WO2023125475A1 - 一种紫外线吸收剂、组合物、化妆品及配制化妆品的工艺 - Google Patents
一种紫外线吸收剂、组合物、化妆品及配制化妆品的工艺 Download PDFInfo
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- WO2023125475A1 WO2023125475A1 PCT/CN2022/142177 CN2022142177W WO2023125475A1 WO 2023125475 A1 WO2023125475 A1 WO 2023125475A1 CN 2022142177 W CN2022142177 W CN 2022142177W WO 2023125475 A1 WO2023125475 A1 WO 2023125475A1
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- ultraviolet absorber
- particle size
- ultraviolet
- particles
- range
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- 239000006097 ultraviolet radiation absorber Substances 0.000 title claims abstract description 103
- 239000002537 cosmetic Substances 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title description 38
- 239000002245 particle Substances 0.000 claims abstract description 184
- 238000009826 distribution Methods 0.000 claims description 49
- 239000002994 raw material Substances 0.000 claims description 21
- 239000006096 absorbing agent Substances 0.000 claims description 19
- 230000000475 sunscreen effect Effects 0.000 claims description 16
- 239000000516 sunscreening agent Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- 238000012545 processing Methods 0.000 claims description 10
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
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- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 229940100539 dibutyl adipate Drugs 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004381 surface treatment Methods 0.000 claims description 2
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000010408 film Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical group CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 abstract description 3
- 229960001630 diethylamino hydroxybenzoyl hexyl benzoate Drugs 0.000 abstract description 2
- AKNXMRHLLPIDLY-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC(N(CC)CC)=C1O AKNXMRHLLPIDLY-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 25
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- 230000000052 comparative effect Effects 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004945 emulsification Methods 0.000 description 7
- 238000007561 laser diffraction method Methods 0.000 description 7
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- 239000007788 liquid Substances 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000007922 dissolution test Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFYLEOHOBYQMJR-UHFFFAOYSA-N N-(3-ethyloctan-3-yl)butanamide Chemical compound C(CCC)(=O)NC(CCCCC)(CC)CC LFYLEOHOBYQMJR-UHFFFAOYSA-N 0.000 description 1
- 206010051246 Photodermatosis Diseases 0.000 description 1
- 239000004904 UV filter Substances 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
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- 230000008845 photoaging Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 238000011112 process operation Methods 0.000 description 1
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Images
Classifications
-
- 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
- A61K8/30—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
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- 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
- A61K8/30—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
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/08—Processes in which the treating agent is applied in powder or granular form
Definitions
- the invention belongs to the field of ultraviolet protection, and more specifically relates to an ultraviolet absorber and its composition and application.
- the application can be to prepare cosmetics by using the above ultraviolet absorber or composition.
- 2-(4-N,N-Diethylamino-2-hydroxybenzoyl) n-hexyl benzoate is a typical and commonly used oil-soluble organic UV absorber, oil The melting temperature is not higher than 50°C, and the sunscreen band is 320-400nm.
- a UVA absorber that absorbs near-ultraviolet rays, it can chemically absorb the energy of ultraviolet rays and convert it into heat energy to prevent ultraviolet rays from penetrating, thereby effectively delaying the penetration of plastics such as plastics. Products made of polymer materials such as rubber and rubber will suffer from photoaging and degradation during use. When used as an additive in sunscreen and other cosmetics, it can effectively prevent the skin from being affected by ultraviolet rays.
- DHHB DHHB
- O/W and W/O systems oil phase and The water phase is usually treated separately, and UV absorbers such as DHHB are usually dissolved in the oil phase for use.
- sunscreen with W/O system put the oil-phase raw materials (including DHHB) into the emulsification pot, stir and heat up to 80-85°C to ensure that all raw materials are completely dissolved or evenly dispersed, and keep warm for 10 minutes.
- the oil phase and the water phase are heated separately in advance, and then the two are mixed and stirred to cool to room temperature. It takes a lot of time or energy to heat the oil phase and water phase to 70°C or above, while the cooling process takes longer or uses auxiliary means, such as water cooling, to make it cool quickly. Not only that, the timing of adding flavors and unstable components in the process is extremely limited.
- Cosmetic companies must consider how to reduce energy consumption and carbon emissions not only in terms of raw materials, transportation and packaging, but also in product technology. Based on this, currently low-energy emulsification (LEE, Low-Energy Emulsification) is usually used for product processing. For example in the so-called cold process of Patent Document 1, ie at room temperature 20-25° C., the solvent and optionally customary other auxiliary substances are converted into sunscreen final formulations.
- the above-mentioned low-energy emulsification method is limited to a certain extent.
- the reason is that the granular DHHB prepared by the new crystallization process will limit the process during use.
- One of the most typical problems is due to the decrease in temperature or concentration. The increase will double the oil-soluble time of DHHB; the second problem is to affect the stability and rhythm of the entire production process. If the production process is restricted by too many factors, it is easy to fluctuate, which will seriously affect the stability of the production process itself and seriously affect production. The stability of the rhythm will affect the quality of the product.
- Patent Document 1 CN105358221B, publication date 2019-08-23, a reagent containing a large amount of UV stabilizers;
- Patent Document 2 CN109908020A, publication date 2019-06-21, a sunscreen composition, its preparation method and its application.
- One of the purposes of the present invention is to provide a UV absorber or a composition based on it that is suitable for both the above-mentioned traditional method and low temperature (room temperature 20-25° C.) processing method;
- the second object of the present invention is to solve the existing ultraviolet absorber or the composition based on it, when being applied to the above-mentioned traditional technology and low temperature (room temperature 20-25 °C) processing technology, it will affect the stability and production of the production process itself.
- the stability of rhythm is seriously adversely affected; the ultraviolet absorber has a maximum particle size of less than 100 ⁇ m.
- the present invention provides a UV absorber, which is 2-(4-N, N-diethylamino-2-hydroxybenzoyl) n-hexyl benzoate, the specific structural formula is as follows :
- the UV absorber has a median particle size d (0.5) below 100 ⁇ m;
- the maximum particle size d (0.9) of the ultraviolet absorber is in the range of 50-100 ⁇ m; at the same time
- the range of the width difference between the minimum particle size d (0.1) and the maximum particle size d (0.9) of the ultraviolet absorber is 30-100 ⁇ m.
- the numerical value of the maximum particle size d (0.9) can be any numerical value selected from any of the following numerical ranges: 50-100 ⁇ m, 50-90 ⁇ m, 50-80 ⁇ m, 50-70 ⁇ m, 50-60 ⁇ m , 60-100 ⁇ m, 60-90 ⁇ m, 60-80 ⁇ m, 60-70 ⁇ m, 70-100 ⁇ m, 70-90 ⁇ m, 70-80 ⁇ m, 80-100 ⁇ m, 80-90 ⁇ m, 90-100 ⁇ m; the minimum particle size d (0.1) to The numerical value of the width difference of the maximum particle size d (0.9) can be any value in any of the following value ranges: 30-100 ⁇ m, 30-90 ⁇ m, 30-80 ⁇ m, 30-70 ⁇ m, 30-60 ⁇ m, 30 ⁇ 50 ⁇ m, 30 ⁇ 40 ⁇ m, 40 ⁇ 100 ⁇ m, 40 ⁇ 90 ⁇ m, 40 ⁇ 80 ⁇ m, 40 ⁇ 70 ⁇ m, 40 ⁇ 60 ⁇ m, 40 ⁇ 50 ⁇
- the minimum particle size d (0.1) of the ultraviolet absorber is in the range of 5-15 ⁇ m.
- the numerical value of the minimum particle size d (0.1) can be any numerical value selected from any of the following numerical ranges: 5-15 ⁇ m, 5-12 ⁇ m, 5-10 ⁇ m, 5-8 ⁇ m, 5-6 ⁇ m , 7-15 ⁇ m, 7-12 ⁇ m, 7-10 ⁇ m, 7-8 ⁇ m, 9-15 ⁇ m, 9-12 ⁇ m, 9-10 ⁇ m, 10-15 ⁇ m, 10-12 ⁇ m, 12-15 ⁇ m, 14-15 ⁇ m.
- the median diameter d (0.5) of the ultraviolet absorber is in the range of 20-40 ⁇ m.
- the numerical value of the median particle diameter d (0.5) can be any numerical value selected from any of the following numerical ranges: 20-40 ⁇ m, 20-35 ⁇ m, 20-30 ⁇ m, 20-25 ⁇ m, 25 ⁇ 40 ⁇ m, 25 ⁇ 35 ⁇ m, 25 ⁇ 30 ⁇ m, 30 ⁇ 40 ⁇ m, 30 ⁇ 35 ⁇ m, 35 ⁇ 40 ⁇ m.
- the ultraviolet absorber has an effective diameter not higher than 3 measured by an instrument.
- the numerical value of the effective radial distance can be any numerical value selected from any of the following numerical ranges: 1 ⁇ 3, 1 ⁇ 2.5, 1 ⁇ 2, 1 ⁇ 1.5, 1.5 ⁇ 3, 1.5 ⁇ 2.5, 1.5 ⁇ 2, 2 ⁇ 3, 2 ⁇ 2.5, 2.3 ⁇ 3.
- the ultraviolet absorber has a consistency ranging from 0.5 to 1.5 measured by an instrument.
- the numerical value of the consistency can be any value selected from any of the following ranges: 0.5-1.5, 0.5-1.2, 0.5-1, 0.5-0.8, 0.5-0.6, 0.7-1.5, 0.7-1.2 , 0.7 ⁇ 1, 0.7 ⁇ 0.8, 1 ⁇ 1.5, 1 ⁇ 1.2.
- the maximum particle size d (0.9) of the ultraviolet absorber is in the range of 50-90 ⁇ m; at the same time
- the minimum particle size d (0.1) of the ultraviolet absorber is in the range of 5-15 ⁇ m.
- the median particle size d (0.5) of the ultraviolet absorber is in the range of 20-40 ⁇ m.
- the ultraviolet absorber has a consistency of not higher than 1 as measured by an instrument.
- the particle size distribution of the ultraviolet absorber meets the following requirements:
- ⁇ d5 is the particle distribution coefficient of 5 ⁇ m particle size
- V d5 is the volume ratio of particles with a particle size below 5 ⁇ m in the particle group to the particle group, %;
- V d100 is the volume ratio of particles with a particle size below 100 ⁇ m in the particle group to the particle group, %;
- the small-diameter particle distribution coefficient of the particle group satisfies ⁇ d5 ⁇ 0.2.
- the particle size distribution of the ultraviolet absorber meets the following requirements:
- ⁇ d10 is the distribution coefficient of 10 ⁇ m particles
- V d10 is the ratio of particles with a particle size below 10 ⁇ m to the total volume of the particles in the ultraviolet absorber, %;
- V d100 is the ratio of particles with a particle size below 100 ⁇ m to the total volume of the particles in the ultraviolet absorber, %;
- the small particle size particle distribution coefficient of the ultraviolet absorber satisfies ⁇ d10 ⁇ 0.2. What needs to be explained here is that the applicant has surprisingly found that when too many small particles or even fine powders are entrained in the ultraviolet absorber, the small particles will fill the gaps between the large particles, which will increase the number of contact points between the particles and promote the formation of solid particles. piece. However, if the volume of the small particles in the ultraviolet absorber is controlled within a certain range, and the difference between the small particle size and the small particle size is controlled, although there will still be agglomeration, compared with the prior art, its agglomeration The degree of blockage is significantly reduced.
- the degree of agglomeration and looseness of the ultraviolet absorber is relatively high.
- the applicant finds that when the product is poured into the container from the package It can be quickly dispersed by collision or simple mechanical stirring, without additional heating or other auxiliary treatment, saving functional energy consumption and reducing process carbon emissions; at the same time, when the ultraviolet absorber of the present invention is usually dissolved in the organic phase for reprocessing, It may be that there is a certain amount of small-sized particles in the absorbent particles, which is more likely to generate liquid bridge force with the organic phase, which increases the adhesion force between the interfaces to a certain extent, making the absorbent particles easier and faster to distribute in the organic phase. in the organic phase.
- the dissolution rate of the absorbent particles with small particle size is faster than that of the absorbent particles with large particle size, which further accelerates the dissolution process of the absorbent particles.
- stirrer any type of stirrer, such as magnetic stirring cores, anchor stirrers, propeller stirrers, inclined blade stirrers or disk stirrers.
- the size of the stirrer relative to the input volume of the raw materials is not critical. It is known that the rate of dissolution can be increased by increasing the stirrer speed, ie stirrer revolutions per minute.
- the stirrer stirs at 100-600 rpm/min, preferably 200-500 rpm/min, and optimally 250-350 rpm/min.
- the small particle size distribution coefficient of the ultraviolet absorber satisfies ⁇ d10 ⁇ 0.15.
- the small particle size distribution coefficient of the ultraviolet absorber satisfies 0.05 ⁇ d10 ⁇ 0.15 ; and the numerical value of the small particle size particle distribution coefficient of the ultraviolet absorber can be selected from any of the following numerical ranges Any value: 0.05 ⁇ 0.15, 0.05 ⁇ 0.12, 0.05 ⁇ 0.1, 0.05 ⁇ 0.08, 0.05 ⁇ 0.06, 0.07 ⁇ 0.15, 0.07 ⁇ 0.12, 0.07 ⁇ 0.1, 0.09 ⁇ 0.15, 0.09 ⁇ 0.12, 0.09 ⁇ 0.1, 0.11 ⁇ 0.15, 0.11 ⁇ 0.12, 0.12 ⁇ 0.15; preferably, the distribution coefficient of the small particle size particles satisfies 0.07 ⁇ d10 ⁇ 0.12.
- V d100 of the ultraviolet absorber is ⁇ 70%; preferably ⁇ 85%, more preferably ⁇ 95%.
- the time for the ultraviolet absorber to be dissolved in the solvent is not more than 30 minutes;
- Described processing condition is specifically as follows:
- the indicator that the ultraviolet absorber is soluble in a solvent is that the solid content in the solvent is less than 0.5%.
- the time for the ultraviolet absorber to be dissolved in the solvent is not more than 25 minutes.
- a composition with ultraviolet absorption comprising: ultraviolet absorbers, dispersants, film-forming agents, antioxidants and lubricants; wherein, the ultraviolet absorbers include any of the above ultraviolet absorbers;
- At least one of the dispersant, film former, antioxidant and lubricant is an oil phase at a temperature not lower than 20°C.
- composition with ultraviolet absorption includes: any one of the above ultraviolet absorption particles 2-(4-N,N-diethylamino-2-hydroxybenzoyl) benzoic acid n-hexyl Dicapryl Carbonate, Dibutyl Adipate, Caprylic/Capric Triglyceride, Tocopheryl Acetate.
- a cosmetic comprising the above-mentioned ultraviolet absorber; or comprising the above-mentioned composition as a raw material.
- Cosmetics as defined in the present invention is a broad definition, "cosmetics" includes but is not limited to whitening agents, sunscreens, sunscreens and the like.
- a cosmetic preparation process characterized in that: using any of the above ultraviolet absorbers or any of the above compositions as raw materials, and when dissolving the raw materials in the oil phase:
- the temperature is not higher than 50°C; preferably 40-50°C;
- the added concentration is not higher than 20wt%; preferably 3-20wt%.
- the present invention also provides the application of the above-mentioned ultraviolet absorbing particle as a sunscreen component of cosmetics, or as an anti-ultraviolet additive component for fabric surface treatment, or as an application of an anti-ultraviolet additive component for polymer materials, and the prepared The final product has high UV absorption coverage and good UV absorption effect.
- the ultraviolet absorbing particles of the present invention can greatly improve the stability of the production process, and can well maintain the rhythm of production. Even when different types and models of products are produced alternately, the stability of the production process can still be maintained, thereby making the production process have corresponding stability, maintaining the continuity of the production cycle, and avoiding changes in production stability affecting the product. Quality stability.
- Fig. 1 is the particle size distribution curve of DHHB ultraviolet absorber in embodiment 1;
- Fig. 2 is the particle size distribution curve of DHHB ultraviolet absorber in embodiment 2;
- Fig. 3 is the particle size distribution curve of DHHB ultraviolet absorber in embodiment 3;
- Fig. 4 is the particle size distribution curve of DHHB ultraviolet absorber in embodiment 4.
- Fig. 5 is the particle size distribution curve of DHHB ultraviolet absorber in embodiment 5;
- Fig. 6 is the particle size distribution curve of DHHB ultraviolet absorber in embodiment 6;
- Fig. 7 is the photo (less than 5min) of the cold melting experiment result of sample in embodiment 1;
- Fig. 8 is the cold melting test result photo (5min) of sample in comparative example 1;
- Fig. 9 is the cold melting test result photo (45min) of sample in comparative example 1;
- Fig. 10 is the cold melting test result photo (105min) of sample in comparative example 1;
- the term "about” is used to provide flexibility and imprecision associated with a given term, measurement or value.
- the degree of flexibility for a particular variable can be readily determined by one skilled in the art. More specifically, although exemplary embodiments of the present invention have been described herein, the present invention is not limited to these embodiments but includes modifications, omissions, Any and all embodiments such as combinations, adaptations, and/or substitutions between the various embodiments.
- the definitions in the claims are to be interpreted broadly according to the language used in the claims and not limited to the examples described in the foregoing detailed description or during the prosecution of this application, which examples should be considered non-exclusive. Any steps recited in any method or process claims may be performed in any order and are not limited to the order presented in the claims. Accordingly, the scope of the present invention should be determined only by the appended claims and their legal equivalents, rather than by the description and examples given above.
- a range of 1-50 should be understood to include the group selected from the group consisting of , 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44 , 45, 46, 47, 48, 49, or 50, any number, combination of numbers, or subrange, and all fractional values between the above integers, for example, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8 and 1.9.
- “nested subranges” that extend from any endpoint within the range are specifically considered.
- a nested subrange of the exemplary range 1-50 could include 1-10, 1-20, 1-30, and 1-40 in one direction, or 50-40, 50-30, 50 in the other direction -20 and 50-10.
- maximum particle size d (0.9) " where "d (0.9) " can also be expressed as “Dv90” or “D90”, means that the cumulative particle size distribution percentage of a sample reaches 90%.
- Particle size its physical meaning is that the particles with a particle size larger than it account for 10%, and the particles smaller than it account for 90%.
- minimum particle size d (0.1) As used herein, the term “minimum particle size d (0.1) ", where “d (0.1) " can also be expressed as “Dv10” or “D10”, means that the cumulative particle size distribution percentage of a sample reaches 10%. Particle size, its physical meaning is that the particles with a particle size larger than it account for 90%, and the particles smaller than it account for 10%.
- the width difference from the smallest particle size d (0.1) to the largest particle size d (0.9) can also be referred to as “effective particle size width” or “particle size width” or “particle size distribution width” or “Effective particle size width” or “particle size width” or “particle size distribution width” specifically means that the particle size corresponding to the cumulative particle size distribution percentage of a sample reaches a certain value d (0.1) and the particle size cumulative distribution percentage of a sample reaches another value.
- the absolute difference between particle sizes corresponding to a value d (0.9) is referred to as "effective particle size width” or "particle size width” or “particle size distribution width” or “Effective particle size width” or “particle size width” or “particle size distribution width” specifically means that the particle size corresponding to the cumulative particle size distribution percentage of a sample reaches a certain value d (0.1) and the particle size cumulative distribution percentage of a sample reaches another value.
- the particle size distribution and characteristics of the ultraviolet absorber described in this article are all measured by laser diffraction method, and the measurement conditions are as follows,
- Particle size analyzer Malvern MS2000 laser particle size analyzer
- Dispersant name water.
- the particle size analyzer used is Malvern MS2000 laser particle size analyzer, and its measurement conditions and detection results are as shown in Table 1 below:
- ⁇ d5 0.0160
- ⁇ d10 0.111 of the ultraviolet absorber in this embodiment
- the difference between D[3,2] and D[4,3] is 11.727 ⁇ m.
- the particle size analyzer used is the Malvern MS2000 laser particle size analyzer, and its measurement conditions and detection results are as shown in Table 3 below:
- the particle size analyzer used is the Malvern MS2000 laser particle size analyzer, and its measurement conditions and detection results are as shown in Table 5 below:
- ⁇ d5 0.019
- ⁇ d10 0.107 of the ultraviolet absorber in this embodiment
- the difference between D[3,2] and D[4,3] is 17.543 ⁇ m.
- the particle size analyzer used is Malvern MS2000 laser particle size analyzer, and its measurement conditions and detection results are as shown in Table 7 below:
- ⁇ d5 0.002
- ⁇ d10 0.074 of the ultraviolet absorber in this embodiment
- the difference between D[3,2] and D[4,3] is 11.215 ⁇ m.
- the particle size analyzer used is Malvern MS2000 laser particle size analyzer, and its measurement conditions and detection results are as shown in Table 9 below:
- the measurement results show that the ultraviolet absorber of this embodiment has the particle size distribution characteristics in Table 10 below, and the specific distribution curve is shown in Figure 5.
- ⁇ d5 0.037
- ⁇ d10 0.095 of the ultraviolet absorber in this embodiment
- the difference between D[3,2] and D[4,3] is 21.881 ⁇ m.
- the DHHB product with the trade name UvinulAPlus produced by BASF was used as a sample.
- the particle size analyzer used is Malvern MS2000 laser particle size analyzer, and its measurement conditions and detection results are as shown in Table 11 below:
- ⁇ d5 0.005
- ⁇ d10 0.122 of the ultraviolet absorber in this comparative example
- the difference between D[3,2] and D[4,3] is 128.616 ⁇ m.
- the dissolution time of the DHHB ultraviolet absorber provided by Examples 1-5 of the present invention is less than 5 minutes. minute.
- the time taken for the dissolution of the DHHB ultraviolet absorber provided by Examples 1-5 of the present invention is also less than 5 minutes, indicating that the time spent for dissolution is Time was not affected by the concentration added.
- the process of actually using DHHB particles to produce sunscreen products involves many links, while the schematic simulation tests listed in the first and second dissolution experiments are only one link in the production process, and this link is in
- the added DHHB has different types and different concentrations, its dissolution time will easily change greatly, causing serious deterioration of the stability of the production process, seriously affecting the stability of the production cycle, and resulting in poor product quality stability.
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Abstract
Description
Claims (21)
- 根据权利要求1所述的紫外线吸收剂,其特征在于:所述最大粒度d (0.9)在50~90μm的范围内。
- 根据权利要求1所述的紫外线吸收剂,其特征在于:所述最大粒度d (0.9)在50~80μm的范围内。
- 根据权利要求1所述的紫外线吸收剂,其特征在于:所述最小粒度d (0.1)到最大粒度d (0.9)的宽度差值的范围为30~70μm。
- 根据权利要求1所述的紫外线吸收剂,其特征在于:所述最小粒度d (0.1)到最大粒度d (0.9)的宽度差值的范围为40~50μm。
- 根据权利要求1所述的紫外线吸收剂,其特征在于:所述最小粒度d (0.1)在5~15μm的范围内。
- 根据权利要求1-6任一所述的紫外线吸收剂,其特征在于:所述紫外线吸收剂具有通过仪器测定的不高于3的有效径距。
- 根据权利要求7所述的紫外线吸收剂,其特征在于:所述紫外线吸收剂具有通过仪器测定的、范围为0.5~1.5的一致性。
- 根据权利要求7所述的紫外线吸收剂,其特征在于:所述紫外线吸收剂具有通过仪器测定的、范围为0.5~1的一致性。
- 根据权利要求7所述的紫外线吸收剂,其特征在于:所述紫外线吸收剂的中值粒径d (0.5)在20~40μm的范围内。
- 根据权利要求11所述的紫外线吸收剂,其特征在于:所述小粒径颗粒分布系数满足α d10≤0.15。
- 根据权利要求11所述的紫外线吸收剂,其特征在于:所述小粒径颗粒分布系数满足0.05≤α d10≤0.15;优选所述小粒径颗粒分布系数满足0.07≤α d10≤0.12。
- 根据权利要求11-13任一所述的紫外线吸收剂,其特征在于:所述紫外线吸收剂的V d100不低于70%;优选不低于85%,进一步优选不低于95%。
- 根据权利要求1-6或者11-13任一所述的紫外线吸收剂,其特征在于:在加工条件下,所述紫外线吸收剂溶于溶剂的时间不高于30分钟;所述加工条件具体如下:溶剂:己二酸二丁酯;添加浓度:3~20wt%;温度:20~30℃;搅拌速度:150±5r/min;所述紫外线吸收剂溶于溶剂的指标为溶剂中固含量低于0.5%。
- 根据权利要求15所述的紫外线吸收剂,其特征在于:所述紫外线吸收剂溶于溶剂的时间不高于25分钟。
- 一种具有紫外线吸收作用的组合物,包括:紫外线吸收剂、分散剂、成膜剂、抗氧化剂及润滑剂;其中,所述紫外线吸收剂包括权利要求1-16任意一项所述的紫外线吸收剂;所述分散剂、成膜剂、抗氧化剂及润滑剂中至少一项在不低于20℃的条件下为油相。
- 根据权利要求17所述的具有紫外线吸收作用的组合物,包括:权利要求1-16任意一项所述的紫外线吸收颗粒2-(4-N,N-二乙基氨基-2-羟基苯甲酰基)苯甲酸正己基酯、碳酸二辛酯、己二酸二丁酯、辛酸/癸酸甘油三酯、生育酚乙酸酯。
- 权利要求1-16任意一项所述的紫外线吸收剂或权利要求17-18任一所述的组合物作为化妆品防晒组分的应用,或作为织物表面处理的防紫外线添加剂组分的应用,或作为高分子材料的防紫外线添加剂组分的应用。
- 一种化妆品,其包括权利要求1-16任意一项所述的紫外线吸收剂;或者其包括权利要求17-18任一所述的组合物作为原料。
- 一种化妆品配制工艺,其特征在于:使用权利要求1-16任意一项所述的紫外线吸收剂或权利要求17-18任一所述的组合物作为原料,且将所述原料溶于油相时:温度不高于50℃;优选为40~50℃;添加浓度不高于20wt%;优选为3~20wt%。
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JP2024508816A JP2024518661A (ja) | 2021-12-28 | 2022-12-27 | 紫外線吸収剤、組成物、化粧品及び化粧品の製造プロセス |
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