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Fluoroalkyl surfactants

A technology of perfluoroalkyl and hydrophilic groups, used in transportation and packaging, organic chemistry, coatings, etc., can solve the problem of high price of fluorinated substances

Inactive Publication Date: 2010-02-10
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorinated substances derived from longer perfluoroalkyl chains are more expensive

Method used

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  • Fluoroalkyl surfactants
  • Fluoroalkyl surfactants
  • Fluoroalkyl surfactants

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-18

[0223] Examples 1-18 illustrate the synthesis of compositions of formula (I) according to route A in Reaction Scheme 1, wherein m is 2, n is 0, and A is hydrogen; i.e. compositions of general formula (Ia) . For each example, the corresponding amount of R listed in Table 2A o -NH 2 and the fluorinated acrylate and methylhydroquinone (0.10 g) were mixed together in a vial equipped with a magnetic stirrer and screw cap. The mixture was stirred at 55-60 °C for 24-72 h as listed in Table 2A. The progress of the reaction was monitored by gas chromatographic analysis to ensure completion, as described below. In Examples 1-13, the crude product was further purified by extraction, conversion to acetate. The sample was transferred to a beaker and mixed with hexane (50 mL). The solution was stirred for 10 min using a magnetic stirrer, then acetic acid (2 mL) was added to separate the product from the hexane layer. The hexane layer (top layer) was removed. Another portion of hexane...

Embodiment 2

[0224] Example 2: 1 H NMR (500MHz, d6-THF,): 4.34(t, 4H, J=6.4Hz), 3.50(t, 2H, J=6.0Hz), 2.73(t, 4H, J=6.9Hz), 2.56(m , 6H), 2.44 (t, 4H, J=7.16), 1.57 (m, 2H, J=6.5Hz). 13 C NMR (126 MHz, d6-THF,): 171.3, 60.2, 55.8, 51.1, 49.3, 32.2, 29.9, 24.8. LC / MS (API-ES+) = 912.1 (M+H).

Embodiment 3

[0225] Example 3: 1 H NMR (500MHz, d6-THF,): 4.43(t, 4H, J=6.4Hz), 3.54(m, 1H, J=6.5Hz), 2.85(m, 4H), 2.68(m, 4H), 2.49 (m, 4H), 2.38 (m, 2H), 1.09 (d, 3H, J = 5.7 Hz). 13 C NMR (126 MHz, d6-THF,): 171.5, 63.9, 62.5, 55.8, 49.6, 32.2, 30.1, 19.8. LC / MS (API-ES+) = 912.1 (M+H).

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Abstract

A composition of formula (I) wherein m and d are each independently an in teger of 1 or 2; n is independently O or 1;each R is independently hydrogen or a C1 to C4 alkyl group; A is independently hydrogen or -C(O)-O-B;Ro is a linear, branched or cyclic aliphatic group, or combination thereof, having f rom about 2 to about 100 carbon atoms, interrupted or substituted by 1 to ab out 50 hydrophilic groups, said hydrophilic groups selected from the group c onsisting of hydroxyl, amino, ether and mixtures thereof; wherein the ratio of hydrophilic groups to carbon atoms is from about 1 :1.1 to about1 : 10, each carbon atom has at most one hydrophilic group bonded to it, and covalen t bonding between hydrophilic groups is absent; each B is independently a mo novalent group of formula (IIa), (IIb) or (IIc): (IIa) Rf 1(CH2)t(R)r- (lib) Rf 2(CH2CF2)p(CH2CH2)q(R1)r- (lie) Rf 3O(CF2CF2)p(CH2CH2)q(R1)r- wherein ea ch of Rf 1 and Rf 2 are C1 - C6 linear or branched perfluoroalkyl; Rf 3 is a C1 to C7 linear or branched perfluoroalkyl group, optionally interrupted by one, two or three ether oxygen atoms; t is an integer of 1 to about 10; p a nd q are each independently integers of 1 to about 3; ris 0 or 1; R1 is a d ivalent radical selected from -S(CH2)r; and provided that when m is 1, n is 1; when m is 2, n is 0, A is hydrogen, and d is1; and when d is 2, m is 1, A is -C(O)-O-B, R0has at least three carbon atoms, and nitrogens and hydrophi lic groups are bonded to different carbon atoms, and its use as a surfactant is disclosed.

Description

field of invention [0001] The field of the invention relates to the synthesis and use of fluorochemical surfactants. Background of the invention [0002] For surfactants and surface treatments with fluorochemical chains, longer perfluoroalkyl chains contain a higher percentage of fluorine and generally provide better performance at a given concentration. However, fluorinated species derived from longer perfluoroalkyl chains are more expensive. Therefore, it is desirable to reduce the fluorine content while yielding the same or higher performance. Reducing the fluorine content will reduce costs, but product performance must be maintained. [0003] US Patent 3,719,698 discloses the reaction of primary alkylamines with two equivalents of fluorinated acrylate esters to provide addition products useful as water and oil repellent finishes for fabrics. [0004] It is desirable to improve surfactant performance and increase fluorine efficiency, that is, to increase the efficiency...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/08C07C229/12C07C229/24C08K5/17C08K5/19C09D7/47C09K23/36
CPCC07C229/08B01F17/0035C07C229/24C08K5/17C07C229/12C09K23/007C07C219/04
Inventor E·J·阿科斯塔S·雷纳茨
Owner EI DU PONT DE NEMOURS & CO