CN112807246B - Ultraviolet-curing optically variable nail polish and preparation method thereof - Google Patents
Ultraviolet-curing optically variable nail polish and preparation method thereof Download PDFInfo
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- CN112807246B CN112807246B CN201911117160.3A CN201911117160A CN112807246B CN 112807246 B CN112807246 B CN 112807246B CN 201911117160 A CN201911117160 A CN 201911117160A CN 112807246 B CN112807246 B CN 112807246B
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/87—Polyurethanes
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
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Abstract
The invention provides an ultraviolet light curing optically variable nail polish, which comprises the following components: a:30-70 parts by weight of a UV-curable resin A; b:10-30 parts by weight of a UV-curable resin B; c:10-50 parts by weight of a diluent monomer; d:0.1 to 10 parts by weight of a photoinitiator; e:0.01-5 parts by weight of a polymerization inhibitor; f:0.01-5 parts by weight of a rheology modifier; g:0.1-15 parts by weight of optically variable pigments; h:0.1 to 10 parts by weight of a conventional pigment. The nail polish can enable the nail to be observed at different angles, presents different color effects, and has the effects of gorgeous color, high color saturation, simple operation, excellent adhesive force, high brightness, good durability and the like.
Description
Technical Field
The invention relates to the technical field of nail coatings, in particular to ultraviolet-curing optically variable nail polish and a preparation method thereof.
Background
The nail polish used by people at present is divided into solvent type nail polish, water-based nail polish and UV light-cured nail polish, wherein the light-cured nail polish becomes one of the main products widely applied in the nail-beautifying market nowadays, and the novel nail-beautifying mode has high gloss and rich and colorful colors which cannot be compared with the conventional nail polish, and has better durability, easy operation and more convenience compared with the conventional nail polish.
In order to make the nail polish obtain richer colors, generate the effects of different decoration appearance states and increase the color richness of the nail polish, the color-changing nail polish is produced. In the early color-changing nail polish, a method of adding a fluorescent dye into the nail polish is mostly adopted, and the effect of fluorescence can be generated under the irradiation of a light source such as ultraviolet rays.
CN1231169A adopts a nail polish formula scheme which is formed by adding 0.5-1.5% of color-changing pigment and 0.3-3.3% of pigment. The nail polish of the invention not only has beautifying and protecting functions of common nail polish in common places, but also can change colors in entertainment places with ultraviolet light sources, such as nightclubs, dance halls, karaoke, bars and the like, and has bright colors. But the light variation effect is more difficult to show in bright occasions when the generated light is weak in dark environments. In order to solve the above limitations and obtain a nail polish for wider light application, patent document CN102631293A discloses a photochromic nail polish prepared by using indoline spiropyran solution as a photochromic agent, wherein the nail polish is coated on nails, is a color under normal weak light, and can be reversibly changed in color under strong light such as sunlight, so that the nail polish has a color change effect, and the color of the nail polish is restored to a primary color after the strong light disappears, thereby increasing interest and aesthetic feeling. Similar patents also include CN103099741A, CN103690453A, CN106580725A, CN107325603A, etc., which all adopt a certain technology to make photochromic nail polish more colorful, respond more quickly, and adapt to nail polish of more dosage forms, but all of them are difficult to respond immediately and require a certain time.
A series of patents of nail polish with both photosensitivity and temperature sensitivity are generated, and the nail polish is basically realized by simultaneously adding reversible temperature-variable pigments and reversible light-variable pigments into a nail polish system. Such patents include: CN103735427A, CN105616182A, CN106924076A, CN109381372A. Although there are two environmental response factors introduced into nail polish systems, such nail polishes cannot fundamentally achieve a visual effect that is viewing-invariant because environmental changes such as temperature and light are slow to change over time. In order to solve the above problems, patent document CN103126938a is prepared by adding pearl powder into a non-toxic, colorless transparent, colored pearl nail polish, which changes color when exposed to light and has not completely the same color in different places and different times. The nail polish has narrow color change range, mostly has gradually changed colors of the same color system, and has weak visual impact.
Disclosure of Invention
The technical problem to be solved by the invention is to provide the ultraviolet curing light-variable nail polish which can show different colors when being observed at different angles and the preparation method thereof, and the ultraviolet curing light-variable nail polish has the effects of gorgeous colors, high color saturation, simple operation, excellent adhesive force, high brightness, good durability and the like.
In a first aspect of the invention, a nail polish is provided, which comprises the following components:
a, 30 to 70 parts by weight, preferably 35 to 65 parts by weight of UV-curable resin A;
10-30 parts by weight, preferably 15-25 parts by weight of UV-curable resin B;
c 10-50 parts by weight, preferably 15-45 parts by weight of a diluent monomer;
0.1 to 10 parts by weight, preferably 1 to 5 parts by weight, of a photoinitiator;
e, 0.01 to 5 parts by weight, preferably 0.1 to 2 parts by weight, of a polymerization inhibitor;
f, 0.01 to 5 parts by weight, preferably 0.1 to 2 parts by weight of a rheology modifier;
g 0.1-15 parts by weight, preferably 1-10 parts by weight of optically variable pigments;
h 0.1 to 10 parts by weight, preferably 1 to 8 parts by weight, of a conventional pigment.
In the methyl oil, the UV curing resin A is a bifunctional polyurethane acrylate oligomer, preferably a product obtained by reacting the following components based on the total mass of raw materials:
sa1: at least one diisocyanate added in an amount of 2 to 25% by weight, preferably 10 to 20% by weight;
sa2: at least one polyether polyol having a number average molecular weight of from 100 to 3000g/mol, preferably a number average molecular weight of from about 200 to 2000g/mol, added in an amount of from 40 to 90% by weight, preferably from 60 to 75% by weight;
sa3: at least one hydroxyalkyl (meth) acrylate, which is added in an amount of 2 to 30% by weight, preferably 10 to 25% by weight;
sa4: at least one catalyst in an amount of 0.01 to 5 wt.%, preferably 0.1 to 0.5 wt.%;
in one embodiment, the preparation process of the UV curable resin a is as follows: firstly, sa1, sa2 and Sa4 are mixed and react for 1 to 5 hours at the temperature of 60 to 90 ℃ to obtain prepolymer terminated by isocyanate groups; and then mixing the obtained prepolymer with Sa3 for end capping reaction, wherein the end capping reaction temperature is preferably 70-90 ℃, and the residual NCO content of the UV curing resin A is controlled to be less than 0.02%.
Preferably, the component Sa1 diisocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate trimer and dicyclohexylmethane diisocyanate, and is preferably one or more of dicyclohexylmethane diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate.
Preferably, the polyether polyol of the component Sa2 is one or more of polyethylene glycol diol, polypropylene glycol diol, polytetramethylene glycol diol, polytetrahydrofuran ether diol and polyethylene glycol-propylene glycol, and preferably polytetramethylene glycol diol and/or polypropylene glycol diol.
Preferably, the hydroxyalkyl group Sa3 (meth) acrylate as the component is one or more of hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxyethyl acrylate and hydroxypropyl acrylate, preferably hydroxyethyl acrylate.
Preferably, the component Sa4 catalyst includes, but is not limited to, one or more of dibutyl tin dilaurate, bismuth neodecanoate, bismuth laurate, bismuth isooctanoate, bismuth naphthenate, preferably bismuth neodecanoate.
The UV curing resin B is a polyurethane acrylate oligomer with the functionality of 3-9, preferably a product obtained by reacting the following components based on the total mass of raw materials:
sb1: at least one diisocyanate, which is added in an amount of 2 to 50% by weight, preferably 10 to 35% by weight;
sb2: at least one polyether polyol having a number average molecular weight of from 100 to 3000g/mol, preferably a number average molecular weight of from about 200 to 2000g/mol, added in an amount of from 40 to 90% by weight, preferably from 50 to 75% by weight;
sb3: at least one hydroxyalkyl (meth) acrylate, which is added in an amount of 5 to 30% by weight, preferably 10 to 25% by weight;
sb4: at least one hydroxy-modified dimethylsiloxane in an amount of 0.5% to 15% by weight, preferably 1 to 10% by weight
Sb5: at least one catalyst in an amount of 0.01 to 1 wt.%, preferably 0.1 to 0.5 wt.%.
In one embodiment, the preparation process of the UV curable resin B is: mixing Sb1, sb2 and Sb5, and reacting at 60-90 ℃ for 1-5h to obtain a prepolymer terminated by isocyanate groups; and then carrying out end capping reaction on the obtained prepolymer and Sb3 and Sb4, wherein the end capping reaction temperature is preferably 70-90 ℃, and the residual NCO content of the UV curing resin B is controlled to be less than 0.02 percent. The obtained UV curing resin B is urethane acrylate oligomer with 3-9 functionality, wherein the functionality refers to the number of double bonds contained in a single curing resin B, and the functionality can be adjusted by adjusting the type of Sb1 isocyanate or the type of Sb3 and Sb4 end-capping monomers by a person skilled in the art.
Preferably, the component Sb1 diisocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate trimer and dicyclohexylmethane diisocyanate, and is preferably one or more of dicyclohexylmethane diisocyanate, hexamethylene diisocyanate trimer and isophorone diisocyanate.
Preferably, the Sb2 polyether polyol as the component is one or more of polyethylene glycol diol, polypropylene glycol diol, polytetramethylene glycol diol, polytetrahydrofuran ether diol and polyethylene glycol-propylene glycol, and polytetramethylene glycol is preferred.
Preferably, the hydroxyalkyl methacrylate of Sb3 (meth) acrylate is one or more of hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, trimethylolpropane triacrylate and ethoxylated and propoxylated derivatives, pentaerythritol tetraacrylate, preferably pentaerythritol tetraacrylate and/or pentaerythritol triacrylate.
Preferably, the component Sb4 hydroxyl modified dimethyl siloxane is one or more of 1,3-bis (3-hydroxy isobutyl) tetramethyl disiloxane, hydroxypropyl pentamethyl disiloxane and 3- (3-hydroxypropyl) heptamethyl trisiloxane.
Preferably, the component Sb5 catalyst includes, but is not limited to, one or more of dibutyl tin dilaurate, bismuth neodecanoate, bismuth laurate, bismuth isooctanoate, bismuth naphthenate, preferably bismuth neodecanoate.
In the methyl oil of the present invention, the diluent monomer includes at least one of a monofunctional (meth) acrylate monomer and a difunctional (meth) acrylate monomer and a trifunctional (meth) acrylate monomer, and further includes trimethylolpropane triacrylate, tripropylene glycol diacrylate, polydipentaerythritol hexaacrylate, isobornyl acrylate, and hydroxyethyl methacrylate, preferably hydroxyethyl methacrylate.
In the methyl oil, the photoinitiator is at least one of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide, and 2,6-difluoro-3-pyrrolyl phenyl titanocene, bistrimethylbenzoyl phenyl phosphine oxide and isopropyl sulfur flavone.
In the methyl oil of the invention, the polymerization inhibitor is at least one of benzenediol, benzenediol derivatives (such as 2-tert-butylcatechol, 2,5-di-tert-butylhydroquinone), tris (N-nitroso-N-phenylhydroxylamine) aluminum salt and p-hydroxyanisole.
In the methyl oil, the rheological regulator is at least one of fumed silica, bentonite, polyamide wax, castor oil derivatives (such as hydrogenated castor oil), polyhydroxycarboxylic acid amide solution (such as RHEOBYK-405 with the concentration of 52%), modified urea solution (such as RHEOBYK-410 with the concentration of 52%) and high molecular weight urea derivative solution (such as RHEOBYK-415 with the concentration of 30%), and preferably modified urea (RHEOBYK-410) solution.
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Preferably, the optically variable pigment comprises one or more of:
1-8 parts of red-to-green light-changing powder, 1-8 parts of green-to-magenta light-changing powder, 1-8 parts of green-to-blue light-changing powder, 1-8 parts of green-to-black light-changing powder, 1-8 parts of gold-to-gray light-changing powder and 1-8 parts of gold-to-green light-changing powder; 0.5-3 parts by weight of interference red pearl powder;
in the nail polish of the invention, the common pigment is at least one of UV special red, yellow, blue, white, black paste or toner.
In a second aspect of the present invention, there is provided a process for preparing said nail polish, comprising: stirring and mixing all the components according to the proportion to a uniform state; preferably, adding the photoinitiator and the polymerization inhibitor into the diluted monomer, stirring for 5-30min at 200-800r/min, and dissolving and mixing uniformly; under the condition of stirring, adding UV curing resin A and UV curing resin B, stirring at 500-2000r/min for 20-30min until the mixture is uniformly mixed, continuously adding rheological regulator, stirring for 20-30min until the mixture is uniformly mixed, then adding optically variable pigment and common pigment, stirring for 20-30min until the mixture is uniformly mixed, filtering and discharging to obtain the optically cured optically variable varnish.
The first oil adopts multilayer interference optical broken film to realize light variation effect, and multilayer optical thin film flaky powder capable of generating optical interference function is used as a dispersing material, has specific spectral characteristics and is substantially an interference principle. The reflection spectrum of the light source changes with the change of an incidence angle; that is, optically variable pigments may appear differently colored as the viewing angle changes. If the viewing angle is changed by 60 degrees, two distinct colors will appear. The first color is observable under total reflection, in other words, at an observation angle of 90 degrees. The first color disappears and the second color appears to intensify when viewed at angles of 60 degrees to about 30 degrees. The color difference at different angles is a result of light reflection, refraction, and interference at the multilayer interfaces of the thin films. The degree of reflection and refraction depends on the wavelength of the light and the material at the interface. For a fixed multilayer structure, the reflected light interferes with the refracted light such that some of the wavelengths of the reflected light on the second surface add and some cancel. As the viewing angle changes, the interference condition that produces a given color disappears, and then the interference condition that produces a second color appears. The choice of material, the number and thickness of the layers determine the color pair. In theory any combination of infrared portions including light. For human eye observation, contrast color pairs such as magenta/green, green/magenta, gold/green, green/blue are preferred. The multilayer optical film flake powder is dispersed in a nail polish matrix by a UV curable resin and a diluent monomer. When irradiated with ultraviolet light, the flakes are fixed to the nail in an oriented manner, and the color is visually changed at visible light incident angles of 90 degrees and 30 degrees, respectively (e.g., magenta/green, gold/green, green/blue, green/magenta, green/black, gold/gray, etc.).
The interference optical broken film is easy to agglomerate due to the size of the interference optical broken film and the interaction force among material molecules of the interference optical broken film, so that the phenomena of unstable nail polish, easy layering and uneven inside are caused. The hydroxyl modified dimethyl siloxane is introduced into the cured resin, so that the coupling effect can be generated between the hydroxyl modified dimethyl siloxane and the interference optical broken film, the interference optical broken film can be uniformly dispersed in the cured resin, the stable arrangement is finally formed, and the light variation effect can be formed after curing. Compared with the addition of a silane coupling agent assistant, the methyl siloxane fixed on the resin B can stabilize the interference optically variable pigment, and the optically variable pigment can be more easily formed into stable uniform arrangement in the curing process, so that an obvious optically variable effect is generated, and the visual impact of the methyl oil product is increased.
The UV light-cured resin is divided into two types, and the physical properties of the cured nail polish can be controlled by regulating the adding proportion of the UV light-cured resin. The UV light-cured resin and the diluent monomer in the nail polish form a cross-linked network structure after light curing, so that a main skeleton of the nail polish is formed, and the physical properties such as glossiness, hardness, toughness and the like are provided for the cured nail polish. Because the power of the UV curing nail lamp is low, the energy of ultraviolet rays emitted by the UV curing nail lamp is low, the functionality of the irradiated nail polish composition participating in the reaction is high or the functional group needs to have stronger reactivity, polyurethane acrylate and acrylate are selected as the main body of the UV light curing resin in the formula, and the carbon-oxygen double bond connected on the acrylate can reduce the minimum energy of the double bond initiated to generate free radicals, so that the light curing is easier to perform in a shorter time. Since the viscosity of the UV light-cured resin is too high, a diluent monomer needs to be added so as to ensure that the UV light-cured resin has good leveling and sagging properties before being coated, and the rheological modifier also plays a role in adjusting the fluid property of a system. As the nail polish product can contact with external light when in use, the nail polish can be cured in advance, so that a polymerization inhibitor needs to be added to improve the storage time of the nail polish.
The invention has the beneficial effects that:
the nail polish can show different color effects when observed at different angles, and has the advantages of gorgeous color, high color saturation, excellent adhesive force, high brightness, good durability and the like.
Detailed Description
In order to better understand the scheme of the present invention, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the following examples and comparative examples, the sources of the main raw materials are as follows:
PPG1000 (Polypropylene glycol, shandong Lanxing Co., ltd.)
PTMG (polytetrahydrofuran ether glycol, hydroxyl value 56mgKOH/g, number average molecular weight =2000, BASF Germany)
HEA (hydroxyethyl acrylate, shanghai Huayi group corporation)
PETA (pentaerythritol triacrylate, futai-Thick functional Polymer materials Co., ltd.)
HPSTS (hydroxypropyl pentamethyldisiloxane, beijing Hua Weirui family chemical Co., ltd.)
8108: organic bismuth catalyst (BiCAT organic bismuth catalyst, leading America)
IBOA (isobornyl acrylate, diluent monomer, shanghai light easy chemical Co., ltd.)
EO15TMPTA (PEG-15 trimethylolpropane triacrylate, diluted monomer, shanghai light chemical Co., ltd.)
HEMA (hydroxyethyl methacrylate, shanghai Huayi group GmbH)
TPGDA (tripropylene glycol diacrylate, BASF, germany)
MEHQ (p-hydroxyanisole, polymerization inhibitor, shanghai Allatin Biotechnology Co., ltd.)
RHEOBYK-405 (52% strength, polyhydroxycarboxylic acid amide solution, germany Bike chemical)
RHEOBYK-410 (52% strength, modified urea solution, germany Bike chemical)
RHEOBYK-415 (30% strength, high molecular weight urea derivative solution, germany Pico chemical)
Red-to-green-to-color (optically variable pigments, beijing Boda Green high tech Co., ltd.)
Changing blue light from green to pigment (optical variable pigment, beijing Boda Green high tech. Co., ltd.)
Gold gray light-to-gray pigment (light-to-gray pigment, beijing Boda Green high-tech Co., ltd.)
CI 77891 (UV white color paste, laien chemical Co., ltd. Of Switzerland)
Preparation of UV-curing resin a:
UV-curable resin A-1:
adding 320g of polytetrahydrofuran ether dihydric alcohol into a four-neck flask provided with a mechanical stirrer, a thermometer and a vacuum device, and dehydrating for 1.5h at 112 ℃ and the vacuum degree of 0.88 MPa; and (3) cooling the dehydrated polytetrahydrofuran ether glycol to 78 ℃, adding 40g of isophorone diisocyanate and 0.5g of bismuth isooctanoate into a four-neck flask, controlling the temperature to be 78 ℃, reacting for 2 hours, cooling to 72 ℃, adding 23g of end capping reagent hydroxyethyl acrylate into the four-neck flask, controlling the temperature to be 72 ℃, and stopping the reaction when the NCO value is reduced to be below 0.02 percent to obtain the UV curing resin A-1 with the functionality of 2.
UV-curable resin A-2:
adding 270g of polypropylene glycol polyether glycol into a four-neck flask provided with a mechanical stirrer, a thermometer and a vacuum device, and dehydrating for 1h at 115 ℃ and under the vacuum degree of 0.82 MPa; cooling the dehydrated polypropylene glycol polyether glycol to 76 ℃, adding 45g of hexamethylene diisocyanate and 0.4g of bismuth neodecanoate into a four-neck flask, controlling the temperature to 76 ℃, reacting for 2 hours, cooling to 70 ℃, adding 39g of end capping agent hydroxyethyl methacrylate into the four-neck flask, controlling the temperature to 70 ℃, stopping the reaction when the NCO value is reduced to be below 0.02 percent, and obtaining the UV curing resin A-2 with the functionality of 2.
UV-curable resin A-3:
adding 270g of polypropylene glycol polyether glycol into a four-neck flask provided with a mechanical stirrer, a thermometer and a vacuum device, and dehydrating for 1h at 115 ℃ and under the vacuum degree of 0.86 MPa; and (2) cooling the dehydrated polypropylene glycol polyether glycol to 74 ℃, adding 60g of isophorone diisocyanate and 0.4g of bismuth neodecanoate into a four-neck flask, controlling the temperature to 74 ℃, reacting for 2 hours, cooling to 72 ℃, adding 35g of end capping agent hydroxyethyl acrylate into the four-neck flask, controlling the temperature to 72 ℃, and stopping the reaction when the NCO value is reduced to be below 0.02 percent to obtain the UV curing resin A-3 with the functionality of 2.
UV-curable resin B-1:
adding 320g of polytetrahydrofuran ether dihydric alcohol into a four-neck flask provided with a mechanical stirrer, a thermometer and a vacuum device, and dehydrating for 1.5h at 112 ℃ and under the vacuum degree of 0.88 MPa; and (3) cooling the dehydrated polytetrahydrofuran ether glycol to 78 ℃, adding 110g of isophorone diisocyanate and 0.6g of bismuth isooctanoate into a four-neck flask, controlling the temperature to be 78 ℃, after 2 trials, cooling to 72 ℃, adding 80g of dipentaerythritol hexaacrylate and 12g of hydroxypropyl pentamethyl disiloxane into the four-neck flask, controlling the temperature to be 72 ℃, and stopping the reaction when the NCO value is reduced to be below 0.02 percent to obtain the UV curing resin B-1 with the functionality of about 7.
UV-curable resin B-2:
adding 240g of polypropylene glycol polyether glycol into a four-neck flask provided with a mechanical stirrer, a thermometer and a vacuum device, and dehydrating for 1h at 115 ℃ and under the vacuum degree of 0.82 MPa; cooling the dehydrated polypropylene glycol polyether glycol to 76 ℃, adding 126g of hexamethylene diisocyanate and 1.1g of bismuth neodecanoate into a four-neck flask, controlling the temperature to 76 ℃, reacting for 2 hours, cooling to 70 ℃, adding 66g of pentaerythritol triacrylate and 6g of hydroxypropyl pentamethyldisiloxane into the four-neck flask, controlling the temperature to 70 ℃, stopping the reaction when the NCO value is reduced to below 0.02 percent, and obtaining the UV curing resin B-2 with the functionality of about 8.
UV-curable resin B-3:
adding 240g of polypropylene glycol polyether glycol into a four-neck flask provided with a mechanical stirrer, a thermometer and a vacuum device, and dehydrating for 1h at 115 ℃ and under the vacuum degree of 0.86 MPa; cooling dehydrated polypropylene glycol polyether glycol to 74 ℃, adding 167g of isophorone diisocyanate and 1.1g of bismuth neodecanoate into a four-neck flask, controlling the temperature to 74 ℃, reacting for 2 hours, cooling to 72 ℃, adding 66g of pentaerythritol triacrylate and 6g of 1, 3-bis (3-hydroxyisobutyl) tetramethyldisiloxane into the four-neck flask, controlling the temperature to 72 ℃, and stopping the reaction when the NCO value is reduced to below 0.02 percent to obtain the UV curing resin B-3 with the functionality of about 6.
Examples 1 to 6
The formula of the light-cured optically variable varnish is shown in the table 1 (in parts by weight), and the preparation method comprises the following steps:
(1) Adding a photoinitiator and a polymerization inhibitor into a diluted monomer according to the proportion, stirring for 10min at 500r/min, and dissolving and mixing uniformly;
(2) Under the condition of stirring, adding UV curing resin A and UV curing resin B, stirring for 30min at 1000r/min until the mixture is uniformly mixed, continuously adding a rheological regulator, stirring for 30min until the mixture is uniformly mixed, then adding optically variable pigment and common pigment, stirring for 30min until the mixture is uniformly mixed, filtering and discharging to obtain the optically cured optically variable varnish.
Table 1:
comparative example 1
A composition was prepared by uniformly mixing 96.3 parts by weight of a commercially available MissCandy small blacksugar P13 clear light-cured nail polish gum, 2.5 parts by weight of a red to green color-changing pigment, and 1.2 parts by weight of a CI 77891 common pigment.
Comparative example 2
A composition was prepared in accordance with 70 parts by weight of UV-curable resin A-1, 20 parts by weight of HEMA,6 parts by weight of TPO,0.05 parts by weight of MEHQ,0.25 parts by weight of RHEOBYKK-410,2.5 parts by weight of red to green changing pigment, 1.2 parts by weight of CI 77891 general pigment with reference to the examples.
A stability test
1-8 from examples 1-6 and comparative examples 1 and 2, respectively # The morphological loading of the light-cured nail polish composition was observed for 30 days of storage at 25 ℃ and 7 days of storage at 50 ℃ as shown in table 2.
Table 2:
as is clear from Table 2, examples 1 to 5 were stable at both 25 ℃ and 50 ℃. Due to the large particle size of the optically variable pigment, the optically variable pigment is difficult to suspend by common nail polish resin, so that a stable ultraviolet curing optically variable nail polish product cannot be obtained.
B performance index
Irradiating a black glass plate coated with light-cured optically-variable nail polish with the thickness of 0.1mm for 2min by a 36W ultraviolet lamp special for nail polish to obtain an ultraviolet-cured optically-variable nail polish coating, and detecting each technical index of the ultraviolet-cured optically-variable nail polish coating as shown in Table 3.
The hardness detection method comprises the following steps: referring to the national standard GB/T6739 'pencil determination method for hardness of paint film', a sharp blade is used for cutting off 5-6 mm of xylem to expose pencil lead, but the pencil lead cannot be damaged; taking 400-mesh sand paper, vertically grinding the pencil on the sand paper at an angle of 90 degrees, and grinding the tip of the pencil lead to be flat (to form a right angle); when the pen point is ground into a plane, the pen can be used for standby; after each measurement, the pen point is retreated, 3 parallel scribes are made on the surface of the horizontally placed UV-cured sample plate coated with the nail polish at an angle of 45 DEG by using a treated pencil, and the hardness level of the paint film is judged.
The glossiness detection method comprises the following steps: the samples were drawn down on a clean black glass plate with a 100 μm wet film maker and cured by uv light, and then the gloss of the nail polish was measured with a gloss meter.
The variable angle light variation detection method comprises the following steps: a sample of nail enamel was drawn down on a clean black glass plate with a 100 μm wet film maker and cured by UV light. Then, visual observation is carried out in the range of 0 to 90 degrees between the sight line and the nail polish sample, and the degree of color change is evaluated.
Table 3:
from the results of the performance tests and the sensory properties after use, it can be seen that examples 1, 2, 3, 4, 5, and 6 can provide bright and durable nail luster and color effects at different angles after curing.
Claims (16)
1. An ultraviolet curing optically variable nail polish comprises the following components:
(a) 30-70 parts by weight of UV curing resin A; the UV curing resin A is a bifunctional urethane acrylate compound which is a product obtained by reacting the following components based on the mass of raw materials:
sa1:2 to 25 weight percent of at least one diisocyanate;
sa2:40-90wt% of at least one polyether polyol having a number average molecular weight of 100-3000g/mol;
sa3:2-30wt% of at least one hydroxyalkyl (meth) acrylate;
sa4:0.01 to 5wt% of at least one catalyst;
the preparation process of the UV curing resin A comprises the following steps: firstly, sa1, sa2 and Sa4 are mixed and react to obtain a prepolymer capped with isocyanate groups; then mixing the obtained prepolymer with Sa3 for end-capping reaction, and controlling the residual NCO content of U V cured resin A to be less than 0.02%;
(b) 10-30 parts by weight of UV curing resin B; the UV curing resin B is a multifunctional urethane acrylate compound with the functionality of 3-9, and is a product obtained by reacting the following components based on the mass of raw materials:
sb1:2 to 50wt% of at least one diisocyanate;
sb2:40-90wt% of at least one polyether polyol having a number average molecular weight of 100-3000g/mol;
sb3:5-30wt% of at least one hydroxyalkyl (meth) acrylate;
sb4: 0.5-15% by weight of at least one hydroxy-modified dimethylsiloxane;
sb5:0.01 to 1wt% of at least one catalyst;
the preparation process of the UV curing resin B comprises the following steps: mixing Sb1, sb2 and Sb5, and reacting to obtain a prepolymer terminated by isocyanate groups; then carrying out end-capping reaction on the obtained prepolymer, sb3 and Sb4, and controlling the residual NCO content of the UV curing resin B to be below 0.02%;
(c) 10-50 parts by weight of a diluent monomer;
(d) 0.1 to 10 parts by weight of a photoinitiator;
(e) 0.01-5 parts by weight of polymerization inhibitor;
(f) 0.01-5 parts by weight of a rheology modifier;
(g) 0.1 to 15 parts by weight of optically variable pigments; the optically variable pigment is at least one of red-to-green-light variable powder, green-to-magenta-light variable powder, green-to-blue-to-black-to-grey-to-light variable powder, gold-to-green-to-light variable powder and interference red pearl powder, the powder fineness of the optically variable pigment is 2-25 micrometers, and the optically variable pigment is produced by Beijing Baddaglin high-tech limited;
(h) 0.1 to 10 weight portions of common pigment.
2. Nail varnish according to claim 1, characterized in that it comprises the following ingredients:
(a) 35-65 parts by weight of UV curing resin A;
(b) 15-25 parts by weight of UV curing resin B;
(c) 15-45 parts by weight of a diluent monomer;
(d) 1-5 parts by weight of a photoinitiator;
(e) 0.1-2 parts by weight of polymerization inhibitor;
(f) 0.1-2 parts by weight of a rheology modifier;
(g) 1-10 parts by weight of optically variable pigment;
(h) 1-8 parts of common pigment.
3. Nail varnish according to claim 1, characterised in that (a) UV-curable resin A is a product obtained by reaction of the following components, based on the raw material mass:
sa1: 10-20wt% of at least one diisocyanate;
sa2: 60-75wt% of at least one polyether polyol having a number average molecular weight of 200-2000g/mol;
sa3: 10-25wt% of at least one hydroxyalkyl (meth) acrylate;
sa4: 0.1 to 0.5wt% of at least one catalyst.
4. The nail polish of claim 1 or 3, wherein the component Sa1 diisocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate trimer and dicyclohexylmethane diisocyanate;
the polyether polyol of the component Sa2 is one or more of polyethylene glycol dihydric alcohol, polypropylene glycol dihydric alcohol, polytetramethylene glycol dihydric alcohol, polytetrahydrofuran ether dihydric alcohol and polyethylene glycol-propylene glycol;
the component Sa3 hydroxyalkyl (meth) acrylate is one or more of hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxyethyl acrylate and hydroxypropyl acrylate.
5. The nail polish of claim 4, wherein the component Sa1 diisocyanate is one or more of dicyclohexylmethane diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate;
the polyether polyol of the component Sa2 is polytetramethylene glycol diol;
the hydroxyalkyl ester of the component Sa3 (methyl) acrylate is hydroxyethyl acrylate.
6. The nail polish of claim 1, wherein (B) the UV-curable resin B is a product obtained by reacting the following components, based on the mass of raw materials:
sb1:10 to 35 weight percent of at least one diisocyanate;
sb2:50-75wt% of at least one polyether polyol having a number average molecular weight of 200-2000g/mol;
sb3:10-25wt% of at least one hydroxyalkyl (meth) acrylate;
sb4:1-10wt% of at least one hydroxy-modified dimethylsiloxane;
sb5:0.1 to 0.5wt% of at least one catalyst.
7. The nail polish of claim 1 or 6, wherein the component Sb1 diisocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate trimer and dicyclohexylmethane diisocyanate;
the Sb2 polyether glycol is one or more of polyethylene glycol dihydric alcohol, polypropylene glycol dihydric alcohol, polytetramethylene glycol dihydric alcohol, polytetrahydrofuran ether dihydric alcohol and polyethylene glycol-propylene glycol;
the component Sb3 (methyl) acrylic acid hydroxyalkyl ester is one or more of hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, trimethylolpropane triacrylate, ethoxylated and propoxylated derivatives and pentaerythritol tetraacrylate;
the component Sb4 hydroxyl modified dimethyl siloxane is one or more of 1,3-bis (3-hydroxy isobutyl) tetramethyl disiloxane, hydroxypropyl pentamethyl disiloxane and 3- (3-hydroxypropyl) heptamethyl trisiloxane.
8. The nail polish of claim 7, wherein the component Sb1 diisocyanate is one or more of dicyclohexylmethane diisocyanate, hexamethylene diisocyanate trimer and isophorone diisocyanate;
the Sb2 polyether polyol is polybutylene glycol diol and/or polypropylene glycol diol;
the component Sb3 hydroxyalkyl (methyl) acrylate is pentaerythritol tetraacrylate and/or pentaerythritol triacrylate.
9. The nail polish of claim 1 or 2, wherein said (c) diluent monomer comprises at least one monomer selected from the group consisting of a monofunctional (meth) acrylate monomer, a difunctional (meth) acrylate monomer, and a trifunctional (meth) acrylate monomer.
10. The nail polish of claim 9, wherein said diluent monomer (c) comprises at least one of trimethylolpropane triacrylate, tripropylene glycol diacrylate, polydipentaerythritol hexaacrylate, isobornyl acrylate, and hydroxyethyl methacrylate.
11. The nail polish of claim 10, wherein said diluent monomer of (c) is hydroxyethyl methacrylate.
12. The nail polish of claim 1 or 2, wherein said photoinitiator (d) is at least one of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis 2,6-difluoro-3-pyrrol-ylphenyltitanocene, bis-trimethylbenzoylphenylphosphine oxide, isopropylthioflavone.
13. The nail polish of claim 1 or 2, wherein (f) the rheology modifier is at least one of fumed silica, bentonite, polyamide waxes, castor oil derivatives, polyhydroxycarboxylic acid amide solutions, modified urea solutions, high molecular weight urea derivative solutions.
14. The nail polish of claim 13, wherein said rheology modifier of (f) is a modified urea solution.
15. Nail varnish according to claim 1, characterised in that the optically variable pigments comprise one or more of the following: 1-8 parts of red-to-green light variable powder, 1-8 parts of green-to-magenta light variable powder, 1-8 parts of green-to-blue color variable powder, 1-8 parts of green-to-black light variable powder, 1-8 parts of gold-to-gray light variable powder and 1-8 parts of gold-to-green light variable powder; 0.5-3 parts by weight of interference red pearl powder.
16. A process for the preparation of nail varnish according to any one of claims 1 to 15, comprising: adding a photoinitiator and a polymerization inhibitor into a diluent monomer, stirring, dissolving and mixing uniformly; under the condition of stirring, adding UV curing resin A and UV curing resin B, stirring until the mixture is uniformly mixed, adding a rheological regulator, stirring until the mixture is uniformly mixed, adding optically variable pigment and common pigment, stirring until the mixture is uniformly mixed, filtering and discharging to obtain the optically cured optically variable nail polish.
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