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UNITED STATES PATENT OFFICE 2,236,530 Sulphocarboxylic ACRED ESTERS of ALCOBO AMNE DERWATWES Albert K

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UNITED STATES PATENT OFFICE 2,236,530 Sulphocarboxylic ACRED ESTERS of ALCOBO AMNE DERWATWES Albert K Patented Apr. 1, 94 2,236,530 UNITED STATES PATENT OFFICE 2,236,530 suLPHoCARBOXYLIC ACRED ESTERS OF ALCOBO AMNE DERWATWES Albert K. Epstein and Morris Katzaraat, Chicago, l, assignors to Ahe Emulso Corporation, Chi cago, Ill., a corporation of Elinois No Drawing. Application September 28, 1939, Serial No. 296.98 18 Claims. (C. 260-401) Our invention relates to a new class of chemical acid group. A more complete understanding of Substances, and more in particular to a new class what may comprise the lipophile group and the of chemical substances having capillary active particular character of the sulpho-carboxylic or properties and particularly adapted for use as sulpho-fatty acid group will be had as the de detergents, wetting, penetrating, emulsifying, , tailed description progreSSeS. lathering, fiotation and anti-spattering agents, The function of the sulphonic acid group is to and for frothing purposes. impart hydrophilic properties, that is, water Wet The principal object of the present invention ting or water attracting properties, to the mole is the provision of a new class of chemical Sub cule as a whole. The groups which are esteri stances capable of satisfactory use in connection fied by the sulpho-carboxylic or sulpho-fatty acid with the problems and fields hereinabove and are in general of a lipophile character. At times hereinafter discussed. they may be strongly lipophilic and at other Another object is the provision of a new class times moderately lipophilic. They may be of of chemical substances which are in general of low molecular weight or of moderately high no relatively simple structure and can be cheaply lecular weight, depending upon the purpose for made in commercial quantities. which the substances may be used. Another object is the provision of a new class More specifically, at least most of the Sub of chemical substances having improved Wetting stances of the invention are lower molecular and detergent characteristics. weight sulpho-carboxylic acid esters of alcohol Other objects and features of the invention Will :20 primary or secondary amines, hydrogen attached be apparent from a consideration of the following to nitrogen of the alcohol primary or Secondary detailed description. amines being replaced by an acyl radical con The substances of the invention are in general taining at least four and preferably from eight esters, preferably of lower molecular Weight car to eighteen carbon atoms. boxylic or fatty acids, with at least one unesteri illustrative examples of compounds falling fied sulphonic acid group in the carboxylic or Within the scope of the invention are as follows: fatty acid radical, wherein. the group esterified with the sulpho-carboxylic or Sulpho-fatty acid (1) C-C-NH-CH-O-C-CH -SO3Na contains nitrogen linked to carbon and a lipophile l & radical with at least four carbon atoms. In cera 30 (2) Cish-C-NH-C.E.-O-C-CH-CH-soak tain circumstances there may be more than one nesterified sulphonic acid group in the car boxylic or fatty acid radical or there Inay be sul (3) CH-CO-NH-CH-O-C-CH2-SO3K phonic acid groups that are esterified and other O sulphonic acid groups that are not esterified but 3 (4) C.E.-- N- CH-CH-C-O-C-C-SO3N in all cases there must be at least One unesteria O O fied sulphonic acid group in preferably the lower molecular weight carboxylic or fatty acid radical. The carboxylic or fatty acid radical with the un (5) CE-O-C-C133 esterified sulphonic acid group is, as indicated, 40 C-CO-N-CH-CH-N preferably of relatively low molecular weight and, for best results, should contain not more C.H-0--C H-SO3Na than eight carbons. Considering the compounds from another C.H.OH aspect, the molecule in each instance contains a 45 relatively high molecular weight lipophile group (6) CH-CO-N and a relatively low molecular Weight hydrophile CH-O--CH-SO.Na group which, in the class of compounds to which the present invention relates, are sulphonic acid O radicals or free or unesterified OH groups in con junction with a sulphonic acid radical. From C.H-0--Caha still another angle, the compounds may be con (7) C-CO-N- W sidered as combinations of a higher molecular weight lipophile group and a relatively low no CH-O--chi-sok lecular weight sulpho-Carboxylic or SulphO-fatty 55 8 2 2,286,580 (8) l', corn oil, cottonseed oil, sardine oil, tallow, soya CH-C-NH-(CH2)-CH-O-C-CH-SOH.NE(('HOH) bean oil, peanut oil, castor oil, seal oil, whale oil, I shark oil, partially or completely hydrogenated animal and vegetable oils such as those men tioned; hydroxy and alphahydroxy higher ali phot phatic and fatty acids such as i-hydroxy stearic (9) Cutta--NH-CH-N--H-CH,- COOK acid, dihydroxy stearic acid, alpha-hydroxy dok stearic acid, alpha-hydroxy palmitic acid, alpha hydroxy lauric acid, alpha-hydroxy coconut oil (10) CH-C-NBI-CE-NH-CH-O-C-C-SONa 10 mixed fatty acids, and the like; other substituted fatty acids such as (ii) CH-C-NH-CH-O-CH-O-C-CH-S OK B-C-COO (12) CiHan-g-NH-CHi-O-g-CH-soH.HN-CHOH 15 Where R is a higher molecular weight hydrocar bon radical; fatty acids derived from various Waxes such as beeswax, spermaceti, montan wax, (13) CH-(CH2)-CH--NH-CH-O-g-CH-s OK and carnauba wax and carboxylic acids derived, by oxidation and other methods, from petrole CH-CH 20 um; cycloaliphatic and hydroaromatic acids such as hexahydrobenzoic acid, resinic acids, naph (14) cá, C-C-NH-C-C-C-O-C-C-SONa thenic acid, and abietic acid; aromatic acids Yoh-cá, such as phthalic acid, benzoic acid, naphtholic O acid, pyridine carboxylic acids; hydroxy aro 25 matic acids such as salicylic acid, hydroxy ben (15) t–NH-CH-O--ch-s ONBI Zoic and naphtholic acids, and the like; and sub stitution and addition derivatives such as amino, halogen, hydroxy, sulphate, sulphonic, phosphate O and the like substitution and addition derivatives 30 of the aforementioned carboxylic substances. It CH-CH-CH-O-(-CH-s O3K will be understood that mixtures of any two or (16) Ciba-C-N, more of said acids may be employed. Yoh-CH-CH-o-c-ch-s OK The alcohol primary and secondary amines or alkylolamines which provide the linkage between the lipophile group and the sulpho-carboxylic Cas group may be selected from a large class and in (17) Culti-c-f-c-b-o-c-CH,- SO3Na clude symmetrical, unsymmetrical, normal and s iso-derivatives, such as monoethanolamine, di O ethanolamine, mono-propanolamine, di-propa 40 nolamine, mono-butanolamine, mono-iso-buta (18) CH-NH--Caha nolamine, mono-pentanolamine, mono-hexanol & HoH amine, mono-decylolamine, mono-laurylolamine, mono-hexadecylolamine, mono-Octodecylolamine, mono-ethyl ethanolamine, mono-butyl ethanol bi-o-on-on-on- OK amine, cyclohexyl ethanolamine, N-cyclohexyl O butanolamine, ethanolandline, alkylolamines of (19) CH-NH-i-Citi, other monovalent or polyvalent alcohols such as glycols, glycerol, sugars, and sugar alcohols such (HoH), as dextrose, sucrose, sorbitol, mannitol and dul CH-0--H-CH, t 50 citol, alkylol polyamines such as alkylol deriva d solk tives of ethylene diamine, diethylene trianine While the above examples represent single and triethylene tetraamine, arylolamines and Substances, it will be understood that, in practice, cyclic hydroxy amines such as N-phenyl ethanol it is, in general, more advantageous to employ amine, p-amino phenol, mixtures of any two or more thereof with or 55 Without diluents. Many different types of compounds may be Ho-ch-{ X-NH. Selected as lipophile groups which are to be re and the like. The alcohol or alkylol radicals of acted with the alcohol primary or secondary the alcohol amines or alkylolamines may contain amines, principally compounds having lipophile 60 substitutent groups such as amino, nitrile, car radicals of relatively high molecular weight. boxyl, hydroxy, halogen, sulphate, Sulphonic, For example, the following materials may be phosphate, and the like and the sequence of car utilized as Sources of lipophile groups: straight bon atoms therein may be interrupted by O, S, chain and branched chain carboxylic, aliphatic, C-O, NH, NR where R is lower alkyl, and the and fatty acids, saturated and unsaturated, such 65 like. as butyric acid, caprylic acid, caproic acid, capric From a study of the compounds which are acid, sebacic acid, behenic acid, arachidic acid, listed hereinabove, those skilled in the art will cerotic acid, erucic acid, melissic acid, Stearic acid, understand that many different expedients may oleic acid, ricinoleic acid, linoleic acid, linolenic be employed for forming the compounds in So acid, lauric acid, myristic acid, palmitic acid, 70 far as the dominant lipophile group and the rel mixtures of any two or more of the above men atively low molecular weight sulpho-carboxylic or tioned acids or other acids, mixed higher fatty fatty acid group are concerned. As stated, how acids derived from animal or vegetable sources, ever, ester linkages are utilized between these for example, lard, COConut oil, rapeseed oil, two portions of the compound, and the skilled sesame oil, palm kernel oil, palm oil, olive oil, 75 chemist will understand in general the most ap a. s 2,286,530 8 proved practices in securing this result. Nu ester of lauric acid may be reacted with mono merous methods are also available for the in ethanolamine at about 150 degrees C. to 80 de troduction of the sulphonic acid group. grees C.
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