CN1541138A - 微胶囊分散体 - Google Patents
微胶囊分散体 Download PDFInfo
- Publication number
- CN1541138A CN1541138A CNA02815925XA CN02815925A CN1541138A CN 1541138 A CN1541138 A CN 1541138A CN A02815925X A CNA02815925X A CN A02815925XA CN 02815925 A CN02815925 A CN 02815925A CN 1541138 A CN1541138 A CN 1541138A
- Authority
- CN
- China
- Prior art keywords
- weight
- microcapsules
- water
- acid
- polyisocyanates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 37
- 239000002775 capsule Substances 0.000 claims abstract description 42
- 239000002904 solvent Substances 0.000 claims abstract description 37
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 25
- 239000006185 dispersion Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 229920002396 Polyurea Polymers 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000005056 polyisocyanate Substances 0.000 claims description 32
- 229920001228 polyisocyanate Polymers 0.000 claims description 32
- 239000000975 dye Substances 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 26
- -1 fatty acid esters Chemical class 0.000 claims description 26
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 239000000839 emulsion Substances 0.000 claims description 17
- 125000005456 glyceride group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 229920001400 block copolymer Polymers 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 11
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000007348 radical reaction Methods 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 22
- 230000008569 process Effects 0.000 abstract description 8
- 239000010696 ester oil Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920003226 polyurethane urea Polymers 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000011162 core material Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 150000002191 fatty alcohols Chemical class 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000004166 Lanolin Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 235000019388 lanolin Nutrition 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000012644 addition polymerization Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 229940039717 lanolin Drugs 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 239000007762 w/o emulsion Substances 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- YJCJVMMDTBEITC-UHFFFAOYSA-N 10-hydroxycapric acid Chemical compound OCCCCCCCCCC(O)=O YJCJVMMDTBEITC-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QNIXMCINXVRKGG-UHFFFAOYSA-N 4-ethyl-1-isocyanato-4-(isocyanatomethyl)octane Chemical compound CCCCC(CC)(CN=C=O)CCCN=C=O QNIXMCINXVRKGG-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- OVSNDJXCFPSPDZ-UHFFFAOYSA-N Reactive red 120 Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=CC(NC=3N=C(NC=4C=CC(NC=5N=C(NC=6C7=C(O)C(N=NC=8C(=CC=CC=8)S(O)(=O)=O)=C(C=C7C=C(C=6)S(O)(=O)=O)S(O)(=O)=O)N=C(Cl)N=5)=CC=4)N=C(Cl)N=3)=C2C(O)=C1N=NC1=CC=CC=C1S(O)(=O)=O OVSNDJXCFPSPDZ-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- GHBFNMLVSPCDGN-UHFFFAOYSA-N caprylic acid monoglyceride Natural products CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- XWZDJOJCYUSIEY-UHFFFAOYSA-L disodium 5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(N=Nc2ccccc2)c(cc2cc(cc(Nc3nc(Cl)nc(Cl)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O XWZDJOJCYUSIEY-UHFFFAOYSA-L 0.000 description 2
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
- 210000004709 eyebrow Anatomy 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000004200 microcrystalline wax Substances 0.000 description 2
- 235000019808 microcrystalline wax Nutrition 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- MCTQNEBFZMBRSQ-UHFFFAOYSA-N (3-amino-4-phenyldiazenylphenyl)azanium;chloride Chemical compound Cl.NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 MCTQNEBFZMBRSQ-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- UGAGPNKCDRTDHP-UHFFFAOYSA-N 16-hydroxyhexadecanoic acid Chemical compound OCCCCCCCCCCCCCCCC(O)=O UGAGPNKCDRTDHP-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 description 1
- AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- MAJRQODVOQXXQQ-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole-4-sulfonic acid Chemical compound N1C=2C(S(=O)(=O)O)=CC=CC=2N=C1C1=CC=CC=C1 MAJRQODVOQXXQQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical compound NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及微胶囊分散体,包含在疏水溶剂中的微胶囊,其中所述疏水溶剂是由50-100重量%的甘油酯油和0-50重量%的能与甘油酯油混溶的溶剂组成,所述微胶囊具有含水溶性有机物质的胶囊芯和基本由聚氨酯和/或聚脲组成的胶囊包衣,以及涉及所述微胶囊分散体的制备方法。
Description
本发明涉及微胶囊分散体,它包含在疏水溶剂中的微胶囊,其中疏水溶剂由50-100重量%的甘油酯油和0-50重量%的能与甘油酯油混溶的溶剂组成,微胶囊具有含水溶性有机物质的胶囊芯和基本由聚氨酯和/或聚脲组成的胶囊包衣,以及涉及它们的制备方法。
微胶囊是球形颗粒,包括胶囊芯和包覆该胶囊芯的胶囊包衣,还称之为胶囊壁。取决于胶囊芯的性质,可以有各种用途。这里关于性能的决定性因素还有壁材料和包封方法,例如在活性成分控释的胶囊的情况下。
微胶囊广泛用于无碳复印纸。因此,包括含有成色剂的芯油的微胶囊很早就为人们所知。以蜜胺-甲醛树脂(EP-A-0 026 914)为基础或以聚脲(EP-A-0 535 384)为基础的胶囊壁通过在水包油型乳液界面处的缩聚或加聚来形成。
与其中油为分散相(即非连续相)和水为连续相的水包油乳液相反,其中两个相被逆转的包封方法也是已知的。这些方法还称为逆微囊包封法。
早期的德国申请10120480.2描述了这种逆包封法。其中教导的微胶囊具有包含水溶性物质的胶囊芯和由蜜胺-甲醛树脂制成的胶囊壁。
另外,US 5,859,075教导的微胶囊是在链烷烃中作为连续相制备的,具有作为胶囊芯的二醇和多元醇以及聚氨酯壁。所得微胶囊适合作为粉末漆组分。根据该教导,水敏性物质也能够用该方法包封。
EP-A-0 148 169描述了在植物油中制备的具有水溶性芯和聚氨酯壁的微胶囊。除了除草剂以外,水溶性染料尤其作为胶囊芯材料提及。
在装饰用化妆品中,通常使用有机或无机颜料作为赋色成分。由于它们的不溶性,颜料对化妆品组合物的其它成分呈现显著的惰性,这与可溶性染料相反。另外,颜料的不溶性具有优点:能够避免已用该化妆品组合物处理的体内部位的持久着色。
然而,使用颜料的缺点是与染料相比,它们的颜色亮度低。
本发明的目的是提供以对溶剂呈惰性的形式用于化妆品组合物的有机水溶性物质,如染料。
我们已经发现,该目的可通过上述微胶囊分散体及其制备方法来实现。
胶囊包括胶囊包衣和胶囊芯。胶囊芯包括作为固体和/或取决于制备方法作为在亲水溶剂中的溶液的至少一种水溶性有机物质。优选的胶囊芯是水溶性有机物质的溶液。
对于本申请来说,反应剂理解为指能与二异氰酸酯基团和/或多异氰酸酯基团反应的携带OH或NH2基团的化合物。
微胶囊包封的基本原理是以界面聚合或加成为基础。在界面加成中,在第一工艺步骤中将所要包封的物质和反应剂溶解在亲水溶剂中,然后添加疏水溶剂,再处理混合物,获得乳液。乳液的连续相通常包括表面活性物质,以便避免液滴的聚结。在该乳液中,亲水溶剂是非连续的滞后分散相,疏水溶剂是连续相。如果亲水溶剂是水,则术语油包水乳液也是适当的。乳化液滴的尺寸大致对应于后来的微胶囊尺寸。为了形成胶囊壁,在第二工艺步骤中乳液与能够形成壁的异氰酸酯混合。反应剂能够在非连续和连续相之间的界面处与溶解在连续相中的异氰酸酯反应,形成聚合物膜。
第三工艺步骤包括新鲜制备的胶囊分散体的后处理。这里,在监控温度和停留时间以及任选使用其它助剂的情况下,终止异氰酸酯和反应剂之间的反应。
亲水溶剂理解为指水或除了水以外包含至多20重量%的水混溶性有机溶剂的那些含水混合物,水混溶性有机溶剂例如是C1-C4链烷醇,尤其甲醇,乙醇,异丙醇或环醚,如四氢呋喃。优选的亲水溶剂是水。
适合的亲水溶剂还有乙二醇,甘油,聚乙二醇和丁二醇,它们的混合物,以及它们与水或上述含水混合物的混合物。优选的亲水溶剂是这些溶剂与水的混合物。
根据本发明,纯甘油酯油或50至<100重量%甘油酯油混合物用作疏水溶剂。甘油酯油理解为指饱和或不饱和脂肪酸与甘油形成的酯。甘油单-、二-和三酯和它们的混合物是适合的。优选的是甘油三脂肪酸酯。
可以提到的脂肪酸的实例是C6-C12脂肪酸,如己酸,辛酸,癸酸和十二烷酸。
优选的甘油酯油是甘油三C6-C12脂肪酸酯,尤其甘油三辛酸酯和三癸酸酯,以及它们的混合物。这种甘油辛酸酯/甘油癸酸酯混合物例如是购自Hüls的Miglyol812。
疏水溶剂由50-100重量%、优选70-100重量%、尤其优选90-100重量%的甘油酯油和0-50重量%、优选0-30重量%、尤其优选0-10重量%的能与甘油酯油混溶的溶剂组成。尤其优选的疏水溶剂是甘油酯油,它们单独或以它们的混合物使用。
能与甘油酯油混溶的油的实例是:
-烃油,如石蜡油,Purcellin油,全氢角鲨烯,以及微晶蜡在这些油中的溶液,
-动物或植物油,甜杏仁油,鳄梨油,胡桐油,羊毛脂及其衍生物,蓖麻油,马油,猪油,芝麻油,橄榄油,霍霍巴油,Carite油,棘胸鱼油,
-其在大气压下的蒸馏起点为大约250℃和其蒸馏终点为410℃的无机油,例如凡士林油,
-饱和或不饱和脂肪酸的酯,如肉豆蔻酸烷基酯,例如肉豆蔻酸异丙酯,肉豆蔻酸丁酯或肉豆蔻酸鲸蜡酯,硬脂酸十六烷基酯,棕榈酸乙酯或异丙酯和蓖麻油酸鲸蜡酯。
可与甘油酯油混溶的其它适合的化合物是硅油,如二甲基聚硅氧烷,甲基苯基聚硅氧烷和硅氧烷-乙二醇共聚物,脂肪酸和脂肪醇或蜡,如巴西棕榈蜡,小烛树蜡,蜂蜡,微晶蜡,地蜡,以及油酸、肉豆蔻酸、亚油酸和硬脂酸的Ca、Mg和Al盐。
水溶性有机物质理解为指在水中至少部分可溶的以碳为基础的化合物。该有机物质对亲水相的亲合力必须大于对疏水相的亲合力。如果该物质具有至少1g/l的在室温下在亲水溶剂中的溶解度,这一般能够确保。该有机物质优选具有≥20g/l的在亲水溶剂中的溶解度。
水溶性有机物质例如是水溶性染料,农用化学品,香料,药物活性成分,肥料或化妆品活性成分。取决于胶囊壁的厚度(这受所选择的工艺条件和原料物质的量的影响),水溶性有机物质不能透过或基本不能透过胶囊。对于基本不能透过的胶囊,能够实现水溶性有机物质的控释。优选的是水溶性染料。
术语“染料”包括这里和以下的有机化合物或有机化合物的盐,以及含有发色团的有机化合物的电荷迁移络合物,发色团在400-850nm的波长范围具有最大吸收和因此使人眼睛产生颜色效果(普通染料)并且本身还可以发射可见区的光(荧光染料)。对于本发明来说,染料也是在250-400nm范围内具有最大吸收的化合物,在用UV光照射时,发射可见区的荧光辐射(荧光增白剂)。对于本发明来说,染料也是能吸收波长<400nm的光和以非辐射方式灭活它的有机化合物(UV稳定剂)。
水溶性染料通常具有能改进在含水溶剂中溶解度的离子官能团。在这方面,能够进行阳离子或阴离子改性。适合的取代基例如是磺酸,羧酸,磷酸基团,以及铵和烷基铵基团。
根据本发明适合的染料包括各种类型的具有各种发色团的染料,例如单偶氮和重氮染料,三芳基甲烷染料,金属配合物染料,如酞菁染料,奎酞酮以及次甲基和氮杂次甲基染料。
作为例子,可以提到以下《色料索引》编号:
直接黄4,5,11,50,127,137,147,153;酸性橙7,8;直接橙15,34,102;直接红81,239,252-255;直接紫9,51;酸性蓝9,86;直接蓝199,218,267,273,279,281;酸性黑194,208,210,221;直接黑19,161,170和171;
碱性红1,碱性红14,碱性蓝7,碱性蓝11,碱性蓝26,碱性紫1,碱性紫4,碱性紫10等;活性染料如活性红120,活性红2等。
染料还包括碱性和酸性染料的络合物以及阴离子和阳离子染料的络合物,例如柯衣定碱和酸性间胺黄酸的络合物。
根据本发明,染料还包括至少部分可溶于水的荧光增白剂。
根据该定义,有机染料还包括以非辐射方式灭活吸收辐射的UV射线吸收化合物(UV稳定剂)。这些化合物常常在防晒组合物中用作UV吸收剂。它们包括对氨基苯甲酸的衍生物,尤其是它的酯;水杨酸酯,肉桂酸酯,二苯甲酮类,2-苯基苯并咪唑-4-磺酸及其盐,尿刊酸,它的盐和它的酯,苯并噁唑类,苯并三唑类,苄叉基樟脑及其衍生物。
还非常适合的是在化妆品中使用的《色料索引)》染料,如42045,42051,42080,42090,42735,44045,61585,62045,73015,74180,溴百里酚蓝,焦糖,10316,13015,18690,18820,18965,19140,45350,47005,75100,核黄素,10020,42053,42100,42170,44090,59040,61570,75810,溴甲酚绿,14270,15510,15980,15985,16230,20170,40215,14700,14720,14815,15620,16035,16185,16255,16290,17200,18050,18130,18736,24790,27290,45100,45220,45380,45405,45410,45425,45430,75470,甜菜根红,花色素类,酸性红195,黑20470,27755,28440,50420,42510,42520,45190和60730。
取决于染料的颜色强度,微胶囊通常包含至少0.1重量%、优选1-50重量%和尤其5-20重量%的至少一种染料,以亲水溶剂为基准计。
根据本发明的胶囊壁主要由聚氨酯和/或聚脲组成。优选的是基本由聚脲,即含NH2基团的反应剂与二异氰酸酯和/或多异氰酸酯的反应产物组成的胶囊壁。
还适合的是二异氰酸酯和多异氰酸酯,如由W.Siefken在JustusLiebigs Annalen der Chemie,562,75-136页中所述的脂族、脂环族、芳脂族、芳族和杂环二异氰酸酯和多异氰酸酯,例如乙二醇二异氰酸酯,1,4-四亚甲基二异氰酸酯,1,6-六亚甲基二异氰酸酯,1,12-十二烷二异氰酸酯,环丁烷1,3-二异氰酸酯,环己烷1,3-和1,4-二异氰酸酯和这些异构体的任何混合物,如在DE-B 1 202 785和US专利3 401 190中所述的1-异氰酸根-3,3,5-三甲基-5-异氰酸根甲基环己烷,2,4-和2,6-己烷-氢化甲苯二异氰酸酯,以及这些异构体的任何混合物,六氢-1,3-和-1,4-亚苯基二异氰酸酯,全氢-1,4’-和-4,4’-二苯基甲烷二异氰酸酯,1,3-和1,4-亚苯基二异氰酸酯,2,4-和2,6-甲苯二异氰酸酯,和这些异构体的任何混合物,二苯基甲烷2,4’-和4,4’-二异氰酸酯,亚萘基-1,5-二异氰酸酯,三苯基甲烷4,4’4”-三异氰酸酯,如通过苯胺-甲醛缩合和后续光气化获得和如在GB专利874 430和848671中所述的多苯基多亚甲基多异氰酸酯,根据US专利3 454 606的间-和对-异氰酸根苯基磺酰基异氰酸酯,如在DE-B 1 157 601中所述的全氯化芳基多异氰酸酯,如在DE专利1 092 007(=US专利3 152 162)中所述的具有碳化二亚胺基团的多异氰酸酯,如在US专利3 492 330中所述的二异氰酸酯,如在GB专利761 626和公开的NL专利申请7 102 524中所述的具有脲基甲酸酯基的多异氰酸酯,如在US专利3 001 973、德国专利1 022789、1 222 067和1 027 394以及德国公开专利1 929 034和2 004 048中所述的具有异氰脲酸酯基的多异氰酸酯,如在BE专利752 261或US专利3394 164中所述的具有脲烷基团的多异氰酸酯,根据德国专利1 230 778的具有酰化脲基的多异氰酸酯,如在德国专利1 101 394和GB专利889 050中所述的具有缩二脲基的多异氰酸酯,如在US专利3 654 106中所述的通过调聚反应制备的多异氰酸酯,如在GB专利965 474和1 072 956、US专利3 567 763和德国专利1 231 688中所述的具有醚基的多异氰酸酯。根据德国专利1 072 385的上述异氰酸酯与缩醛的反应产物和根据US专利3455 883的含有聚合脂肪酸基团的多异氰酸酯。
还可以使用在异氰酸酯工业制备过程中形成的具有异氰酸酯基的蒸馏残余物,任选溶解在上述一种或多种多异氰酸酯中。还可以使用上述多异氰酸酯的任何混合物。
适合的改性、脂族异氰酸酯例如是以六亚甲基1,6-二异氰酸酯、间苯二甲撑二异氰酸酯、4,4’-二异氰酸酯二环己基甲烷和异佛尔酮二异氰酸酯为基础的那些,它们具有至少两个异氰酸酯基/每分子。
还适合的例如是如在DE-B 1 101 394、DE-B 1 453 543、DE-A 1 568 017和DE-A 1 931 055中所述的以具有缩二脲结构的六亚甲基1,6-二异氰酸酯的衍生物为基础的多异氰酸酯。
还可以使用由于含有缩二脲基的六亚甲基1,6-二异氰酸酯用有机磷催化剂进行碳化二亚胺化获得的多异氰酸酯-聚脲酮亚胺,其中首先形成的碳化二亚胺基团与其它异氰酸酯基反应,获得脲酮亚胺基团。
还可以使用具有多于两个异氰酸酯端基的异氰脲酸酯改性的多异氰酸酯,例如在DE-A 2 839 133中描述了以六亚甲基二异氰酸酯为基础制备的那些。其它异氰脲酸酯改性的多异氰酸酯可以与之类似地获得。
还可以使用所述异氰酸酯的混合物,例如脂族异氰酸酯的混合物,芳族异氰酸酯的混合物,脂族和芳族异氰酸酯的混合物,尤其任选包含改性二苯基甲烷二异氰酸酯的混合物。
这里所述的二异氰酸酯和/或多异氰酸酯还可以与以下物质混合使用:二和多碳酰氯,如癸二酰氯,对苯二甲酰氯,己二酰二氯,草酰二氯,丙三酰三氯和1,2,4,5-苯四酰氯;二和多磺酰氯,如1,3-苯二磺酰氯和1,3,5-苯三磺酰氯;光气;以及二氯和多氯甲酸酯,如1,3,5-苯三氯甲酸酯和双氯甲酸乙烯酯。
优选的异氰酸酯是任选与4,4’-二苯基甲烷异氰酸酯和任选的2,4-二苯基甲烷异氰酸酯混合的缩二脲六亚甲基二异氰酸酯,任选与4,4’二苯基甲烷二异氰酸酯和任选的2,4-二苯基甲烷二异氰酸酯混合的三聚六亚甲基二异氰酸酯。
其它优选的二异氰酸酯是在DE-A 3 105 776和3 521 126中给出的烷基苯二异氰酸酯和烷氧基苯二异氰酸酯,包括以它们的缩二脲异氰酸酯脲二酮低聚物形式存在的那些。
优选的二或多异氰酸酯是4,4’-二苯基甲烷二异氰酸酯,单体二苯基甲烷二异氰酸酯和低聚二苯基甲烷二异氰酸酯(聚合物MDI)的混合物,四亚甲基二异氰酸酯,四亚甲基二异氰酸酯三聚物,六亚甲基二异氰酸酯,六亚甲基二异氰酸酯三聚物,异佛尔酮二异氰酸酯三聚物,4,4’-亚甲基双(环己基)二异氰酸酯,苯二甲撑二异氰酸酯,四甲代苯二甲撑二异氰酸酯,十二烷基二异氰酸酯,二异氰酸赖氨酸烷基酯(其中烷基是C1-C10),2,2,4-或2,4,4-三甲基-1,6-六亚甲基二异氰酸酯,2-丁基-2-乙基五亚甲基二异氰酸酯,1,4-二异氰酸根-环己烷或4-异氰酸根甲基-1,8-八亚甲基二异氰酸酯。
特别优选的是具有不同反应活性的NCO基团的多异氰酸酯,如2,4-甲苯二异氰酸酯(2,4-TDI),2,4’-二苯基甲烷二异氰酸酯(2,4’-TDI),三异氰酸根甲苯,异佛尔酮二异氰酸酯(IPDI),2-丁基-2-乙基五亚甲基二异氰酸酯,2-异氰酸根丙基环己基异氰酸酯,3(4)-异氰酸根甲基-1-甲基环己基异氰酸酯,1,4-二异氰酸根-4-甲基戊烷,2,4’-亚甲基-双(环己基)二异氰酸酯和4-甲基环己烷1,3-二异氰酸酯(H-TDI)。还特别优选的是这样的异氰酸酯,其NCO基团的最初反应活性相等,但在第二个NCO基团的情况下,由于首先将醇或胺加成到NCO基团上而诱发反应活性降低。它们的实例是其中NCO基团通过离域电子体系偶联的异氰酸酯,例如1,3-和1,4-亚苯基二异氰酸酯,1,5-亚萘基二异氰酸酯,二苯基二异氰酸酯,联甲苯胺二异氰酸酯或2,6-甲苯二异氰酸酯。
另外,例如可以使用通过利用脲烷、脲基甲酸酯、脲、缩二脲、脲二酮、酰胺、异氰脲酸酯、碳化二亚胺、脲酮亚胺、噁二嗪三酮或亚胺基噁二嗪二酮结构连接而由所述二异氰酸酯或多异氰酸酯或它们的混合物制备的低聚异氰酸酯或聚异氰酸酯。
根据本发明的含NH2反应剂是:肼,胍和它们的盐,羟胺,二胺和多胺和氨基醇。这些化合物可以以纯的形式或以彼此的混合物使用。优选的胍盐是胍碳酸盐。如果使用强酸的胍盐,需要添加碱。
适合的胺一般是具有32-500g/mol、优选60-300g/mol的分子量范围的多官能胺,其含有选自伯和仲氨基中的至少两个氨基。它们的实例是二胺,如二氨基乙烷,二氨基丙烷,二氨基丁烷,二氨基己烷,哌嗪,2,5-二甲基哌嗪,氨基-3-氨基甲基-3,5,5-三甲基环己烷(异佛尔酮二胺,IPDA),4,4’-二氨基二环己基甲烷,1,4-二氨基环己烷,氨基乙基乙醇胺,肼,肼水合物;或三胺,如二亚乙基三胺或1,8-二氨基-4-氨基甲基辛烷。
胺还可以以封闭形式,例如以相应酮亚胺(参看例如CA-A-1 129 128)、酮连氮(参照例如US-A 4 269 748)或胺盐(参看例如US-A 4 292 226)的形式使用。
氨基醇的实例是乙醇胺和三乙醇胺。原则上,水还可以通过加成到NCO基团上和随后消除CO2来产生随后能够与NCO基团交联反应的氨基而起到反应剂的作用。
优选的含NH2反应剂是二胺,尤其优选脂族C2-C6-二胺,如亚乙基二胺和六亚甲基二胺。
根据本发明使用的异氰酸酯的量在通常用于界面加聚方法的范围内变化。因此,使用20-150重量%、优选40-150重量%的异氰酸酯,以提供用于包封的非连续相(亲水溶剂+水溶性物质)为基准计。低至40重量%的量也可以获得胶囊的良好剪切稳定性。150重量%以上的量是可行的,但一般没有获得更加稳定的胶囊壁。
形成壁所需的反应剂的理论量由a)所用反应剂组分的反应性氨基和/或羟基的含量来计算。这些定量比通常用当量来表示。
*)=例如以滴定分析法测定(DIN 53 185)
存在于油相中的所有NCO基团的反应需要至少理论相等数目的NH2和/或OH基。因此有利地以它们的当量比率来使用异氰酸酯和反应剂。然而,反应剂的化学计算量可以偏低,因为在界面加聚方法过程中不能排除异氰酸酯与过量存在的水发生二级反应,或者可以使用过量的反应剂组分,因为这种过量不是关键的。
因此,尤其,反应剂以理论计算量的50-150重量%的量使用。该量优选为50-100重量%,以理论计算量为基准。
本发明进一步提供制备根据本发明的微胶囊分散体的方法,该方法包括使用表面活性物质制备亲水溶剂在疏水溶剂中的乳液,其中亲水相包含水溶性有机物质和能与二异氰酸酯基和/或多异氰酸酯基反应的携带OH或NH2基团的反应剂,并将二异氰酸酯和/或多异氰酸酯加入到该乳液中。
为了获得稳定乳液,需要表面活性物质,如保护胶体和/或乳化剂。通常使用与疏水相混合的表面活性物质。
优选的保护胶体是具有长度≥50的疏水结构单元的线性嵌段共聚物,或其与其它表面活性物质的混合物。线性嵌段共聚物用下式来表示:
其中W是0或1,x是1或1以上,y是0或1,A是亲水结构单元,其具有≥1重量%(>10g/l)的在25℃水中的溶解度和200-50000的分子量,它以共价键连接于B嵌段,以及B是疏水结构单元,其具有300-60000的分子量和<1重量%的在25℃水中的溶解度且能够与A形成共价键;和其中C和D是端基,彼此独立地可以是A或B。端基可以是相同或不同的,与制备方法无关。
亲水基团的实例是聚环氧乙烷,聚(1,3-二氧戊环),聚环氧乙烷或聚(1,3-二氧戊环)的共聚物,聚(2-甲基-2-噁唑啉),聚(氯化缩水甘油基三甲基铵),聚氧化亚甲基。
疏水基团的实例是其中疏水部分是≥50、优选≥75、尤其≥100的立体障碍的聚酯。聚酯由诸如以下组分衍生:2-羟基丁酸,3-羟基丁酸,4-羟基丁酸,2-羟基己酸,10-羟基癸酸,12-羟基十二烷酸,16-羟基十六烷酸,2-羟基异丁酸,2-(4-羟基苯氧基)丙酸,4-羟基苯基丙酮酸,12-羟基硬脂酸,2-羟基戊酸,由己内酯和丁内酯获得的聚内酯,由己内酰胺获得的聚内酰胺,聚氨酯和聚异丁烯。
线性嵌段共聚物同时含有亲水单元和疏水单元。嵌段聚合物具有1000以上的分子量和根据余弦定律计算的≥50的疏水结构部分的长度。计算这些尺寸用于扩展构型,将在文献中给出的键长和键角考虑进去。这些单元的制备一般是已知的。制备方法例如是羟基酸的缩合反应,多元醇(如二醇)与多羧酸(如二羧酸)的缩合。还适合的是内酯和内酰胺的聚合,以及多元醇与多异氰酸酯的反应。疏水聚合物单元与亲水单元反应,如公知的那样,例如通过缩合反应和偶联反应进行。这些嵌段共聚物的制备例如描述在US 4 203 877中,该专利特地引入供参考。线性嵌段共聚物的比例优选是所用表面活性物质总量的20-100重量%。
适合的表面活性物质也是通常用于油包水乳液的乳化剂,例如:
-C12-C18脱水山梨醇脂肪酸酯,
-羟基硬脂酸和C12-C30脂肪醇的酯,
-C12-C18脂肪酸和甘油或聚甘油的单酯和二酯,
-环氧乙烷和丙二醇的缩合物,
-氧丙烯化/氧乙烯化C12-C20脂肪醇,
-多环醇,如甾醇,
-具有高分子量的脂族醇,如羊毛脂,
-氧丙烯化/聚甘油化醇和异硬脂酸镁的混合物,
-聚氧乙基化或聚氧丙烯化脂肪醇的丁二酸酯,
-镁、钙、锂、锌和铝的羊毛脂酸盐和硬脂酸盐,任选作为与氢化羊毛脂、羊毛脂醇或硬脂酸或硬脂醇的混合物。
Span系列的乳化剂(ICI Americas,Inc.)已经证实是特别有利的。它们是环化山梨醇,有时用脂肪酸聚酯化,其中基本结构还可以被已知来自表面活性化合物的其它基团、例如被聚氧乙烯取代。可以提及的实例是与月桂酸、棕榈酸、硬脂酸和油酸的脱水山梨醇酯,如Span 80(脱水山梨醇单油酸酯)和Span 60(脱水山梨醇单硬脂酸酯)。
在优选的实施方案中,氧丙烯化/氧乙烯化C12-C20脂肪醇作为与其它表面活性物质的混合组分使用。这些脂肪醇通常具有3-12个环氧乙烷或环氧丙烷单元。
优选使用C12-C18脱水山梨醇脂肪酸酯作为乳化剂。它们可以单独使用,以它们的混合物和/或以与其它上述类型乳化剂的混合物使用。脱水山梨醇脂肪酸酯的比例优选是所用表面活性物质总量的20-100重量%。
在优选的实施方案中,选择包含以上定义的线性嵌段共聚物和C12-C18脱水山梨醇脂肪酸酯的表面活性物质混合物。
尤其优选的是,选择包含线性嵌段共聚物、C12-C18脱水山梨醇脂肪酸酯和氧丙烯化/氧乙烯化C12-C20脂肪醇的表面活性物质混合物。
优选的是包含20-95重量%、尤其30-75重量%的线性嵌段共聚物和5-80重量%、尤其25-75重量%的C12-C18脱水山梨醇脂肪酸酯的那些混合物,以表面活性物质的重量为基准计算。氧丙烯化/氧乙烯化C12-C20脂肪醇的比例优选是0-20重量%。
尤其优选的是主要包含40-60重量%的线性嵌段共聚物、30-50重量%的C12-C18脱水山梨醇脂肪酸酯和2-10重量%的氧丙烯化/氧乙烯化C12-C20脂肪醇的表面活性物质混合物。
表面活性物质的最佳量首先受表面活性物质本身的影响,其次受反应温度、所需微胶囊尺寸和壁材料的影响。最佳需要量可以通过简单的系列试验来测定。表面活性物质一般以0.01-10重量%、优选0.05-5重量%和尤其0.1-2重量%的量使用,以疏水相为基准计。
为了制备根据本发明的微胶囊,根据一个优选实施方案,可以将水溶性有机物质和携带OH或NH2的反应剂在亲水溶剂中的溶液加入到疏水溶剂中。借助表面活性物质,在搅拌下获得了稳定乳液。根据一个同样优选的变型,只是将水溶性有机物质和反应剂加入到稳定乳液中,或在乳化步骤过程中添加它们。然后可以将异氰酸酯计量加入到这种乳液中。一般,这起动了界面加聚或缩合,因此起动了壁的形成。
界面反应例如可以在-3℃至+70℃下进行,但优选在0-25℃下操作。
取决于所要制备的胶囊的尺寸,以已知方式分散成核材料。对于制备大胶囊,使用有效搅拌器、尤其螺旋桨式或叶轮式搅拌器的分散就是足够的。小胶囊(尤其如果尺寸小于50μm)要求均化或分散机器,这些设备可以配备或不配备强制流动设备。
均化还可以使用超声设备(Branson Sonifier II450)进行。对于利用超声的均化,适合的设备例如是GB 2250930和US 5,108,654中所述的设备。
胶囊尺寸可以通过分散装置/均化装置的速度和/或使用保护胶体的浓度或通过其分子量(即通过在一定限度内的含水连续相的粘度)来控制。在这一点上,当速度增加到极限速度时,分散颗粒的尺寸减小。
在这一点上,重要的是,在胶囊形成的开始使用分散设备。在具有强制流动的连续操作型设备的情况下,有利的是让乳液通过剪切场数次。
使用根据本发明的方法,可以制备具有5-50重量%的微胶囊含量的微胶囊分散体。微胶囊是独立的胶囊。如果在分散过程中选择适当的条件,则可以制备0.5-50μm和更大平均粒度的胶囊。优选的是具有0.5-50μm、尤其至多30μm的平均粒度的胶囊。平均粒径是数均粒径,通过准弹性动态光散射来测定。它通常使用购自Coulter Scientific Instruments的CoulterN4 Plus颗粒分析仪来测定。胶囊的尺寸分布尤其有利地是非常窄的。
根据本发明的微胶囊分散体可以按照已知方式引入到化妆品组合物中。在化妆品组合物中的引入通过用于该目的的常规工序来进行,通常通过搅拌和均化引入到化妆品组合物的其它成分中。
配制为装饰用化妆品组合物的化妆品组合物的例子是用于处理面部皮肤、尤其眼部区域的组合物,如眼影笔,眼线笔,眉笔,眼影膏,胭脂膏,胭脂粉,粉底,化妆品,例如舞台化妆品,唇膏。
在专门由油或脂肪组成的化妆品组合物、尤其具有固态的那些例如笔如眼影笔、眼线笔、眉笔、棒状舞台化妆品、唇膏等的情况下,以及在粉末或细粉化妆品组合物例如眼影膏和胭脂膏或松散粉状胭脂的情况下,优选使用微胶囊分散体。
微胶囊在化妆品组合物中的量主要受装饰用化妆品组合物所要具有的所需颜色效果的控制。取决于化妆品组合物的性质和所需颜色效果,微胶囊在化妆品组合物中的含量为0.1-50重量%,以化妆品组合物的总重量计。
实施例1
将1.5g的Span80(脱水山梨醇单油酸酯)、0.3g的CremophorA6[75重量%的十六/十八醇聚氧乙烯(6)醚(乙氧基化鲸蜡醇),25重量%的硬脂醇,BASF]和2.1g的ArlacelP135(PEG-30二聚羟基硬脂酸酯,AtlasChemie)在860g的Miglyol(甘油癸酸酯/辛酸酯;Hüls)812中的溶液引入到圆柱形2L搅拌容器内。使用分散装置(Turrax 45N,购自Jahnke &Kunkel),在6000rpm转速下通过添加6.7g的乙二胺和4g的Cochenille RedA(E124;C.I.162 55)在80g水中的溶液来制备油包水乳液。将所得乳液在1000rpm的搅拌器速度下在冰浴中冷却到2℃。在冰冷却的同时,在相同的搅拌速度下经300分钟的过程添加23g的BasonatLR 8528(多官能甲苯二异氰酸酯加合物,75重量%乙酸乙酯溶液;BASF)在300g Miglyol中的溶液。当添加完后,将分散体加热到室温,搅拌另外180分钟。所得分散体是红色乳状的,根据显微镜观测结果,它包含直径主要为1-5μm的独立胶囊。粘度是47.5mPas,固含量是11重量%。
粘度根据ISO 3219(DIN 53019)使用Physica MC20粘合剂用测量体系21在100s-1的剪切速度和23℃的温度下测定。胶囊直径使用购自Leitz的显微镜(Diaplan 101/107)在400倍放大倍数下测定。
实施例2
与实施例1类似地制备胶囊分散体,所用染料是4g的活性红120。所得分散体是红色乳状的,根据显微镜观测结果,它包含直径主要为1-5μm的独立胶囊。粘度是43.9mPas,固含量是11重量%。
实施例3
与实施例1类似地制备微胶囊分散体,所用染料是4g的活性红2。所得分散体是红色乳状的,根据显微镜观测结果,它包含直径主要为1-5μm的独立胶囊。粘度是45.2mPas,固含量是11重量%。
实施例4
与实施例1类似,所用水溶液是64g H2O和16g乙醇的混合物。所得分散体是红色乳状的,根据显微镜观测结果,它包含直径主要为1-5μm的独立胶囊。粘度是50.2mPas,固含量是11重量%。
Claims (10)
1、一种微胶囊分散体,包含在疏水溶剂中的微胶囊,其中所述疏水溶剂是由50-100重量%的甘油酯油和0-50重量%的能与甘油酯油混溶的溶剂组成的,所述微胶囊具有含水溶性有机物质的胶囊芯和基本由聚氨酯和/或聚脲组成的胶囊包衣。
2、如权利要求1所要求的微胶囊分散体,其中水溶性有机物质是染料。
3、如权利要求1或2所要求的微胶囊分散体,其中微胶囊包衣是基本由含NH2基团的反应剂与二异氰酸酯和/或多异氰酸酯的反应产物组成。
4、如权利要求1-3所要求的微胶囊分散体,其中疏水溶剂是甘油酯油。
5、如权利要求1-4所要求的微胶囊分散体,其特征在于胶囊芯包含水作为亲水溶剂。
6、一种制备如权利要求1所要求的微胶囊分散体的方法,该方法包括使用表面活性物质制备亲水溶剂在疏水溶剂中的乳液,其中亲水相包含水溶性有机物质和能与二异氰酸酯基和/或多异氰酸酯基反应的携带OH或NH2基团的反应剂,以及将二异氰酸酯和/或多异氰酸酯加入到该乳液中。
8、如权利要求7所要求的方法,其中线性嵌段共聚物是12-羟基硬脂酸嵌段共聚物。
9、如权利要求6所要求的方法,其特征在于所用的表面活性物质是C12-C18脱水山梨醇脂肪酸酯。
10、如权利要求6所要求的方法,其中所用的表面活性物质是包含C12-C18脱水山梨醇脂肪酸酯和如权利要求7的线性嵌段共聚物的混合物。
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- 2002-08-06 US US10/485,266 patent/US6890653B2/en not_active Expired - Fee Related
- 2002-08-06 KR KR1020047002107A patent/KR100886316B1/ko not_active IP Right Cessation
- 2002-08-06 WO PCT/EP2002/008739 patent/WO2003015910A1/de active Application Filing
- 2002-08-06 EP EP02767326A patent/EP1419006A1/de not_active Withdrawn
- 2002-08-06 BR BR0211818-1A patent/BR0211818A/pt not_active IP Right Cessation
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EP1419006A1 (de) | 2004-05-19 |
WO2003015910A1 (de) | 2003-02-27 |
KR100886316B1 (ko) | 2009-03-04 |
DE10138996A1 (de) | 2003-02-27 |
KR20040029424A (ko) | 2004-04-06 |
BR0211818A (pt) | 2004-07-27 |
CN100413575C (zh) | 2008-08-27 |
US20040232575A1 (en) | 2004-11-25 |
US6890653B2 (en) | 2005-05-10 |
JP2004538354A (ja) | 2004-12-24 |
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