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Perfluoroalkyl-substituted amines, acids, amino acids and thioether acids
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A technology of groups and residues, applied in the field of surfactants, can solve problems such as limiting surface tension and insufficient solubility
Inactive Publication Date: 2011-11-23
CIBA SPECIALTY CHEM HLDG INC
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Finally, insufficient solubility of the molecule limits the minimum surface tension that can be achieved
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Embodiment 1
[0079] Synthesis of Perfluoroalkyl-Allyloxy Substituted Carboxybetaine Surfactants
[0080] 1A. 1-allyloxy-3-dimethylamino-2-propanol
[0081] Add 112.7 g (1.00 mol, 40%) dimethylamine into a 500 ml three-neck round bottom flask. With stirring, the amine was heated to 40°C while 114.1 g (1.00 mol) of allyl glycidyl ether was added over 2.5 hours while maintaining the temperature below 50°C. After 3.5 hours at 50°C, GC analysis on a 30M X 0.53mm SPB-5 polysiloxane column showed 98% of the desired product as a single peak. A viscous oil was obtained in quantitative yield. 1 HNMR (500MHz, CDCl 3 ) gives the following result: δ=2.61(6H, s, -N(C H 3 ) 2 ), 2.62 and 2.71 (2H, m, -CH(OH)C H 2 N(CH 3 ) 2 ), 3.40 and 3.51 (2H, dd, -OCH 2 CH(OH)-), 4.04(1H, bm, -CH 2 C H (OH)CH 2 -), 4.36 (2H, m, CH 2 = CHC H 2 -), 5.13 (1H, dd, C H 2 =CH-cis isomer), 5.22 (1H, dd, C H 2 =CH-, trans isomer), 5.80 (1H, m, CH 2 =C H -). The data supports the following structures: ...
Embodiment 2
[0090] Using the method described in Example 1C, using R F A mixture of I homologues (TELA-L, DuPont) with an average molecular weight MW of 506 and the following weight % composition:
[0091] C 6 f 13 C 8 f 17 C 10 f 21 C 12 f 2 C 14 f 2 C 16 f 3 47.0 37.2 11.8 3.0％ 0.8％ 0.2％
[0092] The aqueous solution product was obtained with a yield of 97.5%.
Embodiment 3
[0094] Synthesis of Perfluoroalkyl-[allyloxy / iodopropyloxy]N-oxides
[0095] 3A:R F - Iodine addition:
[0096] In a 500ml three-neck round bottom flask, add 12.7g (0.056mol) of the compound of Example 1A, 25.0g (0.056mol) of perfluorohexyl iodide, 0.4g (2.24mmol) of 2,2'-azobis (2-Methylbutyronitrile) (VAZO-67), 1.1 g (5.60 mmol) sodium metabisulfite and 4.7 g deionized water. With stirring, the mixture was heated to 75-80°C and held for 3-4 hours. After this time, GC analysis on a 30 M X 0.53 mm SPB-5 polysiloxane column showed complete consumption of RFI. The temperature was then controlled to 65°C, and 6.7 g (0.084 mol, 50%) sodium hydroxide was added portionwise to the thick slurry to remove HI. After 2 hours, complete elimination of the desired olefin was demonstrated by titration of iodine with silver nitrate. The aqueous layer was removed and the product was washed three times with 50 ml of deionized water at 65-70°C and then dried under high vacuum to give an amb...
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Abstract
Perfluoroalkyl-substituted amines, acids, amino acids and thioether acid compounds containing a perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkene group as well as derivatives thereof, are described. They are useful as surfactants in a variety of applications where low surface tensions are required, including coating formulations for glass, wood, metal, cement, paper, textiles, as foam control agents in polyurethane foams and especially in aqueous fire-fighting formulations.
Description
[0001] The present invention relates to perfluoroalkyl-substituted amines, acids, amino acids and thioether acids and salts thereof, which are useful as surfactants in various applications. Background technique [0002] Perfluoroalkyl (=R F ) substituted water-soluble compounds are primarily used as specialty surfactants that can reduce the surface energy of aqueous media to well below 20 dynes / cm, while silicone-based surfactants can lower the surface energy to 25 dynes / cm , Conventional hydrocarbon surfactants can be reduced to 30 dynes / cm. They can therefore be used in applications where conventional hydrocarbon and siloxane-based surfactants are unsuitable, for example in the coating of low free energy surfaces such as polyolefins and oil-contaminated surfaces. R F - The surfactants also enable the formulation of aqueous fire protection systems to be used against organic solvent fires, for example where gas oil or alcohol combustion is involved. Such surfactant formulat...
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