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Fluorinated surfactants and method of making the same

A technology of surfactant and fluorination, which is applied in the field of fluorinated surfactant and its preparation, and can solve problems such as reducing the surface tension of solvents or preparations

Inactive Publication Date: 2009-09-02
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, however, the ability of a surfactant to lower the surface tension of a solvent or formulation (i.e., surfactant strength) has little predictive value in determining whether that surfactant will perform well as a leveling agent in a coating formulation

Method used

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  • Fluorinated surfactants and method of making the same
  • Fluorinated surfactants and method of making the same
  • Fluorinated surfactants and method of making the same

Examples

Experimental program
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example

[0160] All parts, percentages, ratios, etc. in the examples and elsewhere in the specification are by weight unless otherwise indicated. The ratios of N-methylperfluorobutanesulfonamidoethyl acrylate (MeFBSEA) to -C(O)OH and -C(O)O- groups reported in the examples below are based on the amount of starting monomer molar ratio.

[0161] In the following examples, MeFBSEA was prepared according to the method in Parts A and B of Example 2 of U.S. Patent No. 6,664,354 (Savu), which is incorporated herein by reference, except that 4270 kg of N-methylperfluorobutanesulfonamidoethanol, 1.6kg of phenothiazine, 2.7kg of methoxyhydroquinone, 1590kg of heptane, 1030kg of acrylic acid, 89kg of methanesulfonic acid (instead of trifluoromethanesulfonic acid ) and 7590kg of water.

[0162] Weight Average Molecular Weight Determination

[0163] The weight average molecular weights in Examples 1-10, 12 and 17 were determined by comparison to linear polystyrene polymer standards using gel p...

example 1

[0167] In a 500-mL flask, blend MeFBSEA (37 grams (g), 0.09 moles (mol)), acrylic acid (4.3 g, 0.06 mol) and mercaptosuccinic acid (4.5 g, 0.03 mol) with isopropanol (IPA) The mixture was diluted to approximately 50% solids. Add 2,2′-azobis(2-methylpropionitrile) (AIBN) (0.1%), use vacuum and nitrogen degassing to react three times, and heat at 70° C. under nitrogen atmosphere for six hours. Additional AIBN (0.05%) was added and heating continued at 70°C for an additional 16 hours. The weight average molecular weight of the polymer was determined to be 1800 by GPC. MeFBSEA with -C(O)OH and -C(O)O - The group ratio was 0.75.

[0168] The reaction was diluted to 30% solids with IPA. Dimethylethanolamine (DMEOA) (12.6 g, 0.12 mol) was added to neutralize the acid and the mixture was further diluted to 25% solids with deionized water. At 25% solids and 50°C, the mixture was visually determined to be a single phase clear and stable solution.

[0169] Deionized water was added...

example 2-6

[0171] Examples 2-6 were prepared as described in Example 1 except that the reagents and amounts indicated in Table 1 (below) were used.

[0172] Table 1

[0173] example

[0174] At 25% solids and 50°C, the mixtures containing the neutralized oligomers of Examples 2, 5 and 6 were visually determined to be single-phase clear and stable solutions, while the mixtures containing the neutralized oligomers of Examples 3 and 4 The mixture was a single-phase cloudy solution. The weight average molecular weights of the oligomers were determined by GPC and are listed in Table 1 (above).

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Abstract

The invention provides a fluorinated surfactants having a weight average molecular weight in a range from 1200 to 10000 grams per mole, wherein the fluorinated surfactant comprises at least one component represented by formula or a salt thereof, wherein: R is H, -CH3, or -CH2CO2H; and m is an integer having a value from 0 to 11. Z is a divalent segment consisting of copolymerized units of perfluoroalkanesulfonamidoalkyl (meth)acrylate and at least one of (meth)acrylic acid, ss-carboxyethyl (meth)acrylic acid, or itaconic acid. The molar ratio of perfluoroalkanesulfonamidoalkyl to carboxylic acid groups in the fluorinated surfactant has a value from 0.5 to 3. Methods of making the fluorinated surfactants are also disclosed.

Description

Background technique [0001] Fluorinated surfactants have been widely used in industrial coatings for many years. Fluorinated surfactants can influence the properties of these coatings, such as wetting behavior, leveling properties and storage stability (for example, with respect to phase separation). The specific properties affected depend, for example, on the specific composition of each surfactant and the specific coating formulation. Surfactants, which are useful leveling agents, lower the surface energy of the formulation and maintain it at an almost constant value during drying. In general, however, the ability of a surfactant to lower the surface tension of a solvent or formulation (i.e., surfactant strength) has little predictive value in determining whether that surfactant will perform well as a leveling agent in a coating formulation . [0002] Many fluorinated surfactants traditionally widely used in industrial coatings contain long-chain perfluoroalkyl groups, su...

Claims

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Application Information

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IPC IPC(8): C08F220/38
CPCC08F220/38C08F220/06C08F220/385
Inventor 乔治·G·I·莫尔鲁道夫·J·达姆斯
Owner 3M INNOVATIVE PROPERTIES CO
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