US2087506A - Quaternary ammonium salts of high molecular weight acids - Google Patents
Quaternary ammonium salts of high molecular weight acids Download PDFInfo
- Publication number
- US2087506A US2087506A US97221A US9722136A US2087506A US 2087506 A US2087506 A US 2087506A US 97221 A US97221 A US 97221A US 9722136 A US9722136 A US 9722136A US 2087506 A US2087506 A US 2087506A
- Authority
- US
- United States
- Prior art keywords
- acid
- radical
- molecular weight
- high molecular
- quaternary ammonium
- 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
- 239000002253 acid Substances 0.000 title description 39
- 150000007513 acids Chemical class 0.000 title description 12
- 150000003242 quaternary ammonium salts Chemical class 0.000 title description 7
- -1 aromatic sulfonic acids Chemical class 0.000 description 45
- 150000003254 radicals Chemical class 0.000 description 27
- 239000000463 material Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000003512 tertiary amines Chemical class 0.000 description 10
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 8
- ZEMPKEQAKRGZGQ-VBJOUPRGSA-N triricinolein Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC)COC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-VBJOUPRGSA-N 0.000 description 8
- ZEMPKEQAKRGZGQ-UHFFFAOYSA-N Triricinolein Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC(O)CCCCCC)COC(=O)CCCCCCCC=CCC(O)CCCCCC ZEMPKEQAKRGZGQ-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 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 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000019635 sulfation Effects 0.000 description 3
- 238000005670 sulfation reaction Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XNVMEUGKSJGWOD-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)(=O)O.S(=O)(=O)(O)C1=CC=CC2=CC=CC=C12 Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.S(=O)(=O)(O)C1=CC=CC2=CC=CC=C12 XNVMEUGKSJGWOD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002193 fatty amides Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical group CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- HDIFHQMREAYYJW-XFXZXTDPSA-N 2,3-dihydroxypropyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XFXZXTDPSA-N 0.000 description 1
- OUNFHIFSLHEIPK-UHFFFAOYSA-N 2-chloronaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=C(Cl)C=CC2=C1 OUNFHIFSLHEIPK-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical group CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- MWCBGWLCXSUTHK-UHFFFAOYSA-N 2-methylbutane-1,4-diol Chemical compound OCC(C)CCO MWCBGWLCXSUTHK-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CJCCRENXOGIKQN-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)(=O)O.S(=O)(=O)(O)C1=C(C=CC=C1)O Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.S(=O)(=O)(O)C1=C(C=CC=C1)O CJCCRENXOGIKQN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000158728 Meliaceae Species 0.000 description 1
- HDIFHQMREAYYJW-UHFFFAOYSA-N Monoricinolein Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical group OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WNYLQLZCIMFUCH-UHFFFAOYSA-N benzenesulfonic acid octadecanoic acid Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.S(=O)(=O)(O)C1=CC=CC=C1 WNYLQLZCIMFUCH-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910001504 inorganic chloride Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 229940074096 monoolein Drugs 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- 150000002889 oleic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/18—Quaternary ammonium compounds
-
- 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
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- This invention relates to a novel composition of matter, and more particularly, to certain quaternary ammonium salts derived from acids of high molecular weight and of the kind hereinafter described.
- Such materials may be employed as wetting, washing, frothing, emulsifying, dispersing, softening, leveling, and plasticizing agents, and they also may be employed as assistants in the textile industry and various other industries.
- Such materials include the following: Salts of higher fatty acids, resinates, rosinates, naphthenates, sulfoabietenes and the like, petroleum sulfonates of both the oil-soluble and oil-insoluble type, sulfated and sulfonated higher alcohols, substituted aromatic sulfonic acids, alkylated polycyclic sulfonic acids, cycloaromatic sulfonic acids, sulfated fatty acids, sulfonated fatty acids, the various cogeners which accompany the sulfo or sulfated fatty acids or sulfonated fatty acids obtained in sulfation or sulfonation processes, and are produced by the hydrolysis of sulfo-fatty acids, followed, in some instances, by condensation; fatty acids of the kind obtained by oxidation, particularly the oxidation of ricinoleic acid, i.
- blown oil, or blown oil fatty acids fatty acid esters in which a sulfoaromatic or sulfo-aliphatic residue has replaced the carboxylic hydrogen
- sulfonated fatty amides, sulfo-amides in which a sulfonated or sulfated alkyl group, or sulfonated or sulfated aryl group has replaced an amino hydrogen in the fatty amide residue
- Sulfo-aromatic fatty acids of the Twitchell reagent type such as sulfo-naphthalene stearic acid, sulfo-benzene stearic acid, sulfo-phenol stearic acid, etc. represent additional examples.
- a maleic acid residue it may, of course, be treated with a bisulfite, so as to be converted into a sulfo-succinic acid residue.
- two moles of a dibasic carboxy acid for example, such as oxalic acid, may combine with two moles of triricinolein.
- the properties are exhibited by materials having at least 8 carbon atoms in the molecule, and not over 120, as in the case of materials where two moles of di-ricinolein have been combined by mean-s of a dibasic acid, as previously pointed out. All these materials referred to are' well known compositions of matter, and the method of manufacturing the same is well known. They have been used in a variety of industries. Some reagents find application in a number of industries, whereas, other reagents are limited to employment, perhaps, in one or two industries,
- T is a hydrocarbon residue without any other concomitant atoms or radicals being present, for instance, in the case of propylated naphthalene sulfonic acid, or in the case of oleic acid, or in the case of petroleum sulfonic acid.
- there may be a hydroxyl group attached to T as in the case ofderivatives of ricinoleic acid, or derivatives of alkylated naphthol sulfonic acids.
- T may contain a halogen atom, such as in the case of chlorinated or brominated oleic acid, alkylated chlornaphthalene sulfonic acid, etc.
- T may have an acid group attached thereto, as in the case of phthalated castor oil, oxylated ricinoleic acid, sulfo-naphthalene stearic acid, etc.
- T is a high molecular weight hydrocarbon residue or its til BaN[ (OH) nD].C1
- each one of the said materials or products is derived from a high molecular weight surface-active acid, whose application in various industries in the form of simple metallic salts is well known.
- the high molecular weight surface-active acids or theirsimpler salts may be described as being polar" compounds, in the sense that the word polar was used by Harkins in about 1917.
- the meaning of the word "polar" in this sense is intended to indicate that into the hydrophobe group or body there has been introduced a hydrophile group, such as a carboxyl group, or a sulfate group, or a sulfonic acid group, which tends to make the material dissolve in water or to spread out on water, or to be wetted by water. Such polarity tends to make the materials orient at interfaces.
- the quaternary ammonium bases themselves, if they be of the kind described, exhibit this same polar property, due to the presence of the hydrocarbon residue, indicated by B, as contributing the hydrophobe portion, and due to the nitrogen atom and the alkylol or alkylol-oxy-alkylol residue introducing' the hydrophile residue.
- such quaternary ammonium bases or simple salts even in their simplest form, such as the chlorides, may show marked surface-active properties and produce a colloidal sol of the kind comparable to that produced by high molecular weight surface-active acids of the kind previously described.
- such materials of the kind herein contemplated are characterized by the fact that one might consider both the anion and the cation as being polar, when considered as an integral part, and without consideration to the natural polar relationship to each other.
- the relationship is comparable to a compound in which both the anion and cation have hydrophobe and hydrophile components bound covalently, whereas, the anion and cation per se are bound electrovalently.
- the quaternary ammonium compounds employed to produce the desired salts may be prepared in various manners.
- Glycerol may be converted by customary procedure into the chlorhydrin, or may be converted into glycidol.
- a glycol such as ethylene glycol, may be converted into the corresponding chlorhydrin.
- the chlorhydrin one may employ the alkylene oxide. It is to be noted that reactions involving glycidol or the alkylene oxides result in the formation of the quaternary base and not in the formation of the chloride. Naturally, such a quaternary base may be used directly to neutralize a high molecular weight surface-active acid of the kind previously described.
- Polyhydric alcohols can be converted into ether alcohols, such as di-glycerol ether or di-ethylene glycol ether.
- ether alcohols such as di-glycerol ether or di-ethylene glycol ether.
- Such polyhydric alcohol ethers can be converted into chlorhydrins in the same manner that glycerol or ethylene glycol can be converted into a chlorhydrin.
- chlorhydrins are entirely satisfactory for reaction with tertiary amines to produce a suitable quaternary ammonium compound. For purpose of illustration, the following examples are presented:
- CHaCl Reactions need not be limited to the simpler tertiary amines, but one may select a secondary amine, such as diamyl-amine, and react it with glycerol chlorhydrin, for example, to produce 1- diamyl amino propane-2,3-diol (l-diamyl amino 2-hydroxy normal propanol).
- a substituted tertiary amine may be indicated by the formula:
- Such a tertiary amine may be reacted further with another mole of the chlorhydrin derived from glycerol, ethylene glycol, or in fact, higher glycols, such as propylene glycol, butylene glycol, hydroxylated glycol, amylene glycol, non-amethylene glycol, decamethylene glycol, etc., or it may be reacted with the alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, amylene oxide, in the presence of water, etc.
- This product can also be considered a tertiary amine, andmay be reacted in the manner previously described in regard to l-diamyl amino propane-2,3-diol.
- a primary amine can be reacted with two moles of a suitable chlorhydrin or its functional derivative, such'as'twomoles of an alkylene oxide to give a product of the kind indicated immediately above.
- aralkyl amine such as benzylamine
- a cyclic amine such as cyclohexylamine, or their homologues.
- Piperidine is also satisfactory for reaction with a chlorhydrin to produce a tertiary amine.
- pyridine or its homologues are satisfactory as tertiary alkyl amines for reactions of the kind described.
- pyridine and its homologues will be considered as trialkylated amines in which the Cal-I5 radical or the like is equivalent to three alkyl radicals.
- Such tertiary amines are reacted with halohydrins of the kind described to form the quaternary ammonium compound.
- My preferred reagent is prepared by employing tri-amylamine or pyridine as the tertiary base and using glycidol for the reaction in which the quaternary ammonium compound is produced. 1,000 lbs. of tri-amylamine or the equivalent amount of pyridine are reacted with 350 lbs. of glycidol in presence of about 75 lbs. of water, until a complete reaction has taken place.
- the tri-amyl propane diol ammonium hydroxide or corresponding pyridinium hydroxide, so produced, is used to neutralize various materials of the kind previously described, and particularly materials derived by the sulfation of castor oil, or by the sulfonation of oleic' acid, inpresence of a molecular amount of naphthalene, so as to produce sulfo-naphthaiene stearic acid, or for the neutralization of propylated or amylated naphthalene sulfonic acids, or for the neutralization of oxalated, phthalated, succinated or maleated tri-ricinolein.”
- I have found that if the material is used for the neutralization of products obtained by the sulfation of castor oil, that one obtains a new kind of Turkey red oil having unusual properties as a dye bath assistant and as a wetting agent or leveling agent in the textile industry.
- the early discussion 3 in the present instance has been limited to products derived from the simplest quaternary compounds, such as indicated by the formulas B3N[(OH)1
- the quaternary ammonium compound maybe indicated as being of the type BmN[(0H)nD]1 n'-OH, in which the various characters have their previous significance, 'with the qualification that B is preferably an alkyl radical having at least two carbon atoms, and m and m represent the numerals 'i, 2 or 3, and m and m' total 4. It is possible that the radical D(OH)1:, where it appears more than one time (in other words, where m has the value of 2 or 3) may #be dissimilar.
- any suitable tertiary amine may serve, such as tertiary propyl amine, tertiary butyl amine, tertiary amyl amine, tertiary hexylamine, etc.
- Mixed alkyl amines such as tertiary amines, in which the alkyl groups are dissimilar, may be employed.
- the corresponding primary or secondary amines may be converted into tertiary amines having at least one alkyl group or the like.
- Such amines may be employed for reaction with halohydrins.
- tri-amylamine, or two moles of pyridine that one obtains corresponding diammonium salts, which are also valuable for neutralization of the high molecular weight surface-active materials of the kind herein described.
- the properties of the acids herein described which indicates their surface activity are well known. They are apt to produce a colloidal sol, particularly if dispersed in water. They tend to adsorb at interfaces; they tend to produce froths or foams; they tend to produce emulsions; they tend to lower the surface tension of the solvent in which they are dissolved; they tend to dissolve in, be wetted by, or spread out on water. In some instances, these properties in regard to water are best observed by dissolving the material in alcohol and adding the alcohol extract to a larger volume of water. The materials tend to have a high molecular weight, etc.
- each of the selected acids exhibit the various surface-active characteristics to the optimum degree, but all of these materials exhibit one or more of the enumerated characteristics surface-active properties to a-greater or lesser degree, or else, some other obvious surface-active property. All these materials are of the kind which are conventionally understood to'be surface-active, or have surface-active properties.
- a new composition of matter consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one hydrocarbon radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
- a new composition of matter consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one aralkyl radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
- a new composition of matter consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one cyclohexyl radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
- a new composition of matter consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one alkyl radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
- A'new composition of matter consisting of a quarternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized. by the presence of at least one alkyl radical and at least one alkylol radical.
- a new composition of matter consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one alkyl radical, said alkyl radical having at least two carbon atoms, and at least one alkylol radical.
- B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OH)nD] is an alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an oil-soluble petroleum sulfonic acid radical.
- B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OHMD] is an alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an alkylated naphthalene sulfonic acid radical.
- B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OH) 1D] is an alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterfication of a hydroxylated fatty body with a dibasic carboxy acid.
- B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(H)1.D] is ar. alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterification of triricinolein with a dibasic carboxy acid.
- B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OHMD] is an alkylol group; n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterification of triricinolein with phthalic acid.
- B is an amyl radical
- m and m are the numerals 1, 2 or 3, and m and m total 4
- HOHMD] is an aikylol group
- n denotes the numeral 1, 2 or 3
- O.X.T represents an acid radical derived by esterification of triricinolein with phthalic acid.
- B is an amyl radical
- m is the numeral 3 and m is the numeral 1
- [(OH)nD] is the C3H5 (OH)2 radical
- n denotes the numeral 1, 2 or 3
- O.X.'I represents an acid radical derived by esterification of triricinoiein with phthalic acid.
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Description
Patented July 20, 1931 UNITED STATES QUATERNARY AMIMONIUM SALTS OF HIGH MOLECULAR WEIGHT ACIDS,
Melvin De Groote, St. Louis, Mo., assignor to Tretolite Company, Webster Groves, Mo., a 1
corporation of Missouri No Drawing. Application August 21, 1936, Serial No. 97,221
15 Claims.
This invention relates to a novel composition of matter, and more particularly, to certain quaternary ammonium salts derived from acids of high molecular weight and of the kind hereinafter described. Such materials may be employed as wetting, washing, frothing, emulsifying, dispersing, softening, leveling, and plasticizing agents, and they also may be employed as assistants in the textile industry and various other industries.
It is well known that various high molecular weight acids, and more particularly, their salts, such as ammonium, potassium, sodium salts, etc., are the kind which exhibit surface-active properties. They give a typical colloidal sol in water or in hydrophobe solvents, in which they happen to be miscible, depending upon the specific agents selected. Examples of such materials include the following: Salts of higher fatty acids, resinates, rosinates, naphthenates, sulfoabietenes and the like, petroleum sulfonates of both the oil-soluble and oil-insoluble type, sulfated and sulfonated higher alcohols, substituted aromatic sulfonic acids, alkylated polycyclic sulfonic acids, cycloaromatic sulfonic acids, sulfated fatty acids, sulfonated fatty acids, the various cogeners which accompany the sulfo or sulfated fatty acids or sulfonated fatty acids obtained in sulfation or sulfonation processes, and are produced by the hydrolysis of sulfo-fatty acids, followed, in some instances, by condensation; fatty acids of the kind obtained by oxidation, particularly the oxidation of ricinoleic acid, i. e., blown oil, or blown oil fatty acids, fatty acid esters in which a sulfoaromatic or sulfo-aliphatic residue has replaced the carboxylic hydrogen; sulfonated fatty amides, sulfo-amides, in which a sulfonated or sulfated alkyl group, or sulfonated or sulfated aryl group has replaced an amino hydrogen in the fatty amide residue; materials of the kind in which the hydroxyl of a fatty acid or of a glyceride has combined with a polybasic carboxy acid, such as phthalated, oxalated, succinated, or maleated esters of ricinoleic acid, triricinolein, monoricinolein, di-ricinolein, mono-olein, di-olein, mono-stearin, di-stearin, mono-naphthenine, etc. Sulfo-aromatic fatty acids of the Twitchell reagent type, such as sulfo-naphthalene stearic acid, sulfo-benzene stearic acid, sulfo-phenol stearic acid, etc. represent additional examples. In the case that a maleic acid residue is present, it may, of course, be treated with a bisulfite, so as to be converted into a sulfo-succinic acid residue. In some instances, two moles of a dibasic carboxy acid, for example, such as oxalic acid, may combine with two moles of triricinolein. Generally speaking, the properties are exhibited by materials having at least 8 carbon atoms in the molecule, and not over 120, as in the case of materials where two moles of di-ricinolein have been combined by mean-s of a dibasic acid, as previously pointed out. All these materials referred to are' well known compositions of matter, and the method of manufacturing the same is well known. They have been used in a variety of industries. Some reagents find application in a number of industries, whereas, other reagents are limited to employment, perhaps, in one or two industries,
or even employment for a single purpose in a 15 particular industry.
It is to be noted that all the chemical compounds above referred to are characterized by the presence of an acid radical, which is either a carboxy acid radical, a sulfonic acid radical, or an acid sulfate radical, as in the case of fatty acid sulfates or alcohol sulfates. The acids themselves may be characterized by the formula T.X.OH, in which T is a high molecular weight residue consisting principally of carbon atoms and hydrogen atoms, and X.OH is the acid radi cal in which X is CO or S02 or S03. In-some instances T is a hydrocarbon residue without any other concomitant atoms or radicals being present, for instance, in the case of propylated naphthalene sulfonic acid, or in the case of oleic acid, or in the case of petroleum sulfonic acid. In other instances, there may be a hydroxyl group attached to T, as in the case ofderivatives of ricinoleic acid, or derivatives of alkylated naphthol sulfonic acids. In other instances, T may contain a halogen atom, such as in the case of chlorinated or brominated oleic acid, alkylated chlornaphthalene sulfonic acid, etc. In still other instances, T may have an acid group attached thereto, as in the case of phthalated castor oil, oxylated ricinoleic acid, sulfo-naphthalene stearic acid, etc. In each case, however, T is a high molecular weight hydrocarbon residue or its til BaN[ (OH) nD].C1,
in which the various characters have their previous significance. If such material is dissolved in alcohol and reacted with an alcoholic solution -of the sodium salt of acids of the kind previously described, there occurs a precipitation of sodium chloride with the formation of the corresponding salt, which may be indicated by the formula BaNE (OH) nD] .O.X.T.
in which the various characters have their previous significance. The materials so obtained from the high molecular weight surface-active acids are much more efiective for various industrial purposes than the corresponding metallic salts or corresponding simpler amine salts. I have also found that such materials are very effective softening agents, cleansing agents, detergent agents, emulsifying agents, wetting agents, and
leveling agents, and that they can be employed as auxiliary agents for the same purpose. I do not contend that any single one of. the said materials will serve for all of the purposes mentioned, but it is believed that no particular difficulty is involved in their application. Each one of the said materials or products is derived from a high molecular weight surface-active acid, whose application in various industries in the form of simple metallic salts is well known. In substantially all instances, it will be found that reagents of the kind described in which one employs the alkylated alkylol or alkylol-oxy-alkylol quaternary ammonium compounds, instead of the simpler compounds, will result in a more effective compound for the particular purpose for which the product is employed, or a compound which will accomplish the same result at a lower cost.
It is to be noted that the high molecular weight surface-active acids or theirsimpler salts may be described as being polar" compounds, in the sense that the word polar was used by Harkins in about 1917. The meaning of the word "polar" in this sense is intended to indicate that into the hydrophobe group or body there has been introduced a hydrophile group, such as a carboxyl group, or a sulfate group, or a sulfonic acid group, which tends to make the material dissolve in water or to spread out on water, or to be wetted by water. Such polarity tends to make the materials orient at interfaces. It is to be noted that the quaternary ammonium bases themselves, if they be of the kind described, exhibit this same polar property, due to the presence of the hydrocarbon residue, indicated by B, as contributing the hydrophobe portion, and due to the nitrogen atom and the alkylol or alkylol-oxy-alkylol residue introducing' the hydrophile residue. Indeed, in some instances, such quaternary ammonium bases or simple salts, even in their simplest form, such as the chlorides, may show marked surface-active properties and produce a colloidal sol of the kind comparable to that produced by high molecular weight surface-active acids of the kind previously described. Briefly stated, then, such materials of the kind herein contemplated are characterized by the fact that one might consider both the anion and the cation as being polar, when considered as an integral part, and without consideration to the natural polar relationship to each other. The relationship is comparable to a compound in which both the anion and cation have hydrophobe and hydrophile components bound covalently, whereas, the anion and cation per se are bound electrovalently.
The quaternary ammonium compounds employed to produce the desired salts may be prepared in various manners. Glycerol may be converted by customary procedure into the chlorhydrin, or may be converted into glycidol. Similarly, a glycol, such as ethylene glycol, may be converted into the corresponding chlorhydrin. Instead of the chlorhydrin one may employ the alkylene oxide. It is to be noted that reactions involving glycidol or the alkylene oxides result in the formation of the quaternary base and not in the formation of the chloride. Naturally, such a quaternary base may be used directly to neutralize a high molecular weight surface-active acid of the kind previously described. Polyhydric alcohols can be converted into ether alcohols, such as di-glycerol ether or di-ethylene glycol ether. Such polyhydric alcohol ethers can be converted into chlorhydrins in the same manner that glycerol or ethylene glycol can be converted into a chlorhydrin. Such chlorhydrins are entirely satisfactory for reaction with tertiary amines to produce a suitable quaternary ammonium compound. For purpose of illustration, the following examples are presented:
CHQOH CH2.0H
CHaCl Reactions need not be limited to the simpler tertiary amines, but one may select a secondary amine, such as diamyl-amine, and react it with glycerol chlorhydrin, for example, to produce 1- diamyl amino propane-2,3-diol (l-diamyl amino 2-hydroxy normal propanol). Such product is in reality a substituted tertiary amine and may be indicated by the formula:
Such a tertiary amine may be reacted further with another mole of the chlorhydrin derived from glycerol, ethylene glycol, or in fact, higher glycols, such as propylene glycol, butylene glycol, hydroxylated glycol, amylene glycol, non-amethylene glycol, decamethylene glycol, etc., or it may be reacted with the alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, amylene oxide, in the presence of water, etc.
Two molecules of glycerol mono-chlorhydrin can be reacted with one mole of mono-amylamine to yield a product of the following type:
This product can also be considered a tertiary amine, andmay be reacted in the manner previously described in regard to l-diamyl amino propane-2,3-diol. Thus, in the reactions previously described, it has been indicated that a primary amine can be reacted with two moles of a suitable chlorhydrin or its functional derivative, such'as'twomoles of an alkylene oxide to give a product of the kind indicated immediately above. However, instead of using mono-amylamine, one can employ an aralkyl amine, such as benzylamine, or a cyclic amine, such as cyclohexylamine, or their homologues. Piperidine is also satisfactory for reaction with a chlorhydrin to produce a tertiary amine. Incidentally, pyridine or its homologues are satisfactory as tertiary alkyl amines for reactions of the kind described. For purposes of classification, pyridine and its homologues will be considered as trialkylated amines in which the Cal-I5 radical or the like is equivalent to three alkyl radicals. Such tertiary amines are reacted with halohydrins of the kind described to form the quaternary ammonium compound.
It has been pointed out that the various reactions above referred to may result in the formation of a quaternary ammonium compound in the form of a chloride. Such chloride can, of course, be reacted with a salt of the high molecular weight surface-active acid in a non-aqueous" solvent, so that an inorganic chloride, such as sodium chloride, potassium chloride, or ammonium chloride is precipitated with the formation of thequaternary ammonium salt of the high molecular weight surface-active acid. On the other hand, it is simpler, as a rule, to convert the quaternary ammonium chloride into the corresponding base by treatment-with an excess of concentrated caustic soda or caustic potash, so as to yield the base itself and to employ the base for neutralization.
My preferred reagent is prepared by employing tri-amylamine or pyridine as the tertiary base and using glycidol for the reaction in which the quaternary ammonium compound is produced. 1,000 lbs. of tri-amylamine or the equivalent amount of pyridine are reacted with 350 lbs. of glycidol in presence of about 75 lbs. of water, until a complete reaction has taken place. The tri-amyl propane diol ammonium hydroxide or corresponding pyridinium hydroxide, so produced, is used to neutralize various materials of the kind previously described, and particularly materials derived by the sulfation of castor oil, or by the sulfonation of oleic' acid, inpresence of a molecular amount of naphthalene, so as to produce sulfo-naphthaiene stearic acid, or for the neutralization of propylated or amylated naphthalene sulfonic acids, or for the neutralization of oxalated, phthalated, succinated or maleated tri-ricinolein." I, have found that if the material is used for the neutralization of products obtained by the sulfation of castor oil, that one obtains a new kind of Turkey red oil having unusual properties as a dye bath assistant and as a wetting agent or leveling agent in the textile industry. I have found that if mahogany acids of the kind derived in the refining of petroleum, as in the manufacture of white oil or medicinal oil, are neutralized with the above product, that one obtains materials of unusual value in various processes involving emulsification, such as the production of cutting oils for use in connection with lathes and the like. I have found that if sulfo-aromatic fatty acids of the kind previously referred to are neutralized with this material, that one obtains an emulsifying agent of unusual effectiveness for producing oilin-water emulsions. I have found that if monophthalated or di-phthalated ricinolein is neutralized with the above material, that one obtains a plasticizer of unusual value in the manufacture of various plastics, or in the manufacture of varnishes or lacquers derived from resinous materials or cellulose bodies. I have found that all the various materials and all the various types previously mentioned are effective in the resolution of oil field emulsions. In each instance where the high molecular weight surface-active fatty acids or its simpler salts are employed in a particular industry, one can invariably find applica- "tion of the new quaternary ammonium compounds, so as to obtain increased efliciency or reduced cost.
For purpose of simplicity, the early discussion 3 in the present instance has been limited to products derived from the simplest quaternary compounds, such as indicated by the formulas B3N[(OH)1|.D].C1 or B3N[(OH1;D].OH. It has been previously indicated that a secondary amine irived from a glycerol ether, or from a glycol ether, the residue not only would contain one 'or more hydroxyl radicals, but might also con tain an oxygen atom, due to the ether group. In such instances, the (OH) nD group might be designated as an alkylol-oxy-alkylol group.
For reasons just indicated, the quaternary ammonium compound maybe indicated as being of the type BmN[(0H)nD]1 n'-OH, in which the various characters have their previous significance, 'with the qualification that B is preferably an alkyl radical having at least two carbon atoms, and m and m represent the numerals 'i, 2 or 3, and m and m' total 4. It is possible that the radical D(OH)1:, where it appears more than one time (in other words, where m has the value of 2 or 3) may #be dissimilar. It has been previously pointed out that any suitable tertiary amine may serve, such as tertiary propyl amine, tertiary butyl amine, tertiary amyl amine, tertiary hexylamine, etc. Mixed alkyl amines, such as tertiary amines, in which the alkyl groups are dissimilar, may be employed. It has been previously indicated how the corresponding primary or secondary amines may be converted into tertiary amines having at least one alkyl group or the like. Such amines may be employed for reaction with halohydrins. It is also interesting as tri-amylamine, or two moles of pyridine, that one obtains corresponding diammonium salts, which are also valuable for neutralization of the high molecular weight surface-active materials of the kind herein described.
The properties of the acids herein described which indicates their surface activity are well known. They are apt to produce a colloidal sol, particularly if dispersed in water. They tend to adsorb at interfaces; they tend to produce froths or foams; they tend to produce emulsions; they tend to lower the surface tension of the solvent in which they are dissolved; they tend to dissolve in, be wetted by, or spread out on water. In some instances, these properties in regard to water are best observed by dissolving the material in alcohol and adding the alcohol extract to a larger volume of water. The materials tend to have a high molecular weight, etc. It is not necessary that each of the selected acids exhibit the various surface-active characteristics to the optimum degree, but all of these materials exhibit one or more of the enumerated characteristics surface-active properties to a-greater or lesser degree, or else, some other obvious surface-active property. All these materials are of the kind which are conventionally understood to'be surface-active, or have surface-active properties.
Having thus described my invention, what I claim as new and desire to secure by Letters Patent, is:
1. A new composition of matter, consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one hydrocarbon radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
2. A new composition of matter, consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one aralkyl radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
3. A new composition of matter, consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one cyclohexyl radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
4. A new composition of matter, consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one alkyl radical, and at least one radical selected from the class consisting of alkylol-oxy-alkylol radicals and alkylol radicals.
5. A'new composition of matter, consisting of a quarternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized. by the presence of at least one alkyl radical and at least one alkylol radical.
6. A new composition of matter, consisting of a quaternary ammonium salt of a high molecular weight surface-active acid of the kind in which the substituted ammonium radical is characterized by the presence of at least one alkyl radical, said alkyl radical having at least two carbon atoms, and at least one alkylol radical.
'7. A new composition of matter indicated by the type formula:
in which B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OH)nD] is an alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an oil-soluble petroleum sulfonic acid radical.
9. A new composition of matter indicated by the type formula:
in which B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OHMD] is an alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an alkylated naphthalene sulfonic acid radical.
10. A new composition of matter indicated by the type formula:
in which B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OH) 1D] is an alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterfication of a hydroxylated fatty body with a dibasic carboxy acid.
11. A new composition of matter indicated by the type formula:
in which B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(H)1.D] is ar. alkylol group, n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterification of triricinolein with a dibasic carboxy acid.
12. A new composition of matter indicated by the type formula:
in which B is an alkyl radical having at least two carbon atoms and not having more than six carbon atoms; m and m are the numerals 1, 2 or 3, and m and m total 4; [(OHMD] is an alkylol group; n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterification of triricinolein with phthalic acid.
13. A new composition of matter indicated by the type formula:
in which B is an amyl radical; m and m are the numerals 1, 2 or 3, and m and m total 4; HOHMD] is an aikylol group; n denotes the numeral 1, 2 or 3, and O.X.T represents an acid radical derived by esterification of triricinolein with phthalic acid.
14. A new composition of matter indicated by the type formula:
in which Bis an amyl radical; m is the numeral 3 a and m is the numeral 1; [(OH) "D1 is an alkylol group; n denotes the numeral 1, 2 or 3, and O.X.T
represents an acid radical derived by esterification of triricinolein with phthalic acid.
15. A new composition of matter indicated by the type formula:
in which B is an amyl radical; m is the numeral 3 and m is the numeral 1; [(OH)nD] is the C3H5 (OH)2 radical; n denotes the numeral 1, 2 or 3, and O.X.'I represents an acid radical derived by esterification of triricinoiein with phthalic acid.
MELVIN DE GROO'IE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US97221A US2087506A (en) | 1936-08-21 | 1936-08-21 | Quaternary ammonium salts of high molecular weight acids |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US97221A US2087506A (en) | 1936-08-21 | 1936-08-21 | Quaternary ammonium salts of high molecular weight acids |
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Publication Number | Publication Date |
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US2087506A true US2087506A (en) | 1937-07-20 |
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ID=22262190
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US97221A Expired - Lifetime US2087506A (en) | 1936-08-21 | 1936-08-21 | Quaternary ammonium salts of high molecular weight acids |
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US (1) | US2087506A (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2585826A (en) * | 1948-11-05 | 1952-02-12 | Gen Aniline & Film Corp | Carbamate-quaternary ammonium compounds and their preparation |
US2623901A (en) * | 1950-01-28 | 1952-12-30 | Nopco Chem Co | Production of choline chloride |
US2655541A (en) * | 1948-10-14 | 1953-10-13 | Hopff Heinrich | Preparation of choline chloride |
US2662885A (en) * | 1950-09-19 | 1953-12-15 | Haarmann & Reimer Chem Fab Zu | Antihistamine compounds |
US2775604A (en) * | 1953-02-09 | 1956-12-25 | Atlas Powder Co | Quaternary ammonium halides |
US3123641A (en) * | 1964-03-03 | Cation-active surface active trilower- | ||
US3123640A (en) * | 1964-03-03 | Cation-active surface active aryldi- | ||
US3274199A (en) * | 1964-03-17 | 1966-09-20 | Millmaster Onyx Corp | Quaternary ammonium salts of higher alpha-sulfo fatty acids |
US3328409A (en) * | 1964-02-10 | 1967-06-27 | Millmaster Onyx Corp | Quaternary salts of dimer acids |
US3819589A (en) * | 1972-02-17 | 1974-06-25 | Petrolite Corp | Polymeric quaternary ammonium betaines |
US3956271A (en) * | 1969-01-20 | 1976-05-11 | Sandoz Ltd. | Process for the production of concentrated solutions of cationic azo dyes |
US4405514A (en) * | 1983-03-08 | 1983-09-20 | The United States Of America As Represented By The Secretary Of Agriculture | Preparation of esters of resin acids, resins, rosins, and derivatives thereof |
US4730081A (en) * | 1986-01-14 | 1988-03-08 | Halliburton Company | Vicinal diol containing monomers and methods of preparing |
US4948535A (en) * | 1986-11-13 | 1990-08-14 | Hoechst Aktiengesellschaft | Process for the sulfation of partial esters of aliphatic polyhydric alcohols |
US4959163A (en) * | 1988-11-03 | 1990-09-25 | Halliburton Company | Polyampholytes-high temperature polymers and method of use |
-
1936
- 1936-08-21 US US97221A patent/US2087506A/en not_active Expired - Lifetime
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3123641A (en) * | 1964-03-03 | Cation-active surface active trilower- | ||
US3123640A (en) * | 1964-03-03 | Cation-active surface active aryldi- | ||
US2655541A (en) * | 1948-10-14 | 1953-10-13 | Hopff Heinrich | Preparation of choline chloride |
US2585826A (en) * | 1948-11-05 | 1952-02-12 | Gen Aniline & Film Corp | Carbamate-quaternary ammonium compounds and their preparation |
US2623901A (en) * | 1950-01-28 | 1952-12-30 | Nopco Chem Co | Production of choline chloride |
US2662885A (en) * | 1950-09-19 | 1953-12-15 | Haarmann & Reimer Chem Fab Zu | Antihistamine compounds |
US2775604A (en) * | 1953-02-09 | 1956-12-25 | Atlas Powder Co | Quaternary ammonium halides |
US3328409A (en) * | 1964-02-10 | 1967-06-27 | Millmaster Onyx Corp | Quaternary salts of dimer acids |
US3274199A (en) * | 1964-03-17 | 1966-09-20 | Millmaster Onyx Corp | Quaternary ammonium salts of higher alpha-sulfo fatty acids |
US3956271A (en) * | 1969-01-20 | 1976-05-11 | Sandoz Ltd. | Process for the production of concentrated solutions of cationic azo dyes |
US3819589A (en) * | 1972-02-17 | 1974-06-25 | Petrolite Corp | Polymeric quaternary ammonium betaines |
US4405514A (en) * | 1983-03-08 | 1983-09-20 | The United States Of America As Represented By The Secretary Of Agriculture | Preparation of esters of resin acids, resins, rosins, and derivatives thereof |
US4730081A (en) * | 1986-01-14 | 1988-03-08 | Halliburton Company | Vicinal diol containing monomers and methods of preparing |
US4948535A (en) * | 1986-11-13 | 1990-08-14 | Hoechst Aktiengesellschaft | Process for the sulfation of partial esters of aliphatic polyhydric alcohols |
US4959163A (en) * | 1988-11-03 | 1990-09-25 | Halliburton Company | Polyampholytes-high temperature polymers and method of use |
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