TWI608055B - Surface-treating agent - Google Patents

Description

Surface treatment agent

The present invention relates to a surface treatment agent, and more particularly to a modified urethane acrylate containing a carbon-carbon double bond and a perfluoropolyether functional group.

The surface treatment agent which can be used for water and oil repellent in the prior art is usually a fluoropolymer having a fluoroalkyl group (meth) acrylate as a structural monomer. These fluoropolymers are disclosed in U.S. Patent Nos. 3,655,732, US Pat. No. 3,773,826, U.S. Pat. However, the water and oil repellency of these fluoropolymers is not sufficient to meet industry standards.

The technical problem to be solved by the present invention is to provide an innovative water- and oil-repellent surface treatment agent, which has strong anti-fingerprint pollution ability and low cost, and is advantageous for application.

The present invention provides a surface treatment agent which can form a film on the surface of a substrate. The surface treating agent of the present invention comprises a triisocyanate obtained by trimerization of a diisocyanate; and a component having at least one active hydrogen compound. The composition further comprises a perfluoropolyether and a monomer having an active hydrogen and a carbon-carbon double bond.

Preferred embodiments of the present invention will be exemplified below. It should be noted that in order to clearly illustrate the present invention, the following description also omits the related materials and related processing techniques.

Comparative example

A comparative sample was prepared with reference to Example 1 of U.S. Patent No. 2004/0181008 A1. The specific process is as follows. Add 5.7 g of HMDI-trimeric isocyanate type triisocyanate (N3300) and 40 ml of dichloropentafluoropropane (HCFC 225) to a stirred 100 ml three-necked flask, add dibutyltin dilaurate, stir, and drop at room temperature. 21.0 g of a mixed solution of a single-end hydroxy-based perfluoropolyether (molecular weight 2100) and 10 ml of HCFC225 was stirred at room temperature for 6 hours, and the temperature was raised to 40 to 45 ° C, and a mixed solution of 2.44 g of hydroxyethyl acrylate and 10 ml of HCFC 225 was added dropwise. After stirring at a constant temperature for 3 hours, it was confirmed by IR that the NCO absorption completely disappeared, and 23.8% of a comparative HCF225 solution was obtained.

Example 1: Preparation of 50 wt% HCFC225 solution of compound (1)

In a three-necked reaction flask equipped with a dropping funnel, a condenser, a thermometer, and a stirring device, SUMIDUR (six-methyl methyl diisocyanate cyclic terpolymer, manufactured by Sumitomo Bayer Urine Co., Ltd., NCO base content: 21.9%) 30 g was dissolved in 120 g of HCFC225, and 0.4 g of dibutyltin dilaurate was further added, and 90 g of hydroxyethyl acrylate was added thereto, and the mixture was stirred at 40 ° C for 5 hours. It was confirmed by IR that the NCO absorption completely disappeared, and a 50 wt% HCF225 solution of the compound (1) was obtained.

Example 2: Preparation of 50 wt% of compound (2) HCFC225 solution

In a three-necked reaction flask equipped with a dropping funnel, a condenser, a thermometer, and a stirring device, 1,1-(bisacryloyloxymethyl)ethyl isocyanate, manufactured by Showa Denko, and 7.5 g was dissolved in 67.5 g of HCFC225, and then dibutyl was added. The dilaurate salt was stirred at 40 ° C in air at 40 ° C and then mixed with a double-end hydroxyl perfluoropolyether (molecular weight 4000) for 5 hours. It was confirmed by IR that the NCO absorption completely disappeared, and a 50 wt% HCF225 solution of the compound (2) was obtained.

Application example

After compound (1) and compound (2) were mixed, the solvent was diluted with a solvent of heptafluorocyclopentane and propylene glycol methyl ether (6:4) to a 20% content of a surface treatment agent.

The following materials were mixed uniformly to obtain a comparative solution: 1,6-ethylene glycol diacrylate (Changxing Chemical Co., Ltd. EM221) 12%, pentaerythritol tripropionate (Changxing Chemical Co., Ltd. EM235-1) 4%, aliphatic polyurethane Acrylate (Changxing Chemical Co., Ltd. EM6150-100) 24%, photoinitiator IRGACURE 907 1.2%, propylene glycol methyl ether 5 6.8% (less than 100%).

A comparative sample and a 20% content of the surface treatment agent of the present invention were added to the above solution in an amount of 2%. Application solution A and a comparative sample were obtained. The blank solution (without adding a surface treatment agent) and the comparative sample and the application solution A were respectively applied to the interface of the polyethylene terephthalate film by wire bar coating, pre-dried at 80 ° C for 4 minutes, and then subjected to high pressure. The mercury lamp is irradiated with a UV-cured layer (radiation energy 2 50 mJ/cm 2 ) to form a transparent hard coat pattern blank, a comparative sample and application A. The above coatings were separately tested for deionized water and n-hexadecane contact angles; the oily note-like wiping and anti-fingerprint performance results were as follows.

Preferred embodiments of the present invention will be exemplified below with reference to the accompanying drawings. Like components in the drawings have the same component symbols. It should be noted that the various elements of the present invention are not drawn to the true aspect of the present invention, and in order to avoid obscuring the present invention, the following description also omits the known components, related materials, and related processing techniques.

Claims (4)

A surface treatment agent comprising a triisocyanate obtained by trimerization of a diisocyanate; 1,1-(bisacryloyloxymethyl)ethyl isocyanate; and having at least one activity The composition of the hydrogen compound further comprises a perfluoropolyether, a monomer having an active hydrogen and a carbon-carbon double bond. The surface treatment agent according to claim 1, wherein the triisocyanate is a hexamethylene diisocyanate cyclic terpolymer. The surface treatment agent according to claim 1, wherein the monomer having an active hydrogen and a carbon-carbon double bond is a hydroxyethyl acrylate. The surface treatment agent according to claim 1, wherein the perfluoropolyether is a double-end hydroxy perfluoropolyether.