Sulfo betaines

CTAB/DTAB = Cetyl/Dodecyl trimethyl ammonium bromide, DSB = Dodecyl sulfo betaine... 

Benzothiazol 2-Carboxy-6-methoxy- E8h, 880 (Ar- NH - CS -COOH/Oxid.) Isoquinolininm 2-Sulfo- (Betain) XI/2, 657, 662... 

Table 1 Ionization constants and solubility behavior of polycarboxybetaines and -sulfo-betaines in salt-free water and 0.1 M KCl solutions...

Babaev and co-workers prepared and isolated several oxazolo[3,2-a]pyridi-nium perchlorates (Scheme 1.284). For example, using Bradsher and Zinn s protocol,the authors treated l-phenacyl-2-pyridone 1077 (R = X = H) with concentrated H2SO4 to produce an intermediate sulfo betaine (not isolated), which was heated in 70% HCIO4 to afford 2-phenyloxazolo[3,2-a]pyridinium perchlorate 1078 (R = X = H) in good yield. 

The classic preparation method of sulfo betaines utilizes the conversion of tertiary amines with propane sultone. Hydroxy sulfo betaines amino oxides are obtained from tertiary amines and chloro hydroxypropane sulfonic acid [32-34]. 

The amphoteric surfactants are relatively expensive products compared to anionic surfactants. Thus, it is not surprising that they are primarily being utilized at low concentrations in cosmetic formulations. A review of 438 shampoos of the U.S. market reveals that appreciable quantities, for example, >5% of alkylamido betaines and imidazolinium surfactants were found in only 8.7% and 13.5%, respectively, of the investigated shampoos. Alkyl betaines were found in a limited number of cases, whereas sulfo betaines were not found in this stndy [4,5]. Since these studies were made, the market has focused on mild products. The change in the U.S. market from bar to liquid soaps has increased the use of alkylamidopropyl betaines. 

The nnmber of chemically conceivable amphoteric snrfactant strnctures is limited in practice to the derivatives of easily accessible and, therefore, economical raw materials. Relative to the amphoteric snrfactants with the combination of cationic nitrogen atom and carboxyl gronps, the so-called sulfo betaines with the sulfonate group, and also the phosphato betaines with the phosphate group as anionic component, play only a subordinate role. 

With zwitterion phases, the charged group nearest to the hydrophobic chain determines whether the sample anions or cations will be retained more strongly. Thus, in a sulfo-betaine (SB) phase, sample anions will be retained more strongly because of the close proximity of the N to the alkyl chain. 

A column coated with n-hexadecylphosphocholine has the hydrophobic head group adjacent to the negative phosphate group. The positive and negative sites on phosphocholine (PC) phases are separated by two -CHj groups. On the sulfo-betaine phases, the oppositely charged sites were separated by three -CH2 groups. 

Sulfopropyl) pyridinium betain N-3-Sulfopropylpyridinium betaine 1-(3-Sulfopropyl) pyridinium hydroxide, inner salt. See Pyridinium propyl sulfo-betaine... 

Hexadecyldimethylammonium)- propan-1-sulfo-betaine separation from nonionic surfactants sulfo-betaines remain at the origin Silica Gel G impregnated with oxalic acid 90 10 CHClj/MeOH Modified Dragendorflf reagent 85... 

Amphoteric (and zwitterionic)—the molecule contains, or can potentially contain, both a negative charge and a positive charge, such as the sulfo-betaines RN+(CH3)2CH2CH2SOi". 

This idea was realized using crown ether styryl dyes (CESD) lc,d, 4c (Scheme 1,4). The compounds lc,d, 4c having betaine structures form supramolecular dimers with a crossed arrangement of molecules (a h-head-to-tail) in the presence of ions, due to the intermolecular interaction between the sulfo group of one of the molecules and a ion located in the crown-ether cavity of the other molecule [20,21], It was shown that photoirradiation of solutions of dimer results in stereospecific PCA giving only one of the 11 possible derivatives of cyclobutane, which is expected in conformity with the concerted superficial (s,s) addition of the reactants (Scheme 5) [22,23], It is noteworthy... 

Sulfobetaines are typically prepared by alkylsulfonation of a monomeric or polymeric tertiary amine with strained sultones, usually 1,3-propanesultone or 1,4-butanesultone. An alternative route is the reaction of tertiary amines with a haloalkylsulfonate. Most of the early investigations on polymeric betaines relate to the sulfo derivatives 23a-e, 24, 25, and 26 listed in Scheme 5 [1-4,178]. 

Zur Herstellung von Essigsdure-imid-(3-sulfo-propylester)-betain (87%)2... 

The presence of monochloroacetic acid (MCA), and dichloroacetic acid (DCA), which is an impurity in MCA, is more critical because of their toxicological implications. While chloroacetic acid is almost completely consumed under proper reaction conditions, dichloroacetic acid takes no part in the carboxymethylation and its hydrolytic degradation is also very limited. Diverse methods have been developed to reduce the residual content of chloroacetic acids. One possibility is the reaction of such acids with sulfonating reagents such as sodium hydrogen sulfite, which leads to a sulfo-carboxy acid (12). A second method is the treatment of the cocamidopropyl betaine at alkaline pH in combination with ammonia or amino acids (13). A more simple way is the hydrolysis of mono- and dichloroacetic acid at elevated temperatures, i.e. > 120°C (14). Contents of mono- and dichloroacetic acid of <5-10 ppm can be reached when using the latter methods. 

Similarly to polyaniline and polythiophene, several other self-doped conducting polymers have been explored including polypyrrole, poly(3,6-(carbaz-9-yl) propanesulfonate), poly(p-phenylene), poly(indolecar-boxylic acid), polyphenylenevinylene, and poly(2-ethynyl-N-(4-sulfo-butyl)pyridinium betaine). The details of synthesis and properties are described in the following sections. 

Sulfaines Coco-amido sulfo propyl betaine Good versatility can be used alone Shows synergy with anionic systems Moderate-High... 

The direct polymerization of betaine monomers in a controlled fashion has been reported by ATRP (288-291), and, most recently, via RAFT (38,43,292,293). Methacrylic derivatives of carboxy-, sulfo-, and phosphobetaines have been prepared via ATRP, while RAFT is more versatile with respect to monomer choice, and examples of styrenic, methacrylic and acrylamido sulfobetaines have been disclosed. 

SLES Cocamido- Sulfo- Cocoampho-propyl betaine succinate acetate... 

All surfactants were tested at 1% of active ingredients. Abbreviations sodium lauryl sulfate (SLS), sodium laureth sulfate with x ethoxylations (SLEX-xEO), ammonium lauryl sulfate (ALS), paraffine sulfonate (PS), linear alkyl benzene sulfonate (LAS), sulfosuccinate (sulfo), sodium cocoyl isethionate (SCI), mono alkyl sulfate (MAP), cocamidopropyl betaine (CAPB), alkyl polyglucoside (APG), alcohol ethoxylate (Ale. ethbx.). 

Propanaminium, N-(2,3-dihydroxypropyl)-N,N-dimethyl-3-[(1-oxococo-alkyl) amino]-, chloride. See Cocamidopropyl PG-dimonium chloride 1-Propanaminium, N-(2,3-dihydroxypropyl)-N,N-dimethyl-3-(1-oxododecy-lamino)-, chloride. See Lauramidopropyl PG-dimonium chloride 1-Propanaminium, N-(2,3-dihydroxypropyl)-N,N-dimethyl-3-[(1-oxoisooctadecyl) amino]-, chloride. See Isostearamidopropyl PG-dimonium chloride 1-Propanaminium, N,N-dimethyl-N-carboxymethyl-3-amino-, N-minkoil acyl derivs., hydroxides, inner salts. See Minkamidopropyl betaine 1-Propanaminium, N,N-dimethyl-N-(2,3-dihydroxypropyl)-3-[(1-oxodocosanyl) amino]-, chloride. See Behenamidopropyl PG-dimonium chloride 1-Propanaminium, N,N-dimethyl-N-ethyl-3-amino-, N-mink oil acyl derivs., ethyl sulfate (salts). See Minkamidopropyl ethyidimonium ethosulfate 1-Propanaminium, N,N-dimethyl-N-ethyl-3[(1-oxodocosanyl) amino]-, ethyl sulfate. See Behenamidopropyl ethyidimonium ethosulfate 1 -Propanaminium, N,N-dimethyl-N-phenylmethyl-3-[(1 -oxobabassu) amino]-, chloride. See Babassamidopropalkonium chloride 1-Propanaminium, N,N-dimethyl-3-sulfo-, N-coco acyl derivs., hydroxides, inner salts. See Coco-sultaine... 

Ablumide LDE Alkamide KD Amide SDO Amidex C Amidex CA Amphoteen 24 Badox 18S Badox 1260 Behenatnidopropyl betaine EsI-Terge T-60 Lauramide 11 Nonoxynol-1 Norfox DCSA Norlbx DGCA Schercomid CDO-Extra Schercomid SCE-Speclal Sodium cocoamphoptopionate Sodium-a-sulfo-methyl cocoate Soyamide DEA Varamide A-83... 

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