CN1774426A - Symmetrical triazine derivatives - Google Patents

Symmetrical triazine derivatives Download PDF

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CN1774426A
CN1774426A CN 200480010224 CN200480010224A CN1774426A CN 1774426 A CN1774426 A CN 1774426A CN 200480010224 CN200480010224 CN 200480010224 CN 200480010224 A CN200480010224 A CN 200480010224A CN 1774426 A CN1774426 A CN 1774426A
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CN100424081C (en
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托马斯·埃里斯
斯蒂芬·穆勒
帕斯卡尔·海奥兹
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Lion Corp
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Abstract

Disclosed is the use of the compounds of formula (1) for the protection of human and animal hair and skin against the damaging effect of UV radiation, wherein A is a radical of formula (1a) or (1b) R, R1 and R5 independently from each other are hydrogen; C1-C18alkyl; or C6-C12aryl; R2, R3 and R4 independently from each other are hydrogen; or a radical of formula wherein at least one of the radicals R2, R3 and R4are a radical of formula (1c); R6, R7, R8, R9 and R10 independently from each other are hydrogen; hydroxy; C1-C18alkyl; C1-C18alkoxy;C6-C12aryl; C6-C12aryloxy; C1-C18alkylthio; carboxy; -COOM; C1-C18alkylcarboxyl; aminocarbonyl; or mono- or di-C1-C18alkylamino; M is an alkali metal ion; x is 1 or 2; and y is a number from 2 to 10; The compounds of formula (1) are high effective UV absorbers for cosmetic formulations aund can - depending on their physical properties - be used in micronized or soluble form.

Description

Striazine derivative
The present invention relates to the purposes of concrete Striazine derivative in the damage of protection humans and animals hair and the anti-UV radiation of skin, comprise the method for make-up preparation and these compounds of preparation of these pyrrolotriazine derivatives.
Triazines by xenyl or the symmetrical replacement of naphthyl is known, and for example by US-A-6,225,467 is disclosed. They are used as electroluminescent device.
Find that unexpectedly these compounds can be as the effective UV absorbent of height of cosmetics.
Therefore, the present invention relates to the non-therapeutical uses of following general formula compound in protection humans and animals hair and the anti-UV radiation injury of skin:
Figure A20048001022400131
Wherein
A is general formula (1a)
Figure A20048001022400132
Or (1b)
Figure A20048001022400133
Group;
R 1And R5Be hydrogen, C independently of one another1-C 18Alkyl or C6-C 12Aryl;
R 2、R 3And R4Be hydrogen or general formula (1c) independently of one another
Figure A20048001022400134
Group,
Radicals R wherein2、R 3And R4In at least one is the group of general formula (1c);
R 6、R 7，、R 8、R 9And R10Be hydrogen, hydroxyl, halogen, C independently of one another1-C 18Alkyl, C1-C 18Alkoxyl, C6-C 12Aryl, xenyl, C6-C 12Aryloxy group, C1-C 18Alkylthio group, carboxyl, COOM, C1-C 18-alkyl carboxyl, amino carbonyl, or one-or two-C1-C 18Alkyl amino, C1-C 10Acylamino-,-COOH;
M is alkali metal ion;
X is 1 or 2; And
Y is the numerical value of 2-10.
According to the definition of mutual-through type (1) compound group, C1-C 18Alkyl is the straight or branched alkyl, such as methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group, amyl group, isopentyl, tertiary pentyl, hexyl, 2-ethylhexyl, heptyl, octyl group, iso-octyl, nonyl, decyl, undecyl, dodecyl, myristyl, pentadecyl, cetyl, heptadecyl or octadecyl.
According to the definition of mutual-through type (1) compound group, C1-C 18Alkyl can be replaced by following groups: methoxy ethyl, ethoxycarbonyl propyl, 2-ethylhexyl, ethoxy, chloropropyl, N, N-lignocaine propyl group, cyano ethyl, phenethyl, benzyl, p-tert-butyl benzene ethyl, p-uncle's Octylphenoxy-ethyl, 3-(2,4-two tertiary pentyl phenoxy groups)-propyl group, ethoxycarbonylmethyl group-2-(2-hydroxyl ethyoxyl) ethyl, or 2-furyl ethyl.
According to the definition of mutual-through type (1) compound group, C1-C 18Alkyl is: for example methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy. , tert-butoxy, amoxy, isoamoxy or uncle's amoxy, own oxygen base, heptan oxygen base, octyloxy, different octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, hendecane oxygen base, dodecyloxy, tetradecyloxyaniline, pentadecane oxygen base, hexadecane oxygen base, heptadecane oxygen base or octadecane oxygen base.
According to the definition of mutual-through type (1) compound group, C6-C 10Aryl is: for example naphthyl and preferably phenyl.
The preferred compound that uses following general formula:
Figure A20048001022400141
R wherein1、R 5、R 6、R 7And R8Such as in the general formula (1) definition.
In general formula (2), R1And R2Be preferably hydrogen.
Most preferably use the compound of general formula (1) or (2), wherein R6And R8Be hydrogen.
The compound of the preferred formula (1) of paying close attention to is, wherein:
R 7Be hydrogen, hydroxyl, C1-C 5Alkyl, C1-C 5Alkoxyl ,-COOM ,-COOH or COOR10；
M is alkali metal ion; And
R 10Be C1-C 5Alkyl.
In addition, preferably use the compound of following general formula:
R wherein1、R 2、R 3、R 9And R10Such as in the general formula (1) definition.
The preferred compound that uses general formula (3), wherein:
R 1、R 2、R 3、R 9And R10For hydrogen or be C independently of one another1-C 18Alkyl.
The example that is preferred for pyrrolotriazine derivatives of the present invention is the compound of following general formula:
Figure A20048001022400161
Or
Figure A20048001022400171
The compound of general formula of the present invention (1) is particularly suitable as the UV filtering agent, namely for the protection of the skin of ultraviolet-sensitive organic matter, particularly humans and animals and the hair illeffects with anti-UV radiation. These compounds are suitable for as the sun-screening agent in cosmetics, medicine and the veterinary drug preparation thus. Can use these compounds with dissolved form and micronized state.
Triazine aryl R according to general formula (1a), 1 (b) or (1c)1、R 2、R 5、R 6、R 7、R 8、R 9And R10Substituent difference, UV absorbent of the present invention can use with dissolved state (organic filtering agent of the organic filtering agent of solubility, dissolving) or with micronized state (nano level organic filtering agent, the organic filtering agent of particle, UV-absorbent pigment).
Without alkyl substituent or only be characterised in that bad oil-soluble and high-melting-point with general formula (1) pyrrolotriazine derivatives of low-grade alkyl substituent. These derivatives are particularly suitable for the UV absorbent as the micronized state form thus.
The mean particle size that thus obtained micronizing UV absorbent has usually is the 0.02-2 micron, preferred 0.03-1.5 micron, and more preferably 0.05-1.0 micron.
UV absorbent of the present invention can also use as the dry matrices of powder type.
UV absorbent of the present invention can also be used for specific cosmetics carrier, for example in solid lipid nano granule (SLN) or the inertia colloidal sol microcapsules, wherein the UV absorbent encapsulated (Pharmazie, 2001 (56), p. 783-786). Such as Internat.J.Phar-maceutics, 2002,242, the lipid nanometer particulate (CLN ,=crystallization lipid nanoparticle) described in P.373-375 can be as the active carrier (for example compound of general formula 6) of UV filtering agent of the present invention.
Make-up preparation of the present invention or pharmaceutical composition can also contain one or more other such as table 1-3 at listed UV filtering agent.
The preparation method of described cosmetic or pharmaceutical preparation is as follows: use common method that UV absorbent and assistant agent are carried out physical property and mix, for example simply each composition is stirred together, especially utilize known cosmetic UV absorbent, such as the dissolution characteristics of OMC, the different monooctyl ester of salicylic acid etc. For example, can be without further processing or using the UV absorbent with micronized state or powder type.
Take the gross weight of described composition as benchmark, make up or pharmaceutical preparation contains UV absorbent or the UV absorber blend of 0.05-40 % by weight.
The UV absorbent of general formula of the present invention (1) or UV filter composition for the protection of skin, hair and/or natural or artificial hair color.
The suitable UV filtering agent material that table 1. can also use with UV absorbent of the present invention
Para-Aminobenzoic derivative, for example 4-dimethylaminobenzoic acid 2-Octyl Nitrite;
Salicyclic acid derivatives, for example BMDBM;
Benzophenone derivative, for example oxybenzone and 5-sulfonic acid thereof;
The dibenzoyl methane derivative, 1-(4-tert-butyl-phenyl)-3-(4-methoxyphenyl)-the third-1 for example, 3-diketone;
Diphenylacrylate ester class, for example octocrylene and 3-(benzofuranyl) 2-cyanoacrylate;
3-imidazol-4 yl acrylicacidandesters class;
Be described in benzofuran derivatives, especially 2-(p-aminophenyl) benzofuran derivatives among EP-A-582 189, US-A-5 338 539, US-A-5 518 713 and the EP-A-613 893;
Polymer UV absorbent for example is described in the benzylidene malonate derivative among the EP-A-709 080;
Cinnamic acid derivative for example is described in Ethylhexyl Methoxycinnamate and isopropyl ester or cinnamic acid derivative among US-A-5 601 811 and the WO97/00851;
Camphor derivatives, 3-(4 '-methyl) benzal-camphane-2-ketone for example, 3-benzal-camphane-2-ketone, N-[2 (with 4)-2-oxygen base borneol-3-subunit-methyl)-benzyl] acrylamide polymer, 3-(4 '-trimethyl ammonium)-benzal-camphane-2-ketone Methylsulfate, 3,3 '-(1, and salt, 3-(4 '-sulfo group) benzal-camphane-2-ketone and salt 4-phenylene two methines)-two (7,7-dimethyl-2-oxo-dicyclo [2.2.1] heptane-1-methanesulfonic acid); Camphor benzalkonium mesylate;
The hydroxy phenyl triaizine compounds, 2-(4 '-methoxyphenyl)-4 for example, 6-two (2 '-hydroxyl-4 '-the n-octyloxy phenyl)-1,3,5-triazines; Two { [4-(3-(2-propoxyl group)-2-hydroxyl-propoxyl group)-2-hydroxyl]-phenyl }-6-(4-the methoxyphenyl)-1,3,5-triazines of 2,4-;
Two { [4-(2-ethyl-own oxygen base)-2-hydroxyl]-phenyl }-6-[4-(2-methoxy ethyl-carboxyl)-phenyl aminos of 2,4-]-1,3,5-triazines; 2,4-pair ([4-(three (trimethylsiloxy-silicyl propoxyl group)-2-hydroxyls]-phenyl }-6-(4-methoxyphenyl)-1,3,5-triazines; 2,4-pair [4-(2 " metacryloxy)-the 2-hydroxyl]-phenyl]-6-(4-methoxyphenyl)-1,3,5-triazines; 2,4-pair [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-triazines; 2,4-pair " 4-(3-(2-propoxyl group)-2-hydroxyl-propoxyl group)-2-hydroxyl]-phenyl }-6-[4-ethyl carboxyl)-phenyl amino]-1,3,5-triazines;
Benzotriazole cpd, for example 2,2 '-methylene-two (6-(2H-BTA-2-yl)-4-(1,1,3,3-tetramethyl butyl)-phenol;
Disclosed triphenylamine base-s-pyrrolotriazine derivatives among US-A-5332568, EP-A-517104, EP-A-507691, WO93/17002 and the EP-A-570838, for example 2,4, the 6-triphenylamine-(p-carbonyl-2 '-ethyl-1 '-the oxygen base)-1,3,5-triazine and UV absorbent;
2-PHENYLBENZIMIDAZOLE-5-SULFONIC ACID and and salt;
Ortho-, meta-or p-amino benzoic Acid ester in Meng class;
Titanium dioxide, zinc oxide, iron oxide, mica, MnO, the Fe of coating or uncoated2O 3、Ce 2O 3、Al 2O 3、ZurO 2The physical sunscreen agent. (face coat: the metallic soap (described in CAS 4086-70-8) of poly-methyl methacrylate base ester, methyl-silicone oil (methylhydrogenpolysi,oxane described in CAS 9004-73-3), dimeticone, three stearic acid isopropyl titaniums (described in CAS 61417-49-0), dolomol, the phosphoric acid perfluor alcohol ester (described in CAS74499-44-8, JP5-86984, JP 4-330007) of C9-15 phosphoric acid fluorine alcohol ester). The mean value that main granular size is 15nm-35nm and the granular size in the dispersion are in the 100nm-300nm scope.
Disclosed hydroxy amino-benzophenone derivative among DE 10011317, EP 1133980 and the EP1046391
Such as disclosed phenyl-benzimidizole derivatives among the EP 1167358
" Sunscreens ", Eds.N.J.Lowe, N.A.Shaath, Marcel Dekker, Inc., New York and Basle or Cosmetics ﹠ Toiletries (107), the UV absorbent described in the 50ff (1992) also can be used as other protective substance.
Preferably following UV being filtered composition is special concern:
-UV-filters composition (A), comprising:
(a 1) Striazine derivative of at least a general formula (1); With
(a 2) the ADP ketone derivatives of at least a following general formula:
Figure A20048001022400191
Wherein:
R 1And R2Be C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkyl, C3-C 10Cycloalkenyl group; Or R1And R2Form 5-or 6-unit heterocycle with the nitrogen-atoms that connects;
n 1Numerical value for 1-4;
Work as n1=1 o'clock,
R 3Be saturated or undersaturated heterocyclic radical, hydroxyl-C1-C 5Alkyl, optional by one or more C1-C 5The cyclohexyl that alkyl replaces, optional by heterocyclic radical, amino carbonyl or C1-C 5The phenyl that alkyl carboxyl replaces;
Work as n1=2 o'clock,
R 3For optional by carbonyl-or alkylidene of replacing of carboxyl-, ring alkylidene, alkylene group or phenylene, general formula *-CH2-C≡C-CH 2-* group; Or
R 3Form the divalent group of general formula (1a) with A
Wherein:
n 2Numerical value for 1-3;
Work as n1Be 3 o'clock,
R 3Be alkane three bases;
Work as n1Be 4 o'clock,
R 3Be alkane four bases;
A is-O-or-N (R5)-; And
R 5Be hydrogen, C1-C 5Alkyl or hydroxyl-C1-C 5Alkyl.
Most preferably UV-filters composition (A1), comprising:
(a 3) compound of general formula (6) and/or (9); With
(a 4) compound of following general formula:
-UV-filters composition (B), comprising:
(b 1) Striazine derivative of at least a general formula (1); With
(b 2) the ADP ketone derivatives of at least a following general formula:
Wherein:
R 1And R2Be hydrogen, C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkenyl group; R wherein1And R2Can form 5-or 6-unit ring;
R 3And R4Be C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkenyl group, C1-C 20Alkoxyl, C1-C 20Alkoxy carbonyl group, C1-C 20Alkylamino, two (C1-C 20Alkyl) amino, optional aryl or the heteroaryl that replaces;
X is hydrogen, COOR5、CONR 6R 7；
R 5、R 6、R 7Be hydrogen, C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkyl, C3-C 10Cycloalkenyl group, (Y-O)q-Z, the optional aryl that replaces;
Y is-(CH2) 2-、-(CH 2) 4-、-CH(CH 3)-CH 2-；
Z is-CH2-CH 3、-CH 2-CH 2-CH 3、-CH 2-CH 2-CH 2-CH 3、CH(CH 3)-CH 3；
M is 0,1,2 or 3;
N is 0,1,2,3 or 4; And
Q is the numerical value of 1-20
Most preferably UV-filters composition (B1), comprising:
(b 3) compound of general formula (6) and/or (9); With
(b 4) compound of following general formula:
Figure A20048001022400212
-UV-filters composition (C), comprising:
(c 1) Striazine derivative of at least a general formula (1); With
(c 2) at least a general formula benzotriazole derivatives:
Figure A20048001022400221
Wherein:
T 2Be C1-C 10The C that alkyl or phenyl replaces1-C 4Alkyl.
Most preferably UV-filters composition (C1), comprising:
(c 3) compound of general formula (6) and/or (9); With
(c 4) micronized compound of following general formula:
Figure A20048001022400222
-UV-filters composition (D), comprising:
(d 1) Striazine derivative of at least a general formula (1); With
(d 2) compound of at least a following general formula:
Figure A20048001022400223
Wherein:
R 1And R2Be C independently of one another3-C 18Alkyl, C2-C 18Alkenyl, general formula-CH2-CH(-OH)-CH 2-O-T 1Group; Or
R 1And R2Group for general formula (4a)
Figure A20048001022400224
R 12Be direct key, straight or branched C1-C 4Alkylidene or general formulaOr
Figure A20048001022400226
Group;
R 13、R 14And R15Be C independently of one another1-C 18Alkyl, C1-C 18The group of alkoxyl or following general formula:
Figure A20048001022400231
R 16Be C1-C 5Alkyl;
m 1And m3Be 1-4 independently of one another;
p 1Be 0 or the numerical value of 1-5;
A 1Group for following general formula:
Figure A20048001022400232
R 3Be hydrogen, C1-C 10Alkyl ,-(CH2CHR 5-O) n1-R 4Or the group of following general formula :-CH2-CH(-OH)-CH 2-O-T 1；
R 4Be hydrogen; M; C1-C 5Alkyl; Or general formula-(CH2)m 2-O-T 1Group;
R 3Be hydrogen or methyl;
T 1Be hydrogen or C1-C 8Alkyl;
Q 1Be C1-C 18Alkyl;
M is metal cation;
m 2Be 1-4; And
N is 1-16.
Most preferably UV-filters composition (D1), comprising:
(d 3) compound of general formula (6) and/or (9); With
(d 4) compound of following general formula:
Figure A20048001022400241
-UV-filters composition (E), comprising:
(e 1) Striazine derivative of at least a general formula (1); With
(e 2) the hydroxy phenyl triaizine compounds of at least a following general formula:
Figure A20048001022400242
Wherein:
R 1、R 2And R3Be C independently of one another1-C 18Alkyl, C2-C 10Alkenyl or phenyl-C1-C 4Alkyl;
R 4Be hydrogen or C1-C 5Alkyl.
Most preferably UV-filters composition (E1), comprising:
(e 3) compound of general formula (6) and/or (9); With
(e 4) compound of following general formula:
-UV-filters composition (F), comprising:
(f 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) or (9); With
(f 2) the dibenzoyl methane Derivatives of at least a following general formula:
Figure A20048001022400251
Or
Figure A20048001022400252
Most preferably UV-filters composition (F1), comprising:
(f 3) compound of general formula (6) and/or (9); With
(f 4) 1-[4-(1,1-dimethyl ethyl) phenyl]-3-(4-methoxyphenyl the third-1,3-diketone (Avobenzone);
-UV-filters composition (G), comprising:
(g 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(g 2) phenyl bisbenzimidazole tetrasulfonic acid sodium (Heliopan AP).
-UV-filters composition (H), comprising:
(h 1) Striazine derivative of at least a general formula (1), and
(h 2) triazine of benzoxazole-replacement of following general formula:
Wherein:
R 1、R 2And R3Be side chain or non-side chain C independently of one another1-C 12Alkyl.
Most preferably UV-filters composition, comprising:
(h 3) compound of general formula (6) and/or (9), and
(h 4) 1,3,5-triazines-2,4,6-triamine, N, N '-two [4-[5-(1,1-dimethyl propyl)-2-benzoxazolyl] phenyl]-N " (2-ethylhexyl) (CAS No.288254-16-0).
In addition, preferred UV filters composition (H2), comprising:
(h 5) compound of general formula (6) or (9), and
(h 6) at least a general formula (h21) compound, wherein
(h 61)R 1And R2Be tertiary pentyl and R3Be the tert-butyl group; Or wherein
(h 62)R 1And R2Be the tert-butyl group and R3Be uncle's octyl group; Or wherein
(h 63)R 1And R2Be the tert-butyl group and R3Be the 2-ethylhexyl; Or wherein
(h 64)R 1And R2Be tertiary pentyl and R3Be the 2-ethylhexyl.
-UV-filters composition (I), comprising:
(i1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(i2) 2-(2H-BTA-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl) the oxygen base] the disiloxane base] propyl group]-; (CAS-No.155633-54-8; The Drometrizole trisiloxanes; Mexoryl XL);
-UV-filters composition (K), comprising:
(k 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(k 2) siloxanes and silicone, two-Me, 1-[[4-[3-ethyoxyl-2-(carbethoxyl group)-3-oxo-1-acrylic] phenoxy group] methyl] vinyl Me, 3-[4-[3-ethyoxyl-2-(carbethoxyl group)-3-oxo-1-acrylic] phenoxy group]-1-acrylic Me, Me hydrogen (dimethyl siloxane diethyl toluenyl malonic ester (Dimethicodiethylbenzalmalonate); CAS-No.207574-74-1);
-UV-filters composition (L), comprising:
(l 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(l 2) (+/-)-1,7,7-trimethyl-3-[(4-aminomethyl phenyl) methylene] dicyclo [2.2.1] heptan-2-ketone; P-methyl benzylidene camphor;
-UV-filters composition (M), comprising:
(m 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(m 2) α-(2-oxo borneol-3-subunit) toluene-4-sulfonic acid and salt (Mexoryl SL) thereof;
-UV-filters composition (N), comprising:
(n 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(n 2) N, N, N-trimethyl-4-[(4,7,7-trimethyl-3-oxo dicyclo [2,2,1] heptan-2-subunit) methyl]-anilinomethyl sulfate (Mexoryl SO);
-UV-filters composition (O), comprising:
(o 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(o 2) 2-cyano group, 3,3-diphenylacrylate 2-ethylhexyl (octocrylene);
-UV-filters composition (P), comprising:
(p 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(p 2) Uvinul MC 80 (OMC);
-UV-filters composition (Q), comprising:
(q 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(q 2) benzoic acid, 4,4 ', 4 " (1,3,5-acetal-2,4,6-three basic three imino groups) three-, three (2-ethylhexyl) ester; 2,4,6-triphenylamine base-(p-carbonyl-2 '-ethylhexyl-1 '-oxygen base (oxi))-1,3,5-triazines (octyl triazone);
-UV-filters composition (R), comprising:
(r 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(r 2) 2-phenyl-1H-benzimidazole-5-sulfonic acid (Phenylbenzimidazolesulfonic acid);
-UV-filters composition (S), comprising:
(s 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(s 2) benzoic acid, 4,4 '-[[the 6-[[4-[[(1-dimethyl ethyl) amino] carbonyl] phenyl] amino] 1,3,5-triazines-2,4-two bases] diimino] two-, two (2-ethylhexyl) ester; Uvasorb HEB (Uvasorb HEB).
In composition (A)-(S), the compound of general formula (1), (6) and (9) preferably exists with micronizing form composition respectively.
The compound of general formula (1) can also be used as wrinkle resistant sensation conditioning agent (referring to embodiment 29). This is another object of the present invention.
Can be according to for example US-A-6, the known method described in 225,467 prepares the compound of general formula (1).
In addition, can be take corresponding halogenated aromatic compound and three halo triazines as raw material with the compound that obtains general formula (1) in the Grignard reaction.
The ring trimerizing of aromatic nitrile compound is the another kind of good method of the Striazine derivative of preparation general formula (1), and the productive rate that obtains is lower.
Found unexpectedly the straightforward procedure of preparation general formula (1) compound. Three halos-1,3,5-triazines class and aromatic compounds are reacted in friedel-crafts-reaction and are obtained the Striazine derivative of high yield.
Suitable aromatic compounds is:
Figure A20048001022400281
And/or
Figure A20048001022400282
Wherein: R1-R 10Such as in the general formula (1) definition.
According to the method, can prepare according to following reaction scheme the compound of general formula (101):
 
Preferably cyanuric chloride is used as three halos-1,3,5-triazines.
Reaction temperature is-10-250 ℃, and preferred 5-150 ℃, most preferably 70-130 ℃.
Can be listed in the following table as the type of compounds of catalyst:
Acid halide   AlCl 3，AlBr 3，SnCl 4，SbCl 5，FeCl 3
Metal alkyl and metal alkoxide   AlR 3，BR 3，ZnR 2，Al(OPh) 3
Bronsted acid   HCl，HCl-AlCl 3，H 2SO 4，HF，H 3PO 4
Acidic oxide and derivative Zeolites, the oxide of mixing and solid peracid, clay, heteropoly acid, modified clay
Carrier acid   H 3PO 4-SiO 2，BF 3-Al 2O 3
Cationic ion-exchange resin   Permutit Q，Amberlite IR 112，DoWex 50，   Nafion-silica，Deloxan
Other catalyst The solid peracid, heteropoly acid, the proton on the carrier or lewis acid, Nafion and Nafion class compound
Preferred catalyst is (as single compound or composition: AlCl3、AlBr 3、BF 3、Boys、 BBr 3、BeCl 2、CdCl 2、ZnCl 2、GaCl 3、GaBr 3、FeCl 3、SbCl 3、BiCl 3、TiCl 4、 ZrCl 4、SnCl 4、UCl 4And SbCl5。
Advantageously with listed compound in the table in stoichiometric amount or the excessive use.
The co-catalyst that uses: alcohols, water, HCl, HF, H2SO 4、H 3PO 4, RCOOH (organic acid), sulphonic acids, for example p-methyl benzenesulfonic acid.
Also can be with stoichiometric amount or with excessive use co-catalyst.
Preferably gas HCl is used as co-catalyst.
As catalyst, co-catalyst or promoter, the classes of compounds of use:
-form cationic compound: preferred alkyl-and acyl group-halide and contain oxygen-, sulphur-or the compound of halogen-donor atom.
-adduct: ZnCl2-AlCl 3、SnCl 4、AlCl 3-ketone, AlCl3-pyridine, AlCl3-RNO 2、 AlBr 3-RNO 2、GaCl 3-RNO 2、SbF 5、BF 3-OEt 2、BF 3-C 6H 5OH；AlCl 3-sulfolane. (R-NO2: nitro aliphatic series and nitro-aromatics).
Suitable solvent is: aliphatic hydrocarbon, aromatic hydrocarbons, sulfur-bearing-hydro carbons, halogenated aromatic compound, halogenated aliphatic compound, alkyl (alyl)-aryl ethers, alkyl-alkyl ether, sulfolane, nitro-aromatics and nitro aliphatic compounds.
Most preferably: chlorobenzene, 1,2-dichloro-benzenes, Isosorbide-5-Nitrae-dichloro-benzenes, nitrobenzene, nitromethane, tetrachloromethane.
In addition; reaction is at ionic liquid, and for example s.1-1-butyl-pyridinium father-in-law chloride-aluminium chloride (III) and 1-butyl-3-methylimidazole father-in-law chloride-aluminium chloride (III) (carry out in the solvent of ethyl-3-methylimidazole father-in-law halogenated aluminum hydrochlorate ionic liquid as the friedel-crafts acylation reaction of ferrocene. Journal of the Chemical Society, Dalton Transactions:Inorganic Chemistry 1999 (1), 63).
Find unexpectedly reaction not as 1, the solvent of 2-dichloro-benzenes situation under carry out. When gas HCl was put into reactant mixture, reaction was carried out well especially.
This preparation method has special significance, because the application of halogenated aromatic solvent is so that unique what be difficult to remove in end-product is the solvent residues thing. These types of solvents are not suitable for cosmetic applications.
For example, cosmetic or pharmaceutical preparation can be creme, gel, lotion, alcohol and water/alcoholic solution, emulsion, wax/fat composition, patch, powder or ointment. Except above-mentioned UV filtering agent, cosmetic or pharmaceutical preparation can contain other assistant agent as described below.
As moisture and emulsion (for example W/O, O/W, O/W/O and W/O/W emulsion or microemulsion) oil-containing, described preparation contains: for example, 0.1-30 % by weight, one or more UV absorbents (take composition total weight as benchmark) of preferred 0.1-15 % by weight and especially 0.5-10 % by weight; At least a oil component (take composition total weight as benchmark) of 1-60 % by weight, especially 5-50 % by weight and preferred 10to 35 % by weight; At least a emulsifying agent (take composition total weight as benchmark) of 0-30 % by weight, especially 1-30 % by weight and preferred 4-20 % by weight; 10-90 % by weight, the especially water of 30-90 % by weight, (take composition total weight as benchmark); With the 0-88.9 % by weight, especially acceptable assistant agent is gone up in other cosmetic of 1to 50 % by weight.
Cosmetic of the present invention or pharmaceutical composition/preparation can also contain one or more other compounds, such as the aliphatic alcohol ester class of aliphatic acid; Natural or synthetic glycerine three ester classes comprise glyceride type and derivative; Pearlescent waxes: hydrocarbon ils, silicone or siloxanes (organic replacement polysiloxane-based); Fluoridize or the perfluorinate emulsifier; Superfatting agent; Surfactant; Consistency modifiers/thickener and rheology modifier; Polymer; Biological active component; The deodorant activities component; Dandruff removing agent; Antioxidant; Hydrotropic agent; Anticorrisive agent and bacteriostatic agent; Aromatic oil; Colouring agent; Polymeric beads or hollow ball as SPF promoter.
Comprise in the various cosmetic products and make up or pharmaceutical preparation. Consider, for example, especially descend series preparation: skin conditioner, bath agent, cosmetic personal nursing agent, foodcare agent; The hair remover (depilation) of lucifuge agent, skin tanning agent, depigmenting agent, pest repellant, deodorant, antiperspirant, the preparation that is used for cleaning and nursing stained skin, chemicals form, shave a mao agent, aromatic or cosmetic hair nursing agent.
Listed final preparation can exist with various forms, for example:
-liquid preparation form is such as W/O, O/W, O/W/O, W/O/W or PIT emulsion and all types of microemulsion; Gel, oil, creme, milk or lotion, powder, lacquer, tablet or cosmetics, rod, spray or aerosol, foam or paste form.
Be anti-day photo etching as the make-up preparation with particular importance that is used for skin, such as day cream, toner, creme, oil, sunscreen or summer using agent after newborn, pre-suntan or the Exposure to Sunlight, also claim the skin tanning agent, for example from shining black frost. The special meaningfully sun-screening agent of suncream, suntan lotion, sunscreen and spray form.
Be above-mentioned preparation for hair-care as the make-up preparation with particular importance that is used for hair, the shampoo of especially shampoo form, hair conditioner, conditioner, pre-care formulations for example, hair oil, hair styling cream, hair styling gel having, pomade, hair conditioner; The nursing bag, strong conditioner, hair straighten, liquid hair mousse, hair foaming agent and hair jelly. The shampoo of special meaningfully shampoo form.
The notable feature of make-up preparation of the present invention is that application on human skin is to the splendid protective action of daylight detrimental effect.
Embodiment
The preparation of UV absorbent
Embodiment 1: the preparation of general formula (101) compound
Figure A20048001022400311
Cyanuric chloride (36.9g, 0.20mol) is dissolved in 1,2-dichloro-benzenes (500ml). Add aluminium chloride (96.0g, 0.72mol) and this reactant mixture is heated to 140 ℃. Slowly drip and be dissolved in 200ml 1, the biphenyl (111.0g, 0.72mol) of 2-dichloro-benzenes also maintains 140-145 ℃ of lower 1-4 hour with temperature.
With this reactant mixture be cooled to about 60 ℃ and join the dense HCl of 150ml and the mixture of 350g ice in. After being separated under about 110 ℃, remove the dichloro-benzenes phase, with Na2CO 3Stir together and at 100-110 ℃ of lower heat filtering. Required compound is recrystallized from filtrate.
For purifying, make this compound from dichloro-benzenes be recrystallized the diox.
13C NMR(90MHz，CDCl 3，TMS)：
   The peak    δ(ppm)    ％Int.    Peak Nr.    δ(ppm)    ％Int.
  1   171.8   15.6   6   129.3   98.6
  2   145.6   21.6   7   128.4   32.5
  3   140.8   18.3   8   127.8   62.9
  4   135.6   26.4   9   127.7   100.0
  5   129.9   62.2
Embodiment 2:
Provide biphenyl (200.0g, 1.28mol) and fusing under 70-75 ℃. Add cyanuric chloride (9.2g, 0.05mol) and discharged hydrogen chloride 10 minutes. Minute 5 equal portions add aluminium chloride (20.0g, 0. 15mol) in 40 minutes, wherein again emit hydrogen chloride after front two parts of addings. Behind reaction terminating, slowly drip 95% ethanol (200ml), under reflux state, this reactant mixture was heated 1 hour. Final adding acetone (400ml) also stirred 1 hour, is cooled to room temperature and filters out defective product under puffing regimens.
The productive rate of three (biphenyl)-1,3,5-triazines (general formula 101): about 65%
Embodiment 3: the preparation of general formula (102) compound
Obtain the compound of general formula (102) according to the method described in the embodiment 1, condition is to substitute biphenyl with naphthalene.
Embodiment 4: the preparation of general formula (103) compound
Figure A20048001022400331
Reaction scheme:
Figure A20048001022400332
Embodiment 4a:
With 0.5g 2,4,6-three-(4-bromophenyl)-1,3,5-triazines (CAS Nr.30363-03-2) and 0.816g 4-xenyl boric acid join in the 10m toluene in ar gas environment. The 2.238g cesium carbonate is dissolved in 3.5ml water and joins in the above-mentioned reactant mixture. After adding 0.03 equivalent palladium (II) catalyst, this reactant mixture was heated 4 hours under reflux state. This reactant mixture is cooled to room temperature and then filtration. Filter cake is dissolved in hot DMF, filter and under cooling condition crystallization go out required product. The brilliant fusing point of white fine needle be 360 ℃ and1H-NM has confirmed this structure.
NMR-data: 1H-NMR (340MHz, CDCl3)：δ＝8.83(d，6H)，7.82(d，6H)，7.75 (d，6H)，7.67(d，6H)，7.62-7.60(m，6H)，7.44-7.40(m，6H)，7.34-7.30ppm(m， 3H)。
Also can use chloride, iodide or toluene fulfonate to replace bromide as raw material. Preferred bromide
Embodiment 4b:
The compound that can synthesize by following approach on the other hand, general formula (103):
X=Cl, Br, I, adjacent tosyl (the preferred Br of x=)
Embodiment 4c:
Another kind of approach for the preparation of the compound of general formula (103) is as follows:
Figure A20048001022400342
Embodiment 4d:
Obtain the compound of general formula (103) according to the method described in the embodiment 1, condition is to substitute biphenyl with para-terpheny.
Embodiment 5: the preparation of general formula (104) compound
Obtain the compound of general formula (104) according to the method described in the embodiment 1, condition is with right, and quaterphenyl is substituted biphenyl as starting compound.
Embodiment 6: the preparation of micronizing UV absorbent
Respectively with the compound of 100 parts of general formulas (101), (102), (103) or (104) with as the zirconium silicate grain (bells) of grinding aid (diameter: 0,1-4mm), dispersant (15 parts of C8-C 16Poly glucoside) and water (85 parts) jointly to be ground to mean particle size in ball mill be d50＝130nm。
Make the little pigment dispersion that has obtained in this way the UV absorbent.
Embodiment 7: the preparation of micronizing UV absorbent
Respectively with 100 parts of general formulas (101), (102), (103) or (104) compound with as the zirconium silicate grain of grinding aid (diameter: 0,1-4mm), dispersant (15 parts of C12Glyceride (gyceride)-polyethylene glycol 10) and water (85 parts) jointly to be ground to mean particle size in ball mill be d50＝130nm。
Make the little pigment dispersion that has obtained in this way the UV absorbent.
Application Example
   Embodiment 8a:UV-A/UV-B day care UV protective liquid
   The INCI-title    %w/w (providing)
   8a    8b    8c    8d    8e    8f
The A part Oil base polyoxyethylene (3) ether phosphate   0.60   0.60   0.60   0.60   0.60   0.60
Stearyl polyoxyethylene (21) ether   2.50   250   2.50   2.50   2.50   250
Stearyl polyoxyethylene (2) ether   1.00   1.00   1.00   1.00   1.00   1.00
Cetanol   0.80   0.80   0.80   0.80   0.80   0.80
Octadecanol   1.50   1.50   1.50   1.50   1.50   1.50
  Tribehenin   0.80   0.80   0.80   0.80   0.80   0.80
Isohexadecane   8.00   8.00   8.00   8.00   8.00   8.00
Ethylhexyl methoxy cinnamate   3.00   3.00   3.00   3.00   3.00   3.00
General formula (a4) compound   2.00
General formula (d as described in claim 184) compound   1.30  
General formula (h described in claim 212, 1) compound   1.50  
General formula (i2) compound (Mexoryl DTS)   2.00
The compound of the general formula described in claim 26 (I2)   1.50  
General formula (b4) compound   2.00
The B part Water In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100
Glycerine   2.00   2.00   2.00   2.00   2.00   2.00
UV-absorbent dispersion as described in example 6 above; The compound of general formula (101)   3.00     3.00     3.00     3.00     3.00     3.00  
Phenylbenzimidazolesulfonic acid (Eusolex 232)   2.00
EDETATE SODIUM   0.10   0.10   0.10   0.10   0.10   0.10
The C part Water   20.00   20.00   20.00   20.00   20.00   20.00
N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15       0.15       0.15       0.15       0.15       0.15    
Propane diols   4.00   4.00   4.00   4.00   4.00   4.00
The D part Sodium acrylate copolymer (with) atoleine (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   1.50       1.50       1.50       1.50       1.50       1.50    
Cyclopentasiloxane   4.00   4.00   4.00   4.00   4.00   4.00
Polyethylene glycol-12 dimeticone   2.00   2.00   2.00   2.00   2.00   2.00
Alpha-tocopherol acetate   0.45   0.45   0.45   0.45   0.45   0.45
Water (with) citric acid In right amount In right amount In right amount In right amount In right amount In right amount
The E part Spices In right amount In right amount In right amount In right amount In right amount In right amount
   Embodiment 8b:UV-A/UV-B day care UV protective liquid
   NCL, title    %w/w (providing)
   8a    8b    8c    8d    8e    8f
The A part Oil base polyoxyethylene (3) ether phosphate   0.60   0.60   0.60   0.60   0.60   0.60
Stearyl polyoxyethylene (21) ether   2.50   2.50   2.50   2.50   2.50   2.50
Stearyl polyoxyethylene (2) ether   1.00   1.00   1.00   1.00   1.00   1.00
Cetanol   0.80   0.80   0.80   0.80   0.80   0.80
Octadecanol   1.50   1.50   1.50   1.50   1.50   1.50
  Tribehenin   0.80   0.80   0.80   0.80   0.80   0.80
Isohexadecane   8.00   8.00   8.00   8.00   8.00   8.00
Ethylhexyl methoxy cinnamate   3.00   3.00   3.00   3.00   3.00   3.00
General formula (a4) compound   2.00
General formula (d as described in claim 184) compound   1.30  
General formula (h described in claim 212, 1) compound   1.50  
General formula (i2) compound (Mexoryl DTS)   2.00
The compound of the general formula described in claim 26 (I2)   1.50  
General formula (b4) compound   2.00
The B part Water In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100
Glycerine   2.00   2.00   2.00   2.00   2.00   2.00
UV-absorbent dispersion as described in example 6 above; The compound of general formula (103)   3.00     3.00     3.00     3.00     3.00     3.00  
Phenylbenzimidazolesulfonic acid (Eusolex 232)   2.00
EDETATE SODIUM   0.10   0.10   0.10   0.10   0.10   0.10
The C part Water   20.00   20.00   20.00   20.00   20.00   20.00
N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15       0.15       0.15       0.15       0.15       0.15    
Propane diols   4.00   4.00   4.00   4.00   4.00   4.00
The D part Sodium acrylate copolymer (with) atoleine (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   1.50       1.50       1.50       1.50       1.50       1.50    
Cyclopentasiloxane   4.00   4.00   4.00   4.00   4.00   4.00
Polyethylene glycol-12 dimeticone   2.00   2.00   2.00   2.00   2.00   2.00
Alpha-tocopherol acetate   0.45   0.45   0.45   0.45   0.45   0.45
Water (with) citric acid In right amount In right amount In right amount In right amount In right amount In right amount
The E part Spices In right amount In right amount In right amount In right amount In right amount In right amount
   Embodiment 8c:UV-A/UV-B day care UV protective liquid
   The INCl-title    %w/w (providing)
   8a    8b    8c    8d    8e    8f
The A part Oil base polyoxyethylene (3) ether phosphate   0.60   0.60   0.60   0.60   0.60   0.60
Stearyl polyoxyethylene (21) ether   2.50   2.50   2.50   2.50   2.50   2.50
Stearyl polyoxyethylene (2) ether   1.00   1.00   1.00   1.00   1.00   1.00
Cetanol   0.80   0.80   0.80   0.80   0.80   0.80
Octadecanol   1.50   1.50   1.50   1.50   1.50   1.50
  Tribehenin   0.80   0.80   0.80   0.80   0.80   0.80
Isohexadecane   8.00   8.00   8.00   8.00   8.00   8.00
Ethylhexyl methoxy cinnamate   3.00   3.00   3.00   3.00   3.00   3.00
The B part Water In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100
Glycerine   2.00   2.00   2.00   2.00   2.00   2.00
UV-absorbent dispersion as described in example 6 above; The compound of general formula (101)   3.00     3.00     3.00     3.00     3.00     3.00  
General formula (m2) compound (Mexoryl SL)   2.00
The compound of general formula (n2) (Mexoryl SO)   1.50
Ubiquinone   0.0I
General formula (c4) micronized compound   2.00
Phenylbenzimidazolesulfonic acid (Eusolex 232)   2.00
EDETATE SODIUM   0.10   0.10   0.10   0.10   0.10   0.10
The C part Water   20.00   20.00   20.00   20.00   20.00   20.00
N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15       0.15       0.15       0.15       0.15       0.15    
Propane diols   4.00   4.00   4.00   4.00   4.00   4.00
The D part Sodium acrylate copolymer (with) atoleine (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   1.50       1.50       1.50       1.50       1.50       1.50    
Cyclopentasiloxane   4.00   4.00   4.00   4.00   4.00   4.00
Polyethylene glycol-12 dimeticone   2.00   2.00   2.00   2.00   2.00   2.00
Alpha-tocopherol acetate   0.45   0.45   0.45   0.45   0.45   0.45
Water (with) citric acid In right amount In right amount In right amount In right amount In right amount In right amount
The E part Spices In right amount In right amount In right amount In right amount In right amount In right amount
   Embodiment 8d:UV-A/UV-B day care UV protective liquid
The INCI-title %w/w (providing)
   8a    8b    8c    8d    8e    8f
The A part Oil base polyoxyethylene (3) ether phosphate   0.60   0.60   0.60   0.60   0.60   0.60
Stearyl polyoxyethylene (21) ether   2.50   2.50   2.50   2.50   2.50   2.50
Stearyl polyoxyethylene (2) ether   1.00   1.00   1.00   1.00   1.00   1.00
Cetanol   0.80   0.80   0.80   0.80   0.80   0.80
Octadecanol   1.50   1.50   1.50   1.50   1.50   1.50
  Tribehenin   0.80   0.80   0.80   0.80   0.80   0.80
Isohexadecane   8.00   8.00   8.00   8.00   8.00   8.00
Ethylhexyl methoxy cinnamate   3.00   3.00   3.00   3.00   3.00   3.00
The B part Water In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100 In right amount to 100
Glycerine   2.00   2.00   2.00   2.00   2.00   2.00
UV-absorbent dispersion as described in example 6 above; The compound of general formula (103)   3.00     3.00     3.00     3.00     3.00     3.00  
General formula (m2) compound (Mexoryl SL)   2.00
The compound of general formula (n2) (Mexoryl SO)   1.50
Ubiquinone   0.01
General formula (c4) micronized compound   2.00
Phenylbenzimidazolesulfonic acid (Eusolex 232)   2.00
EDETATE SODIUM   0.10   0.10   0.10   0.10   0.10   0.10
The C part Water   20.00   20.00   20.00   20.00   20.00   20.00
N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15       0.15       0.15       0.15       0.15       0.15    
Propane diols   4.00   4.00   4.00   4.00   4.00   4.00
The D part Sodium acrylate copolymer (with) atoleine (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   1.50       1.50       1.50       1.50       1.50       1.50    
Cyclopentasiloxane   4.00   4.00   4.00   4.00   4.00   4.00
Polyethylene glycol-12 dimeticone   2.00   2.00   2.00   2.00   2.00   2.00
Alpha-tocopherol acetate   0.45   0.45   0.45   0.45   0.45   0.45
Water (with) citric acid In right amount In right amount In right amount In right amount In right amount In right amount
The E part Spices In right amount In right amount In right amount In right amount In right amount In right amount
The preparation explanation of embodiment 8a-8d:
Respectively A part and B partly are heated to 75 ℃. Continuing under the stirring A part impouring B part. To sneak into described mixture from D part cyclopentasiloxane and polyethylene glycol-12 dimeticone immediately after the emulsification. After this, use Ultra Turrax with 11000rpm with this mixture homogenize 30 seconds. After being cooled to 65 ℃, sneak into sodium acrylate copolymer (with) atoleine (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether. Under＜50 ℃ temperature, add the C part. Under＜35 ℃ temperature, sneak into alpha-tocopherol acetate and subsequently water (with) the lemon acid for adjusting pH. At room temperature add the E part.
Lotion between embodiment 9:UV day
   The INCI-title    %w/w (providing)
The A part The phosphoric acid cetyl   1.75
Benzoic acid C12-C15 Arrcostab   4.00
16/18 alcohol/polyethylene glycol-20 stearate   2.00
The ethoxydiglycol oleate   2.00
Stearic acid   1.50
Ethylhexyl methoxy cinnamate   3.00
Isononyl isononanoate   2.00
Bemotrizinol (Tinosorb S)   1.00
The B part Water In right amount to 100
Xanthan gum   0.35
UV-absorbent dispersion as described in example 6 above   5.00
EDETATE SODIUM   0.20
Propane diols   2.00
N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) methyl p-hydroxybenzoate (with) propylparaben (with) propane diols   0.70
Glycerine   1.50
The C part Cyclopentasiloxane (with) dimeticone   1.00
Ethoxydiglycol   3.00
Dimeticone   2.00
The D part Triethanolamine In right amount
The preparation explanation:
Prepare the A part by sneaking into all components, then under middling speed, stir and be heated to 75 ℃. Preparation B part also is heated to 75 ℃. In this temperature with progressively increase progressively under the mixing speed B part impouring A part. Then this mixture of homogenize (30 seconds, 15000rpm). Under the temperature of＜50C, add the C part. Then this compound of cooling under middling speed stirs detects pH and regulates with triethanolamine.
Embodiment 10: sunscreen
The INCI-title %w/w (providing)
The A part 16/18 alcohol/polyethylene glycol-20 stearate   4.00
Benzoic acid C12-C15 Arrcostab   2.00
Dicaprylyl ether (Dicaprylyl Ether)   3.00
The ethoxydiglycol oleate   2.00
Stearic acid   1.00
Ethylhexyl methoxy cinnamate   3.00
Sodium acrylate copolymer (with) Glycine Soja (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   0.30  
Saualane   3.50
The B part Water In right amount to 100
UV-absorbent dispersion as described in example 6 above   5.00
The C part N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15  
Propane diols   2.50
Water   10.00
The D part Cyclopentasiloxane (with) dimeticone   2.00
Ethoxydiglycol   5.00
Cyclopentasiloxane (with) dimeticone/vinyl-dimeticone friendship   2.00
Linked polymer
The E part NaOH   0.10
The preparation explanation:
Prepare the A part by sneaking into all components, then under middling speed, stir and be heated to 75 ℃. Preparation B part also is heated to 75 ℃. In this temperature with progressively increase progressively under the mixing speed B part impouring A part. Be lower than 65 ℃ of lower D parts that add separately. After under middling speed stirs, being cooled to 55 ℃, add the C part. Then detect pH and regulate with NaOH. With 16000rpm with this mixture homogenize 30 seconds.
Embodiment 11: daily lotion
   The INCI-title   %w/w (providing)
The A part The phosphoric acid stearyl   5.00
  Tricontanyl PVP   1.00
The ethoxydiglycol oleate   3.00
Saualane   5.00
Benzoic acid C12-C15 Arrcostab   5.00
Ethylhexyl methoxy cinnamate   3.00
Tristerin   2.00
Cetanol   2.00
Butyl methoxydibenzoylmethise (Parsol 1789)   1.50
The B part Water   20.00
UV-absorbent dispersion as described in example 5 above   3.00
Bisoctrizole (TinosorbM)   2.00  
The C part Water In right amount to 100
Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.50  
Glycerine   2.50
N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidine   0.15
Base-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester
Sodium lauroyl glutamate   0.70
The D part Cyclopentasiloxane (with) dimeticone   1.50
Triethanolamine   1.85
The preparation explanation:
Prepare the A part by sneaking into all components, then under middling speed, stir and be heated to 75 ℃. Preparation C part also is heated to 75 ℃. In this temperature with progressively increase progressively under the mixing speed C part impouring A part. After emulsification, add immediately the B part, then with the neutralization of part triethanolamine. With this mixture homogenize 30 seconds. After under middling speed stirs, cooling off, the adding cyclopentasiloxane (with) dimeticone. Be lower than 35 ℃ of lower pH of inspection and regulating with triethanolamine.
Embodiment 12: sprayable sunscreen
   The INCI-title    %w/w (providing)
The A part 16/octodecyl alcohol polyoxyethylene (15) ether (with) tristerin   3.00
Octadecanol   1.00
The castor oil acid cetyl   0.80
Dicaprylyl ether   3.00
Benzoic acid C12-C15 Arrcostab   3.00
Isohexadecane   2.50
The stearyl dimeticone   1.00
Ethylhexyl methoxy cinnamate   4.00
Cetanol   0.80
Tartaric acid two-C12-13 Arrcostab   3.00
The B part Water In right amount to 100
Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.45
Polyethylene glycol-7 glyceryl cocounut oil acid esters   2.50
Glycerine   2.00
Propane diols   3.00
The C part N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15  
Water   20.00
UV-absorbent dispersion as described in example 6 above   12.00
Titanium dioxide (with) silica (with) Sodium Polyacrylate   8.00
The D part Cyclopentasiloxane (with) dimeticone   0.85
The E part NaOH (with) water In right amount to pH 6.50-7.00
The F part Spices In right amount
The preparation explanation：
A part and B partly are heated to 80 ℃. Under agitation A is partly mixed the B part and use UltraTurrax with 11000rpm homogenize 30 seconds. C partly is heated to 60 ℃ also slowly to be joined in the described emulsion. After being cooled to 40 ℃, at room temperature sneaking into the D part and add the E part.
Embodiment 13: day care liquid
   The INCI-title   %w/w (providing)
The A part Polyglyceryl methyl glucoside distearate   2.50
16/18 alcohol   2.00
Octyl stearate   3.00
Caprylic/capric triglyceride   4.00
Isohexadecane   4.00
Ethylhexyl methoxy cinnamate   2.70
The B part Water   64.80
Glycerine   5.00
Phenoxetol (with) methyl p-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) propylparaben   0.50    
UV-absorbent dispersion as described in example 6 above   8.00
The C part The ring dimeticone (with) dimeticone   3.00
The D part Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.50  
The preparation explanation：
A part and B partly are heated to 75 ℃. Under continuous stirring, A partly added the B part and with 11000rpm homogenize 1 minute. After being cooled to 50 ℃, under continuous stirring, add the C part.
After being cooled to 30 ℃, add the D part. After this pH is adjusted to 6.00-6.50.
Embodiment 14: the day care agent with UV protective action
   The INCI-title    %w/w (providing)
The A part Tristerin SE   3.00
Tristerin and polyethylene glycol-100 stearates   3.50
Cetanol   1.50
Myristyl myristate   2.00
Isopropyl palmitate   2.50
Atoleine   5.00
Octyldimethyl PABA   3.00
The B part Water In right amount to 100
Propane diols   7.50
Phenoxetol (with) methyl p-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) propylparaben   1.00    
The C part Water   30.00
UV-absorbent dispersion as described in example 6 above   10.00
The D part Sodium acrylate copolymer (with) atoleine (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   2.00  
The E part Citric acid   0.30
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃. After B partly being added the A part, use UltraTurrax with 11000rpm homogenize 1 minute in this mixture. After being cooled to 50 ℃, add the C part. After this with this mixture with 16000rpm homogenize 1 minute. During in temperature＜40 ℃, add the D part. At room temperature with the E part pH value is adjusted to 6.00-6.50.
Embodiment 15:O/W day is used the UV protective liquid
   The INCl-title    %w/w (providing)
The A part Tristerin and polyethylene glycol-100 stearates   5.00
Octadecanol   1.00
Glyceryl tripalmitate   0.70
Dimeticone   2.00
Benzoic acid C12-15 Arrcostab   5.00
Isopropyl palmitate   5.00
Ethylhexyl methoxy cinnamate   3.00
The B part Water In right amount to 100
Polysorbate60   0.50
Glycerine   3.00
The C part Water   10.00
UV-absorbent dispersion as described in example 6 above   8.00
The D part Phenoxetol (with) methyl p-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) propylparaben   0.70    
Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   1.50
The E part Water (with) NaOH In right amount
The F part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃, C partly is heated to 60 ℃. After this under agitation with B part impouring A part. With this mixture with UltraTurrax with 11 000rpm homogenizes 30 seconds and sneak into the C part. After being cooled to 40 ℃, add the D part. At room temperature with NaOH the pH value is adjusted to 6.30-6.70 and adds the F part.
Embodiment 16:O/W day is used the UV protective agent
   The INCI-title    %w/w (providing)
The A part Tristerin and polyethylene glycol-100 stearates   5.00
Octadecanol   1.00
Glyceryl tripalmitate   0.70
Dimeticone   2.00
Benzoic acid C12-15 Arrcostab   4.00
Isopropyl palmitate   4.00
Ethylhexyl methoxy cinnamate   3.00
OXYBENZONE   1.00
UVNUL MS-40   1.00
The B part Water In right amount to 100
Polysorbate60   0.50
Glycerine   3.00
The C part Water   10.00
UV-absorbent dispersion as described in example 6 above   8.00
The D part Phenoxetol (with) methyl p-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) propylparaben   0.70    
Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   1.50
The E part Water (with) NaOH In right amount
The F part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃, C partly is heated to 60 ℃. After this under agitation with B part impouring A part. With this mixture with UltraTurrax with 11000rpm homogenize 30 seconds and sneak into the C part. After being cooled to 40 ℃, add the D part. At room temperature with NaOH the pH value is adjusted to 6.30-6.70 and adds the F part.
Embodiment 17: suncream
   The INCI-title %w/w (providing)
The A part 16/18 alcohol (with) DCP (with) hexadecanol polyoxyethylene (10) ether   4.50  
Benzoic acid C12-15 Arrcostab   6.00
Caprylic/capric triglyceride   7.00
Pentaerythritol tetraoctyl stearate   2.00
Ethylhexyl methoxy cinnamate   3.00
Neo Heliopan E1000   2.00
The B part Water In right amount to 100
Glycerine   2.00
Propane diols   1.50
Magnesiumaluminumsilicate   1.20
The C part Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.50  
UV-absorbent dispersion as described in example 5 above   12.00
The D part Phenyl front three silicone oil   1.50
Phenoxetol (with) methyl p-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) propylparaben   0.70    
The E part NaOH   0.90
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃. Under continuous stirring, B is partly added A partly and after this use UltraTurrax with 11000rpm homogenize 30 seconds. After being cooled to 60 ℃, add the C part. Add the C part at 40 ℃, and with 11000rpm homogenize 15 seconds. At room temperature partly regulate the pH value with E.
Embodiment 18:UVA/UVB O/W type day care liquid
   The INCI-title    %w/w (providing)
The A part Tristerin and polyethylene glycol-100 stearates   5.00
Octadecanol   1.00
Glyceryl tripalmitate   0.70
Mineral oil   15.00
The B part Water In right amount to 100
Polysorbate60   0.50
Glycerine   3.00
The C part Water   10.00
UV-absorbent dispersion as described in example 6 above   8.00
The D part Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   1.50
Phenoxetol (with) methyl p-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) propylparaben   0.70    
The E part Water (with) NaOH In right amount
The F part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃, C partly is heated to 60 ℃. Under agitation with B part impouring A part. , after 1 minute C is partly being joined in the A/B mixture with the 11000rpm homogenize. After being cooled to 40 ℃, sneak into the D part. At room temperature with the E part pH value is adjusted to 6.3-7.0. The final F part that adds.
Embodiment 19:UVA/UVB O/W type day care liquid
   The INCI-title    %w/w (providing)
The A part Oil base polyoxyethylene (3) ether phosphate   0.60
Stearyl polyoxyethylene (21) ether   2.50
Stearyl polyoxyethylene (2) ether   1.00
Cetanol   0.80
The B part Octadecanol   1.50
  tribehenin   0.80
Isohexadecane   8.00
The C part Water In right amount to 100
Glycerine   2.00
EDETATE SODIUM   0.10
Cyclopentasiloxane   4.50
Polyethylene glycol-12 dimeticone   2.00
The D part Sodium acrylate copolymer (with) mineral oil (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   1.50  
The E part UV-absorbent dispersion as described in example 6 above   10.00
The F part Alpha-tocopherol acetate   0.45
DMDMH (with) butyl carbamic acid iodine propynyl ester (with) water (with) butanediol   0.85  
The G part Water (with) citric acid In right amount
Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃. Under continuous stirring with A part impouring B part. Immediately C is partly joined after the emulsification and also use UltraTurrax with 11000rpm homogenize 30 seconds in the described mixture. After being cooled to 65 ℃, under 50 ℃ with sodium acrylate copolymer (with) mineral oil (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether slowly joins in the UV absorbent dispersion. Under about 35-30 ℃, sneak into the F part. With the G part pH value is adjusted to 5.5-6.5.
The daily protective liquid of embodiment 20:UV-A/UV-B O/W type
   The INCI-title    %w/w (providing)
The A part GLYCERYL DILAURATE   2.00
The own ester of palm acid ethyl   6.00
Cetanol   1.00
Tristerin   2.00
Lauryl polyoxyethylene (23) ether   1.00
Isopropyl palmitate   2.00
  Tribehenin   0.80
Beeswax   1.50
Lanolin oil   1.00
The B part Water In right amount to 100
Propane diols   4.00
Water (with) titanium dioxide (with) aluminium oxide (with) sodium metaphosphate (with) phenoxetol (with) methyl P-hydroxybenzoic acid sodium   4.00  
The C part Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   1.00
Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   1.00    
The D part UV-absorbent dispersion as described in example 6 above   8.00
The E part Water (with) NaOH In right amount
The preparation explanation：
Respectively A part and B partly are heated to 80 ℃. When stirring, also use UltraTurrax with 11000rpm homogenize 30 seconds A part impouring B part. After being cooled to 60 ℃, sneak into the C part. Under 40 ℃ and continuous stirring, slowly add the D part. With the E part pH is adjusted to 6.50-7.00.
Embodiment 21: sprayable suntan lotion
   The INCI-title    %w/w (providing)
The A part The cetyl potassium phosphate   0.20
Isohexadecane   7.00
VP/ eicosylene copolymer   1.50
Tartaric acid two-C12-13 Arrcostab   6.00
Uvinul T 150   2.50
Benzoic acid C12-15 Arrcostab   4.50
Water In right amount to 100
Sorbitol polyoxyethylene (30) ether   2.00
Sorbitan stearate (with) sucrose cocounut oil acid esters   4.00
The B part Titanium dioxide (with) aluminium oxide (with) silica (with) Sodium Polyacrylate   2.50
Water   30.00
UV-absorbent dispersion as described in example 6 above   12.00
Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   0.70    
Water (with) NaOH In right amount
The preparation explanation：
Respectively A part and B partly are heated to 80 ℃, C partly is heated to 50 ℃. Also use UltraTurrax with 11000rpm homogenize 1 minute B part impouring A part. After being cooled to 50 ℃, under continuous stirring, add the C part. Under 40 ℃, sneak into the D part also again with 11000rpm homogenize 10 seconds. Partly regulate pH with E.
Embodiment 22:O/W day is used the UV protective liquid
  The INCI-title    %w/w (providing)
The A part Tristerin and polyethylene glycol-100 stearates   5.00
Octadecanol   1.00
Glyceryl tripalmitate   0.70
Dimeticone   2.00
Caprylic/capric triglyceride   5.00
Isopropyl palmitate   5.00
Ethylhexyl methoxy cinnamate   3.00
The B part Water In right amount to 100
Polysorbate60   0.50
Glycerine   3.00
The C part Water   10.00
UV-absorbent dispersion as described in example 6 above   8.00
ZnO (Nanox zinc oxide)   3.00
The D part Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   0.70    
Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   1.50
The E part Water (with) NaOH In right amount
The F part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃, C partly is heated to 60 ℃. After this under agitation with B part impouring A part. With this mixture with UltraTurrax with 11000rpm homogenize 30 seconds and sneak into the C part. After being cooled to 40 ℃, add the D part. At room temperature with NaOH the pH value is adjusted to 6.30-6.70 and adds the F part.
Embodiment 23: the water proofing property sunscreen
  The INCI-title    %w/w (providing)
The A part Polyglycereol (10) five stearates (with) behenyl alcohol (with) stearyl dilactic acid sodium   2.50  
VP/ eicosylene copolymer   1.50
Octadecanol   1.50
Saualane   4.00
Benzoic acid C12-15 Arrcostab   5.50
Octocrylene   1.50
4 methyl benzylidene camphor   3.00
Ethylhexyl methoxy cinnamate   2.00
Neo Heliopan OS (Neoheliopan OS)   2.00
The B part Water In right amount to 100
Glycerine   1.80
Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.80
The C part UV-absorbent dispersion as described in example 6 above   9.00
The D part VP/ hexadecylene copolymer   2.70
The ring dimethicone   1.50
Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   0.70    
The E part Water (with) alpha-tocopherol acetate (with) caprylic/capric triglyceride (with) polysorbate80 (with) lecithin   3.50  
The F part Spices In right amount
Water (with) NaOH In right amount
The preparation explanation：
Respectively A part and B partly are heated to 80 ℃. Under continuous stirring with A part impouring B part. After this use UltraTurrax with 11 000rpm with this mixture homogenize 1 minute. After being cooled to 60 ℃, sneak into the C part. Also this mixture is carried out the short time homogenize again 40 ℃ of lower D parts that add. Also at room temperature add spices 35 ℃ of lower E parts that add. Finally regulate pH with NaOH.
Embodiment 24:UVA/UVB O/W type suntan lotion
   The INCI-title    %w/w (providing)
The A part The cetyl potassium phosphate   2.00
  Tricotanyl PVP   1.00
Caprylic/capric triglyceride   5.00
Benzoic acid C12-15 Arrcostab   5.00
Different n-nonanoic acid 16/octadecyl ester   5.00
Stearine   3.00
Cetanol   1.00
Dimeticone   0.10
Ethylhexyl methoxy cinnamate   5.00
The B part Water In right amount to 100
Glycerine   3.00
2,2 '-two (Isosorbide-5-Nitrae-phenylene)-1H-benzimidazoles-4,6-disulfonic acid one sodium salt (Neoheliopan AP)   2.00  
The C part Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.50  
The D part UV-absorbent dispersion as described in example 6 above   8.00
The E part Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   1.00    
The F part Water (with) NaOH In right amount to pH 7.00
The G part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 80 ℃. Under middling speed stirs with B part impouring A part. After this use UltraTurrax with 11000rpm with this mixture homogenize 1 minute. After being cooled to 70 ℃, under agitation add the C part. After being cooled to 50 ℃, sneak into the D part very slowly. 40 ℃ of lower E parts that add. At room temperature with F part pH is adjusted to 7.00 and add the G part.
Embodiment 25:UVA/UVB O/W type suntan lotion
  The INCI-title    %w/w (providing)
The A part The cetyl potassium phosphate   2.00
 Tricotanyl PVP   1.00
Caprylic/capric triglyceride   5.00
Benzoic acid C12-15 Arrcostab   5.00
Different n-nonanoic acid 16/stearyl   5.00
Stearine   3.00
Cetanol   1.00
Dimeticone   0.10
Ethylhexyl methoxy cinnamate   4.00
Uvasorb HEB (UVASORB HEB)   1.00
The B part Water In right amount to 100
Glycerine   3.00
The C part Stearyl polyoxyethylene (10) ether allyl ether/acrylate copolymer   0.50
The D part UV-absorbent dispersion as described in example 6 above   20.00
The E part Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   1.00    
The F part Water (with) NaOH In right amount to pH 7.00
The G part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 80 ℃. Under middling speed stirs with B part impouring A part. With UltraTurrax with 11000rpm with this mixture homogenize 1 minute. After being cooled to 70 ℃, under agitation add the C part. After further being cooled to 50 ℃, sneak into the D part very slowly. 40 ℃ of lower E parts that add. At room temperature with F part pH is adjusted to 7.00 and add the G part.
Embodiment 26: suntan lotion
   The INCI-title    %w/w (providing)
The A part 16/18 alcohol (with) DCP (with) hexadecanol polyoxyethylene (15) ether phosphate   4.00  
Benzoic acid C12-15 Arrcostab   2.00
Dicaprylyl ether   3.00
Oleic acid ethoxydiglycol ester   2.00
Stearic acid   1.00
Ethylhexyl methoxy cinnamate   2.00
Sodium acrylate copolymer (with) Glycine soja (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   0.30  
Saualane   3.50
VP/ eicosylene copolymer   2.00
Toluenyl malonic ester polysiloxanes (Parsol SLX)   2.00
The B part Water In right amount to 100
UV-absorbent dispersion as described in example 6 above   5.00
The C part N-(methylol)-N-(the two methylols-2 of 1,3-, 5-dioxy-4-imidazolidinyl-N '-(methylol) urea (with) butyl carbamic acid iodine propynyl ester   0.15  
Propane diols   2.50
Water   10.00
The D part Cyclopentasiloxane (with) dimeticone   2.00
Ethoxydiglycol   5.00
Cyclopentasiloxane (with) dimeticone/vinyl-dimethyl silicone oil cross-linked polymer   2.00  
The E part Water (with) NaOH In right amount
The F part Spices In right amount
The preparation explanation：
Respectively A part and B partly are heated to 75 ℃. Increasing progressively under the mixing speed B part impouring A part. During in temperature＜65 ℃, add separately the component of D part. After being cooled to 55 ℃, under stirring, middling speed adds the C part. During in temperature＜35 ℃, detect pH and with NaOH regulate and with Ultra Turrax with 11 000rpm homogenizes 30 seconds. At room temperature add the F part.
Embodiment 27:W/O suntan lotion
  The INCI-title    %w/w (providing)
The A part Polyethylene glycol-7 rilanit special   3.00
Two isostearic acid polyglycereol (3) esters   4.00
Microwax   1.00
Dolomol   1.50
Propylparaben   0.10
Mineral oil   15.00
Octyl dodecanol   8.30
Uvinul T 150   1.00
Ethylhexyl methoxy cinnamate   2.00
Uvinul A+ (Uvinul A+)   1.50  
The B part Water In right amount to 100
Water (with) citric acid   0.05
Methyl p-hydroxybenzoate   0.15
Dolomol   0.50
The C part UV-absorbent dispersion as described in example 6 above   9.00
Spices In right amount
The preparation explanation：
When stirring, A partly is heated to 80 ℃. B is partly added the A part and uses Ultra Turrax with 11 000rpm homogenizes 1 minute. After being cooled to 30 ℃, sneak into the C part.
Embodiment 28:W/O type skin care suntan lotion
   The INCI-title    %w/w (providing)
The A part Dimerization hydroxy stearic acid polyglycereol (2) ester   3.00
Olein   3.00
Different n-nonanoic acid 16/stearyl   7.00
Lauric acid hexyl ester   6.00
Dicaprylyl ether   6.00
Propylparaben   0.10
The hexyl decyl alcohol   3.00
Dolomol   1.00
Beeswax   1.00
Ethylhexyl methoxy cinnamate   4.00
The B part Water In right amount to 100
Methyl p-hydroxybenzoate   0.15
Magnesium sulfate   1.00
The C part UV-absorbent dispersion as described in example 6 above   6.00
The preparation explanation：
When slowly stirring, separately A partly is heated to 80C. B partly added A part and with 11000rpm homogenize 1 minute. After being cooled to 30 ℃, under continuous stirring, add the C part.
Embodiment 29: sun-screening agent
   The INCI-title    %w/w (providing)
The A part The hexyl decyl alcohol   2.70
Polyoxyethylene (2) octadecane alcohol ether   2.20
Dimerization hydroxy stearic acid polyethylene glycol (30) ester   1.10
Dispersion UV-absorbent dispersion as described in example 6 above; Regulate pH=7 with citric acid   6  
The B part The thylhexoic acid cetyl   4.00
Isohexadecane   4.00
Ethylhexyl methoxy cinnamate   0.00
Bemotrizinol (Tinosorb S)   0.00  
Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   0.60    
The C part Water In right amount to 100
Glycerine   3.00
The D part Sodium acrylate copolymer (with) mineral oil (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   2.00  
The E part Cyclopentasiloxane   2.00
This sun-screening agent also can be used as wrinkle resistant sensation conditioning agent.
The preparation explanation
Mix the A part and be heated to 60 ℃-65 ℃ and slowly adding split under rapid stirring.
Under stirring, 60 ℃ and middling speed add the B part.
60 ℃-75 ℃ and stir under B is partly added the A part.
Under agitation add C part to homogenize (can with ultra turrax emulsification when the rapid stirring).
Under stirring, middling speed adds D part (60 ℃).
Finally under agitation add E part (60 ℃) and cooling under middling speed stirs.
Embodiment 30: the sun-screening agent that does not contain polyethylene glycol
  The INCI-title    %w/w (providing)
The A part The hexyl decyl alcohol   2.30
Polyglycereol (3) methyl glucoside distearate   1.40
Polyglycereol gathers hydroxy stearic acid ester   1.40
Dispersion UV-absorbent as described in example 6 above; Regulate pH=7 with citric acid   5.00  
The thylhexoic acid cetyl   3.00
Isohexadecane   3.00
Ethylhexyl methoxy cinnamate   3.00
Bemotrizinol (Tinosorb S)   2.00
Phenoxetol (with) methyl p-hydroxybenzoate (with) ethyl-para-hydroxybenzoate (with) butyl p-hydroxybenzoate (with) propylparaben (with) p-Hydroxybenzoic acid isobutyl ester   0.60    
The B part Water In right amount to 100
Glycerine   3.00
Sodium acrylate copolymer (with) mineral oil (with) polypropylene glycol-1 tridecyl polyoxyethylene (6) ether   1.50  
The C part Cyclopentasiloxane   1.50

Claims (37)

1. the purposes of general formula (1) compound in protection humans and animals hair and the anti-UV radiation injury of skin:
Figure A2004800102240002C1
Wherein
A is general formula (1a)
Figure A2004800102240002C2
Or (1b)
Figure A2004800102240002C3
Group;
R 1And R5Be hydrogen, C independently of one another1-C 18Alkyl or C6-C 12Aryl;
R 2、R 3And R4Be hydrogen or general formula (1c) independently of one another
Figure A2004800102240002C4
Group,
Wherein in general formula (1a), radicals R2、R 3And R4In at least one is the group of general formula (1c);
R 6、R 7，、R 8、R 9And R10Be hydrogen, hydroxyl, halogen, C independently of one another1-C 18Alkyl, C1-C 18Alkoxyl, C6-C 12Aryl, xenyl, C6-C 12Aryloxy group, C1-C 18Alkylthio group, carboxyl, COOM, C1-C 18-alkyl carboxyl, amino carbonyl or-or two-C1-C 18Alkyl amino, C1-C 10Acylamino-,-COOH;
M is alkali metal ion;
X is 1 or 2; And
Y is the numerical value of 2-10.
2. the purposes of claim 1 relates to the compound of general formula (2):
Figure A2004800102240002C5
Wherein:
R 1、R 5、R 6、R 7And R8As defined in claim 1.
3. claim 1 or 2 purposes, wherein R1And R5Be hydrogen.
4. the purposes of one of claim 1-3, wherein R6And R8Be hydrogen.
5. the purposes of one of claim 1-4, wherein:
R 7Be hydrogen, hydroxyl, C1-C 5Alkyl, C1-C 5Alkoxyl ,-COOM ,-COOH or COOR10；
M is alkali metal ion; And
R 10Be C1-C 5Alkyl.
6. the purposes of claim 1 relates to the compound of general formula (3):
Wherein
R 1、R 2、R 3、R 9And R10As defined in claim 1.
7. the purposes of claim 6, wherein:
R 1、R 2、R 3、R 9And R10For hydrogen or be C independently of one another1-C 18Alkyl.
8. each purposes according to claim 1-5, wherein use the compound of general formula (6):
Figure A2004800102240003C2
9. make-up preparation comprises that permissible carrier or assistant agent are gone up in compound and the cosmetic of at least a general formula (1) of claim 1.
10. the make-up preparation of claim 9 comprises that UV filters composition (A), and said composition (A) comprising:
(a 1) Striazine derivative of at least a general formula (1); With
(a 2) the ADP ketone derivatives of at least a following general formula:
Wherein:
R 1And R2Be C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkyl, C3-C 10Cycloalkenyl group; Or R1And R2Form 5-or 6-unit heterocycle with the nitrogen-atoms that connects;
n 1Numerical value for 1-4;
Work as n1=1 o'clock,
R 3Be saturated or undersaturated heterocyclic radical, hydroxyl-C1-C 5Alkyl, optional by one or more C1-C 5The cyclohexyl that alkyl replaces, optional by heterocyclic radical, amino carbonyl or C1-C 5The phenyl that alkyl carboxyl replaces
Work as n1=2 o'clock,
R 3For the optional alkylidene that is replaced by carbonyl or carboxyl-, ring alkylidene, alkylene group or phenylene, general formula *-CH2-C≡C-CH 2-* group; Or
R 3Form the divalent group of general formula (1a) with A
Figure A2004800102240004C2
Wherein:
n 2Numerical value for 1-3;
Work as n1Be 3 o'clock,
R 3Be alkane three bases;
Work as n1Be 4 o'clock,
R 3Be alkane four bases;
A is-O-or-N (R5)-; And
R 5Be hydrogen, C1-C 5Alkyl or hydroxyl-C1-C 5Alkyl.
11. the make-up preparation of claim 10 comprises that UV filters composition (A1), said composition (A1) comprising:
(a 3) compound of general formula (6) or (9); With
(a 4) compound of following general formula:
Figure A2004800102240005C1
12. the make-up preparation of claim 9 comprises that UV filters composition (B), said composition (B) comprising:
(b 1) Striazine derivative of at least a general formula (1); With
(b 2) the ADP ketone derivatives of at least a following general formula:
Figure A2004800102240005C2
Wherein:
R 1And R2Be hydrogen, C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkenyl group; R wherein1And R2Can form 5-or 6-unit ring;
R 3And R4Be C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkenyl group, C1-C 20Alkoxyl, C1-C 20Alkoxy carbonyl group, C1-C 20Alkylamino, two (C1-C 20Alkyl) amino, optional aryl or the heteroaryl that replaces;
X is hydrogen, COOR5、CONR 6R 7；
R 5、R 6、R 7Be hydrogen, C independently of one another1-C 20Alkyl, C2-C 20Alkenyl, C3-C 10Cycloalkyl, C3-C 10Cycloalkenyl group, (Y-O)q-Z, the optional aryl that replaces;
Y is-(CH2) 2-、-(CH 2) 4-、-CH(CH 3)-CH 2-；
Z is-CH2-CH 3、-CH 2-CH 2-CH 3、-CH 2-CH 2-CH 2-CH 3、CH(CH 3)-CH 3；
M is 0,1,2 or 3;
N is 0,1,2,3 or 4; And
Q is the numerical value of 1-20
13. the make-up preparation of claim 12 comprises that UV filters composition (B1), said composition (B1) comprising:
(b 3) compound of general formula (6) or (9); With
(b 4) compound of following general formula:
Figure A2004800102240006C1
14. the make-up preparation of claim 9 comprises that UV filters composition (C), said composition (C) comprising:
(c 1) Striazine derivative of at least a general formula (1); With
(c 2) at least a general formula benzotriazole derivatives:
Figure A2004800102240006C2
Wherein:
T 2Be C1-C 10The C that alkyl or phenyl replaces1-C 4Alkyl.
15. the make-up preparation of claim 14 comprises that UV filters composition (C1), said composition (C1) comprising:
(c 3) compound of general formula (6) or (9); With
(c 4) compound of following general formula:
Figure A2004800102240006C3
16. the make-up preparation of claim 9 comprises that UV filters composition (D), said composition (D) comprising:
(d 1) Striazine derivative of at least a general formula (1); With
(d 2) compound of at least a following general formula:
Wherein:
R 1And R2Be C independently of one another3-C 18Alkyl, C2-C 18Alkenyl, general formula-CH2-CH(-OH)-CH 2-O-T 1Group; Or
R 1And R2Group for general formula (4a)
Figure A2004800102240007C2
R 12Be direct key, straight or branched C1-C 4Alkylidene or general formula-Cm1H 2m1-or-Cm1H 2m1The group of-O-;
R 13、R 14And R15Be C independently of one another1-C 18Alkyl, C1-C 18The group of alkoxyl or following general formula:
R 16Be C1-C 5Alkyl;
m 1And m3Be 1-4 independently of one another;
p 1Be 0 or the numerical value of 1-5;
A 1Group for following general formula
Figure A2004800102240007C4
Or
Figure A2004800102240007C5
R 3Be hydrogen, C1-C 10Alkyl ,-(CH2CHR 5-O) n1-R 4Or the group of following general formula :-CH2-CH(-OH)-CH 2-O-T 1；
R 4Be hydrogen; M; C1-C 5Alkyl; Or general formula-(CH2) m2-O-T 1Group;
R 3Be hydrogen or methyl;
T 1Be hydrogen or C1-C 8Alkyl;
Q 1Be C1-C 18Alkyl;
M is metal cation;
m 2Be 1-4; And
N is 1-16.
17. the make-up preparation of claim 16 comprises that UV filters composition (D1), said composition (D1) comprising:
(d 3) compound of general formula (6) or (9); With
(d 4) compound of following general formula:
18. the make-up preparation of claim 9 comprises that UV filters composition (E), said composition (E) comprising:
(e 1) Striazine derivative of at least a general formula (1); With
(e 2) the hydroxy phenyl pyrrolotriazine derivatives of at least a following general formula:
Wherein:
R 1、R 2And R3Be C independently of one another1-C 18Alkyl, C2-C 10Alkenyl or phenyl-C1-C 4Alkyl;
R 4Be hydrogen or C1-C 5Alkyl.
19. the make-up preparation of claim 18 comprises that UV filters composition (E1), said composition (E1) comprising:
(e 3) compound of general formula (6) or (9); With
(e 4) compound of following general formula:
20. the make-up preparation of claim 9 comprises that UV filters composition (F), said composition (F) comprising:
(f 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) or (9); With
(f 2) dibenzoylmethane derivative of at least a following general formula:
Figure A2004800102240009C2
Or
Figure A2004800102240009C3
21. the make-up preparation of claim 9 comprises that UV filters composition (G), said composition (G) comprising:
(g 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) or (9); With
(g 2) Neo Heliopan AP.
22. the make-up preparation of claim 9 comprises that UV filters composition (H), said composition (H) comprising:
(h 1) Striazine derivative of at least a general formula (1), and
(h 2) triazine of benzoxazole-replacement of at least a following general formula:
Figure A2004800102240010C1
Wherein:
R 1、R 2And R3Be side chain or non-side chain C independently of one another1-C 12Alkyl.
23. the make-up preparation of claim 22 comprises that UV filters composition (H1), said composition (H1) comprising:
(h 3) compound of general formula (6) or (9), and
(h 4) 1,3,5-triazines-2,4,6-triamine, N, N '-two [4-[5-(1,1-dimethyl propyl)-2-benzoxazolyl] phenyl]-N " (2-ethylhexyl).
24. the make-up preparation of claim 22 or 23 comprises that UV filters composition (H2), said composition (H2) comprising:
(h 5) compound of general formula (6) or (9), and
(h 6) at least a general formula (h21) compound, wherein
(h 61)R 1And R2Be tertiary pentyl and R3Be the tert-butyl group; Or wherein
(h 62)R 1And R2Be the tert-butyl group and R3Be uncle's octyl group; Or wherein
(h 63)R 1And R2Be the tert-butyl group and R3Be the 2-ethylhexyl; Or wherein
(h 64)R 1And R2Be tertiary pentyl and R3Be the 2-ethylhexyl.
25. the make-up preparation of claim 9 comprises that UV filters composition (I), said composition (I) comprising:
(i 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) or (9); With
(i 2) 2-(2H-BTA-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethyl silyl) the oxygen base] the disiloxane base] propyl group]-.
26. the make-up preparation of claim 9 comprises that UV filters composition (K), said composition (K) comprising:
(k 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) or (9); With
(k 2) siloxanes and silicone, two-Me, 1-[[4-[3-ethyoxyl-2-(carbethoxyl group)-3-oxo-1-acrylic] phenoxy group] methyl] vinyl Me, 3-[4-[3-ethyoxyl-2-(carbethoxyl group)-3-oxo-1-acrylic] phenoxy group]-1-acrylic Me, wherein:
Me is hydrogen.
27. the make-up preparation of claim 9 comprises that UV filters composition (L), said composition (L) comprising:
(l 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) or (9); With
(l 2) (+/-)-1,7,7-trimethyl-3-[(4-aminomethyl phenyl) methylene] dicyclo [2.2.1] heptan-2-ketone.
28. the make-up preparation of claim 9 comprises that UV filters composition (M), said composition (M) comprising:
(m 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(m 2) α-(2-oxo borneol-3-subunit) toluene-4-sulfonic acid and salt thereof.
29. the make-up preparation of claim 9 comprises that UV filters composition (N), said composition (N) comprising:
(n 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(n 2) N, N, N-trimethyl-4-[(4,7,7-trimethyl-3-oxo dicyclo [2,2,1] heptan-2-base subunit) methyl]-anilinomethyl sulfate.
30. the make-up preparation of claim 9 comprises that UV filters composition (O), said composition (O) comprising:
(o 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(o 2) 2-cyano group, 3,3-diphenylacrylate 2-ethylhexyl.
31. the make-up preparation of claim 9 comprises that UV filters composition (P), said composition (P) comprising:
(p 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(p 2) Uvinul MC 80.
32. the make-up preparation of claim 9 comprises that UV filters composition (Q), said composition (Q) comprising:
(q 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(q 2) benzoic acid, 4,4 ', 4 " (1,3,5-triazines-2,4,6-three basic three imino groups) three-, three (2-ethylhexyl) ester.
33. the make-up preparation of claim 9 comprises that UV filters composition (R), said composition (R) comprising:
(r 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(r 2) 2-phenyl-1H-benzimidazole-5-sulfonic acid.
34. the make-up preparation of claim 9 comprises that UV filters composition (S), said composition (S) comprising:
(s 1) Striazine derivative of at least a general formula (1), the compound of preferred formula (6) and/or (9); With
(s 2) benzoic acid, 4,4 '-[[the 6-[[4-[[(1-dimethyl ethyl) amino] carbonyl] phenyl] amino] 1,3,5-triazines-2,4-two bases] diimino] two-, two (2-ethylhexyl) ester.
35. each make-up composition among the claim 9-34, the compound of its formula of (1), general formula (6) or general formula (9) is present in the described composition with micronized state.
36. the compound of general formula (1) is as the purposes of wrinkle resistant sensation conditioning agent.
37. prepare the method for general formula (1) compound, comprise the halo triaizine compounds that makes general formula (1d) according to following reaction scheme with Friedel-Crafts reaction and the optional general formula (1e) that replaces or the reaction of aromatic hydrocarbon (1f) and obtain the compound of general formula (1):
Figure A2004800102240012C1
Wherein:
X is fluorine, chlorine or (oder) bromine; And
R 1、R 2、R 3、R 9、R 10, x and y as defined in claim 1.
CNB2004800102245A 2003-03-24 2004-03-19 Symmetrical triazine derivatives Expired - Fee Related CN100424081C (en)

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CN108635244A (en) * 2011-06-07 2018-10-12 拜尔斯道夫股份有限公司 Use of polyglycerol-10 stearate in sunscreen formulations to increase contact angle and thereby improve water resistance
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CN101854904B (en) * 2007-08-30 2012-08-15 巴斯夫欧洲公司 Stabilization of cosmetic compositions
CN107049819A (en) * 2007-12-14 2017-08-18 巴斯夫欧洲公司 Sunscreen composition comprising color pigment
CN108635244A (en) * 2011-06-07 2018-10-12 拜尔斯道夫股份有限公司 Use of polyglycerol-10 stearate in sunscreen formulations to increase contact angle and thereby improve water resistance
CN108635244B (en) * 2011-06-07 2023-07-14 拜尔斯道夫股份有限公司 Use of polyglycerol-10 stearate in sunscreen formulations to improve contact angle and thus water resistance
CN110372620A (en) * 2019-08-07 2019-10-25 天津利安隆新材料股份有限公司 A kind of preparation method of ultraviolet absorbing agent UV-1600 intermediate
CN110372620B (en) * 2019-08-07 2021-06-22 天津利安隆新材料股份有限公司 Preparation method of ultraviolet absorbent UV-1600 intermediate
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