US2165356A - Dry-cleaning fluid - Google Patents
Dry-cleaning fluid Download PDFInfo
- Publication number
- US2165356A US2165356A US68137A US6813736A US2165356A US 2165356 A US2165356 A US 2165356A US 68137 A US68137 A US 68137A US 6813736 A US6813736 A US 6813736A US 2165356 A US2165356 A US 2165356A
- Authority
- US
- United States
- Prior art keywords
- bromide
- ammonium
- cetyl
- dodecyl
- dry cleaning
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000005108 dry cleaning Methods 0.000 title description 28
- 239000012530 fluid Substances 0.000 title description 11
- -1 aliphatic radical Chemical class 0.000 description 21
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 17
- 150000002500 ions Chemical class 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- 150000004714 phosphonium salts Chemical group 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 5
- KRBFFJIZAKABSA-UHFFFAOYSA-N 2-bromooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(Br)C(O)=O KRBFFJIZAKABSA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- VIXPKJNAOIWFMW-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC VIXPKJNAOIWFMW-UHFFFAOYSA-M 0.000 description 3
- 125000001453 quaternary ammonium group Chemical class 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N 3-Methoxy-4,5-methylenedioxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ZLBYHIUFEATEMX-UHFFFAOYSA-N CCCCCCCCCCC(C(=O)NC1=CC=CC=C1)Br Chemical compound CCCCCCCCCCC(C(=O)NC1=CC=CC=C1)Br ZLBYHIUFEATEMX-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000001117 oleyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005496 phosphonium group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- AKKWBJYDDSGXHQ-UHFFFAOYSA-O trimethyl-[4-(octadecanoylamino)phenyl]azanium Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C([N+](C)(C)C)C=C1 AKKWBJYDDSGXHQ-UHFFFAOYSA-O 0.000 description 2
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
- UPFKHSKRCBUWTH-UHFFFAOYSA-M 1,1-dihexadecylpiperidin-1-ium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+]1(CCCCCCCCCCCCCCCC)CCCCC1 UPFKHSKRCBUWTH-UHFFFAOYSA-M 0.000 description 1
- VYCNDXYSPKUVGD-UHFFFAOYSA-M 1-(hexadecoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCOC[N+]1=CC=CC=C1 VYCNDXYSPKUVGD-UHFFFAOYSA-M 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- LFYSWCFSJAZQJJ-UHFFFAOYSA-L 1-dodecylpyridin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCCCCC[N+]1=CC=CC=C1.CCCCCCCCCCCC[N+]1=CC=CC=C1 LFYSWCFSJAZQJJ-UHFFFAOYSA-L 0.000 description 1
- QYYNAIAURMHJOQ-UHFFFAOYSA-M 1-hexadecyl-1-methylpiperidin-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+]1(C)CCCCC1 QYYNAIAURMHJOQ-UHFFFAOYSA-M 0.000 description 1
- KQVYBYSUVFRMGE-UHFFFAOYSA-M 1-hexadecylpyridin-1-ium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 KQVYBYSUVFRMGE-UHFFFAOYSA-M 0.000 description 1
- TTXLFUJSPVEFDO-UHFFFAOYSA-M 1-octadecylpyridin-1-ium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 TTXLFUJSPVEFDO-UHFFFAOYSA-M 0.000 description 1
- HJNAJKBRYDFICV-UHFFFAOYSA-M 1-tetradecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[N+]1=CC=CC=C1 HJNAJKBRYDFICV-UHFFFAOYSA-M 0.000 description 1
- DPRAYRYQQAXQPE-UHFFFAOYSA-N 2-bromohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(Br)C(O)=O DPRAYRYQQAXQPE-UHFFFAOYSA-N 0.000 description 1
- IYSADSHHFXGLFH-UHFFFAOYSA-N 2-bromooctadecanamide Chemical compound CCCCCCCCCCCCCCCCC(Br)C(N)=O IYSADSHHFXGLFH-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- LWUBNLXPDJHRNE-UHFFFAOYSA-M 2-methyl-1-octadecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1C LWUBNLXPDJHRNE-UHFFFAOYSA-M 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- IEZDTNCUMWPRTD-UHFFFAOYSA-N 346704-04-9 Chemical compound [O-][N+](=O)C1=CC=C(N2CCNCC2)C=C1N1CCCCC1 IEZDTNCUMWPRTD-UHFFFAOYSA-N 0.000 description 1
- SJZKAXVGSIOYBN-UHFFFAOYSA-M 4-ethyl-4-octadecylmorpholin-4-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+]1(CC)CCOCC1 SJZKAXVGSIOYBN-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- SGFBLYBOTWZDDE-UHFFFAOYSA-N Choline stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)C SGFBLYBOTWZDDE-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- AMRFLURHGMTLOF-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].C(C)[P+](CCCCCCCCC=C/CCCCCCCC)(CCCCCCCCC=C/CCCCCCCC)CC.C(C)[P+](CC)(CCCCCCCCC=C/CCCCCCCC)CCCCCCCCC=C/CCCCCCCC Chemical compound S(=O)(=O)([O-])[O-].C(C)[P+](CCCCCCCCC=C/CCCCCCCC)(CCCCCCCCC=C/CCCCCCCC)CC.C(C)[P+](CC)(CCCCCCCCC=C/CCCCCCCC)CCCCCCCCC=C/CCCCCCCC AMRFLURHGMTLOF-UHFFFAOYSA-L 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- YRCOEIBVPXHKSP-UHFFFAOYSA-M [Br-].C(CC)[S+](CCCCCCCCCCCC)CCC Chemical compound [Br-].C(CC)[S+](CCCCCCCCCCCC)CCC YRCOEIBVPXHKSP-UHFFFAOYSA-M 0.000 description 1
- IWRPWXHFCMKJSU-UHFFFAOYSA-M [Br-].C[S+](CCCCCCCCCCCCCC)C Chemical compound [Br-].C[S+](CCCCCCCCCCCCCC)C IWRPWXHFCMKJSU-UHFFFAOYSA-M 0.000 description 1
- FAUOTMBLHSCGMP-UHFFFAOYSA-M [Cl-].C(C)[S+](CCCCCCCCCCCCCCCCCC)CC Chemical compound [Cl-].C(C)[S+](CCCCCCCCCCCCCCCCCC)CC FAUOTMBLHSCGMP-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 229960001040 ammonium chloride Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- KBGBDGQCRFNDLU-UHFFFAOYSA-N benzyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CC1=CC=CC=C1 KBGBDGQCRFNDLU-UHFFFAOYSA-N 0.000 description 1
- PKFHWYATRRWVSF-UHFFFAOYSA-M benzyl-dodecyl-methylsulfanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[S+](C)CC1=CC=CC=C1 PKFHWYATRRWVSF-UHFFFAOYSA-M 0.000 description 1
- HXEBZFWZFJEYQY-UHFFFAOYSA-N benzyl-hexadecyl-methylsulfanium Chemical compound CCCCCCCCCCCCCCCC[S+](C)CC1=CC=CC=C1 HXEBZFWZFJEYQY-UHFFFAOYSA-N 0.000 description 1
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- BYMSUMXRXSDTBV-UHFFFAOYSA-M cyclohexyl-dodecyl-dimethylazanium bromide Chemical compound [Br-].C[N+](CCCCCCCCCCCC)(C1CCCCC1)C BYMSUMXRXSDTBV-UHFFFAOYSA-M 0.000 description 1
- HMMQEAPPBOFQSP-UHFFFAOYSA-M cyclohexyl-dodecyl-methylsulfanium iodide Chemical compound [I-].C1(CCCCC1)[S+](CCCCCCCCCCCC)C HMMQEAPPBOFQSP-UHFFFAOYSA-M 0.000 description 1
- URRISVSZHXGKJJ-UHFFFAOYSA-M cyclohexyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C1CCCCC1 URRISVSZHXGKJJ-UHFFFAOYSA-M 0.000 description 1
- UHUYXVHRGTYTEM-UHFFFAOYSA-M decyl(trimethyl)azanium;iodide Chemical compound [I-].CCCCCCCCCC[N+](C)(C)C UHUYXVHRGTYTEM-UHFFFAOYSA-M 0.000 description 1
- KAOPHVRFVWFGRN-UHFFFAOYSA-M decyl(trimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCC[N+](C)(C)C KAOPHVRFVWFGRN-UHFFFAOYSA-M 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DASXZANXANBHCF-UHFFFAOYSA-M docosyl(trimethyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C DASXZANXANBHCF-UHFFFAOYSA-M 0.000 description 1
- 150000002027 dodecanoic acid esters Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NCZFYMIPOHPCCG-UHFFFAOYSA-N dodecyl(dimethyl)sulfanium Chemical compound CCCCCCCCCCCC[S+](C)C NCZFYMIPOHPCCG-UHFFFAOYSA-N 0.000 description 1
- QYNBOUXUYXSEIW-UHFFFAOYSA-M dodecyl(dimethyl)sulfanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[S+](C)C QYNBOUXUYXSEIW-UHFFFAOYSA-M 0.000 description 1
- PBUIQGLFQJJIME-UHFFFAOYSA-L dodecyl(triethyl)phosphanium sulfate Chemical compound S(=O)(=O)([O-])[O-].C(C)[P+](CCCCCCCCCCCC)(CC)CC.C(C)[P+](CC)(CC)CCCCCCCCCCCC PBUIQGLFQJJIME-UHFFFAOYSA-L 0.000 description 1
- CBURDXCEXJBUAJ-UHFFFAOYSA-M dodecyl(triethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[P+](CC)(CC)CC CBURDXCEXJBUAJ-UHFFFAOYSA-M 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- QNALZNMQKPAXNA-UHFFFAOYSA-M dodecyl(trimethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[P+](C)(C)C QNALZNMQKPAXNA-UHFFFAOYSA-M 0.000 description 1
- AOFLSGCSQROFFU-UHFFFAOYSA-N dodecyl-ethyl-methylsulfanium Chemical compound CCCCCCCCCCCC[S+](C)CC AOFLSGCSQROFFU-UHFFFAOYSA-N 0.000 description 1
- ARJMGEOMIVYGLN-UHFFFAOYSA-M dodecyl-ethyl-methylsulfanium;iodide Chemical compound [I-].CCCCCCCCCCCC[S+](C)CC ARJMGEOMIVYGLN-UHFFFAOYSA-M 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 235000021183 entrée Nutrition 0.000 description 1
- OJGQURDBUGGMOC-UHFFFAOYSA-M ethyl-hexadecyl-dimethylphosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](C)(C)CC OJGQURDBUGGMOC-UHFFFAOYSA-M 0.000 description 1
- QBSNQUFFRJVUBO-UHFFFAOYSA-N ethyl-hexadecyl-methylsulfanium Chemical compound CCCCCCCCCCCCCCCC[S+](C)CC QBSNQUFFRJVUBO-UHFFFAOYSA-N 0.000 description 1
- XBWDYHBJVKIFGB-UHFFFAOYSA-M ethyl-hexadecyl-methylsulfanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[S+](C)CC XBWDYHBJVKIFGB-UHFFFAOYSA-M 0.000 description 1
- XFYICZOIWSBQSK-UHFFFAOYSA-N ethylazanium;iodide Chemical compound [I-].CC[NH3+] XFYICZOIWSBQSK-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- CPKBQTMHOYYDJW-UHFFFAOYSA-N hexadecyl(dimethyl)sulfanium Chemical compound CCCCCCCCCCCCCCCC[S+](C)C CPKBQTMHOYYDJW-UHFFFAOYSA-N 0.000 description 1
- LGPJVNLAZILZGQ-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[N+](C)(C)C LGPJVNLAZILZGQ-UHFFFAOYSA-M 0.000 description 1
- HNTXFQLKQWBPLG-UHFFFAOYSA-M hexadecyl(trimethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](C)(C)C HNTXFQLKQWBPLG-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- MIKQUZGJQABVKX-UHFFFAOYSA-M icosyl(trimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCCCC[N+](C)(C)C MIKQUZGJQABVKX-UHFFFAOYSA-M 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- PSRABQSGTFZLOM-UHFFFAOYSA-N n-ethyl-n-methylcyclohexanamine Chemical compound CCN(C)C1CCCCC1 PSRABQSGTFZLOM-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 239000000126 substance Substances 0.000 description 1
- HNJXPTMEWIVQQM-UHFFFAOYSA-M triethyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC HNJXPTMEWIVQQM-UHFFFAOYSA-M 0.000 description 1
- QFGWYYQGDCVPFQ-UHFFFAOYSA-M triethyl(hexadecyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC QFGWYYQGDCVPFQ-UHFFFAOYSA-M 0.000 description 1
- MBXYEKQOJQZLHR-UHFFFAOYSA-M triethyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CC)(CC)CC MBXYEKQOJQZLHR-UHFFFAOYSA-M 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-O triethylphosphanium Chemical compound CC[PH+](CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-O 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- HIACZXUUKNSHAN-UHFFFAOYSA-M trimethyl(octadecyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C HIACZXUUKNSHAN-UHFFFAOYSA-M 0.000 description 1
- UJLZFWKVBBDKKP-UHFFFAOYSA-M trimethyl(octadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[P+](C)(C)C UJLZFWKVBBDKKP-UHFFFAOYSA-M 0.000 description 1
- ZBXQFQUWIWNCEP-UHFFFAOYSA-M trimethyl(octyl)phosphanium;iodide Chemical compound [I-].CCCCCCCC[P+](C)(C)C ZBXQFQUWIWNCEP-UHFFFAOYSA-M 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- This invention relates to new fluids for use in dry cleaning processes and more particularly to new drycleaning processes wherein surface active organic compounds, the positive ion of which contains an aliphatic radical having a chain of eight or more carbon atoms, are added to the conventional dry cleaning solvents which are employed.
- That part of the molecule of the dissolved soap in such a composition which is believed to be mainly active is the negatively charged long chain radical to which the carboxylic group is attached.
- This invention has as an object to provide new processes for dry cleaning textile fabrics.
- a further object is to provide novel dry cleaning fluids for use in said processes.
- a still further object is to provide new uses for surface active organic compounds which contain a long chain aliphatic radical in their positive ions.
- this invention in its broadest aspect involves the use in a dry-cleaning fluid of any surface active organic compound, the positive ion ofwhich contains an aliphatic radical having a chain of eight or more carbon atoms.
- this invention relates to the use in a dry cleaning solvent of a quaternary ammonium salt, the positive ion of which contains an aliphatic radical having a chain of eight or more carbon atoms.
- this invention relates to dry cleaning fluids which contain a quaternary ammonium salt, the positive ion of which contains a straight chain alkyl group having from twelve to eighteen carbon atoms directly linked to the nitrogen atom.
- dry cleaning solvents in 50 which are dissolved organic quaternary ammonium salts, one or more radicals of which consist of a carbon chain, either saturated or unsaturated, containing eight or more carbon atoms and directly or indirectly linked to the nitrogen atom, are exceedingly potent as dry cleaning agents; and the present invention consists in a process for dry cleaning textile materials by means of a solution as above described of an organic quaternary ammonium salt.
- Such agents are distinguished from the soaps hitherto employed in dry cleaning in that the effective properties may be regarded as due to the positively charged and not the negatively charged portion of the molecule.
- Quaternary ammonium salts which are at present preferred for use in the processes of this invention are: cetyl pyridinium bromide, cetyl trimethyl ammonium bromide, dimethyl dicetyl ammonium bromide, p-stearophenyl trimethylammonium methyl sulphate and p-stearamidophenyl trimethyl ammonium'methosulphate, but others may be employed.
- Example 1 Example 2 Serge suiting is cleaned by immersing in a cold solution of 1 part ofcetyl trimethyl ammonium bromide in 1000' parts of trichlorethylene, work- .ing gently for 10 minutes or longer, and drying.
- Example 3 Serge suiting may also be cleaned by immersing it in white spirit containing 0.2 per centv of dimethyl dicetyl ammonium bromide.
- Example 4 A cotton fabric is cleaned by immersing in a cold solution of 0.5 part of cetyl pyridinium bromide in 1000 parts of trichlorethylene and working gently for 15 minutes or longer and drying.
- Numerous quaternary ammonium salts. containing a long chain aliphatic radical in the positive ion may be used in connection with the present invention.
- cetyl pyridinium bromide use may be made of dodecyl pyridinium bromide, dodecyl pyridinium sulphate, tetradecyl pyridinium bromide, cetyl pyridinium iodide, octadecyl pyridinum bromide, octadecyl pyridinium iodide, octadecyl picolinium bromide, undecyl quinolium chloride, and other similar quaternary ammonium salts which may be prepared by the methods set forth in British Patents 379,896, 392,763, and 434,856.
- quaternary ammonium salts which are useiul are methyl cetyl piperidinium methyl sulphate, the preparation or which is described in British Patent 424,410; dicetyl piperidinium bromide hydroxy- I ethyl octadecyl morpholinium bromide, the prepa- I mide, oleyl amide-ethyl methyl piperidiniumration of which is set forth in U. 8.
- Patent 2,004,476 and the stearic, oleic, ricinoleic, palmitic, myristic, and lauric acid esters of hydroxy ethyl pyridiniurn chloride and dihydroxy propyl pyridinium chloride, which are described in British Patent 390,553, French Patent 125,637, and U. 5. Patent 2,004,476.
- Still other useful quaternary ammonium salts are those obtained according to French Patent 788,898 such as the addition product of pyridine and the ethyl ester of alpha bromostearic acid, the addition product 01' pyridine and the ethyl ester of alpha bromopalmitic acid, the addition product of pyridine .and alpha bromostearic acid amide, the addition product of pyridine and alpha bromostearic acid, the addition product oi trimethyl amine and alpha bromostearic acid, the addition prodnot 01' trimethyl amine and the methyl ester of alpha bromostearlc acid, the addition product of pyridine and alpha bromostearic acid anilide, the addition product of pyridine and alpha. bromolauric acid anilide, the addition product of trimethyl amine and alpha bromolauric acid anilide, the addition product" of dimethyl cyclohexyl amine and alpha bromostearic acid, etc.
- cetyl trimethyl ammonium bromide and dimethyl dicetyl ammonium bromide there may be employed octadecyl trimethyl ammonium bromide, octadecyl trimethyl ammonium iodide, cetyl trimethyl ammonium iodide, cetyl triethyl ammonium iodide, cetyl triethyl ammonium bromide, cetyl benzyl diethyl'ammonium chloride, eicosyl trimethyl ammonium bromide, ,docosyl trimethyl ammonium iodide, cetyl benzyl dimethyl ammonium chloride, octadecyl trimethyl ammonium methosulphate, decyl trimethyl ammoniumiodide, cetyl cyclohexyl dimethyl ammonium bromide, dodecyl cyclohexyl dimethyl ammonium bromide
- Still further quaternary ammonium salts which may be used in place of those set forth in the preceding paragraphs are the products described in Examples 1 and 3 of the German Patent 275,344; the products described in British Patent 394,196; the alkylated acidyl polyalkylene polyamines described in U. 8. Patent 1,924,698; stearoyl choline chloride; the nitrogen-containing esters described by Harris in U. 8, Patent 2,023,075; and the long chain betaines disclosed in French Patent 789,304 such as the dodecyl dimethyl, the cetyl dimethyl, the octadecyl dimethyl, and the dodecyl dibutyl betaines which are derived from chloracetic acid. 7
- quaternary ammonium salts which contain a long chain aliphatic radical in their positive ion
- use. may be made of the analogous quaternary phosphoniumsalts.
- the custernary phosphonium salts which may be employed are cetyl trimethyl phosphonium bromide, cetyl triethyl phosphonium bromide, dodecyl trimethyl phosphonium bromide, dodecyl triethyl phosphonium bromide, cetyl ethyl dimethyl phosphonium chloride, diethyl dioleyl phosphonium sulphate, dodecyl triethyl phosphonium sulphate, octyl trimethyl phosphonium iodide, octadecyl bromide, octadecyl trimethyl phosphonium bromide, tetradecyl trlethyi phosphonium bromide
- quaternary phosphonium salts may be prepared according to the methods described in British Patents 424,410, 434,810, 434,856, and 435,443. If desired, oneor more of these quaternary phosphonium salts may be used in combination with one or more of the above mentioned.
- ternary ammonium and phosphonium salts use may be made 01' ternary sulphonium salts, the positive ion of which contains an aliphatic radical having a chain of eight or more carbon atoms.
- suitable ternary sulphonium compounds are cetyl dimethyl sulphonium methosuiphate, cetyl methyl benzyl sulphonium methosulphate, dodecyl dimethyl sulphonium bromide, cetyl methyl ethyl sulphonium iodide, cetyl methyl ethyl sulphonium methosulphate, octadecyl diethyl sulphonium chloride, dodecyl dipropyl sulphonium bromide, decyl dimethyl sulphonlum iodide, tetradecyl dimethyl sulphonium bromide, dodecyl methyl
- sulphonium iodide dodecyl methyl ethyl sulphonium methosulphate, dodecyl methyl ethyl sulphonium iodide, dodecyl dimethyl sulphonium methosulp'hate, dodecyl benzyl methyl sulphonium chloride, etc.
- These sulphonium compounds may be prepared by the methods set forth in British Patents 424,410, 434,810, 434,856, and 435,444. If desired, these sulphonium salts may be used in admixture with one or more of the ammonium and phosphonium salts rather than in place of these latter salts.
- I claim: 1 A .dry cleaning fluid consisting of a dry cleaning solvent containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an aliphatic radical having a chain of eightto twenty-two carbon atoms.
- a dry cleaning fluid consisting of a dry cleaning solvent containing from 0.2 to 0.5% of a surface active organic compound selected from the group consisting of quaternary ammonium, quaternary phosphonium and ternary sulphonium salts, the positive ion of which compound contains an aliphatic radical having a chain of 8 to 22 carbon atoms.
- a dry cleaning fluid consisting of a dry cleaning solvent containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an alkyl group having from twelve to eighteen carbon atoms in a straight chain.
- a dry cleaning fluid consisting of a chlorinated hydrocarbon dry cleaning solvent containing from 0.2% to 0.5% of a surface active organic compound selected from the group consisting of quaternary ammonium, quaternary phosphonium, and ternary sulphonium salts, the positive ion of which compound contains an aliphatic hydrocarbon radical having a chain of 8 to 22 carbon atoms.
- a dry cleaning fluid consisting of a chicrinated hydrocarbon dry cleaning solvent containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an aliphatic hydrocarbon radical having a chain of 8 to 22 carbon atoms.
- a dry cleaning solvent consisting of trichlorethylene containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an alkyl group having from 12 to 18 carbon atoms in a straight chain.
Description
Patented dilly it, l3
entree stares DRY-CLEANING mum Charles Dunbar, Manchester, England,
to Imperial Chemical Industries nssignor Limited, a
corporation oi Great Britain No Drawing. Application March 10, 1936, Serial No. 68,137. In Great Britain March 13, 1935 6 Claims.
This invention relates to new fluids for use in dry cleaning processes and more particularly to new drycleaning processes wherein surface active organic compounds, the positive ion of which contains an aliphatic radical having a chain of eight or more carbon atoms, are added to the conventional dry cleaning solvents which are employed.
In the dry cleaning of textiles, e. g., materials of wool or silk, it has been a common practice to employ an organic solvent, such as benzene, white spirit or trlchlorethylene, in which is dissolved a. soap, for. instance, potassium or triethanol ammonium oleate, frequently with the addition of a higher fatty acid, for instance, oleic acid, and, if desired, water. (See, e. g., Farrell and May, Journal of the Society of Dyers and Colourists, 1908, p. 43; Bird, ibid., 1933, p. 316; Harvey, American Dyestufi Reporter, 1980, p. 249.)
That part of the molecule of the dissolved soap in such a composition which is believed to be mainly active is the negatively charged long chain radical to which the carboxylic group is attached.
This invention has as an object to provide new processes for dry cleaning textile fabrics. A further object is to provide novel dry cleaning fluids for use in said processes. A still further object is to provide new uses for surface active organic compounds which contain a long chain aliphatic radical in their positive ions. Other objects will appear hereinafter.
These objects are accomplished by the following invention which in its broadest aspect involves the use in a dry-cleaning fluid of any surface active organic compound, the positive ion ofwhich contains an aliphatic radical having a chain of eight or more carbon atoms. In a more restricted sense this invention relates to the use in a dry cleaning solvent of a quaternary ammonium salt, the positive ion of which contains an aliphatic radical having a chain of eight or more carbon atoms. In its preferred embodiment this invention relates to dry cleaning fluids which contain a quaternary ammonium salt, the positive ion of which contains a straight chain alkyl group having from twelve to eighteen carbon atoms directly linked to the nitrogen atom.
I have discovered that dry cleaning solvents in 50 which are dissolved organic quaternary ammonium salts, one or more radicals of which consist of a carbon chain, either saturated or unsaturated, containing eight or more carbon atoms and directly or indirectly linked to the nitrogen atom, are exceedingly potent as dry cleaning agents; and the present invention consists in a process for dry cleaning textile materials by means of a solution as above described of an organic quaternary ammonium salt. Such agents are distinguished from the soaps hitherto employed in dry cleaning in that the effective properties may be regarded as due to the positively charged and not the negatively charged portion of the molecule. By the use of the process of the present invention, certain advantages are secured.
Quaternary ammonium salts which are at present preferred for use in the processes of this invention are: cetyl pyridinium bromide, cetyl trimethyl ammonium bromide, dimethyl dicetyl ammonium bromide, p-stearophenyl trimethylammonium methyl sulphate and p-stearamidophenyl trimethyl ammonium'methosulphate, but others may be employed.
The following examples illustrate but do not limit the invention. The parts are by weight.
Example 1 Example 2 Serge suiting is cleaned by immersing in a cold solution of 1 part ofcetyl trimethyl ammonium bromide in 1000' parts of trichlorethylene, work- .ing gently for 10 minutes or longer, and drying.
Example 3 Serge suiting may also be cleaned by immersing it in white spirit containing 0.2 per centv of dimethyl dicetyl ammonium bromide.
Example 4 A cotton fabric is cleaned by immersing in a cold solution of 0.5 part of cetyl pyridinium bromide in 1000 parts of trichlorethylene and working gently for 15 minutes or longer and drying.
Numerous quaternary ammonium salts. containing a long chain aliphatic radical in the positive ion may be used in connection with the present invention. In place of cetyl pyridinium bromide, use may be made of dodecyl pyridinium bromide, dodecyl pyridinium sulphate, tetradecyl pyridinium bromide, cetyl pyridinium iodide, octadecyl pyridinum bromide, octadecyl pyridinium iodide, octadecyl picolinium bromide, undecyl quinolium chloride, and other similar quaternary ammonium salts which may be prepared by the methods set forth in British Patents 379,896, 392,763, and 434,856. Other quaternary ammonium salts which are useiul are methyl cetyl piperidinium methyl sulphate, the preparation or which is described in British Patent 424,410; dicetyl piperidinium bromide hydroxy- I ethyl octadecyl morpholinium bromide, the prepa- I mide, oleyl amide-ethyl methyl piperidiniumration of which is set forth in U. 8. Patent 2,019,124; the'products described in Examples 2, 3, and 4 01' British Patent 394,196; the cetyloxymethyl pyridinium chloride mentioned in British Patent 390,553, French Patent 725,637, and U. 8. Patent 2,004,476; and the stearic, oleic, ricinoleic, palmitic, myristic, and lauric acid esters of hydroxy ethyl pyridiniurn chloride and dihydroxy propyl pyridinium chloride, which are described in British Patent 390,553, French Patent 125,637, and U. 5. Patent 2,004,476. Still other useful quaternary ammonium salts are those obtained according to French Patent 788,898 such as the addition product of pyridine and the ethyl ester of alpha bromostearic acid, the addition product 01' pyridine and the ethyl ester of alpha bromopalmitic acid, the addition product of pyridine .and alpha bromostearic acid amide, the addition product of pyridine and alpha bromostearic acid, the addition product oi trimethyl amine and alpha bromostearic acid, the addition prodnot 01' trimethyl amine and the methyl ester of alpha bromostearlc acid, the addition product of pyridine and alpha bromostearic acid anilide, the addition product of pyridine and alpha. bromolauric acid anilide, the addition product of trimethyl amine and alpha bromolauric acid anilide, the addition product" of dimethyl cyclohexyl amine and alpha bromostearic acid, etc.
In place 0! cetyl trimethyl ammonium bromide and dimethyl dicetyl ammonium bromide, there may be employed octadecyl trimethyl ammonium bromide, octadecyl trimethyl ammonium iodide, cetyl trimethyl ammonium iodide, cetyl triethyl ammonium iodide, cetyl triethyl ammonium bromide, cetyl benzyl diethyl'ammonium chloride, eicosyl trimethyl ammonium bromide, ,docosyl trimethyl ammonium iodide, cetyl benzyl dimethyl ammonium chloride, octadecyl trimethyl ammonium methosulphate, decyl trimethyl ammoniumiodide, cetyl cyclohexyl dimethyl ammonium bromide, dodecyl cyclohexyl dimethyl ammonium bromide, dodecyl cyclohexyl diethyl ammonium bromide, dodecyl trimethyl ammo nium chloride, cetyl trimethyl ammonium chloride, octyl t ethyl ammonium iodide, 'octadecyl triethyl ammonium bromide, dodecyl trimethyl ammonium bromide, octadecyl benzyl dimethyl ammonium chloride, cetyl triethanol'ammonium bromide. dodecyl ethanol dimethyl ammonium sulphate,-etc.
In place of p-stearamidophenyl trimethyl ammonium methosulphate, use may be made of oleylamido-ethyl diethyl methyl ammonium iodide, oleyiamido-ethyl diethyl methyl ammonium methosulphate, stearamido-ethyl diethyl methyl ammonium methosulphate, oleylamidoethyl diethyl benzyl ammonium chloride, oieyiamido-propyl diethyl methyl ammonium iodide, oleylamido-ethyl diethyl allyl ammonium bromethosulphate, oleyl'amido-ethyl ethyl cyclohexyl methyl ammonium methosulphate, oleylamidoethyl trimethyl ammonium methosulphate, stearamido-ethyl trimethyl ammonium methosulphate, and other similar compounds which may be prepared according to the methods set triethyl phosphonium forth in German Patent %,500, British Patent 294,582, and U. 3. Patent 1,737,458.
Still further quaternary ammonium salts which may be used in place of those set forth in the preceding paragraphs are the products described in Examples 1 and 3 of the German Patent 275,344; the products described in British Patent 394,196; the alkylated acidyl polyalkylene polyamines described in U. 8. Patent 1,924,698; stearoyl choline chloride; the nitrogen-containing esters described by Harris in U. 8, Patent 2,023,075; and the long chain betaines disclosed in French Patent 789,304 such as the dodecyl dimethyl, the cetyl dimethyl, the octadecyl dimethyl, and the dodecyl dibutyl betaines which are derived from chloracetic acid. 7
The various quaternary ammonium salts mentioned above are generally used individually in a dry-cleaning fluid, but it is contemplated that two or more oi them may be used coniointly.
In place of quaternary ammonium salts-which contain a long chain aliphatic radical in their positive ion, use. may be made of the analogous quaternary phosphoniumsalts. Among the custernary phosphonium salts which may be employed are cetyl trimethyl phosphonium bromide, cetyl triethyl phosphonium bromide, dodecyl trimethyl phosphonium bromide, dodecyl triethyl phosphonium bromide, cetyl ethyl dimethyl phosphonium chloride, diethyl dioleyl phosphonium sulphate, dodecyl triethyl phosphonium sulphate, octyl trimethyl phosphonium iodide, octadecyl bromide, octadecyl trimethyl phosphonium bromide, tetradecyl trlethyi phosphonium bromide, etc. These quaternary phosphonium salts may be prepared according to the methods described in British Patents 424,410, 434,810, 434,856, and 435,443. If desired, oneor more of these quaternary phosphonium salts may be used in combination with one or more of the above mentioned.
In place or the quaternary ammonium and phosphonium salts, use may be made 01' ternary sulphonium salts, the positive ion of which contains an aliphatic radical having a chain of eight or more carbon atoms. Among the suitable ternary sulphonium compounds are cetyl dimethyl sulphonium methosuiphate, cetyl methyl benzyl sulphonium methosulphate, dodecyl dimethyl sulphonium bromide, cetyl methyl ethyl sulphonium iodide, cetyl methyl ethyl sulphonium methosulphate, octadecyl diethyl sulphonium chloride, dodecyl dipropyl sulphonium bromide, decyl dimethyl sulphonlum iodide, tetradecyl dimethyl sulphonium bromide, dodecyl methyl cyclohexyl sulphonium iodide, octadecyl dimethyl su1phon-. ium iodide, dodecyl methyl ethyl sulphonium methosulphate, dodecyl methyl ethyl sulphonium iodide, dodecyl dimethyl sulphonium methosulp'hate, dodecyl benzyl methyl sulphonium chloride, etc. These sulphonium compounds may be prepared by the methods set forth in British Patents 424,410, 434,810, 434,856, and 435,444. If desired, these sulphonium salts may be used in admixture with one or more of the ammonium and phosphonium salts rather than in place of these latter salts.
The compounds mentioned above may be used in solution in any of the dry-cleaning solvents quaternary ammonium salts hereindeparting from the spirit and scope thereof; it
is to be understood that the invention is not limited to the specific embodiments thereof except as defined in the appended claims.
I claim: 1 A .dry cleaning fluid consisting of a dry cleaning solvent containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an aliphatic radical having a chain of eightto twenty-two carbon atoms.
2. A dry cleaning fluid consisting of a dry cleaning solvent containing from 0.2 to 0.5% of a surface active organic compound selected from the group consisting of quaternary ammonium, quaternary phosphonium and ternary sulphonium salts, the positive ion of which compound contains an aliphatic radical having a chain of 8 to 22 carbon atoms.
'3. A dry cleaning fluid consisting of a dry cleaning solvent containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an alkyl group having from twelve to eighteen carbon atoms in a straight chain.
4. A dry cleaning fluid consisting of a chlorinated hydrocarbon dry cleaning solvent containing from 0.2% to 0.5% of a surface active organic compound selected from the group consisting of quaternary ammonium, quaternary phosphonium, and ternary sulphonium salts, the positive ion of which compound contains an aliphatic hydrocarbon radical having a chain of 8 to 22 carbon atoms.
5. A dry cleaning fluid consisting of a chicrinated hydrocarbon dry cleaning solvent containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an aliphatic hydrocarbon radical having a chain of 8 to 22 carbon atoms.
6. A dry cleaning solvent consisting of trichlorethylene containing from 0.2% to 0.5% of a quaternary ammonium salt, the positive ion of which contains an alkyl group having from 12 to 18 carbon atoms in a straight chain.
CHARLES DUNBAR.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7865/35A GB453523A (en) | 1935-03-13 | 1935-03-13 | Improved process of dry cleaning |
Publications (1)
Publication Number | Publication Date |
---|---|
US2165356A true US2165356A (en) | 1939-07-11 |
Family
ID=9841263
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US68137A Expired - Lifetime US2165356A (en) | 1935-03-13 | 1936-03-10 | Dry-cleaning fluid |
Country Status (2)
Country | Link |
---|---|
US (1) | US2165356A (en) |
GB (1) | GB453523A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2577773A (en) * | 1947-03-26 | 1951-12-11 | Gen Aniline & Film Corp | Ternary detergent compositions |
US2729576A (en) * | 1953-09-29 | 1956-01-03 | Davies Young Soap Company | Method of dry cleaning fabric and simultaneously rendering the same antistatic |
US2820719A (en) * | 1952-08-27 | 1958-01-21 | Davies Young Soap Company | Process for rendering fabrics water repellent |
US2941952A (en) * | 1955-05-27 | 1960-06-21 | Monsanto Chemicals | Dry-cleaning detergent composition |
US2950253A (en) * | 1953-07-29 | 1960-08-23 | Bohme Fettchemie Gmbh | Methods of washing textile fabrics |
US2980624A (en) * | 1957-01-04 | 1961-04-18 | Gen Aniline & Film Corp | Dry cleaning compositions |
US3003247A (en) * | 1957-07-31 | 1961-10-10 | Ici Ltd | Process for drying metal articles |
US3005266A (en) * | 1957-03-30 | 1961-10-24 | Philips Corp | Method of removing surface water from articles |
US3124536A (en) * | 1964-03-10 | Composition for cleaning synthetic fur | ||
US3124535A (en) * | 1964-03-10 | Fur cleaning composition | ||
US3635656A (en) * | 1971-01-11 | 1972-01-18 | Emery Industries Inc | Drycleaning method |
US3962151A (en) * | 1972-08-11 | 1976-06-08 | Lever Brothers Company | Solvent type cleaners |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE970293C (en) * | 1953-01-10 | 1958-09-04 | Julius Rupert Zink | Cleaning with non-aqueous solvents |
DE976341C (en) * | 1953-11-12 | 1963-07-11 | Stockhausen & Cie Chem Fab | Dry cleaning methods |
DE1112240B (en) * | 1956-06-14 | 1961-08-03 | Stockhausen & Cie Chem Fab | Dry cleaning method |
-
1935
- 1935-03-13 GB GB7865/35A patent/GB453523A/en not_active Expired
-
1936
- 1936-03-10 US US68137A patent/US2165356A/en not_active Expired - Lifetime
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3124536A (en) * | 1964-03-10 | Composition for cleaning synthetic fur | ||
US3124535A (en) * | 1964-03-10 | Fur cleaning composition | ||
US2577773A (en) * | 1947-03-26 | 1951-12-11 | Gen Aniline & Film Corp | Ternary detergent compositions |
US2820719A (en) * | 1952-08-27 | 1958-01-21 | Davies Young Soap Company | Process for rendering fabrics water repellent |
US2950253A (en) * | 1953-07-29 | 1960-08-23 | Bohme Fettchemie Gmbh | Methods of washing textile fabrics |
US2729576A (en) * | 1953-09-29 | 1956-01-03 | Davies Young Soap Company | Method of dry cleaning fabric and simultaneously rendering the same antistatic |
US2941952A (en) * | 1955-05-27 | 1960-06-21 | Monsanto Chemicals | Dry-cleaning detergent composition |
US2980624A (en) * | 1957-01-04 | 1961-04-18 | Gen Aniline & Film Corp | Dry cleaning compositions |
US3005266A (en) * | 1957-03-30 | 1961-10-24 | Philips Corp | Method of removing surface water from articles |
US3003247A (en) * | 1957-07-31 | 1961-10-10 | Ici Ltd | Process for drying metal articles |
US3635656A (en) * | 1971-01-11 | 1972-01-18 | Emery Industries Inc | Drycleaning method |
US3962151A (en) * | 1972-08-11 | 1976-06-08 | Lever Brothers Company | Solvent type cleaners |
Also Published As
Publication number | Publication date |
---|---|
GB453523A (en) | 1936-09-14 |
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