, carbonat-, cit-rat- og tartrationer og av disse foretrukkes de monovalente ioner. with a higher solubility constant than sodium chloride or by ion exchange in an anion exchanger. As anions, in addition to the chloride ions, hydroxyl, bromide, methylsulphate, acetate, sulphate, carbonate, citrate and tartrates can be mentioned, and of these the monovalent ions are preferred.
Den her beskrevne fremgangsmåte kan sammenfattes i folgende to reaksjonstrinn: The procedure described here can be summarized in the following two reaction steps:
I reaksjonsformlene har R^, R^, R4, X og n^ den tidligere In the reaction formulas, R^, R^, R4, X and n^ have the former
angitte betydning. stated meaning.
Reaksjonen mellom alkoholen, alternativt et alkylenoxyd-addukt derav, og epiklorhydrin utfores ved en temperatur på ca. 100-150°C i nærvær av en katalysator. Som katalysator har spesielt SnCl^, BFg og HCIO^ vist seg utmerkede, og de gir en hurtig og lett The reaction between the alcohol, alternatively an alkylene oxide adduct thereof, and epichlorohydrin is carried out at a temperature of approx. 100-150°C in the presence of a catalyst. As a catalyst, especially SnCl^, BFg and HCIO^ have proven to be excellent, and they provide a quick and easy
kontrollerbar reaksjon, men også andre sure katalysatorer, som tolu-ensulfonsyre og svovelsyre kan anvendes. For å erholde en fullsten-dig omsetning av alkoholforbindelsen tilsettes epiklorhydrin vanligvis i overskudd. Kvaterni se ringen av det sekundære amin med klorglyceryletheren utfores i nærvær av alkali, f.eks. natriumhydroxyd, ved en temperatur på ca. lOO - 150°C. Vanligvis utfores reaksjonen i nærvær av et organisk opplosningsmiddel med kokepunkt på minst 60°C, controllable reaction, but also other acid catalysts, such as toluenesulfonic acid and sulfuric acid can be used. In order to obtain a complete conversion of the alcohol compound, epichlorohydrin is usually added in excess. Quaternary ringing of the secondary amine with the chloroglyceryl ether is carried out in the presence of alkali, e.g. sodium hydroxide, at a temperature of approx. 100 - 150°C. Usually the reaction is carried out in the presence of an organic solvent with a boiling point of at least 60°C,
hvorved opplosningsmidlet f.eks. utgjores av methanol, ethanol og monoethylether av diethylenglycol. whereby the solvent e.g. consists of methanol, ethanol and monoethyl ether of diethylene glycol.
Forbindelsene ifolge oppfinnelsen kan også fremstilles The compounds according to the invention can also be prepared
ved forskjellige variasjoner av den ovenfor beskrevne fremgangsmåte. Således kan klorglyceryletheren bringes til å reagere med ammoniakk eller et primært amin med en methyl- eller ethylsubstituent og deref-ter utfore kvatærneringen med f.eks. methyl- eller ethylklorid eller dimethyl- eller diethylsulfat. Denne fremgangsmåte er imidlertid mere komplisert enn den tidligere beskrevne og omfatter flere reaksjonstrinn samtidig, som forårsaker et storre antall biprodukter og lavere totalutbytte. by different variations of the method described above. Thus, the chloroglyceryl ether can be made to react with ammonia or a primary amine with a methyl or ethyl substituent and then carry out the quaternization with e.g. methyl or ethyl chloride or dimethyl or diethyl sulfate. However, this method is more complicated than the one previously described and includes several reaction steps at the same time, which causes a larger number of by-products and a lower overall yield.
De alkoholer med 8-22 carbonatomer som anvendes ved fremstilling av forbindelser ifolge oppfinnelsen kan være såvel syntetiske som avledet fra naturprodukter. De naturlig forekommende, de såkallte fettalkoholer, fremstilles vanligvis ved reduksjon av fett-syrer eller fettsyreestre erholdt fra vegetabilske oljer, som kokos-olje, palmeolje, soyaolje, linolje, maisolje eller ricinusolje, ani-malske oljer eller fett, som fiskeolje, hvalolje,"talg eller ister. Som eksempel på passende alkoholer bor folgende nevnes: octylalkohol, decylalkohol, dodecylalkohol, tetradecylalkohol, cetylalkohol, stea-rylalkohol, eicosylalkohol, oleylalkohol og eicosenylalkohol. Syntetiske alkoholer fremstilles fortrinnsvis i henhold til Zieglermetoden eller ved oxoprosessen. De fleste i henhold til oxoprosessen frem-s ti Hede alkoholer har en mere eller mindre forgrenet carbonkjede, hvorfor i dette tilfelle et stort antall isomerer er mulige. Disse alkoholers fysikalske og kjemiske egenskaper ligner meget egenskapene hos de rettkjedede primære alkoholer. The alcohols with 8-22 carbon atoms used in the preparation of compounds according to the invention can be both synthetic and derived from natural products. The naturally occurring, so-called fatty alcohols, are usually produced by reducing fatty acids or fatty acid esters obtained from vegetable oils, such as coconut oil, palm oil, soya oil, linseed oil, corn oil or castor oil, animal oils or fats, such as fish oil, whale oil, "tallow or lard. The following should be mentioned as examples of suitable alcohols: octyl alcohol, decyl alcohol, dodecyl alcohol, tetradecyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, oleyl alcohol and eicosenyl alcohol. Synthetic alcohols are preferably produced according to the Ziegler method or by the oxo process. Most according to to the oxo process forward-p ten Hede alcohols have a more or less branched carbon chain, which is why in this case a large number of isomers are possible.The physical and chemical properties of these alcohols are very similar to the properties of the straight-chain primary alcohols.
Passende sekundære aminer ved fremgangsmåten Appropriate secondary amines in the process
er dimethylamin og diethylamin, hvilke er kommersielt til-gjengelige. De primære aminer som kan anvendes er methyl- og ethyl-amin. are dimethylamine and diethylamine, which are commercially available. The primary amines that can be used are methyl and ethyl amine.
Forbindelsene ifolge oppfinnelsen har vist seg spesielt The compounds according to the invention have proved particularly effective
egnede til å bibringe tekstilmaterialet et mykt grep og redusere vis-se materialers tendens til statisk oppladning. Således kan forbindelsene med fordel tilsettes ved skylling av tekstilmateriale, og efter-som de har god affinitet til tekstilfibre, kan tilsetningen i prin-sipp finne sted under hvilken som helst skylling, selvom den beste virkning erholdes når tilsetningen benyttes i det siste skyllevann. Tilsetningsmengden av de kvartære forbindelser ved skylling av tek- suitable for giving the textile material a soft grip and reducing certain materials' tendency to static charge. Thus, the compounds can advantageously be added when rinsing textile material, and as they have a good affinity for textile fibres, the addition can in principle take place during any rinse, although the best effect is obtained when the additive is used in the final rinse water. The amount of addition of the quaternary compounds when rinsing the
stilmateriale varierer med tekstilmaterialet, vaskeforholdende og den virkning som onskes, men generelt kan der sies at tilsetningen bor utgjore 0,01 - 0,50 g, fortrinnsvis 0,05 - 0,15 g pr. liter skyllevann, eller 0,1 - 5,0 g, fortrinnsvis 0,5 - 1,5 g pr. kg tekstilmateriale. Forbindelsene kan også tilsettes ved forvask eller hoved-vask, men i disse tilfelle blir virkningen noe mindre. Tekstilmaterialet kan være uvevet eller vevet og består av såvel, syntetiske som naturlige materialer, som bomull, lin, ull, rayon, polyvinylklorid-fibre, polyethylenfibre, polypropylenfibre, polyaminfibre, polyester-fibre og polyamidfibre. Ved fremstilling av produkter basert på papir, som laken, papirklær, servietter, håndklær, bleier, sanitetsbind og adsorpsjonsdyner, kan forbindelser ifolge oppfinnelsen tilsettes den vannholdige massesuspensjon i en mengde på 0,02 - 2 % regnet på cel-lulosens vekt for å gi det ferdige produkt god mykhet og vannabsorp-sjon. Videre har det vist seg hensiktsmessig å påfdre materiale med tendens til uonsket elektrostatisk oppladning oppldsninger av foreliggende forbindelser f.eks. ved sproytning eller bestrykning. Denne teknikk er spesielt anvendelig for materiale eller gjenstander som normalt vaskes meget sjelden eller overhodet ikke. Eksempler på slike produkter er heldekkende tepper og stoppede mobler, skinntoy av poly-acrylnitril eller rayonull; skinn og lær; papir og papirprodukter; glass- og annen mineralull; grammofonplater:, lyd- og bildeopptag-ningsbånd; farve- og lakkoverflater; metallfolier; chassiser for elek-trisk og elektronisk apparatur etc. På fiber- og tekstilgjenstander som tepper, produkter basert på cellulosefibre, skinntoy og mineralull har forbindelsene også en utpreget myknende virkning. style material varies with the textile material, washing conditions and the desired effect, but in general it can be said that the addition should amount to 0.01 - 0.50 g, preferably 0.05 - 0.15 g per liter of rinse water, or 0.1 - 5.0 g, preferably 0.5 - 1.5 g per kg textile material. The compounds can also be added during pre-wash or main wash, but in these cases the effect is somewhat less. The textile material can be non-woven or woven and consists of both synthetic and natural materials, such as cotton, linen, wool, rayon, polyvinyl chloride fibres, polyethylene fibres, polypropylene fibres, polyamine fibres, polyester fibers and polyamide fibres. In the manufacture of products based on paper, such as sheets, paper clothes, napkins, towels, diapers, sanitary pads and absorbent pads, compounds according to the invention can be added to the aqueous pulp suspension in an amount of 0.02 - 2% calculated on the weight of the cellulose to give the finished product good softness and water absorption. Furthermore, it has proven appropriate to apply solutions of present compounds to material with a tendency to unwanted electrostatic charging, e.g. by spraying or coating. This technique is particularly applicable to material or objects that are normally washed very rarely or not at all. Examples of such products are full-covering carpets and upholstered furniture, leather toys made of poly-acrylonitrile or rayon wool; skins and leather; paper and paper products; glass and other mineral wool; gramophone records, audio and video recording tapes; paint and varnish surfaces; metal foils; chassis for electrical and electronic equipment etc. On fiber and textile items such as carpets, products based on cellulose fibres, leather toys and mineral wool, the compounds also have a distinct softening effect.
Forbindelsene ifolge oppfinnelsen anvendes vanligvis i form av en 5 - 10 %'s vannoppldsning som foruten den aktive substans også inneholder f.eks. opplbselighetsformidlende tilsetninger som ethyldiglycol, for senkning av oppløsningens viskositet. Man kan også på kjent måte innarbeide ikke-ioniske tensider, såsom addukter mellom ethylenoxyd eller propylenoxyd og alifatiske alkoholer eller alkylfe-noler og derved oke det behandlede tekstilmateriales evne til gjen-fuktning. The compounds according to the invention are usually used in the form of a 5-10% water solution which, in addition to the active substance, also contains e.g. solubilising additives such as ethyldiglycol, to lower the viscosity of the solution. One can also incorporate non-ionic surfactants in a known manner, such as adducts between ethylene oxide or propylene oxide and aliphatic alcohols or alkylphenols and thereby increase the rewetting ability of the treated textile material.
For spesielle anvendelsesområder kan det være onskelig at forbindelsen ifolge oppfinnelsen er opplost i et flyktig opplosningsmiddel slik at dette hurtig kan dunste bort. I slike tilfelle kan f.eks. aceton, methanol, ethanol, isopropanol eller blandinger derav anvendes som oppløsningsmiddel. For special areas of application, it may be desirable for the compound according to the invention to be dissolved in a volatile solvent so that this can evaporate quickly. In such cases, e.g. acetone, methanol, ethanol, isopropanol or mixtures thereof are used as solvents.
Følgende eksempler har til hensikt ytterligere å forklare oppfinnelsen. The following examples are intended to further explain the invention.
Eksempel 1 Example 1
I et kar forsynt med anordninger for oppvarmning og omrør-ing samt tilbakelopskjoler ble innført 300 g (1 mol) av en smelte av talgfettalkohol (blanding av cetyl-, stearyl- og eicosylalkohol) omsatt med 0,5 mol ethylenoxyd pr. mol alkohol under anvendelse av natriumhydroxyd som alkalisk katalysator. Smeiten ble holdt ved 75°C under omrøring, hvorefter 3 g SnCl^ ble innført og lOl g (1,1 mol) epiklorhydrin ble tilsatt i løpet av 1 time. Temperaturen ble forhøy-et til 125°C og holdt ved denne temperatur i ytterligere 2 timer. Gjenværende epiklorhydrin ble fjernet ved vakuumbehandling, og det erholdte reaksjonsprodukt utgjorde 390 g av en svakt gulfarvet, tyktfly-tende væske. 300 g (1 mol) of a melt of tallow fatty alcohol (mixture of cetyl, stearyl and eicosyl alcohol) reacted with 0.5 mol of ethylene oxide per moles of alcohol using sodium hydroxide as an alkaline catalyst. The melt was kept at 75°C with stirring, after which 3 g of SnCl 2 were introduced and 10 g (1.1 mol) of epichlorohydrin was added over the course of 1 hour. The temperature was raised to 125°C and held at this temperature for a further 2 hours. Remaining epichlorohydrin was removed by vacuum treatment, and the reaction product obtained amounted to 390 g of a slightly yellow-coloured, viscous liquid.
I en autoklav forsynt med anordning for oppvarmning og om-røring ble innført 350 g (0,9 mol) av det ovenfor angitte reaksjonsprodukt, 20 g(0,45 mol) dimethylamin oppløst i 125 g ethanol, samt 23 g (0,56 mol) natriumhydroxyd og 15 g vann. Blandingen ble holdt i autoklav ved 125°C 3 timer, hvorefter gjenværende dimethylamin ble fjernet ved nitrogengassgjennomblåsning. Reaksjonsproduktet besto av en svakt beige substans med smeltepunkt 37 - 40°C og viste seg ved an-alyse å bestå av 57 % kvartært amin, 10 % tertiært amin, 23 % ethanol, 6 % NaCl og 4 % vann. Dette produkt vil herefter bli betegnet med A. 350 g (0.9 mol) of the above reaction product, 20 g (0.45 mol) dimethylamine dissolved in 125 g ethanol, and 23 g (0.56 mol) of sodium hydroxide and 15 g of water. The mixture was kept in an autoclave at 125°C for 3 hours, after which residual dimethylamine was removed by nitrogen gas blowing. The reaction product consisted of a faint beige substance with a melting point of 37 - 40°C and was shown by analysis to consist of 57% quaternary amine, 10% tertiary amine, 23% ethanol, 6% NaCl and 4% water. This product will henceforth be denoted by A.
Eksempler 2- 7 Examples 2-7
På lignende måte som i eksempel 1 ble fremstillet ytterligere produkter ifølge oppfinnelsen. Disse forbindelser som betegnes med B - G var folgende: B. Reaksjonsprodukt av 2 mol cetylalkohol, 2. mol epiklorhydrin In a similar way as in example 1, further products according to the invention were produced. These compounds, denoted by B - G, were as follows: B. Reaction product of 2 moles of cetyl alcohol, 2. moles of epichlorohydrin
og 1 mol dimethylamin. and 1 mole of dimethylamine.
C. Reaksjonsprodukt av 2 mol talgfettalkohol, 2 mol epiklorhydrin og 1 mol dimethylamin. D. Reaksjonsprodukt av 2 mol talgfettalkohol, 1 mol butylenoxyd, 2 mol epiklorhydrin og 1 mol dimethylamin. C. Reaction product of 2 moles of tallow fatty alcohol, 2 moles of epichlorohydrin and 1 mole of dimethylamine. D. Reaction product of 2 mol of tallow fatty alcohol, 1 mol of butylene oxide, 2 mol of epichlorohydrin and 1 mol of dimethylamine.
E. Reaksjonsprodukt av 2 mol talgfettalkohol, 4 mol ethylenoxyd, 2 mol epiklorhydrin og 1 mol dimethylamin. E. Reaction product of 2 mol of tallow fatty alcohol, 4 mol of ethylene oxide, 2 mol of epichlorohydrin and 1 mol of dimethylamine.
F. Reaksjonsprodukt av 2 mol talgfettalkohol, 8 mol ethylenoxyd, 2 mol epiklorhydrin og 1 mol dimethylamin. F. Reaction product of 2 mol of tallow fatty alcohol, 8 mol of ethylene oxide, 2 mol of epichlorohydrin and 1 mol of dimethylamine.
G. Reaksjonsprodukt av 2 mol av en fettalkoholblanding av C^q- og <C>^<->alkoholer, 8 mol ethylenoxyd, 2 mol epiklorhydrin og 1 mol dimethylamin. G. Reaction product of 2 moles of a fatty alcohol mixture of C^q- and <C>^<->alcohols, 8 moles of ethylene oxide, 2 moles of epichlorohydrin and 1 mole of dimethylamine.
Eksempel 8 Example 8
I dette eksempel ble sammenlignet et kommersielt produkt bestående av 75 % distearyldimethylammoniumklorid i en rekke vaskeforsok i en sylindervaskemaskin, hvorved prøvestykker av bomullsfrot-te forst ble vasket med et kommersielt storvaskmiddel ved 90°C I det siste skyllevann ble tilsatt noen av forbindelsene A - E i en mengde tilsvarende 0,5 g pr. kg vasketoy. Denne vask og efterbehandling ble gjentatt fem ganger. Efter hver avsluttet vask ble frottéstoffets mykhet bedomt subjektivt av seks personer. Folgende resultater ble erholdt: In this example, a commercial product consisting of 75% distearyldimethylammonium chloride was compared in a series of washing trials in a cylinder washing machine, whereby test pieces of cotton terry were first washed with a commercial detergent at 90°C. In the last rinse water, some of the compounds A - E in an amount corresponding to 0.5 g per kg laundry. This washing and finishing was repeated five times. After each wash, the softness of the terry cloth was judged subjectively by six people. The following results were obtained:
Av resultatene fremgår at produktene A og D hadde de beste tekstilmyknende egenskaper og var klart bedre enn sammenligningsforsoket, og at produktene B og C uten ethylenglycolénheter oppviste go-de mykgjorende egenskaper og likeledes var klart bedre enn sammenlig-ningsf orsoket. Når antall alkylenglycolenheter oker over 1 enhet pr. alkoholkjede, avtar den mykgjorende effekt påny, og ved 2 en-heter pr. alkoholkjede erholdes en mykgjorende effekt som er sammen-lignbar med sammenligningsforsoket. The results show that products A and D had the best fabric softening properties and were clearly better than the comparison trial, and that products B and C without ethylene glycol units showed good softening properties and were likewise clearly better than the comparison trial. When the number of alkylene glycol units increases above 1 unit per alcohol chain, the emollient effect decreases again, and at 2 units per alcohol chain, a softening effect is obtained which is comparable to the comparative experiment.
Eksempel 9 Example 9
I dette eksempel ble undersøkt de antistatiske egenskaper hos forbindelsene A-E samt for sammenligning,det kommersielle produkt som beskrevet i eksempel 8, i en rekke vaskeforsok i en sylindervaskemaskin, hvorved prøvestykkene av nylon forst ble vasket med ett kommersielt storvaskmiddel ved 22°C. I det siste skyllevann ble tilsatt et produkt ifolge oppfinnelsen i en mengde tilsvarende 0,5 g pr. kg vasketoy. Efter avsluttet behandling ble den tid bestemt som krevdes for utladning av halvdelen av den elektriske oppladning som var påført nylonet i en Rothschild, Static Voltmeter R 1020. Følgen-de resultater ble erholdt: In this example, the antistatic properties of compounds A-E and, for comparison, the commercial product as described in example 8, were examined in a series of washing trials in a cylinder washing machine, whereby the test pieces of nylon were first washed with a commercial detergent at 22°C. In the last rinse water, a product according to the invention was added in an amount corresponding to 0.5 g per kg laundry. After completion of the treatment, the time required for the discharge of half of the electrical charge which had been applied to the nylon was determined in a Rothschild, Static Voltmeter R 1020. The following results were obtained:
Av resultatene fremgår at de forbindelser ifolge oppfinnelsen B og C som ikke inneholder noen alkylenglycolenheter har bedre antistatiske egenskaper enn det kommersielle produkt. Nærvær av al-kylglycolenheter forbedrer den antistatiske effekt ytterligere, slik at halveringstiden for nylon behandlet med forbindelser A, D, E, F, G utgjør omtrent halvparten eller mindre enn for det kommersielle produkt . The results show that the compounds according to the invention B and C which do not contain any alkylene glycol units have better antistatic properties than the commercial product. The presence of alkylglycol units further improves the antistatic effect, so that the half-life of nylon treated with compounds A, D, E, F, G is about half or less than that of the commercial product.
Av sammenligningseksempler 8 og 9 fremgår at forbindelsene ifølge oppfinnelsen har bedre antistatisk effekt og/eller bedre myk-gjørende effekt enn nærbeslektede tidligere anvendte forbindelser. Videre fremgår at forbindelser hvor n^ og n i den tidligere angitte strukturformel er fra 0 til 2, har bedre egenskaper i begge disse henseender. From comparative examples 8 and 9 it appears that the compounds according to the invention have a better antistatic effect and/or a better softening effect than closely related previously used compounds. Furthermore, it appears that compounds where n^ and n in the previously stated structural formula are from 0 to 2 have better properties in both of these respects.
Eks empe1 10 Eg empe1 10
På samme måte som i eksempel 1 ble omsatt en fettalkoholblanding (1 mol) med epiklorhydrin (1,1 mol) og dimethylamin (0,5 mol) under anvendelse av ethyIdiglycol som opplosningsmiddel. Fett-alkoholblandingen besto av 15 % decylalkohol, 47 % dodecylalkohol og 38 % tetradecylalkohol. Den resulterende produktblanding besto av 57 % kvartær ammoniumforbindelse ifolge oppfinnelsen, 2,8 % av et tertiært amin inneholdende en alkylethergruppe og to methylgrupper samt 25 % ethyldiglycol. Resten utgjordes av vann, natriumklorid og ikke omsatte utgangsprodukter. Produktblandingen utviste flytepunkt ved 12°C, stivningspunkt ved 10°C samt klarpunkt ved 33°C. In the same way as in example 1, a fatty alcohol mixture (1 mol) was reacted with epichlorohydrin (1.1 mol) and dimethylamine (0.5 mol) using ethyl diglycol as solvent. The fatty alcohol mixture consisted of 15% decyl alcohol, 47% dodecyl alcohol and 38% tetradecyl alcohol. The resulting product mixture consisted of 57% quaternary ammonium compound according to the invention, 2.8% of a tertiary amine containing an alkyl ether group and two methyl groups and 25% ethyl diglycol. The rest consisted of water, sodium chloride and unconverted starting products. The product mixture showed a pour point at 12°C, a solidification point at 10°C and a clear point at 33°C.
Av denne produktblanding ble 12 vektdeler opplost i 88 vektdeler vann. Den erholdte oppløsning var flytende ved romtemperatur og hadde stivningspunkt 0°C. Når vannopplosningen ble frosset og siden opptint, var der ingen tendens til geldannelse. Of this product mixture, 12 parts by weight were dissolved in 88 parts by weight of water. The resulting solution was liquid at room temperature and had a solidification point of 0°C. When the water solution was frozen and then thawed, there was no tendency to gel.
Stykker av bomullsfrotté ble forst vasket med et kommersielt storvaskmiddel ved 90°C i en sylindervaskemaskin. I det siste skyllevann ble tilsatt den erholdte produktblanding eller distearyldimethylammoniumklorid som tekstilmykgjoringsmiddel i en mengde på 1,2 g torrsubstans pr. kg tekstilvare. Denne fremgangsmåte ble gjentatt 5 ganger. Efter hver avsluttet vask ble frottéstykkenes mykhet beddmt subjektivt av seks personer, hvorav de tre fant frottéstykkene efterbehandlet med produktet ifolge oppfinnelsen mykest, mens de gjenværende tre ikke merket noen forskjell. Pieces of cotton terry were first washed with a commercial detergent at 90°C in a cylinder washing machine. In the last rinse water, the obtained product mixture or distearyldimethylammonium chloride was added as textile softener in an amount of 1.2 g of dry substance per kg of textiles. This procedure was repeated 5 times. After each finished wash, the softness of the terry cloth pieces was assessed subjectively by six people, three of whom found the terry cloth pieces after-treated with the product according to the invention to be the softest, while the remaining three did not notice any difference.
Frottéstykkenes vannoppsugningsevne ble bestemt ved at et sirkulært provestykke ble presset mot oppsiden av en glassfiberplate hvis underside var helt i kontakt med et visst vannvolum. Ved å av-lese vannvolumets minskning som funksjon av tiden, kunne oppsugnings-hastigheten bestemmes. Folgende resultat ble erholdt: The water absorption capacity of the terry cloth pieces was determined by pressing a circular test piece against the top of a fiberglass plate whose underside was completely in contact with a certain volume of water. By reading the decrease in water volume as a function of time, the absorption rate could be determined. The following results were obtained:
Nylonmateriale vasket ved 22°C ble underkastet samme vas-kefremgangsmåte som frottématerialet. Efter kondisjonering 1 døgn ved 65% relativ luftfuktighet og 20°C ble ledningsevnen bestemt i et. Rotschild Static Voltmeter R 1020, hvorved en tøyremse ble spent opp mellom to metallklemmer, over hvilken ble påført en spenning på 100 volt. Tiden som medgikk til å senke spenningen til det halve, ble bestemt. Folgende resultat ble erholdt: Nylon material washed at 22°C was subjected to the same washing procedure as the terry cloth material. After conditioning for 1 day at 65% relative humidity and 20°C, the conductivity was determined in a Rotschild Static Voltmeter R 1020, whereby a strip of cloth was stretched between two metal clamps, across which a voltage of 100 volts was applied. The time taken to lower the voltage by half was determined. The following results were obtained:
Av ovenstående resultat fremgår at forbindelsen er flytende ved romtemperatur, og at den er frysnings- og opptiningsstabil i vann-opplosning. Sammenlignet med distearyldimethylammoniumklorid som er det vanlig anvendte tekstilmykgjoringsmiddel gir dessuten forbindelsen ifolge oppfinnelsen tekstilene bedre egenskaper med hensyn til mykhet, antistatisk virkning og absorpsjonsevne. From the above result it appears that the compound is liquid at room temperature, and that it is freezing and thawing stable in water solution. Compared to distearyldimethylammonium chloride, which is the commonly used textile softening agent, the compound according to the invention also gives the textiles better properties with regard to softness, antistatic effect and absorbency.
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE7114793A SE382630B (en) | 1971-11-19 | 1971-11-19 | CATHIONIC ACTIVE QUARTER ASSOCIATION, WHICH REDUCES MATERIAL'S CAPACITY TO ELECTROSTATIC CHARGING AND / OR IMPROVES ITS SOFTNESS |
SE7213069A SE387333B (en) | 1972-10-11 | 1972-10-11 | CATHIONIC ACTIVE QUARTER ASSOCIATION, WHICH REDUCES MATERIAL'S CAPACITY TO ELECTROSTATIC CHARGING AND / OR IMPROVES ITS SOFTNESS |
Publications (2)
Publication Number | Publication Date |
---|---|
NO135523B true NO135523B (en) | 1977-01-10 |
NO135523C NO135523C (en) | 1977-04-20 |
Family
ID=26655916
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO420672A NO135523C (en) | 1971-11-19 | 1972-11-17 |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5141034B2 (en) |
BE (1) | BE791118A (en) |
DK (1) | DK136221B (en) |
ES (1) | ES408761A1 (en) |
FI (1) | FI56372C (en) |
IT (1) | IT975641B (en) |
NO (1) | NO135523C (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5545610B2 (en) * | 2008-08-07 | 2014-07-09 | 東邦化学工業株式会社 | Cleaning composition |
-
0
- BE BE791118D patent/BE791118A/en not_active IP Right Cessation
-
1972
- 1972-11-17 DK DK573072A patent/DK136221B/en not_active IP Right Cessation
- 1972-11-17 IT IT7062772A patent/IT975641B/en active
- 1972-11-17 NO NO420672A patent/NO135523C/no unknown
- 1972-11-17 FI FI324272A patent/FI56372C/en active
- 1972-11-17 JP JP11611772A patent/JPS5141034B2/ja not_active Expired
- 1972-11-18 ES ES408761A patent/ES408761A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS4862682A (en) | 1973-09-01 |
BE791118A (en) | 1973-03-01 |
FI56372C (en) | 1980-01-10 |
FI56372B (en) | 1979-09-28 |
DK136221C (en) | 1978-02-06 |
JPS5141034B2 (en) | 1976-11-08 |
NO135523C (en) | 1977-04-20 |
ES408761A1 (en) | 1976-03-16 |
DK136221B (en) | 1977-09-05 |
IT975641B (en) | 1974-08-10 |
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