GB415718A - Process for the manufacture of acid amide derivatives - Google Patents
Process for the manufacture of acid amide derivativesInfo
- Publication number
- GB415718A GB415718A GB6144/33A GB614433A GB415718A GB 415718 A GB415718 A GB 415718A GB 6144/33 A GB6144/33 A GB 6144/33A GB 614433 A GB614433 A GB 614433A GB 415718 A GB415718 A GB 415718A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- oil
- acids
- products
- oils
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 title abstract 9
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title 1
- 239000000047 product Substances 0.000 abstract 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 14
- 239000002253 acid Substances 0.000 abstract 11
- 150000007513 acids Chemical class 0.000 abstract 11
- 239000003921 oil Substances 0.000 abstract 8
- 235000019198 oils Nutrition 0.000 abstract 8
- 229910021529 ammonia Inorganic materials 0.000 abstract 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 6
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 6
- 239000000194 fatty acid Substances 0.000 abstract 6
- 229930195729 fatty acid Natural products 0.000 abstract 6
- 150000004665 fatty acids Chemical class 0.000 abstract 6
- 230000001804 emulsifying effect Effects 0.000 abstract 5
- -1 heptadecylene amines Chemical class 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 239000002480 mineral oil Substances 0.000 abstract 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 4
- 239000007858 starting material Substances 0.000 abstract 4
- 239000010698 whale oil Substances 0.000 abstract 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 3
- FVFPYKAQLMWGMZ-UHFFFAOYSA-N 20,20-dichloroicosan-1-amine Chemical compound C(CCCCCCCCCC(Cl)Cl)CCCCCCCCCN FVFPYKAQLMWGMZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 3
- 239000004753 textile Substances 0.000 abstract 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Chemical class CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 2
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 abstract 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 2
- MVGQUEVXCCJTOO-UHFFFAOYSA-N 1-hydroxynaphthalene-2-sulfonamide Chemical compound C1=CC=CC2=C(O)C(S(=O)(=O)N)=CC=C21 MVGQUEVXCCJTOO-UHFFFAOYSA-N 0.000 abstract 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical class OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 abstract 2
- SXNBVULTHKFMNO-UHFFFAOYSA-N 2,2-dihydroxyoctadecanoic acid Chemical class CCCCCCCCCCCCCCCCC(O)(O)C(O)=O SXNBVULTHKFMNO-UHFFFAOYSA-N 0.000 abstract 2
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 abstract 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Chemical class CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Chemical class CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 2
- 102000009027 Albumins Human genes 0.000 abstract 2
- 108010088751 Albumins Proteins 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- 239000001828 Gelatine Substances 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 239000005639 Lauric acid Chemical class 0.000 abstract 2
- 229920000715 Mucilage Polymers 0.000 abstract 2
- 239000005642 Oleic acid Chemical class 0.000 abstract 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Chemical class CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 2
- 235000019482 Palm oil Nutrition 0.000 abstract 2
- 235000021355 Stearic acid Nutrition 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000853 adhesive Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 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 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000003240 coconut oil Substances 0.000 abstract 2
- 235000019864 coconut oil Nutrition 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 239000002537 cosmetic Substances 0.000 abstract 2
- 238000005520 cutting process Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 239000007857 degradation product Substances 0.000 abstract 2
- 150000004985 diamines Chemical class 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000003925 fat Substances 0.000 abstract 2
- 235000019197 fats Nutrition 0.000 abstract 2
- 229920000159 gelatin Polymers 0.000 abstract 2
- 235000019322 gelatine Nutrition 0.000 abstract 2
- 239000003292 glue Substances 0.000 abstract 2
- 125000005456 glyceride group Chemical group 0.000 abstract 2
- 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 abstract 2
- 150000008282 halocarbons Chemical class 0.000 abstract 2
- CRPAPNNHNVVYKL-UHFFFAOYSA-N hexadecane-1-sulfonamide Chemical compound CCCCCCCCCCCCCCCCS(N)(=O)=O CRPAPNNHNVVYKL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 238000007689 inspection Methods 0.000 abstract 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Chemical class CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000000944 linseed oil Substances 0.000 abstract 2
- 235000021388 linseed oil Nutrition 0.000 abstract 2
- 125000002960 margaryl 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])[H] 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000012170 montan wax Chemical class 0.000 abstract 2
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002674 ointment Substances 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 239000002540 palm oil Substances 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 239000010491 poppyseed oil Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000010499 rapseed oil Substances 0.000 abstract 2
- 239000011347 resin Chemical class 0.000 abstract 2
- 229920005989 resin Chemical class 0.000 abstract 2
- 239000000344 soap Substances 0.000 abstract 2
- 239000008117 stearic acid Chemical class 0.000 abstract 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 2
- 229940124530 sulfonamide Drugs 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000002383 tung oil Substances 0.000 abstract 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 229960002703 undecylenic acid Drugs 0.000 abstract 2
- VBGWJYKQNCXGSY-UHFFFAOYSA-N 1,1,18-trichlorooctadecane Chemical compound ClC(CCCCCCCCCCCCCCCCCCl)Cl VBGWJYKQNCXGSY-UHFFFAOYSA-N 0.000 abstract 1
- JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000010000 carbonizing Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000005352 clarification Methods 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 238000009963 fulling Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- BOKZEYLMVZFSMR-UHFFFAOYSA-N n,n-dibutylnaphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N(CCCC)CCCC)=CC=CC2=C1 BOKZEYLMVZFSMR-UHFFFAOYSA-N 0.000 abstract 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 229920001195 polyisoprene Polymers 0.000 abstract 1
- 238000004513 sizing Methods 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
Classifications
-
- 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
- C09K23/26—Sulfonamides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09G—POLISHING COMPOSITIONS; SKI WAXES
- C09G1/00—Polishing compositions
-
- 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
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Carboxylic and sulphonic acid amides stated to be useful as emulsifying agents in the textile industry are prepared by treating one molecular proportion of an acid amide having the formula RCON <R>1H or RSO2N <R>1H in which R is an organic residue containing at least eight carbon atoms directly connected together and R1 is hydrogen or alkyl, aralkyl, aryl or cycloalkyl groups which must be free from hydroxyalkyl and oxyalkyloxy groups, with not more than three molecular proportions of alkylene oxide for each reactive hydrogen atom in the amide group. In order to improve their solubility, the products may be treated with polybasic mineral acids containing oxygen, e.g. phosphoric or sulphuric acid. The acid amides used as starting material may be prepared by condensing the carboxylic or sulphonic acids with ammonia, or mono or diamines. Fatty acids obtained by oxidation of paraffins, undecylenic acid, lauric acid, stearic acid, oleic acid, dihydroxystearic acid, resin and montan wax acids, naphthenic acids, phthalic acid, phthalamic acid, 1 : 8-naphthalenedicarboxylic acid and cyclohexylpropionic acid may serve as the parent acids for the amides as well as the fatty acids of palm oil, coco nut oil, poppy seed oil, rape oil, linseed oil, soya bean oil, train oil, chinawood oil and castor oil. Palmitic sulphonamide, cetylsulphonamide, 1-hydroxynaphthalene-2-sulphonamide and dichlorstearylethylamide are mentioned as starting materials. Aniline, aminonaphthols and phenols, phenylenediamine and methyl, butyl, benzyl, undecyl, cyclohexyl, heptadecyl and heptadecylene amines are bases which are specified. The more soluble products may be used for emulsifying oils, fats and hydrocarbons. The lipoid soluble products may be used in the production of salves, cosmetics, pharmaceutical preparations, greasing and stuffing agents and cutting and boring oils. Soaps, turkey red oils, mineral oils, fatty alcohol sulphonates, alkylated-naphthalenesulphonic acids, glue, gelatine, sulphite cellulose liquor, gums, mucilages, alcohols, ketones, hydrocarbons and halogenated hydrocarbons may be used with the products. In examples: (1) ethylene oxide is introduced into a product derived from partially hydrogenated train oil and ammonia (cf. Specification 384,665, [Group IV]) whereby a product is obtained which may be used for emulsifying mineral oils: (2) dibutylnaphthalenesulphonamide is treated with ethylene oxide. The Specification as open to inspection under Sect. 91 comprises also the treatment with ethylene oxide of crude acid amides derived from glycerides, to obtain similar products. The use of the products together with condensation products of fatty acids with hydroxy and aminoalkylsulphonic acids, albumin degradation products and enzymes is referred to. The following components are also mentioned: dodecylsulphuric ester amide (obtainable by treating with ammonia the acid chloride prepared by reacting dodecylsulphuric ester with phosphorus pentachloride) and 4-hydroxyphenylethyl-amine. This subject-matter does not appear in the Specification as accepted.ALSO:Carboxylic and sulphonic acid amides stated to be useful as wetting, cleaning, emulsifying and levelling agents in the textile industry are prepared by treating one molecular proportion of an acid amide having the formula, <FORM:0415718/IV/1> organic residue containing at least eight carbon atoms directly connected together and R1 is hydrogen or an alkyl, aralkyl, aryl or cycloalkyl group which must be free from hydrooxyalkyl and oxyalkyloxy groups, with not more than three molecular proportions of alkylene oxide for each reactive hydrogen atom in the amide group. Alkaline substances may be used to assist the reaction and water is preferably excluded as far as possible. In order to improve their solubility, the products may be treated with polybasic mineral acids containing oxygen, e.g., phosphoric or sulphuric acid. The acid amides used as starting material may be prepared by condensing the carboxylic or sulphonic acids with ammonia, or mono or diamines. Fatty acids obtained by oxidation of paraffins, undecylenic acid, lauric acid, stearic acid, oleic acid, dihydroxystearic acid, resin and montan wax acids, naphthenic acids, phthalic acid, phthalamic acid, 1 : 8-naphthalenedicarboxylic acid and cyclohexylpropionic acid may serve as the parent acids for the amides as well as the fatty acids of palm oil, coconut oil, poppyseed oil, rape oil, linseed oil, soya bean oil, train oil, chinawood oil and castor oil. Palmitic sulphonamide, cetyl-sulphonamide, 1-hydroxynaphthalene-2-sulphonamide and dichlorstearylethylamide are mentioned as starting materials. Aniline, aminonaphthols and phenols, phenylenediamine and methyl, butyl, benzyl, undecyl, cyclohexyl, heptadecyl, and heptadecylene amines are bases which are specified. The more soluble products may be added to dyeing, mercerizing, carbonizing and fulling baths and may be used for improving the fastness of dyeings to rubbing, preparing dyepastes and emulsifying oils, fats and hydrocarbons. The lipoid soluble products may be used in preparations for oiling, sizing and softening textiles and in the production of salves, cosmetics, pharmaceutical preparations, greasing and stuffing agents, cutting and boring oils, polishes, protecting preparations for metals, lacquers, varnishes and caoutchouc. Soaps, turkey red oils, mineral oils, fatty alcohol sulphonates, alkylated naphthalenesulphonic acids, glue, gelatine, sulphite cellulose liquor, gums, mucilages, alcohols, ketones, hydrocarbons and halogenated hydrocarbons may be used with the products. In examples: (1) ethylene oxide is introduced into a product derived from partially hydrogenated train oil and ammonia (cf. Specification 384,665), whereby a product is obtained which may be used for emulsifying mineral oils: (2) dibutyl naphthalenesulphonamide (obtained by treating dibutylnaphthalene sulphonic acid with phosphorus pentachloride and condensing the acid-chloride with ammonia) is treated with ethylene oxide. Dichlorstearylethylamide may be obtained by chlorinating stearic acid chloride to form dichlorstearylchloride and condensing the latter with ethylamine. The Specification as open to inspection under Sect. 91 comprises also the treatment with ethylene oxide of crude acid amides derived from glycerides, the clarification of the products by treating with peroxides, hypochlorites, decolorizing carbon or Fuller's earth and their use for stabilizing diazo solutions. The use of the products together with condensation products of fatty acids with hydroxy and aminoalkylsulphonic acids, albumin degradation products and enzymes is referred to. The following components are also mentioned; dodecylsulphuric ester amide (obtainable by treating with ammonia the acid chloride prepared by reacting dodecylsulphuric ester with phosphorus pentachloride) and 4-hydroxyphenylethylamine. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE415718X | 1932-02-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB415718A true GB415718A (en) | 1934-08-28 |
Family
ID=6448508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6144/33A Expired GB415718A (en) | 1932-02-29 | 1933-02-28 | Process for the manufacture of acid amide derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB415718A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2730428A (en) * | 1950-10-21 | 1956-01-10 | Tepha Ges Fur Pharmazeutische | Method and composition for washing and bleaching fibrous materials |
| DE938728C (en) * | 1949-04-26 | 1956-02-09 | Henkel & Cie Gmbh | Process for the preparation of derivatives of alkylbenzenesulfamides |
| DE952800C (en) * | 1951-02-24 | 1956-11-22 | Huels Chemische Werke Ag | Process for the production of non-ionic, surface-active compounds |
| US2883277A (en) * | 1956-10-12 | 1959-04-21 | Gen Aniline & Film Corp | Synergistic corrosion inhibiting composition for gasoline |
| DE1086514B (en) * | 1954-10-06 | 1960-08-04 | Prod Chim Ind Et Organiques So | N-polyglycol ether derivatives as corrosion protection agents |
| US3200139A (en) * | 1960-12-22 | 1965-08-10 | Pure Oil Co | beta-sulfatosulfonamides |
| US4200465A (en) | 1974-11-12 | 1980-04-29 | Konishiroku Photo Industry Co., Ltd. | Antistatic light-sensitive silver halide photographic element |
-
1933
- 1933-02-28 GB GB6144/33A patent/GB415718A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE938728C (en) * | 1949-04-26 | 1956-02-09 | Henkel & Cie Gmbh | Process for the preparation of derivatives of alkylbenzenesulfamides |
| US2730428A (en) * | 1950-10-21 | 1956-01-10 | Tepha Ges Fur Pharmazeutische | Method and composition for washing and bleaching fibrous materials |
| DE952800C (en) * | 1951-02-24 | 1956-11-22 | Huels Chemische Werke Ag | Process for the production of non-ionic, surface-active compounds |
| DE1086514B (en) * | 1954-10-06 | 1960-08-04 | Prod Chim Ind Et Organiques So | N-polyglycol ether derivatives as corrosion protection agents |
| US2883277A (en) * | 1956-10-12 | 1959-04-21 | Gen Aniline & Film Corp | Synergistic corrosion inhibiting composition for gasoline |
| US3200139A (en) * | 1960-12-22 | 1965-08-10 | Pure Oil Co | beta-sulfatosulfonamides |
| US4200465A (en) | 1974-11-12 | 1980-04-29 | Konishiroku Photo Industry Co., Ltd. | Antistatic light-sensitive silver halide photographic element |
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