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Nail color coating system

a nail color and coating technology, applied in the field of cross-sectional nail color coating systems, can solve the problems of affecting the success of uv nail gel in the mass market for home use, affecting the success of uv nail gel in the mass market, and taking some effort to remove a fully cured uv nail gel from the nail surfa

Inactive Publication Date: 2018-12-13
ELEMENTIS SPECIALTIES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a nail polish composition that includes a crosslinkable coating composition containing an ingredient A that has at least two protons that can be activated to form a Michael carbanion donor, an ingredient B that functions as a Michael acceptor with at least two ethylenically unsaturated functionalities each activated by an electron-withdrawing group, and a carbonate initiator of Formula (1). The composition also includes a dye, an inorganic pigment, or a colorant independently selected from the group consisting of D&C Red 21, D&C Red No. 22, D&C Red No. 30, D&C Red No. 40, D&C Black No. 2, D&C Yellow No. 5, D&C Green No. 5, Annatto, and Caramel. The composition can further include ammonium carbamate. The inorganic pigment can be selected from the group consisting of red iron oxide, yellow iron oxide, titanium dioxide, brown iron oxide, chromium oxide green, ultramarine blue, ultramarine pink, black iron oxide, bismuth oxychloride, aluminum powder, manganese violet, mica, and combinations thereof. The dye can be selected from the group consisting of D&C Red 21, D&C Red No. 22, D&C Red No. 30, D&C Red No. 40, D&C Black No. 2, D&C Yellow No. 5, D&C Green No. 5, Annatto, and Caramel. The ingredient A can be selected from the group consisting of compounds, oligomers, or polymers containing a malonate group or an acetoacetate group. The ingredient B can be selected from the group consisting of acrylates, fumarates, maleates, and combinations thereof. The composition can further include a lake. The patent text provides various options for ingredients and combinations to create a nail polish composition with desired properties.

Problems solved by technology

UV nail gel coatings can easily last for two weeks or more and still look like new whereas conventional nail polishes are easily scratched and will chip or peel from the natural nail in one to five days.
However, conventional nail polish is easily removed with solvent whereas it can take some effort to remove a fully cured UV nail gel from the nail surface.
An expensive UV light also is required for UV nail gel application and this has limited the success of UV nail gels in the mass market for home use.
This limits the pot life, working time and general use as a coating.
However, malonate esters are known to be susceptible to base hydrolysis, particularly when water is present.
The hydrolysis product furthermore can result in undesirable destruction of base catalyst by means of formation of malonate salt; a reaction which is cloaked as longer pot life and gel time.
Presence of water can also be quite problematic in certain coatings applications.
Wood grain raising is a significant problem when water is present in wood coatings; water penetrates into wood, which causes swelling and lifting of fibers and this leaves a rough surface.
Water also can cause flash rust, i.e. appearance of rust spots on a metal surface during drying of newly applied paint that contains water.
Longer term rust formation in terms of corrosion may also be a problem when dealing with formulations that contain water.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0068]General Synthesis of Carbonate Catalyst from Diethylcarbonate.

[0069]Most of the methanol solvent from a 40 g tetrabutylammonium hydroxide (TBA OH) solution in methanol (1 M) was removed with a rotary evaporator. The material was not allowed to become completely dry without solvent as dry quaternary ammonium hydroxide base is susceptible to decomposition. Next, 40 grams of ethanol was added and most of the solvent was again removed. This procedure was repeated at least two more times until the methanol effectively had been replaced as determined by NMR. The solution strength is determined by titration (typically 1.7 mmol base / g solution). Next, a precise amount of the TBA OH in solution was mixed with diethyl carbonate (DEtC) in a 1:5 molar ratio respectively and stirred for 1 hour at room temperature using magnetic stirrer. The final clear initiator solution was analyzed by means of titration and NMR. In a similar manner, clear solutions were obtained in 1-propanol and 2-propa...

example 2

Malonate Resin (I) Synthesis.

[0070]A 500 ml reactor was charged with 149.8 g of Polyethylene glycol (PEG 300), 100 g of diethyl malonate (DEM), 32.5 g of 1-octanol and 4-5 drops of titanium (IV) butoxide. The reactor was equipped with a Dean-Stark apparatus, mechanical stirrer, nitrogen flow and heating equipment. The mixture was heated to about 180° C. with stirring under nitrogen atmosphere. During an eight-hour reaction time, about 70 ml of ethanol was collected. The final product was a lightly yellow colored liquid with less than 0.15 wt. % of residual DEM as determined by gas chromatography (GC). Gel permeation chromatography (GPC) analysis showed Mw / Mn (PDI) of 4191 / 2818 (1.49) in gram / mole and a malonate methylene equivalent molecular weight of 360 g / mole.

example 3

Basic Nail Color Formulation

[0071]FD&C and D&C dyes commonly used in nail enamel formulations were evaluated in Michael addition based crosslinkable compositions. Such colorants may also be used in other coating application industries such as automotive and industrial paints, architectural paints, plastics, adhesives and others. Concentrated dispersions of dye in Malonate resin from example 2 were prepared first. Said dispersions were then used to formulate simple nail enamel color coat formulations. All nail enamel color coats were formulated to contain dye concentrations at 3% dye loading by weight. Finally, nail enamel coatings of controlled thickness are prepared to evaluate certain applications and color properties. The following is an example how a dye dispersion and color nail enamel coat is prepared and serves as general preparative example:

Dye Dispersion:

[0072]First, 10.04 g of Malonate resin (I) from example 2 was weighed directly into a tared 60 ml capacity mortar and 3.0...

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Abstract

A nail polish composition containing a crosslinkable coating composition. The composition comprises ingredient A that has at least two protons that can be activated to form a Michael carbanion donor; ingredient B that functions as a Michael acceptor having at least two ethylenically unsaturated functionalities each activated by an electron-withdrawing group; and a carbonate initiator of Formula (1)wherein R7 is selected from hydrogen, a linear or branched substituted or unsubstituted alkyl group having 1 to 22 carbon atoms; 1 to 8 carbon atoms; 1 to 3 carbon atoms; and An+ is a cationic species or polymer and n is an integer equal or greater than 1 with the proviso that An+ is not an acidic hydrogen; at least one colorant independently selected from the group consisting of (i) a dye; (ii) an inorganic pigment; or an (iii) a lake; and optionally further comprising ammonium carbamate (H2NR8R9+—OC═ONR8R9), wherein R8 R9 are each independently selected from hydrogen, a linear or branched substituted or unsubstituted alkyl group having 1 to 22 carbon atoms; 1 to 8 carbon atoms; 1 to 3 carbon atoms.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority benefit from U.S. Provisional Patent Application 62 / 518,791 filed Jun. 13, 2017 which is incorporated by reference herein in its entirety.FIELD OF THE INVENTION[0002]The invention provides for a crosslinkable composition for use in nail coating compositions containing dyes, inorganic pigments or lakes.BACKGROUND[0003]The coatings industry continues to develop new chemistries as performance requirements for decorative and functional coatings evolve. Drivers for change are varied and these can include: regulatory controls to reduce VOC emissions, concerns about toxic hazards of coating raw materials, a desire for cost reduction, commitments to sustainability, and a need for increased product effectiveness.[0004]UV nail gel coatings have gained rapid popularity with fashion conscious individuals who apply nail polish to fingernails or toenails to decorate and protect nail plates. UV nail gels can produce coat...

Claims

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Application Information

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IPC IPC(8): A61K8/33A61Q3/02A61K8/44A61K8/41A61K8/73A61K8/85A61K8/49
CPCA61K8/33A61Q3/02A61K8/44A61K8/416A61K8/731A61K8/85A61K8/4986A61K8/494A61K2800/95C09D7/45C09D7/63C09D4/06C09D7/20C09D167/02C08F265/04C08F265/06C08F222/103C08J3/24C08G63/21C08K5/17C08K5/109C08J2367/02
Inventor IJDO, WOUTERCHEN, YANHUIDESHMUKH, PRASHANTGUPTA, RAJNIHECK, JAMES A.HOYTE, WAYNEGRAY, MAURICE
Owner ELEMENTIS SPECIALTIES INC