CN1897911A - Merocyanine derivatives for cosmetic use - Google Patents
Merocyanine derivatives for cosmetic use Download PDFInfo
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- CN1897911A CN1897911A CN 200480038027 CN200480038027A CN1897911A CN 1897911 A CN1897911 A CN 1897911A CN 200480038027 CN200480038027 CN 200480038027 CN 200480038027 A CN200480038027 A CN 200480038027A CN 1897911 A CN1897911 A CN 1897911A
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Abstract
Described are merocyanine derivatives of formula (1a) or (1b) wherein n and o are integers from 2 to 4 and aminocyclohexenone intermediates. They are used in protecting human and animal hair and skin from UV radiation.
Description
The present invention relates to Merocyanine derivatives (merocyanine derivative) avoids the purposes in the ultraviolet radiation and comprises the cosmetic composition of such chemical compound at protection human and animal's hair and skin.
The chemical compound that is used for purposes of the present invention has formula (1a) or (1b):
Wherein
R
2Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or cyano group;
R
4Be cyano group; Or-Q
1-R
5
Q
1For-COO-;-CONH-;-CO-;-SO
2-; Or-CONR
6-;
R
5Be C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Or unsubstituted or C
1-C
6The C that alkyl replaces
6-C
20Aryl;
R
6Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
Cyclohexene part (cyclohexene radical) C is unsubstituted or by one or more C
1-C
5Alkyl replaces;
N is 2 to 4;
O is 2 to 4;
If n=2 is then in formula (1a)
R
1Be alkylidene (alkylene), cycloalkylidene (cycloalkylene) or phenylene (phenylene); Or R
1And R
2Form alkylidene, cycloalkylidene or phenylene simultaneously; With
R
3Be cyano group; Or-Q
1-R
5Or R
3And R
4Form 5-to 7-unit monocycle carbocyclic ring together, its randomly by-O-or-NR
7-cut off (interrupted);
If o=2 is then in formula (1b)
R
3Be alkylidene, cycloalkylidene or phenylene, it is randomly by C
1-C
4Alkyl, C
1-C
4Alkoxyl ,-COR
6,-COOR
6Or-CONHR
6Replace; With
R
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
7-cut off;
R
7Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
M is 3 to 7 number;
If n=3 is then in formula (1a)
R
1Be the trivalent alkyl, its randomly by one or more O-or-NR
7-group cut off; With
R
3Be cyano group; Or-Q
1-R
5Or R
3And R
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=3 is then in formula (1b)
R
3Be 1,1-alkylidene (alkylidene), 1,1-cycloalkylidene (cycloalkylidene) or cyclohexadienylene (phenylidene); With
R
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, wherein randomly by O-or-NR
7-cut off;
If n=4 is then in formula (1a)
R
1Be the tetravalence alkyl; With
R
3For cyano group or-Q
1-R
5Or R
3And R
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=4 is then in formula (1b)
R
3Be the tetravalence alkyl; With
R
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
7-cut off.
C
1-C
22Alkyl is represented straight or branched, the unsubstituted or alkyl that replaces, for example methyl, ethyl, propyl group, isopropyl, normal-butyl, n-hexyl, cyclohexyl, positive decyl, just-dodecyl, just-octadecyl, eicosyl, methoxyethyl, ethoxy propyl group, 2-ethylhexyl, ethoxy, chloropropyl, N, N dimethylamine base propyl group, cyanoethyl, phenethyl, benzyl, to the tert-butyl benzene ethyl, to uncle's Octylphenoxy ethyl, 3-(2,4-two tertiary pentyl phenoxy groups)-propyl group, ethoxycarbonylmethyl group-2-(2-hydroxyl-oxethyl) ethyl or 2-furyl ethyl.
C
1-C
6Alkoxyl is represented methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amoxy, isoamoxy or uncle's amoxy.
C
6-C
10Aryl represents, for example phenyl, tolyl, anisyl (anisyl), mesityl (mesityl), chlorphenyl, 2,4-di-tert-pentyl-phenyl and naphthyl.
Heterocyclic radical comprises one, two, three or four ring hetero atoms identical or inequality.Particularly preferably be, comprise one, two or three, one or two identical or different heteroatomic heterocycle especially.Described heterocycle can be a monocycle or multi-ring, and is for example monocyclic, bicyclic or tricyclic.Preferably monocycle or bicyclo-, especially monocycle.Described ring preferably comprises 5,6 or 7 annular atomses.The monocycle of formula of can deriving (1a) and the group that (1b) exists in the chemical compound and the example of bicyclic system, pyrroles, furan, thiophene, imidazoles, pyrazoles, 1 are arranged, 2,3-triazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pyrans, thiapyran, 1,4-diox, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, indole, benzothiophene, benzofuran, pyrrolidine, piperidines, piperazine, morpholine and thiomorpholine.
Work as R
5And R
6When forming 5-to 7-unit monocycle carbocyclic ring or heterocycle together, such ring is for for example, and 1,3-dioxy cyclohexane ring, 1,1-Dimethyl-3,5-diketocyclohexane ring (dimedone ring), 1 for example, 3-dioxy-5,5-diethyl cyclohexylamine ring; 1,3-diaza-2,4,6-three oxygen cyclohexane rings, barbiturates ring (barbituric acid ring), 1 for example, 3-dimethyl barbituric acid ring, 1-phenyl barbiturates ring, 1-methyl-3-octyl group barbiturates ring, 1-ethyl-3-octyloxy carbonyl ethyl barbiturates ring; 1,2-diaza-3,5-dioxolanes, ring for example 1,2-diaza-1,2-dimethyl-3,5-dioxy ring penta ring, 1,2-diaza-1,2-diphenyl-3,5-dioxy ring penta ring; Or 2,4-diaza-1-alkoxyl-3,5-dioxy cyclohexene ring, for example 2,4-diaza-1-ethyoxyl-4-ethyl-3,5-dioxy cyclohexene ring, 2,4-diaza-1-ethyoxyl-4-[3-(2,4-two tertiary pentyl phenoxy groups) propyl group]-3,5-dioxy cyclohexene ring etc.
It is further preferred that, the chemical compound of formula (1a), wherein
R
1As the definition in formula (1a);
R
2Be hydrogen;
R
3Be cyano group;
R
4For-CONHR
5With
R
5Be C
1-C
22Alkyl; Or C
6-C
20Aryl.
If in the formula (1a), n=2
Further preferably, the purposes of the chemical compound of use formula (1c),
Wherein
R
1Be *-(CH
2)
m-* group is unsubstituted or by one or more C
1-C
5Group replaces;
Formula (1a
1) divalent group
Formula (1a
2) divalent group
Or
R
1And R
2Nitrogen-atoms with two connections forms formula (1a
3) divalent group
R
8Be hydrogen; Or C
1-C
5Alkyl;
R
3Be cyano group; Or-Q
1-R
5
P is 0 to 3 number;
Cyclohexenyl group C is unsubstituted or by one or more C
1-C
5Alkyl replaces; With
R
2, R
4, R
5, Q
1With m as in formula (1a) with the definition (1b).
Further preferably, the purposes of formula (1d) chemical compound
Wherein,
R
1Be formula (1d
1)
Or (1d
2)
The trivalent group,
R
2Be hydrogen; Or C
1-C
5Alkyl;
R
3And R
4Be cyano group independently of each other; Or-Q
1-R
5
Q
1For-COO-;-CONH-;-CO-;-SO
2-;-CONR
12-;
R
5Be C
1-C
5Alkyl;
R
9And R
10Be C independently of each other
1-C
4Alkyl;
R
11And R
12Be hydrogen independently of each other; Or C
1-C
5Alkyl; With
P is 0 to 5 number.
Further preferably, the purposes of the chemical compound of formula (1e),
Wherein, R
1And R
2Be C independently of each other
1-C
22Alkyl; Or cyano group; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
7-cut off;
R
4Be cyano group; Or-Q
1-R
5
N is 3; Or 4;
If o=3, then
R
3Be divalent alkyl;
If o=4, then
R
3Be the tetravalence alkyl;
R
5, R
7, R
9, R
10, Q
1With m as the definition in formula (1b).
Further preferably, comprise monomeric compound, oligomeric compound or the polymerizable compound of formula (2) construction unit purposes as UV chromophore (chromophore),
Wherein,
The group of at least one asterisk labelling can be connected on monomer, the oligomeric or polymer-based group;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces; And R
2And R
4As in formula (1a) with the definition (1b).
Preferably, monomeric compound, oligomeric compound or polymerizable compound are formula (3)
Wherein
Z is the group of formula (2);
R
13Be hydrogen; Halogen; Or C
1-C
5Alkyl;
R
14For-CONH-;-COO-; Or phenylene;
R
15Be C
1-C
20Alkylidene; Or C
6-C
20Arlydene;
R
16For-COO-;-OCO-;-CONH-;-NH-CO-O-;-NH-CO-;-SO
2NH-;-NHSO
2-;-SO
2-or-O-;
Q is 0; Or integer; With
R is 0; Or integer.
Chemical compound with formula (2) construction unit is known, is disclosed in for example US-A-4, and in 749,643, the representative example of these chemical compounds is the example 3.1-3.7 on 11-13 hurdle in described list of references.
These examples for compounds with formula (3) construction unit are the example 2.1-2.9 on 11-13 hurdle in described list of references.
Other chemical compound that is used for purposes of the present invention is listed in following table MC1 herein:
In some cases, formula that the present invention uses (1a) and merocyanine chemical compound (1b) are compound known, but also comprise noval chemical compound.
Described noval chemical compound has formula
Wherein
R '
2Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Cyano group; Or R '
1And R '
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
R '
4For-Q '
1-R '
5
Q '
1For-COO-;-CONH-;-CO-;-SO
2-; Or-CONR '
6-;
R '
5Be C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Or unsubstituted or C
1-C
6The C that alkyl replaces
6-C
20Aryl;
R '
6Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
R '
7Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces;
M is 3 to 7;
N is 2 to 4;
O is 2 to 4;
If n=2 is then in formula (in 1 ' a)
R '
1Be alkylidene, cycloalkylidene or phenylene; Or R '
1And R '
2Form alkylidene, cycloalkylidene or phenylene simultaneously; With
R '
3For cyano group or-Q '
1-R '
5Or R '
3And R '
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=2 is then in formula (in 1 ' b)
R '
3Be alkylidene, cycloalkylidene or phenylene; With
R '
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
If n=3 is then in formula (in 1 ' a)
R '
1Be the trivalent alkyl, its randomly by one or more-O-or-NR '
7-group cuts off; With
R '
3For cyano group or-Q '
1-R '
5Or R '
3And R '
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=3 is then in formula (in 1 ' b)
R '
3Be 1,1-alkylidene, 1,1-cycloalkylidene or cyclohexadienylene; With
R '
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R '
1And R '
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
If n=4 is then in formula (in 1 ' a)
R '
1Be the tetravalence alkyl; With
R '
3For cyano group or-Q '
1-R '
5Or R '
3And R '
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=4 is then in formula (in 1 ' b)
R '
3Be the tetravalence alkyl; With
R '
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R '
1And R '
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
The preparation of formula (1a) and chemical compound (1b) can be according to methods known in the art, and for example at US-A-4, the method for 749,643 the 66th row-Di 14 hurdles, the 13rd hurdle the 57th line description is carried out, and this paper is introduced into as a reference.
The chemical compound of formula (1a) can be that initiation material is by the condensation reaction preparation of resorcinol class (dihydroxyresorcines) with primary amine or secondary amine compound with the amino Ketohexamethylene-3 of the 1-of formula (3)
R wherein
1, R
2With n as in formula (1a) definition.With suitable alkylating agent such as the dithyl sulfate alkylation of dimethyl sulfate or other and react with the active chemical compound of suitable methylene (methyllene-active compound compound) subsequently after, obtain the chemical compound of formula (1a).
The initial compounds of formula (3) can carry out the preferred dimethyl sulfoxine of described solvent, N-Methyl pyrrolidone, dimethyl formamide or dimethyl acetylamide with the alkylating agent that suits such as the alkylated reaction of dimethyl sulfate in The suitable solvent.Proton solvent also suits as methanol, ethanol, isobutanol, the tert-butyl alcohol or isopropyl alcohol.This reaction also can be carried out in aliphatic or aromatic solvent such as hexane, toluene or dimethylbenzene.The mixture of ether compound such as diethyl ether and oxolane or halogenated solvent such as chloroform or dichloromethane and these solvents also suits.
This reaction can be carried out-80 ℃ of temperature to the boiling point of reactant mixture, preferred 60 to 120 ℃.
The intermediate of formula (3) is new, and is another theme of the present invention, wherein
R
2Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
3-cut off;
R
3Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Or unsubstituted or C
1-C
6The C that alkyl replaces
6-C
20Aryl;
M is 3 to 7;
N is 2 to 4;
Cyclohexenyl group C is unsubstituted or by one or more C
1-C
5Alkyl replaces;
When n=2,
R
1And R
2Form alkylidene, cycloalkylidene or phenylene simultaneously;
When n=3,
R
1Be the trivalent alkyl, its randomly by one or more-O-or-NR
3-group cuts off;
When n=4,
R
1Be the tetravalence alkyl, its randomly by one or more-O-or-NR
3-group cuts off.
They are the intermediate that can be used for preparing the UV absorbent, and they self are also represented the UV-B absorbent, are used to protect human and animal's hair and skin to avoid the UV irradiation.
Other chemical compound that is used for purposes of the present invention is listed in the table MC1a below this paper:
Suitable especially according to formula of the present invention (1a) and chemical compound (1b) as the UV filter, promptly be used to protect skin and the hair of ultraviosensitive organic substance being avoided the adverse effect, particularly human and animal of UV irradiation.Therefore, these chemical compounds are suitable to the opacifier in cosmetics, pharmaceutical composition and the veterinary formulation.Can use the dissolved form and the micronize state (micronizedstate) of these chemical compounds.
UV absorbent according to the present invention can use its The dissolved (organic filter of the organic filter of solubility, solubilising (solubelized organic filter)) or micronize state (nanoscale filter, the organic filter of microgranule, UV-absorbent colorant).
The formula (1a) and the Merocyanine derivatives (1b) that do not contain alkyl substituent or only comprise low-grade alkyl substituent have poor oil-soluble and dystectic feature.Therefore, suitable to especially the TUV absorbent during their micronize states.
Any known method that is applicable to the preparation microgranule can be used for preparing micronized UV absorbent; for example wet grinding, wet method mediate (wet-kneading), from The suitable solvent spray drying, according to RESS method (supercritical solution rapid expanding method, Rapid Expansion of Supercritical Solutions) carry out swelling, redeposition (the anti-solvent recrystallization of GASR method=gas/PCA method=with spissated anti-solvent deposition) from the suitable solvent that comprises supercritical fluid.
So the micronize UV absorbent that obtains has 0.02 to 2 usually, and preferably from 0.03 to 1.5,0.05 to 1.0 micron average particle size particle size more preferably.
Also can be according to UV absorbent of the present invention as the dry matrices (drysubstrates) of powder type.
Also can be used for the specific support of used for cosmetic according to UV absorbent of the present invention, for example in solid lipid nanoparticle (SLN) or the inertia collosol and gel microcapsule, wherein the UV absorbent be encapsulation (Pharmazie, 2001 (56), p.783-786).
Can also comprise one or more other UV filter according to cosmetic formulations of the present invention or pharmaceutical composition.
Cosmetic formulations or pharmaceutical preparation can use conventional method by physical mixed UV absorbent and the preparation of one or more adjuvants, for example by stirring each composition simply together, especially by utilizing for example dissolution properties of cinnamic acid octyl group methoxyl group ester, the different monooctyl ester of salicylic acid etc. of known cosmetic UV absorbent.The UV absorbent that uses can be, for example do not need further processing, or with the micronize state or with form of powder.
Cosmetic formulations or pharmaceutical preparation comprise a kind of UV absorbent or the UV absorber blend based on the gross weight meter 0.05-40% weight of compositions.
Preferably, the formula according to the present invention (1a) of use and (1b) and the blending ratio of other optional bright protective agent be 1: 99 to 99: 1, be preferably 1: 95 to 95: 1, most preferably be 10: 90 to 90: 10, by weight.Particularly advantageous is that blending ratio is 20: 80 to 0: 20, is preferably 40: 60 to 60: 40, most preferably from about 50: 50.In particular, use such compositions to improve dissolubility or increase UV absorption.
In addition, can be with the suitable other UV filter material of UV absorbent use of the present invention, for example para-amino benzoic acid derivant, for example 4-dimethylaminobenzoic acid 2-ethyl hexyl ester; Salicyclic acid derivatives, for example salicylic acid 2-ethyl hexyl ester; Benzophenone derivates is 2-hydroxyl-4-methoxy benzophenone and its 5-sulfonic acid for example; The dibenzoyl methane derivant, 1-(4-tert-butyl-phenyl)-3-(4-methoxyphenyl) propane-1 for example, 3-diketone; The diphenylacrylate ester, 2-ethylhexyl 2-cyano group-3 for example, 3-diphenylacrylate ester, and 3-(benzofuranyl) 2-cyanoacrylate; 3-imidazol-4 yl acrylic acid and ester thereof; Benzofuran derivatives, especially 2-(p-aminophenyl) benzofuran derivatives is described among EP-A-582 189, US-A-5 338 539, US-A-5 518 713 and the EP-A-613893; Polymer UV absorbent for example is described in the toluenyl malonic ester derivant among the EP-A-709 080; Cinnamic acid derivative, for example 4-methoxy cinnamic acid 2-ethyl hexyl ester and isopentyl ester or be described in US-A-5 601 811 and WO 97/00851 in cinnamic acid derivative; Camphor derivatives, for example 3-(4 '-methyl) benzal-camphane-2-ketone (3-(4 '-methyl) benzylidene-bornan-2-one, 3-benzylidenebornan-2-one); 3-benzal camphane-2-ketone (3-benzylidenebornan-2-one), N-[2 (with 4)-2-oxygen camphane-3-subunit-methyl)-benzyl] acrylamide polymer (N-[2 (and4)-2-oxyborn-3-ylidene-methyl)-benzyl] acrylamide polymer), 3-(4 '-trimethyl ammonium)-benzal-Camphora-2-ketone methylsulfuric acid ester (3-(4 '-trimethyl-ammonium)-benzylidene-bornan-2-one methyl sulfate), 3,3 '-(1,4-phenylene two methines)-two (7,7-dimethyl-2-oxygen-bicyclo-[2.2.1] heptane-1-methanesulfonic acid) (3,3 '-(1,4-phenylenedi-methine)-bis (7,7-dimethyl-2-oxo-bicyclo[2.2.1] heptane-1-methanesulfonic acid)) and salt, 3-(4 '-sulfo group) benzal-Camphora-2-ketone (3-(4 '-sulfo) benzylidene-bornan-2-one) and salt thereof; Camphora benzalkonium methylsulfuric acid ester; The hydroxyphenyltriazinuv chemical compound, 2-(4 '-methoxyphenyl)-4 for example, 6-two (2 '-hydroxyl-4 '-the n-octyloxy phenyl)-1,3, the 5-triazine, 2,4-two { [4-(3-(2-propoxyl group)-2-hydroxyl-propoxyl group)-2-hydroxyl]-phenyl }-6-(4-methoxyphenyl)-1,3, the 5-triazine, 2,4-two { [4-(2-ethylhexyl oxygen)-2-hydroxyl]-phenyl }-6-[4-(2-methoxy ethyl carboxyl)-phenylamino]-1,3, the 5-triazine, 2,4-two [4-(three (trimethyl silyl oxygen base-silicyl propoxyl group)-2-hydroxyls]-phenyl }-6-(4-methoxyphenyl)-1,3, the 5-triazine, 2,4-two [4-(2 " methylpropenyl oxygen base)-the 2-hydroxyl]-phenyl }-6-(4-methoxyphenyl)-1; 3; 5-triazine; 2,4-two [4-(1 ', 1 '; 1 '; 3 ', 5 ', 5 ', 5 '-seven methyl trimethoxy silylation-2 " methyl-propoxyl group)-the 2-hydroxyl]-phenyl }-6-(4-methoxyphenyl)-1; 3,5-triazine; 2,4-two { [4-(3-(2-propoxyl group)-2-hydroxyl-propoxyl group)-2-hydroxyl]-phenyl }-6-[4-ethyl carboxyl)-phenylamino]-1; 3, the 5-triazine; Benzotriazole cpd, for example 2,2 '-methylene-two (6-(2H-benzotriazole-2-yl)-4-(1,1,3, the 3-tetramethyl butyl)-phenol; Three phenylaminos-s-pyrrolotriazine derivatives, for example 2,4,6-three phenylaminos-(to phosphinylidyne-2 '-ethyl-1 '-oxygen)-1,3,5-triazines (2,4,6-trianiline-(p-carbo-2 '-ethyl-1 '-oxy)-1,3,5-triazine) with the UV absorbent that is described among US-A-5 332568, EP-A-517 104, EP-A-507 691, WO 93/17002 and the EP-A-570 838; 2-Phenylbenzimidazole-5-sulfonic acid and salt thereof; Ortho-aminobenzoic acid ester (menthylo-aminobenzoates); The physical sunscreen agent of coating or non-coating, for example titanium dioxide, zinc oxide, ferrum oxide, Muscovitum, MnO, Fe
2O
3, Ce
2O
3, Al
2O
3, ZrO
2(surface coatings: poly-methyl methacrylate base ester, methyl-silicone oil (methylhydrogenpolysi,oxane, be described in CAS 9004-73-3), dimethyl polysiloxane, isopropyl titanium three isostearates (being described in CAS 61417-49-0), metallic soap, for example magnesium stearate (being described in CAS 4086-70-8), perfluor alcohol phosphate ester C for example
9-15Perfluor alcohol phosphate ester (being described in CAS 74499-44-8, JP 5-86984 JP 4-330007).Primary particle size average out to 5nm-35nm, the particle size in dispersion liquid is 100nm-300nm.Also can use the hydroxy amino-benzophenone derivates that is disclosed in DE10011317, EP 1133980 and EP 1046391, be disclosed in phenyl-benzimidizole derivatives of EP 1167358; Be described in " Sunscreens ", Eds.N.J.Lowe, N.A.Shaath, Marcel Dekker, Inc., New York and Basle or in Cosmetics ﹠amp; Toiletries (107), the UV absorbent of 50ff (1992) is as other UV protective substance.
Preferably, following UV filter compositions is particularly advantageous.
-UV-filter compositions (T) comprises
(t
1) at least a formula (1a) or Merocyanine derivatives (1b); With
(t
2) following formula (t
21) triaizine compounds
Wherein,
R
1And R
5Be hydrogen; C
1-C
18Alkyl; Or C
6-C
12Aryl; With
R
6, R
7And R
8Be hydrogen independently of each other; Hydroxyl; Halogen; C
1-C
18Alkyl; C
1-C
18Alkoxyl; C
6-C
12Aryl; Xenyl (biphenylyl); C
6-C
12Aryloxy group; C
1-C
18Alkylthio group; Carboxyl;-COOM; C
1-C
18-alkyl carboxyl; Amino carbonyl; Or single-or two-C
1-C
18Alkylamino; C
1-C
10Acylamino-; Or-COOH.
Most preferably following UV-filter combination comprises
(t
3) chemical compound of formula (MC02); With
(t
4) 1,3,5-triazines; 2,4,6-three [1,1 '-biphenyl]-the 4-base-(9CI) (2,4,6-tris[1,1 '-biphenyl]-4-yl-(9CI)).
Also can use formula (1a) and chemical compound (1b) as wrinkle resistant sensory modifier.
Cosmetic formulations or pharmaceutical preparation can be, for example emulsifiable paste, gel, lotion, alcoholic solution and water/alcoholic solution, emulsion ,/fat composition, bar-shaped preparation (stick preparations), powder or ointment.Except the above-mentioned UV filter of mentioning, cosmetic formulations or pharmaceutical preparation also can further comprise following adjuvant.
As moisture and when containing fat liquor (for example W/O, O/W, O/W/O and W/O/W emulsion or microemulsion), described preparation for example comprises, based on gross weight meter 0.1 to 30% weight of compositions, one or more UV absorbent of preferred 0.1 to 15% weight, especially 0.5 to 10% weight; Based on gross weight meter 1 to 60% weight, especially 5 to 50% weight of compositions, at least a oil ingredient of preferred 10 to 35% weight; Based on gross weight meter 0 to 30% weight, especially 1 to 30% weight of compositions, at least a emulsifying agent of preferred 4 to 20% weight; Gross weight meter 10 to 90% weight, the especially water of 30 to 90% weight based on compositions; With 0 to 88.9% weight, but the other cosmetic adjuvant of 1 to 50% weight especially.
Also comprise one or more additional compounds according to cosmetics of the present invention or pharmaceutical composition/preparation, aliphatic alcohol for example, fatty acid ester, natural or synthetic triglyceride comprises glyceride type and derivant, pearlescent waxes class (pearlescent waxes), hydrocarbon oils, silicone or type siloxane (organic replacement polysiloxane-based), fluorizated or fluoridized oils, emulsifying agent, superfatting agent, surfactant, consistency modifiers/thickening agent and rheology modifier, polymer, bioactive ingredients, the deodorize active component, antidandruff agent, antioxidant, hydrotropic solvent, antiseptic and antibacterial, aromatic oil, coloring agent, polymeric beads (polymeric beads) or hollow ball as the SP reinforcing agent.
Cosmetic formulations or pharmaceutical preparation
Cosmetics or pharmaceutical preparation are included in the cosmetics goods that extensively are.For example, especially following goods:
Skin care, shower goods, cosmetic personal care product, nursing foot goods, sunscreen, skin tanning goods, depigmentation goods, deodorizer, antiperspirant, cleaning or nurse the goods of skin defective (blemished skin), the goods of having a shave, fragrance product or cosmetic hair treatment goods.
The goods that are used for the particular importance of batch skin as the cosmetics goods are sunscreen (light-protective preparations), for example sunscreen (sunmilks), lotion, emulsifiable paste, oil, opacifier (sunblock) or tropicals, pre-tanned goods (pretanning preparation) or solarization back also comprise the skin tanning goods for example from tanned emulsifiable paste (self-tanningcream) with goods (after-sun preparations).Particularly advantageous is the sunscreen of sun-proof emulsifiable paste, sunlight lotion, sunscreen and Sprayable.
Cosmetic formulations of the present invention has the anti-sun damage effect of excellent protection human skin.
Preparation embodiment
Embodiment 1: the preparation of chemical compound MC20
1a. the preparation of starting stage (chemical compound MC01a)
Used water separator reflux 6.04 gram ethylenediamines and the mixture of 31.15 gram 1,1-Dimethyl-3,5-diketocyclohexanes in 200ml toluene 3 hours.Behind the cooling mixture, leach product, with the amount of ethyl acetate washing, at 80 ℃ of vacuum dryings.Productive rate is for almost quantitative.
Mp.＞250℃。
The preparation of embodiment 1b. chemical compound MC2
Under 100 ℃, the 7.61 chemical compound MC14a that restrain are dissolved in the 375ml N-Methyl pyrrolidone, drip 6.50 gram sulphuric acid dimethyl esters and mix.100 ℃ of following stirred reaction mixtures 60 minutes.After being cooled to 80 ℃, 5.81g ethyl cyanoacetate, 5.14 gram triethylamines and 4.3ml isopropyl alcohol are dropwise slowly added.Stirred reaction mixture is 90 minutes under 100 ℃ temperature.After the reaction mixture, leach crude product.Use the mixture of toluene and methanol (6: 4) to carry out the silica gel column chromatography analysis subsequently,, obtain 1.28 gram (10%o.th.) pure products at 80 ℃ of following vacuum dryings.
λ
Max(acetonitrile)=389nm.
Embodiment 2a: the preparation of chemical compound MC06a
Used water separator reflux 9.06 gram 1,1-Dimethyl-3,5-diketocyclohexanes and the mixture of 2.78 gram piperazines in 64ml toluene 5 hours.Behind the cooling mixture, leach product, with the amount of ethyl acetate washing, at 80 ℃ of following vacuum dryings.Productive rate: 75%.
Embodiment 2b: the preparation of chemical compound MC07
3.34 gram dimethyl sulfate are added drop-wise to 4.33 to be digested among the compound MC06a (preparing among the embodiment 2a).Under 100 ℃, stirred reaction mixture 60 minutes.After being cooled to 80 ℃, drip the mixture of the triethylamine of 2.89 gram ethyl cyanoacetates and 5.21 grams.Stirred reaction mixture is 90 minutes under 110 ℃ temperature.After the cooling, add 300ml water, leach crude product.Use the mixture of toluene and methanol (6: 4) to carry out the silica gel column chromatography analysis subsequently,, obtain the pure products of 4.5 grams (65%o.th.) at 80 ℃ of following vacuum dryings.
λ
Max(ethanol)=406nm.
Embodiment 3a: the preparation of chemical compound MC08a
Use water separator reflux 9.06 gram 1,1-Dimethyl-3,5-diketocyclohexanes and 4.30 grams 1, the mixture of 2-diamino-cyclohexane in 64ml toluene 3 hours.
Behind the cooling mixture, leach product, with the amount of ethyl acetate washing, at 80 ℃ of following vacuum dryings.Productive rate 95% product.
The preparation of embodiment 3b. chemical compound MC10
22.86 gram dimethyl sulfate are added drop-wise among the chemical compound MC06a of 16.99 grams.Under 100 ℃, stirred reaction mixture 60 minutes.After being cooled to 80 ℃, the triethylamine treatment mixture with 13.50 grams stirred 10 minutes.Slowly drip the mixture of 16,72 gram diethyl malonates and 28.89 gram DBU then.100 ℃ of following stirred reaction mixtures 90 minutes.After the cooling, add 300mL water, leach crude product.Use the mixture of toluene and methanol (6: 4) to carry out the silica gel column chromatography analysis subsequently,, obtain 21.28 gram (70%o.th.) pure products at 80 ℃ of following vacuum dryings.
λ
Max(ethanol)=373nm.
Embodiment 3c: the preparation of chemical compound MC09
MC09a and 30ml dimethyl sulfate with 17.93 grams (0.05mol) in oil bath are heated to 100 ℃, and stir 40 minutes in this temperature.Reaction mixture to 60 ℃ adds the mixture of 11.93 gram (0.103mol) ethyl cyanoacetates and 8.25 gram (0.120mol) Sodium ethylate in the 50ml alcoholic solution, stirs 40 minutes down at 110 ℃, wherein steams in reaction and removes ethanol.Reaction mixture is used H
2O precipitates chemical compound, the suction extraction.Use 9: 1 toluene and acetone mixture to carry out column chromatography (Kieselgel) subsequently,, obtain pure products at 80 ℃ of following vacuum dryings.
Productive rate: 23.3 grams (85%d.Th.).
Embodiment 4: the preparation of micronized UV absorbent
With the chemical compound of 100 parts formula MC2 and zirconium silicate particles (diameter: 0,1 to 4mm), dispersant (15 parts C as grinding aid
8-C
16Polyglucoside) and water (85 parts) to be milled to average particle size particle size in ball mill be d
50=200nm.Obtain little dispersible pigment dispersion of UV absorbent with this method.
Application Example
Embodiment 5:UV-A/UV-B daily nursing UV protects lotion (Daily care UV protectionlotion)
| The INCI-title | %w/w (according to what supply) | |
| Part A | Oleic alcohol polyoxyethylene ether-3 phosphate ester (Oleth-3Phosphate) | 0.60 |
| Brij-721-21 | 2.50 | |
| Brij-721-2 | 1.00 | |
| Spermol | 0.80 | |
| Stearyl alcohol | 1.50 | |
| Mountain Yu acid glycerol three esters (Tribehenin) | 0.80 | |
| 2-Methylpentadecane | 8.00 | |
| Ethylhexyl Methoxycinnamate (Ethylhexyl Methoxycinnamate) | 5.00 | |
| Part B | Water | In right amount to 100 |
| Glycerol | 2.00 | |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 3.00 | |
| The EDTA disodium | 0.10 | |
| Portion C | Water | 20.00 |
| Diimidazole ureine (Diazolidinyl Urea) and butyl carbamic acid iodo propinyl ester (Iodopropynyl Butylcarbamate) | 0.15 | |
| Propylene glycol | 4.00 | |
| Part D | Sodium acrylate copolymer (with) vaseline oil (with) PPG-1 tridecyl polyoxyethylene ether-6 (PPG-1Trideceth-6) | 1.50 |
| D5 | 4.50 | |
| PEG-12 dimethyl polysiloxane (PEG-12Dimethicone) | 2.00 | |
| Alpha-tocopherol acetate | 0.45 | |
| Water (with) citric acid | In right amount | |
| Part E | Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 75 ℃ respectively.Under continuous stirring, part A is poured among the part B.Immediately D5 and the PEG-12 dimethyl polysiloxane of part D joined in the mixture after the emulsifying.Use Ultra Turrax with 11000rpm homogeneous mixture 30 seconds then.After being cooled to 65 ℃, the adding sodium acrylate copolymer (with) vaseline oil (with) PPG-1 tridecyl polyoxyethylene ether-6.Under＜50 ℃ temperature, add portion C.Under≤35 ℃ temperature, add alpha-tocopherol acetate, then water (with) the Fructus Citri Limoniae acid for adjusting pH.Add part E under the room temperature.
Lotion between embodiment 6:UV day (day lotion)
| The INCI-title | %w/w (according to what supply) | |
| Part A | Phosphoric acid hexadecane ester | 1.75 |
| Benzoic acid C12-C15 Arrcostab | 5.00 | |
| Cetearyl alcohol/PEG-20 stearate (Cetearyl Alcohol/PEG-20Stearate) | 2.00 | |
| Ethoxydiglycol oleate (Ethoxydiglycol Oleate) | 2.00 | |
| Stearic acid | 1.50 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Isononyl isononanoate (Isononyl Isononanoate) | 2.00 | |
| Part B | Water | In right amount to 100 |
| Xanthan gum | 0.35 | |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 5.00 | |
| The EDTA disodium | 0.20 | |
| Propylene glycol | 2.00 | |
| The diimidazole ureine (with) methyl parahydroxybenzoate (with) propyl p-hydroxybenzoate (with) propylene glycol | 0.70 | |
| Glycerol | 1.50 | |
| Portion C | D5 (with) dimethyl polysiloxane alcohol (Dimethiconol) | 1.00 |
| Ethoxydiglycol | 3.00 | |
| Dimethyl polysiloxane | 2.00 | |
| Part D | Triethanolamine | In right amount |
The preparation explanation
Part A is by all the components is mixed, and stirs and be heated to 75 ℃ of preparations then under appropriate speed.Preparation part B also is heated to 75 ℃.Under this temperature, under increasing progressively mixing speed with in the part B impouring part A.Then homogeneous mixture (30 seconds, 15000rpm).Under＜55 ℃ temperature, add the composition of portion C.Cooling mixture under appropriateness stirs is checked pH then, and is regulated with triethanolamine.
Embodiment 7: sun-proof Emulsion (sun protection emulsion)
| The INCI-title | %w/w (according to what supply) | |
| Part A | Cetearyl alcohol (with) DCP (with) spermaceti polyoxyethylene ether-10 phosphate ester (Ceteth-10Phosphate) | 4.00 |
| Benzoic acid C12-15 Arrcostab | 2.00 | |
| Dicaprylyl ether | 3.00 | |
| The ethoxydiglycol oleate | 2.00 | |
| Stearic acid | 1.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Sodium acrylate copolymer (with) Glycine Soja (with) PPG-1 tridecyl polyoxyethylene ether-6 | 0.30 | |
| Squalane | 3.50 | |
| Part B | Water | In right amount to 100 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 5.00 | |
| Portion C | The diimidazole ureine (with) butyl carbamic acid iodo propinyl ester | 0.15 |
| Propylene glycol | 2.50 | |
| Water | 10.00 | |
| Part D | D5, dimethyl polysiloxane alcohol | 2.00 |
| Ethoxydiglycol | 5.00 | |
| D5 (with) dimethyl polysiloxane/vinyl-dimethyl polysiloxane cross linked polymer | 2.00 | |
| Part E | Sodium hydroxide | 0.10 |
The preparation explanation
Part A is by all the components is mixed, and stirs and be heated to 75 ℃ of preparations then under appropriate speed.Preparation part B also is heated to 75 ℃.Under this temperature, under increasing progressively mixing speed with in the part B impouring part A.Being lower than under 65 ℃, add the composition of part D respectively.After under appropriateness stirs, being cooled to 55 ℃, add portion C.Check pH then, regulate with sodium hydroxide.Homogeneous mixture is 30 seconds under 16000rpm.
Embodiment 8: daily lotion (every day lotion)
| The INCI-title | %w/w (according to what supply) | |
| Part A | The phosphoric acid stearyl | 5.00 |
| Tricontanyl PVP | 1.00 | |
| The ethoxydiglycol oleate | 3.00 | |
| Squalane | 5.00 | |
| Benzoic acid C12-15 Arrcostab | 5.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Tristerin | 2.00 | |
| Spermol | 2.00 | |
| Part B | Water | 20.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 3.00 | |
| Portion C | Water | In right amount to 100 |
| The INCI-title | %w/w (according to what supply) | |
| Brij-721-10 allyl ethers/acrylate copolymer | 0.50 | |
| Glycerol | 2.50 | |
| The diimidazole ureine (with) butyl carbamic acid iodo propinyl ester | 0.15 | |
| The lauryl sodium glutamate | 0.70 | |
| Part D | D5 (with) dimethyl polysiloxane alcohol | 1.50 |
| Triethanolamine | 1.85 |
The preparation explanation
Part A is by all the components is mixed, and stirs and be heated to 75 ℃ of preparations then under appropriate speed.The preparation portion C also is heated to 75 ℃.Under appropriateness stirs, portion C is joined in the part A.Add part B after the emulsifying immediately, then with the neutralization of part triethanolamine.Homogeneous mixture 30 seconds.After under appropriateness stirs, cooling off, the adding D5 (with) dimethyl polysiloxane alcohol.Be lower than under 35 ℃, checking pH, and regulating with triethanolamine.
Embodiment 9: the sun-proof Emulsion that can spray
| The INCI-title | %w/w (according to what supply) | |
| Part A | Cetearyl alcohol polyoxyethylenated alcohol-15 (with) tristerin | 3.00 |
| Stearyl alcohol | 1.00 | |
| The castor oil acid cetyl | 0.80 | |
| Dicaprylyl ether (Dicaprylyl Ether) | 3.00 | |
| Benzoic acid C12-15 Arrcostab | 3.00 | |
| 2-Methylpentadecane | 2.50 | |
| The stearyl dimethyl polysiloxane | 1.00 | |
| The ethylhexyl Methoxycinnamate | 4.00 | |
| Spermol | 0.80 | |
| Two-C12-13 alkyl tartrate | 3.00 | |
| Part B | Water | In right amount to 100 |
| Brij-721-10 allyl ethers/acrylate copolymer | 0.45 | |
| PEG-7 glycerol cocoa ester | 2.50 | |
| Glycerol | 2.00 | |
| Propylene glycol | 3.00 | |
| Portion C | The diimidazole ureine (with) butyl carbamic acid iodo propinyl ester | 0.15 |
| Water | 20.00 | |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 12.00 | |
| Titanium dioxide (with) Silicon stone (with) sodium polyacrylate | 8.00 | |
| Part D | D5 (with) dimethyl polysiloxane alcohol (Dimethiconol) | 0.85 |
| Part E | Sodium hydroxide (with) water | In right amount to pH 6.50-7.00 |
| Part F | Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 80 ℃.Under agitation part A is sneaked among the part B usefulness Ultra Turrax even 30 seconds with 11000rpm.C to 60 ℃ of heating part, and slowly join in the Emulsion.After being cooled to 40 ℃, at room temperature, add part D and part E.
Embodiment 10: the daily nursing lotion
| The INCI-title | %w/w (according to what supply) | |
| Part A | Polyglyceryl methyl glucoside distearate | 2.50 |
| Cetearyl alcohol (Cetearyl Alcohol) | 2.00 | |
| Octyl stearate | 3.00 | |
| Caprylic/capric triglyceride | 4.00 | |
| 2-Methylpentadecane | 4.00 | |
| The ethylhexyl Methoxycinnamate | 2.70 | |
| Part B | Water | 64.80 |
| Glycerol | 5.00 | |
| Phenoxyethanol (with) methyl parahydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethylparaben (with) propyl p-hydroxybenzoate | 0.50 | |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 | |
| Portion C | Cyclomethicone (with) dimethyl polysiloxane | 3.00 |
| Part D | Brij-721-10 allyl ethers/acrylate copolymer | 0.50 |
The preparation explanation
Part A and part B are heated to 75 ℃.Under agitation part A is sneaked among the part B even 1 minute minute with 11000rpm.After being cooled to 50 ℃, under continuous stirring, add portion C.After being cooled to 30 ℃, add part D.Regulating pH afterwards is 6.00-6.50.
The agent of embodiment 11:UV protection daily nursing
| The INCI-title | %w/w (according to what supply) | |
| Part A | Tristerin SE | 3.00 |
| Tristerin and PEG-100 stearate | 3.50 | |
| Spermol | 1.50 | |
| Myristyl myristate | 2.00 | |
| Isopropyl palmitate | 2.50 | |
| Vaseline oil (Paraffinum Perliquidum) | 5.00 | |
| Octyldimethyl para-amino benzoic acid (Octyl diemthyl PABA) | 3.00 | |
| Part B | Water | In right amount to 100 |
| Propylene glycol | 7.50 | |
| Phenoxyethanol (with) methyl parahydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethylparaben (with) propyl p-hydroxybenzoate | 1.00 | |
| Portion C | Water | 30.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 10.00 | |
| Part D | Sodium acrylate copolymer (with) vaseline oil (with) PPG-1 tridecyl polyoxyethylene ether-6 | 2.00 |
| The INCI-title | %w/w (according to what supply) | |
| Part E | Citric acid | 0.30 |
The preparation explanation
Part A and B are heated to 75 ℃ respectively.After joining part B in the part A, with Ultra Turrax with 11000rpm homogeneous mixture 1 minute.After being cooled to 50 ℃, add portion C.Afterwards, with 16000rpm homogeneous mixture 1 minute.Under＜40 ℃ temperature, add part D.At room temperature regulating the pH-value with part E is 6.00 to 6.50.
Embodiment 12:O/W day is protected lotion with UV
| The INCI-title | %w/w (according to what supply) | |
| Part A | Tristerin (with) the PEG-100 stearate | 5.00 |
| Stearyl alcohol | 1.00 | |
| Tripalmitin | 0.70 | |
| Dimethyl polysiloxane | 2.00 | |
| Benzoic acid C12-15 Arrcostab | 5.00 | |
| Isopropyl palmitate | 5.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Part B | Water | In right amount to 100 |
| Polysorbate 60 | 0.50 | |
| Glycerol | 3.00 | |
| Portion C | Water | 10.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 | |
| Part D | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.70 |
| Brij-721-10 allyl ethers/acrylate copolymer | 1.50 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Part F | Aromatic | In right amount |
The preparation explanation
Part A and B are heated to 750 ℃ respectively, part ℃ is heated to 60 ℃.Afterwards, under agitation with in the part B impouring part A.With 11000rpm homogeneous mixture 30 seconds, add portion C with Ultra Turrax.After being cooled to 40 ℃, add part D.At room temperature, regulating the pH-value with sodium hydroxide is 6.30 to 6.70, adds part F.
Embodiment 13:O/W day is used the UV protective agent
| The INCI-title | %w/w (according to what supply) |
| The INCI-title | %w/w (according to what supply) | |
| Part A | Tristerin (with) the PEG-100 stearate | 5.00 |
| Stearyl alcohol | 1.00 | |
| Tripalmitin | 0.70 | |
| Dimethyl polysiloxane | 2.00 | |
| Benzoic acid C12-15 Arrcostab | 5.00 | |
| Isopropyl palmitate | 5.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Part B | Water | In right amount to 100 |
| Polysorbate 60 | 0.50 | |
| Glycerol | 3.00 | |
| Portion C | Water | 10.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 | |
| Part D | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.70 |
| Brij-721-10 allyl ethers/acrylate copolymer | 1.50 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Part F | Aromatic | In right amount |
The preparation explanation
Part A and B are heated to 75 ℃ respectively, portion C is heated to 60 ℃.Afterwards, under agitation with in the part B impouring part A.With 11000rpm homogeneous mixture 30 seconds, add portion C with Ultra Turrax.After being cooled to 40 ℃, add part D.At room temperature, regulating the pH-value with sodium hydroxide is 6.30 to 6.70, adds part F.
Embodiment 14: sunscreen cream (Sunscreen Cream)
| The INCI-title | %w/w (according to what supply) | |
| Part A | Cetearyl alcohol (with) DCP (with) spermaceti polyoxyethylene ether-10 phosphate ester | 4.50 |
| Benzoic acid C12-15 Arrcostab | 6.00 | |
| Caprylic/capric triglyceride | 7.00 | |
| Pentaerythritol tetraoctyl stearate | 2.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| P-methoxycinnamic acid isopentyl ester | 2.00 | |
| Part B | Water | In right amount to 100 |
| Glycerol | 2.00 | |
| Propylene glycol | 1.50 | |
| Magnesiumaluminumsilicate | 1.20 | |
| Portion C | Brij-721-10 allyl ethers/acrylate copolymer | 0.50 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 12.00 | |
| Part D | Phenyl trimethyl polysiloxanes (phenyl Trimethicone) | 1.50 |
| Phenoxyethanol (with) methyl parahydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethylparaben (with) propyl p-hydroxybenzoate | 0.70 | |
| Part E | Sodium hydroxide | 0.90 |
The preparation explanation
Part A and B are heated to 75 ℃ respectively, under continuous stirring, part B are joined in the part A, use Ultra Turrax then with 11000rpm homogeneous mixture 30 seconds.After being cooled to 60 ℃, add portion C.Add down portion C at 40 ℃, even 15 seconds with 11000rpm.At room temperature, regulate the pH-value with part E.
Embodiment 15:UVA/UVB daily nursing lotion, type O/W
| The INCI-title | %w/w (according to what supply) | |
| Part A | Tristerin (with) the PEG-100 stearate | 5.00 |
| Stearyl alcohol | 1.00 | |
| Tripalmitin | 0.70 | |
| Mineral oil | 15.00 | |
| Part B | Water | In right amount to 100 |
| Polysorbate 60 | 0.50 | |
| Glycerol | 3.00 | |
| Portion C | Water | 10.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 | |
| Part D | Brij-721-10 allyl ethers/acrylate copolymer | 1.50 |
| Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.70 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Part F | Aromatic | In right amount |
The preparation explanation
Part A and B are heated to 75 ℃ respectively, portion C is heated to 60 ℃.Under agitation with in the part B impouring part A., portion C is joined in the mixture of A/B after even 1 minute with 11000rpm.After being cooled to 40 ℃, add part D.At room temperature, regulating the pH-value with sodium hydroxide is 6.30 to 6.70, adds part F.
Embodiment 16:UVA/UVB daily nursing lotion, type O/W
| The INCI-title | %w/w (according to what supply) | |
| Part A | Oleic alcohol polyoxyethylene ether-3 phosphate ester | 0.60 |
| Brij-721-21 | 2.50 | |
| Brij-721-2 | 1.00 | |
| Spermol | 0.80 | |
| Stearyl alcohol | 1.50 | |
| Mountain Yu acid glycerol three esters | 0.80 | |
| 2-Methylpentadecane | 8.00 | |
| Part B | Water | In right amount to 100 |
| The INCI-title | %w/w (according to what supply) | |
| Glycerol | 2.00 | |
| The EDTA disodium | 0.10 | |
| Portion C | D5 | 4.50 |
| The PEG-12 dimethyl polysiloxane | 2.00 | |
| Part D | Sodium acrylate copolymer (with) mineral oil (with) PPG-1 tridecyl polyoxyethylene ether-6 | 1.50 |
| Part E | The UV-absorbent dispersion liquid of describing among the embodiment 4 | 10.00 |
| Part F | Alpha-tocopherol acetate | 0.45 |
| DMDM Hydantoin (with) butyl carbamic acid iodo propinyl ester (with) water (with) butanediol | 0.85 | |
| Part G | Water (with) citric acid | In right amount |
| Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 75 ℃ respectively.Under agitation part A is poured among the part B.After emulsifying, immediately portion C is joined in the mixture, and with Ultra Turrax with 11000rpm even 30 seconds.After being cooled to 65 ℃, at 50 ℃, with sodium acrylate copolymer (with) mineral oil (with) PPG-1 tridecyl polyoxyethylene ether-6 slowly joins in the UV absorbent dispersion liquid.Under about 35-30 ℃, add part F.Regulating pH with part G is 5.5 and 6.5.
Embodiment 17:UV-A/UV-B day is with protecting lotion O/W
| The INCI-title | %w/w (according to what supply) | |
| Part A | GLYCERYL DILAURATE | 2.00 |
| The palm acid ethyl hexyl ester | 6.00 | |
| Spermol | 1.00 | |
| Tristerin | 2.00 | |
| Polyoxyethylene lauryl ether-23 | 1.00 | |
| Isopropyl palmitate | 2.00 | |
| Mountain Yu acid glycerol three esters | 0.80 | |
| Cera Flava | 1.50 | |
| Lanolin oil | 1.00 | |
| Part B | Water | In right amount to 100 |
| Propylene glycol | 4.00 | |
| Water (with) titanium dioxide (with) aluminium oxide (with) Polymeric sodium metaphosphate. (with) phenoxyethanol (with) methyl P-hydroxybenzoic acid sodium | 4.00 | |
| Portion C | Brij-721-10 allyl ethers/acrylate copolymer | 1.00 |
| Part D | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 1.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 | |
| Part E | Water (with) sodium hydroxide | In right amount |
The preparation explanation
Part A and part B are heated to 80 ℃ respectively.Under agitation part A is poured among the part B usefulness Ultra Turrax even 30 seconds with 11000rpm.After being cooled to 60 ℃, add portion C,, under continuous stirring, slowly add part D at 40 ℃.Regulating pH with part E is 6.50-7.00.
Embodiment 18: the sunlight lotion that can spray (sunscreen lotion)
| The INCI-title | %w/w (according to what supply) | |
| Part A | Cetyl potassium phosphate (Potassium Cetyl Phosphate) | 0.20 |
| 2-Methylpentadecane | 7.00 | |
| VP/ eicosylene copolymer | 1.50 | |
| Two-C12-13 alkyl tartrate | 6.00 | |
| The ethylhexyl triazinone | 2.50 | |
| Benzoic acid C12-15 Arrcostab | 4.50 | |
| Part B | Water | In right amount to 100 |
| Sorbitol polyoxyethylene ether-30 (Sorbeth-30) | 2.00 | |
| Sorbitan monostearate (with) sucrose cocoa ester | 4.00 | |
| Titanium dioxide (with) aluminium oxide (with) Silicon stone (with) sodium polyacrylate | 2.50 | |
| Portion C | Water | 30.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 12.00 | |
| Part D | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.70 |
| Part E | Water (with) citric acid | In right amount |
The preparation explanation
Part A and part B are heated to 80 ℃ respectively, and portion C is heated to 50 ℃..Part A is poured among the part B usefulness Ultra Turrax even 1 minute with 11000rpm.After being cooled to 50 ℃, under continuous stirring, add portion C,, add part D, even 10 seconds with 11000rpm at 40 ℃.Regulate pH with part E.
Embodiment 19:O/W day is protected lotion (protection lotion) with UV
| The INCI-title | %w/w (according to what supply) | |
| Part A | Tristerin (with) the PEG-100 stearate | 5.00 |
| Stearyl alcohol | 1.00 | |
| Tripalmitin | 0.70 | |
| Dimethyl polysiloxane | 2.00 | |
| Caprylic/capric triglyceride | 5.00 | |
| Isopropyl palmitate | 5.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Part B | Water | In right amount to 100 |
| Polysorbate 60 | 0.50 | |
| Glycerol | 3.00 | |
| Portion C | Water | 10.00 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 |
| The INCI-title | %w/w (according to what supply) | |
| Part D | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.70 |
| Brij-721-10 allyl ethers/acrylate copolymer | 1.50 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Part F | Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 75 ℃ respectively, portion C is heated to 60 ℃.Afterwards, under agitation, B is poured in the part A with part.With 11000rpm homogeneous mixture 30 seconds, add portion C with Ultra Turrax.After being cooled to 40 ℃, add part D.At room temperature, regulating the pH-value with sodium hydroxide is 6.30 to 6.70, adds part F.
Embodiment 20: the sun-proof Emulsion of water proofing property
| The INCI-title | %w/w (according to what supply) | |
| Part A | Polyglyceryl-10-the five kinds of stiffness in infant fat acid ester (with) docosanol (with) sodium stearoyl lactate (Sodium Stearoyl Lactylate) | 2.50 |
| VP/ eicosylene copolymer | 1.50 | |
| Stearyl alcohol | 1.50 | |
| Squalane | 4.00 | |
| Benzoic acid C12-15 Arrcostab | 7.50 | |
| Octocrylene (Octocrylene) | 1.50 | |
| 4 methyl benzylidene camphor | 3.00 | |
| The ethylhexyl Methoxycinnamate | 2.00 | |
| Part B | Water | In right amount to 100 |
| Glycerol | 1.80 | |
| Brij-721-10 allyl ethers/acrylate copolymer | 0.80 | |
| Portion C | The UV-absorbent dispersion liquid of describing among the embodiment 4 | 9.00 |
| Part D | VP/ hexadecene copolymer | 2.70 |
| Cyclomethicone | 1.50 | |
| Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.70 | |
| Part E | Water (with) alpha-tocopherol acetate (with) caprylic/capric triglyceride (with) polyoxyethylene sorbitan monoleate (with) lecithin | 3.50 |
| Part F | Aromatic | In right amount |
| Water (with) sodium hydroxide | In right amount |
The preparation explanation
Part A and part B are heated to 80 ℃ respectively.Under continuous stirring, part A is poured among the part B.Use Ultra Turrax with 11000rpm homogeneous mixture 1 minute afterwards.After being cooled to 60 ℃, add portion C.Under 40 ℃, add part D, once more the homogeneous mixture short period.Under 35 ℃, add part E, add aromatic in room temperature.Regulate pH with sodium hydroxide at last.
Embodiment 21:UVA/UVB sunlight lotion, the O/W type
| The INCI-title | %w/w (according to what supply) | |
| Part A | The cetyl potassium phosphate | 2.00 |
| Tricontanyl PVP | 1.00 | |
| Caprylic/capric triglyceride | 5.00 | |
| Benzoic acid C12-15 Arrcostab | 5.00 | |
| Different n-nonanoic acid cetearyl ester (Cetearyl Isononanoate) | 5.00 | |
| Tristerin | 3.00 | |
| Spermol | 1.00 | |
| Dimethyl polysiloxane | 0.10 | |
| The ethylhexyl Methoxycinnamate | 5.00 | |
| Part B | Water | In right amount to 100 |
| Glycerol | 3.00 | |
| Portion C | Brij-721-10 allyl ethers/acrylate copolymer | 0.50 |
| Part D | The UV-absorbent dispersion liquid of describing among the embodiment 4 | 8.00 |
| Part E | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 1.00 |
| Part F | Water (with) sodium hydroxide | In right amount to pH 7.00 |
| Part G | Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 80 ℃ respectively.Under appropriateness stirs, in part B impouring part A.With Ultra Turrax with 11000rpm homogeneous mixture 1 minute.After being cooled to 70 ℃, under agitation add portion C.After being cooled to 50 ℃, add part D very slowly.At 40 ℃, add part E.At room temperature, regulating pH with part F is 7.00, adds part G.
Embodiment 22:UVA/UVB sunlight lotion, the O/W type
| The INCI-title | %w/w (according to what supply) | |
| Part A | The cetyl potassium phosphate | 2.00 |
| Tricontanyl PVP | 1.00 | |
| Caprylic/capric triglyceride | 5.00 | |
| Benzoic acid C12-15 Arrcostab | 5.00 | |
| Different n-nonanoic acid cetearyl ester | 5.00 | |
| Tristerin | 3.00 | |
| Spermol | 1.00 | |
| Dimethyl polysiloxane | 0.10 | |
| The ethylhexyl Methoxycinnamate | 5.00 |
| The INCI-title | %w/w (according to what supply) | |
| Part B | Water | In right amount to 100 |
| Glycerol | 3.00 | |
| Portion C | Brij-721-10 allyl ethers/acrylate copolymer | 0.50 |
| Part D | The UV-absorbent dispersion liquid of describing among the embodiment 4 | 20.00 |
| Part E | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 1.00 |
| Part F | Water (with) sodium hydroxide | In right amount to pH 7.00 |
| Part G | Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 80 ℃ respectively.Under appropriateness stirs, in part B impouring part A.With Ultra Turrax with 11000rpm homogeneous mixture 1 minute.After being cooled to 70 ℃, under agitation add portion C.After being cooled to 50 ℃, add part D very slowly.At 40 ℃, add part E.At room temperature, regulating pH with part F is 7.00, adds part G.
Embodiment 23: sunlight lotion
| The INCI-title | %w/w (according to what supply) | |
| Part A | Cetearyl alcohol (with) DCP (with) spermaceti polyoxyethylene ether-10 phosphate ester | 4.00 |
| Benzoic acid C12-15 Arrcostab | 2.00 | |
| Dicaprylyl ether | 3.00 | |
| The ethoxydiglycol oleate | 2.00 | |
| Stearic acid | 1.00 | |
| The ethylhexyl Methoxycinnamate | 3.00 | |
| Sodium acrylate copolymer (with) glycine Soja (with) PPG-1 tridecyl polyoxyethylene ether-6 | 0.30 | |
| Squalane | 3.50 | |
| VP/ eicosylene copolymer | 2.00 | |
| Part B | Water | In right amount to 100 |
| The UV-absorbent dispersion liquid of describing among the embodiment 4 | 5.00 | |
| Portion C | The diimidazole ureine (with) butyl carbamic acid iodo propinyl ester | 0.15 |
| Propylene glycol | 2.50 | |
| Water | 10.00 | |
| Part D | D5 (with) dimethyl polysiloxane alcohol | 2.00 |
| Ethoxydiglycol | 5.00 | |
| D5 (with) dimethyl polysiloxane/vinyl-dimethyl based polysiloxane cross linked polymer | 2.00 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Part F | Aromatic | In right amount |
The preparation explanation
Part A and part B are heated to 75 ℃ respectively.Under the mixing speed that increases progressively, B is poured in the part A with part.Under＜65 ℃ temperature, add the composition of part D respectively.After being cooled to 55 ℃, under stirring, appropriateness adds portion C.Under＜35 ℃ temperature, check that pH is, and regulate, usefulness Ultra Turrax even 30 seconds with 11000rpm with sodium hydroxide.At room temperature, add part F.
Embodiment 24:W/O sunlight lotion
| The INCI-title | %w/w (according to what supply) | |
| Part A | The PEG-7 castor oil hydrogenated | 3.00 |
| Polyglyceryl-3 diisopstearate | 4.00 | |
| Microwax | 1.00 | |
| Magnesium stearate | 1.50 | |
| Propyl p-hydroxybenzoate | 0.10 | |
| Mineral oil | 15.00 | |
| Octyldodecanol | 8.00 | |
| The ethylhexyl triazinone | 1.00 | |
| The ethylhexyl Methoxycinnamate | 2.00 | |
| Part B | Water | In right amount to 100 |
| Water (with) citric acid | 0.05 | |
| Methyl parahydroxybenzoate | 0.15 | |
| Magnesium sulfate | 0.50 | |
| Portion C | The UV-absorbent dispersion liquid of describing among the embodiment 4 | 9.00 |
| Aromatic | In right amount |
The preparation explanation
Under agitation part A is heated to 80 ℃.B joins part A with part, usefulness UltraTurrax even 1 minute with 11000rpm.After being cooled to 30 ℃, add portion C.
Embodiment 25: skin protection sunlight lotion W/O
| The INCI-title | %w/w (according to what supply) | |
| Part A | Polyglyceryl-2 dimerization hydroxy stearic acid ester | 3.00 |
| Olein | 3.00 | |
| Different n-nonanoic acid cetearyl ester | 7.00 | |
| Lauric acid hexyl ester | 6.00 | |
| Dicaprylyl ether | 6.00 | |
| Propyl p-hydroxybenzoate | 0.10 | |
| Hexyldecanol | 3.00 | |
| Magnesium stearate | 1.00 | |
| Cera Flava | 1.00 | |
| The ethylhexyl Methoxycinnamate | 4.00 | |
| Part B | Water | In right amount to 100 |
| Methyl parahydroxybenzoate | 0.15 | |
| Magnesium sulfate | 1.00 |
| The INCI-title | %w/w (according to what supply) | |
| Portion C | The UV-absorbent dispersion liquid of describing among the embodiment 4 | 6.00 |
The preparation explanation
Under gentle agitation, part A is heated to 80 ℃.B joins part A with part, with 11000rpm even 1 minute.After being cooled to 30 ℃, under continuous stirring, add portion C.
Embodiment 26:O/W Emulsion
| The INCI-title | %w/w (according to what supply) | |
| Part A | The UV absorbent of formula (MC10) | 3 grams |
| Oleum sesami | 10 grams | |
| Tristerin | 4 grams | |
| Stearic acid | 1 gram | |
| Spermol | 0.5 gram | |
| Polysorbate 20 | 0.2 gram | |
| Part B | Propylene glycol | 4 grams |
| Propyl p-hydroxybenzoate | 0.05 gram | |
| Methyl parahydroxybenzoate | 0.15 gram | |
| Triethanolamine | 0.1 gram | |
| Carbomer 934 | 0.1 gram | |
| Water | Add to 100ml |
The preparation of Emulsion
Phase (A):
At first, the UV absorbent is dissolved in the Oleum sesami.Other component and the mixing that add (A).
Phase (B):
Propyl p-hydroxybenzoate and methyl parahydroxybenzoate are dissolved in the propylene glycol.The water that adds 60ml then is heated to 70 ℃, then emulsifying carbomer 934 therein.
Emulsifying
Can descend in powerful application machine (A) slowly joined in (B).By adding the entry adjusted volume to 100ml.
Embodiment 27: daily nursing frost (daily care cream), type O/W
| The INCI title | %w/w (during use) | |
| Part A | Tristerin (with) cetearyl alcohol (with) hexadecyl palmitate (with) cocoa glyceride | 4.0 |
| Cetearyl alcohol polyoxyethylenated alcohol-12 | 4.0 |
| The INCI title | %w/w (during use) | |
| Cetearyl alcohol | 2.0 | |
| Dicaprylyl ether | 4.5 | |
| The stearic acid ethyl hexyl ester | 4.0 | |
| Lauric acid hexyl ester | 3.5 | |
| The ethylhexyl triazinone | 1.0 | |
| The toluenyl malonic ester polysiloxanes | 2.0 | |
| HDI/ trihydroxy methyl hexyl lactone cross-linked copolymer (with) Silicon stone | 5.0 | |
| The stearyl dimethyl polysiloxane | 1.0 | |
| Dimethyl polysiloxane | 2.0 | |
| Spermol | 0.8 | |
| The chemical compound of formula (MC10) | 2.0 | |
| Part B | Water | In right amount to 100 |
| Water (with) scleroglucan (with) phenoxyethanol | 2.0 | |
| Glycerol | 2.0 | |
| Portion C | Brij-721-10 allyl ethers/acrylate copolymer | 0.45 |
| Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.7 | |
| Part D | Water (with) alpha-tocopherol acetate (with) caprylic/capric triglyceride (with) polyoxyethylene sorbitan monoleate (with) lecithin | 4.0 |
| Part E | Water (with) sodium hydroxide | In right amount |
| Aromatic | In right amount |
Preparation method
Part A and part B are heated to 80 ℃ respectively.Under agitation with among the part A impouring part B.Use Ultra Turrax with 11000rpm homogeneous mixture 20 seconds afterwards.Mixture is cooled to 60 ℃, adds portion C.Being lower than under 30 ℃ the temperature, add part D, regulating pH value with sodium hydroxide is 6.5 to 7.0.Add aromatic at last.
Embodiment 28: sun-proof emulsifiable paste, type O/W
| The INCI title | %w/w (during use) | |
| Part A | Polyglyceryl-3-methyl glucoside distearate | 2.0 |
| Decyl oleate | 5.7 | |
| Isopropyl palmitate | 5.8 | |
| Caprylic/capric triglyceride | 6.5 | |
| The chemical compound of formula (MC10) | 2.0 | |
| The ethylhexyl Methoxycinnamate | 5.0 | |
| Spermol | 0.7 | |
| Part B | Glycerol | 3.0 |
| Carbomer | 0.3 | |
| Water | In right amount to 100 | |
| Portion C | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.5 |
| Part D | Di-2-ethylhexylphosphine oxide-benzotriazole base tetramethyl butyl phenol (Methylene bis-benzotriazolyl | 8.0 |
| The INCI title | %w/w (during use) | |
| Tetramethylbutylphenol) (with) water (with) decyl glucoside (with) propylene glycol (with) xanthan gum | ||
| Water | 20.0 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Aromatic | In right amount |
Preparation method
Part A and part B are heated to 75 ℃ respectively.Under agitation with among the part A impouring part B.Use Ultra Turrax with 11000rpm homogeneous mixture 15 seconds afterwards.Mixture is cooled to 60 ℃, adds portion C and part D.Homogeneous mixture was than (5 seconds/11000rpm), cool off once more short time once more.At room temperature, regulating pH value with sodium hydroxide is 5.5 to 6.0.Add aromatic at last.
Embodiment 29: daily nursing is prevented the UV lotion
| The INCI title | %w/w (during use) | |
| Part A | Oleic alcohol polyoxyethylene ether-3 phosphate ester | 0.6 |
| Brij-721-21 | 2.5 | |
| Brij-721-2 | 1.0 | |
| Spermol | 0.8 | |
| Stearyl alcohol | 1.5 | |
| Mountain Yu acid glycerol three esters | 0.8 | |
| 2-Methylpentadecane | 8.0 | |
| Formula (MC10) or chemical compound (MC37) | 5.0 | |
| Part B | Water | In right amount to 100 |
| Glycerol | 2.0 | |
| Di-2-ethylhexylphosphine oxide-benzotriazole base tetramethyl butyl phenol (with) water (with) decyl glucoside (with) propylene glycol (with) xanthan gum | 3.0 | |
| The EDTA disodium | 0.1 | |
| Portion C | Water | 20.0 |
| The diimidazole ureine (with) butyl carbamic acid iodo propinyl ester | 0.15 | |
| Propylene glycol | 4.0 | |
| Part D | Sodium acrylate copolymer (with) liquid paraffin (with) PPG-1 tridecyl polyoxyethylene ether-6 | 1.5 |
| D5 | 4.5 | |
| The PEG-12 dimethyl polysiloxane | 2.0 | |
| Alpha-tocopherol acetate | 0.45 | |
| Water (with) citric acid | In right amount | |
| Part E | Aromatic | In right amount |
Preparation method
Add B to 75 ℃ of part A and part respectively.Under agitation with among the part A impouring part B.The SF 1202 and SF 1288 mixture that add part D after the emulsifying immediately.Use Ultra Turrax with 11000rpm homogeneous mixture 30 seconds afterwards.Allow to be cooled to 65 ℃, add SALCARE
SC91.Being lower than under 50 ℃ the temperature, add portion C, under 35 ℃ or lower temperature, use the Fructus Citri Limoniae acid for adjusting pH value.Add part E in room temperature earlier.
Embodiment 30: sun-proof emulsifiable paste, type O/W
| The INCI title | %w/w (during use) | |
| Part A | Polyglyceryl-3-methyl glucoside distearate | 2.0 |
| Decyl oleate | 5.7 | |
| Isopropyl palmitate | 5.8 | |
| Caprylic/capric triglyceride | 6.5 | |
| Formula (MC14) or chemical compound (MC37) | 2.0 | |
| The ethylhexyl Methoxycinnamate | 5.0 | |
| Spermol | 0.7 | |
| Part B | Glycerol | 3.0 |
| Carbomer | 0.3 | |
| Water | In right amount to 100 | |
| Portion C | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.5 |
| Part D | Di-2-ethylhexylphosphine oxide-benzotriazole base tetramethyl butyl phenol (with) water (with) decyl glucoside (with) propylene glycol (with) xanthan gum | 8.0 |
| Water | 20.0 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Aromatic | In right amount |
Preparation method
Part A and part B are heated to 75 ℃ respectively.Under agitation with among the part A impouring part B.With Ultra Turrax with 11000rpm homogeneous mixture 15 seconds.Mixture is cooled to 60 ℃, adds portion C and part D.Once more short time of homogeneous mixture (5 seconds/11000rpm).After the cooling, under stirring and room temperature, regulate pH once more with sodium hydroxide.Obtain pH and be 5.50 to 6.00 solution.Add aromatic at last.
Embodiment 31: sun-proof emulsifiable paste; Type O/W
| The INCI title | %w/w (during use) | |
| Part A | Polyglyceryl-3-methyl glucoside distearate | 2.0 |
| Decyl oleate | 5.7 | |
| Isopropyl palmitate | 5.8 | |
| Caprylic/capric triglyceride | 6.5 | |
| Formula (MC10) (50%) or (MC37) chemical compound of (50%) and the mixture of Uvinul A Plus CAS Reg. No.302776-68-7 (50%) | 2.0 | |
| The ethylhexyl Methoxycinnamate | 5.0 |
| The INCI title | %w/w (during use) | |
| Spermol | 0.7 | |
| Part B | Glycerol | 3.0 |
| Carbomer | 0.3 | |
| Water | In right amount to 100 | |
| Portion C | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.5 |
| Part D | Di-2-ethylhexylphosphine oxide-benzotriazole base tetramethyl butyl phenol (with) water (with) decyl glucoside (with) propylene glycol (with) xanthan gum | 8.0 |
| Water | 20.0 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Aromatic | In right amount |
Preparation method
Part A and part B are heated to 75 ℃ respectively.Under agitation with among the part A impouring part B.With Ultra Turrax with 11000rpm homogeneous mixture 15 seconds.Mixture is cooled to 60 ℃, adds portion C and part D.Once more short time of homogeneous mixture (5 seconds/11000rpm).After the cooling, under appropriateness stirring and room temperature, regulating pH value with sodium hydroxide solution is 5.50 to 6.00 once more.Add aromatic at last.
Embodiment 32: sun-proof emulsifiable paste, type O/W
| The INCI title | %w/w (during use) | |
| Part A | Polyglyceryl-3-methyl glucoside distearate | 2.0 |
| Decyl oleate | 5.7 | |
| Isopropyl palmitate | 5.8 | |
| Caprylic/capric triglyceride | 6.5 | |
| Formula (MC10) (50%) or (MC37) mixture of the chemical compound of (50%) and benzylidene camphor, CAs Reg. No.36861-47-9 (50%) | 2.0 | |
| The ethylhexyl Methoxycinnamate | 5.0 | |
| Spermol | 0.7 | |
| Part B | Glycerol | 3.0 |
| Carbomer | 0.3 | |
| Water | In right amount to 100 | |
| Portion C | Phenoxyethanol (with) methyl parahydroxybenzoate (with) ethylparaben (with) butyl p-hydroxybenzoate (with) propyl p-hydroxybenzoate (with) p-Hydroxybenzoic acid isobutyl ester | 0.5 |
| Part D | Di-2-ethylhexylphosphine oxide-benzotriazole base tetramethyl butyl phenol (with) water (with) decyl glucoside (with) propylene glycol (with) xanthan gum | 8.0 |
| Water | 20.0 | |
| Part E | Water (with) sodium hydroxide | In right amount |
| Aromatic | In right amount |
Preparation method
Part A and part B are heated to 75C respectively.Under agitation with among the part A impouring part B.With Ultra Turrax with 11000rpm homogeneous mixture 15 seconds.Mixture is cooled to 60 ℃, adds portion C and part D.Once more short time of homogeneous mixture (5 seconds/11000rpm).After the cooling, under appropriateness stirring and room temperature, regulate pH value once more with sodium hydroxide.Obtain pH and be 5.50 to 6.00 solution.Add aromatic at last.
Claims (15)
1. formula (1a) or chemical compound (1b) are avoided purposes in the ultraviolet radiation at protection human and animal's hair and skin
Wherein
R
2Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or cyano group;
R
4Be cyano group; Or-Q
1-R
5
Q
1For-COO-;-CONH-;-CO-;-SO
2-; Or-CONR
6-;
R
5Be C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Or unsubstituted or C
1-C
6The C that alkyl replaces
6-C
20Aryl;
R
6Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces;
N is 2 to 4;
O is 2 to 4;
If n=2 is then in formula (1a)
R
1Be alkylidene, cycloalkylidene or phenylene; Or R
1And R
2Form alkylidene, cycloalkylidene or phenylene simultaneously; With
R
3For cyano group or-Q
1-R
5Or R
3And R
4Form 5-to 7-unit monocycle carbocyclic ring together, its randomly by-O-or-NR
7-cut off;
If o=2 is then in formula (1b)
R
3Be alkylidene, cycloalkylidene or phenylene, it is randomly by C
1-C
4Alkyl, C
1-C
4Alkoxyl ,-COR
6,-COOR
6Or-CONHR
6Replace; With
R
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2With the nitrogen-atoms that is connected them
Formation-(CH together
2)
m-ring, its randomly by-O-or-NR
7-cut off;
R
7Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
M is 3 to 7 number;
If n=3 is then in formula (1a)
R
1Be the trivalent alkyl, its randomly by one or more-O-or-NR
7-group cuts off; With
R
3For cyano group or-Q
1-R
5Or R
3And R
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=3 is then in formula (1b)
R
3Be 1,1-alkylidene, 1,1-cycloalkylidene or cyclohexadienylene; With
R
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
7-cut off;
If n=4 is then in formula (1a)
R
1Be the tetravalence alkyl; With
R
3Be cyano group; Or-Q
1-R
5Or R
3And R
4Form 5-to 7-unit monocycle carbocyclic ring together;
If n=4 is then in formula (1b)
R
3Be the tetravalence alkyl; With
R
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
7-cut off.
2. the purposes of claim 1 is wherein in formula (1a)
R
1As the definition in formula (1a)
R
2Be hydrogen;
R
3Be cyano group;
R
4For-CONHR
5With
R
5Be C
1-C
22Alkyl; Or C
6-C
20Aryl.
3. the purposes of claim 1, wherein
If n=2, the chemical compound of use formula (1c),
Wherein
R
1Be *-(CH
2)
m-* group is unsubstituted or by one or more C
1-C
5Group replaces; Formula (1a
1) divalent group
Formula (1a
2) divalent group
Or R
1
And R
2Nitrogen-atoms with 2 connections forms formula (1a
3) divalent group
R
8Be hydrogen; Or C
1-C
5Alkyl;
R
3Be cyano group; Or-Q
1-R
5
P is 0 to 3 number;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces; With
R
2, R
4, R
5, Q
1With the definition in m such as the claim 1.
4. the purposes of claim 1 is wherein used the chemical compound of formula (1d)
Wherein
R
1Be formula (1d
1)
The trivalent group,
R
2Be hydrogen; Or C
1-C
5Alkyl;
R
3And R
4, be cyano group independently of each other; Or-Q
1-R
5
Q
1For-COO-;-CONH-;-CO-;-SO
2-; CONR
12-;
R
5Be C
1-C
5Alkyl;
R
9And R
10Be C independently of each other
1-C
4Alkyl;
R
11And R
12Be hydrogen independently of each other; C
1-C
5Alkyl; With
P is 0 to 5 number.
5. the purposes of claim 1 is wherein used the chemical compound of formula (1e)
Wherein
R
1And R
2C independently of each other
1-C
22Alkyl; Or cyano group; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR
7-cut off;
R
4Be cyano group; Or-Q
1-R
5
O is 3; Or 4;
If o=3, then
R
2Be the trivalent alkyl;
If o=4, then
R
2Be the tetravalence alkyl;
R
5, R
7, Q
1With the definition in m such as the claim 1; With
R
9And R
10As the definition in the claim 4.
6. according to each purposes in the claim 1 to 5, wherein use other UV absorbent.
7. according to the purposes of claim 6, wherein other UV absorbent is selected from formula (t
21) triaizine compounds
Wherein,
R
1And R
5Be hydrogen; C
1-C
18Alkyl; Or C
6-C
12Aryl; With
R
6, R
7And R
8Be hydrogen independently of each other; Hydroxyl; Halogen; C
1-C
18Alkyl; C
1-C
18Alkoxyl; C
6-C
12Aryl; Xenyl; C
6-C
12Aryloxy group; C
1-C
18Alkylthio group; Carboxyl;-COOM; C
1-C
18-alkyl carboxyl; Amino carbonyl; Or single or two-C
1-C
18Alkylamino; C
1-C
10Acylamino-; Or-COOH.
8. according to the purposes of claim 6 or 7, wherein use UV filter compositions, described UV filter compositions comprises:
(t3) chemical compound of formula (MC02)
(t
4) 1,3,5-triazines; 2,4,6-three [1,1 '-biphenyl]-the 4-base-(9CI).
9. monomeric compound, oligomeric compound or the polymerizable compound that comprises formula (2) construction unit avoided purposes in the ultraviolet radiation as the UV chromophore at protection human and animal's hair and skin,
Wherein,
The group of at least one asterisk labelling can be connected to monomer, oligomeric or polymer-based group;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces; With
R
2And R
4As the definition in claim 1.
10. according to the purposes of claim 9, wherein monomeric compound, oligomeric compound or polymerizable compound are formula (3) chemical compound
Wherein,
Z is the group of formula (2);
R
13Be hydrogen; Halogen; Or C
1-C
5Alkyl;
R
14For-CONH-;-COO-; Or phenylene;
R
15Be C
1-C
20Alkylidene; Or C
6-C
20Arlydene;
R
16For-COO-;-OCO-;-CONH-;-NH-CO-O-;-NH-CO-; SO
2NH-;-NHSO
2-; SO
2-or-O-;
Q is 0; Or integer; With
R is 0; Or integer.
11. formula (1 ' a) or (1 ' b) chemical compound
R '
2Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Cyano group; Or R '
1And R '
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
R '
4For-Q '
1-R '
5
Q '
1For-COO-;-CONH-;-CO-;-SO
2-; Or-CONR '
6-;
R '
5Be C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Or unsubstituted or C
1-C
6The C that alkyl replaces
6-C
20Aryl;
R '
6Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
R '
7Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces;
M is 3 to 7;
N is 2 to 4;
O is 2 to 4;
If n=2 is then in formula (in 1 ' a)
R '
1Be alkylidene, cycloalkylidene or phenylene; Or R '
1And R '
2Form alkylidene, cycloalkylidene or phenylene simultaneously; With
R '
3For cyano group or-Q '
1-R '
5Or R '
3And R '
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=2 is then in formula (in 1 ' b)
R '
3Be alkylidene, cycloalkylidene or phenylene; With
R '
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
If n=3 is then in formula (in 1 ' a)
R '
1Be the trivalent alkyl, its randomly by one or more-O-or-NR '
7-group cuts off; With
R '
3For cyano group or-Q '
1-R '
5Or R '
3And R '
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=3 is then in formula (in 1 ' b)
R ' 3 is 1,1-alkylidene, 1,1-cycloalkylidene or cyclohexadienylene; With
R '
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R '
1And R '
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
If n=4 is then in formula (in 1 ' a)
R '
1Be the tetravalence alkyl; With
R '
3For cyano group or-Q '
1-R '
5Or R '
3And R '
4Form 5-to 7-unit monocycle carbocyclic ring together;
If o=4 is then in formula (in 1 ' b)
R '
3Be the tetravalence alkyl; With
R '
1Be hydrogen; Cyano group; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R '
1And R '
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
12. the chemical compound of formula (4)
Wherein,
R
2Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Unsubstituted or C
1-C
6Alkyl or C
1-C
6The C that alkoxyl replaces
6-C
20Aryl; Or R
1And R
2Form-(CH with the nitrogen-atoms that connects them
2)
m-ring, its randomly by-O-or-NR '
7-cut off;
R
3Be hydrogen; C
1-C
22Alkyl; C
3-C
8Cycloalkyl; Or unsubstituted or C
1-C
6The C that alkyl replaces
6-C
20Aryl;
M is 3 to 7;
N is 2 to 4;
The cyclohexene portion C is unsubstituted or by one or more C
1-C
5Alkyl replaces;
When n=2,
R
1And R
2Form alkylidene, cycloalkylidene or phenylene simultaneously;
When n=3,
R
1Be the trivalent alkyl, its randomly by one or more-O-or-NR
3-group cuts off;
When n=4,
R
1Be the tetravalence alkyl, its randomly by one or more-O-or-NR
3-group cuts off;
13. the formula of claim 12 (4) chemical compound is avoided purposes in the ultraviolet radiation as the UV-B absorbent at protection human and animal's hair and skin.
14. the formula of claim 12 (4) chemical compound is as the purposes of the intermediate that is used to prepare the UV absorbent.
15. cosmetic formulations comprises the formula (1a) of at least a or multiple claim 1 or 12, the chemical compound and the cosmetics acceptable auxiliary of (1b) or (4).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03104746 | 2003-12-17 | ||
| EP03104746.7 | 2003-12-17 | ||
| EP04102155.1 | 2004-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1897911A true CN1897911A (en) | 2007-01-17 |
| CN100591319C CN100591319C (en) | 2010-02-24 |
Family
ID=34924143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200480038027A Expired - Fee Related CN100591319C (en) | 2003-12-17 | 2004-12-08 | Merocyanine derivatives for cosmetic use |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100591319C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103619313A (en) * | 2011-04-29 | 2014-03-05 | 欧莱雅 | Solid cosmetic makeup and/or care composition |
| CN105358123A (en) * | 2013-07-08 | 2016-02-24 | 帝斯曼知识产权资产管理有限公司 | Uv screening composition comprising a uv filter, an organopolysiloxane functionalized with a uv absorber and porous silica and/or polymethylmethacrylate particles |
| CN107260561A (en) * | 2011-07-21 | 2017-10-20 | 莱雅公司 | Cosmetics and/or dermatological compositions containing Merocyanine derivatives |
| CN112424162A (en) * | 2018-07-12 | 2021-02-26 | 巴斯夫欧洲公司 | Method for crystallizing merocyanine |
-
2004
- 2004-12-08 CN CN200480038027A patent/CN100591319C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103619313A (en) * | 2011-04-29 | 2014-03-05 | 欧莱雅 | Solid cosmetic makeup and/or care composition |
| CN107661224A (en) * | 2011-04-29 | 2018-02-06 | 欧莱雅 | Solic cosmetic and/or care composition |
| US9974719B2 (en) | 2011-04-29 | 2018-05-22 | L'oreal | Solid cosmetic makeup and/or care composition |
| CN107260561A (en) * | 2011-07-21 | 2017-10-20 | 莱雅公司 | Cosmetics and/or dermatological compositions containing Merocyanine derivatives |
| CN107260561B (en) * | 2011-07-21 | 2022-05-17 | 莱雅公司 | Cosmetic and/or dermatological composition containing merocyanine derivatives |
| CN105358123A (en) * | 2013-07-08 | 2016-02-24 | 帝斯曼知识产权资产管理有限公司 | Uv screening composition comprising a uv filter, an organopolysiloxane functionalized with a uv absorber and porous silica and/or polymethylmethacrylate particles |
| CN105358123B (en) * | 2013-07-08 | 2018-11-13 | 帝斯曼知识产权资产管理有限公司 | Including UV lightscreening agents, with the UV shielding compositions of the functionalized organopolysiloxane of UV absorbents and porous silica and/or poly methyl methacrylate particle |
| CN112424162A (en) * | 2018-07-12 | 2021-02-26 | 巴斯夫欧洲公司 | Method for crystallizing merocyanine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100591319C (en) | 2010-02-24 |
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