USRE39993E1 - Emulsions - Google Patents
Emulsions Download PDFInfo
- Publication number
- USRE39993E1 USRE39993E1 US10/893,704 US89370404A USRE39993E US RE39993 E1 USRE39993 E1 US RE39993E1 US 89370404 A US89370404 A US 89370404A US RE39993 E USRE39993 E US RE39993E
- Authority
- US
- United States
- Prior art keywords
- mol
- esters
- oligoesters
- cosmetic emulsion
- dicarboxylic acids
- 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.)
- Expired - Fee Related
Links
- 239000000839 emulsion Substances 0.000 title abstract description 16
- 229920002601 oligoester Polymers 0.000 claims abstract description 26
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 37
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 22
- -1 aromatic dicarboxylic acids Chemical class 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 11
- 239000003755 preservative agent Substances 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 238000006068 polycondensation reaction Methods 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000000035 biogenic effect Effects 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 239000008271 cosmetic emulsion Substances 0.000 claims 9
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000002689 soil Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 19
- 229920000728 polyester Polymers 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 7
- 230000002335 preservative effect Effects 0.000 description 7
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 5
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 125000003827 glycol group Chemical group 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 230000037072 sun protection Effects 0.000 description 3
- 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 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007957 coemulsifier Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 229940119170 jojoba wax Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229920000223 polyglycerol Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- LAWHHRXCBUNWFI-UHFFFAOYSA-N 2-pentylpropanedioic acid Chemical compound CCCCCC(C(O)=O)C(O)=O LAWHHRXCBUNWFI-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 1
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000000973 cosmetic coloring agent Substances 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- GXJPKIGCMGAHTL-UHFFFAOYSA-N dipropyl benzene-1,4-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)C=C1 GXJPKIGCMGAHTL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SFFVATKALSIZGN-UHFFFAOYSA-N hexadecan-7-ol Chemical compound CCCCCCCCCC(O)CCCCCC SFFVATKALSIZGN-UHFFFAOYSA-N 0.000 description 1
- XYXCXCJKZRDVPU-UHFFFAOYSA-N hexane-1,2,3-triol Chemical compound CCCC(O)C(O)CO XYXCXCJKZRDVPU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960001173 oxybenzone Drugs 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003996 polyglycerol polyricinoleate Substances 0.000 description 1
- 235000010958 polyglycerol polyricinoleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
Definitions
- oligoesters are used as soil release polymers in detergents and cleaners. These oligoesters are condensation products of dimethyl terephthalate, ethylene glycol, propylene glycol and polyalkylene glycols. As a consequence of a molar excess of the alcohol component, these oligoesters contain terminal OH groups which may, wholly or in part, be terminated by alkoxy groups (endcaps). Compounds of this type are available commercially under the names ®Milease T, ®Permalose, ®Repel-O-Tex.
- the invention thus provides emulsions comprising an oligoester.
- oligoesters are preferably obtained by polycondensation of one or more aromatic dicarboxylic acids or esters thereof and one or more polyhydric alcohols, such as, for example, ethylene glycol and/or propylene glycol.
- these esters can also contain polyethylene glycol, polypropylene glycol, sulfoisophthalic acid, sulfobenzoic acid, isethionic acid, C 1 -C 4 -alcohols, oxalkylated C 1 -C 24 -alcohols, oxalkylated C 6 -C 18 -alkylphenols and/or oxalkylated C 8 -C 24 -alkylamines as monomers.
- Suitable as component a) for the preparation of the oligoesters are aromatic dicarboxylic acids, such as, for example, terephthalic acid, phthalic acid, isophthalic acid, and the mono- and dialkyl esters with C 1 - to C 6 -alcohols, such as dimethyl terephthalate, diethyl terephthalate and di-n-propyl terephthalate.
- aromatic dicarboxylic acids such as, for example, terephthalic acid, phthalic acid, isophthalic acid
- mono- and dialkyl esters with C 1 - to C 6 -alcohols such as dimethyl terephthalate, diethyl terephthalate and di-n-propyl terephthalate.
- compositions which can be used as component a) for the preparation of the polyesters are oxalic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, itaconic acid, and the mono- and dialkyl esters of the carboxylic acids with C 1 -C 6 -alcohols, e.g. diethyl oxalate, diethyl succinate, diethyl glutarate, methyl adipate, diethyl adipate, di-n-butyl adipate, ethyl fumarate and dimethyl maleate.
- the anhydrides of the carboxylic acids having at least two carboxyl groups are also suitable as compound of component a) for the preparation of the oligoesters, e.g. maleic anhydride, phthalic anhydride or succinic anhydride.
- compound of component a particular preference is given to using terephthalic acid, phthalic acid, isophthalic acid, and the dimethyl, diethyl, dipropyl and dibutyl esters thereof. It is of course possible to use mixtures of different carboxylic acids or of different esters. Likewise, it is also possible to use, for example, mixtures of carboxylic acids and esters or mixtures of carboxylic acids and anhydrides in the condensation.
- polyethylene glycols having molar masses of from 500 to 5000, preferably from 1000 to 3000, are used.
- Suitable as component d) for the preparation of the oligoesters are water-soluble addition products of from 5 to 80 mol of at least one alkylene oxide with 1 mol of C 1 -C 24 -alcohols, C 6 -C 18 -alkylphenols or C 8 -C 24 -alkylamines. Preference is given to monomethyl ethers of polyethylene glycols.
- the alkylene oxides used for the preparation of the compounds of component d) are preferably ethylene oxide, and mixtures of ethylene oxide and propylene oxide.
- mixtures of ethylene oxide together with propylene oxide and/or butylene oxide are also suitable.
- These water-soluble addition products of the alkylene oxide are surfactants. If mixtures of alkylene oxides are used for their preparation, then they may contain the alkylene oxides in blocks or else in random distribution.
- Suitable alcohols which are alkoxylated are, for example, octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol or stearyl alcohol, but in particular methanol, and the alcohols having 8 to 24 carbon atoms obtainable by the Ziegler process, or the corresponding oxo alcohols.
- octylphenol, nonylphenol and dodecylphenol are of particular importance.
- the alkylamines used are, in particular, the C 12 -C 18 -monoalkylamines.
- Suitable polyols are, for example, pentaerythritol, trimethylolethane, trimethylolpropane, 1,2,3-hexanetriol, sorbitol, mannitol and glycerol.
- the oligoesters according to the invention are synthesized by processes known per se, by heating components a, b and c, and optionally d with the addition of a catalyst firstly at atmospheric pressure to temperatures of from 160 to about 220° C. The reaction is then continued under reduced pressure at temperatures of from 160 to about 240° C. with removal by distillation of excess glycols.
- the known transesterification and condensation catalysts of the prior art are suitable for the reaction, such as, for example, titanium tetraisopropoxide, dibutyltin oxide and/or antimony trioxide/calcium acetate.
- polyesters known from EP 241 985 which, in addition to oxyethylene groups and terephthalic acid units, contain 1,2-propylene, 1,2-butylene and/or 3-methoxy-1,2-propylene groups and glycerol units and are terminally capped with C 1 - to C 4 -alkyl groups;
- the soil release polymers, described in EP 253 567 having a molar mass of from 900 to 9000 g/mol of ethylene terephthalate and polyethylene oxide terephthalate, where the polyethylene glycol units have molecular weights of from 300 to 3000 g/mol and the molar ratio of the ethylene terephthalate to polyethylene oxide terephthalate is 0.6 to 0.95;
- oligoesters of ethylene terephthalate and polyethylene oxide terephthalate in which the polyethylene glycol units have molecular weights of from 750 to 5000 g/mol and the molar ratio of ethylene terephthalate to polyethylene oxide terephthalate is 50:50 to 90:10 and whose use in detergents is described in German Patent Specification DE 28 57 292, and oligoesters having molecular weights of from 15 000 to 50 000 g/mol of ethylene terephthalate and polyethylene oxide terephthalate, where the polyethylene glycol units have molecular weights of from 1000 to 10 000 g/mol and the molar ratio of ethylene terephthalate to polyethylene oxide terephthalate is 2:1 to 6:1, which, according to DE 33 24 258, can be used in detergents.
- the described oligoesters are usually present in the emulsions according to the invention in amounts of from 0.1 to 5% by weight, preferably 0.3 to 3% by weight, based on the finished emulsion.
- the emulsions may either be water-in-oil emulsions or oil-in-water emulsions.
- the nonaqueous proportion of the emulsions which is composed largely of the emulsifier and the oil substance and generally corresponds to the solids content, is usually 5 to 95% and preferably 15 to 75% by weight.
- the emulsions may comprise 5 to 95% by weight and preferably 25 to 85% by weight of water, depending on whether the intention is to prepare lotions of comparatively low viscosity, or creams and ointments of high viscosity.
- suitable oil substances are Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C 6 -C 13 -fatty acids with linear C 6 -C 20 -fatty alcohols, esters of branched C 6 -C 13 -carboxylic acids with linear C 6 -C 20 -fatty alcohols, esters of linear C 6 -C 18 -fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, dimerdiol or trimerdiol) and/or Guerbet alcohols, triglycerides based on C 6 -C 10 -fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates, dialkyl ethers and/or aliphatic or aromatic hydrocarbons.
- polyhydric alcohols such as, for example
- the emulsions can be used as skin care compositions, such as, for example, day creams, night creams, care creams, nourishing creams, body lotions, ointments and the like, and can comprise, as further auxiliaries and additives, coemulsifiers, superfatting agents, fats, waxes, stabilizers, biogenic active ingredients, glycerol, preservatives, dyes and fragrances.
- the described oligoesters can also be used without the co-use of a nonionic surfactant as emulsifier.
- the co-use of emulsifiers is therefore not obligatory, but possible.
- Suitable nonionogenic O/W coemulsifiers are addition products of from 2 to 30 mol of ethylene oxide and/or 0 to 5 mol of propylene oxide with linear fatty alcohols having 8 to 22 carbon atoms, with fatty acids having 12 to 22 carbon atoms and with alkylphenols having 8 to 15 carbon atoms in the alkyl group; C 12 -C 18 -fatty acid mono- and diesters of addition products of from 1 to 30 mol of ethylene oxide with glycerol; glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and the ethylene oxide addition products thereof; addition products of from 15 to 60 mol of ethylene oxide with castor oil and/or hydrogenated castor oil; polyol and, in particular, polyglycerol esters, such as e.g.
- polyglycerol polyricinoleate and polyglycerol poly-12-hydroxystearate are also suitable are mixtures of compounds of two or more of these classes of substance.
- the addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. They are homolog mixtures whose average degree of alkoxylation corresponds to the ratio of the quantitative amounts of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out.
- C 12 -C 18 -fatty acid mono- and diesters of addition products of ethylene oxide with glycerol are known from DE 20 24 051 as refatting agents for cosmetic preparations.
- Superfatting agents which can be used are substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter also serving as foam stabilizers.
- Typical examples of fats are glycerides, and suitable waxes are, inter alia, beeswax, paraffin wax or microcrystalline waxes, optionally in combination with hydrophilic waxes, e.g. cetyl stearyl alcohol.
- Stabilizers which can be used are metal salts of fatty acids, such as e.g. magnesium stearate, aluminum stearate and/or zinc stearate.
- Biogenic active ingredients means, for example, plant extracts and vitamin complexes.
- suitable preservatives are phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
- Suitable pearlizing agents are, for example, glycol distearic esters, such as ethylene glycol distearate, but also fatty acid monoglycol esters. Dyes which can be used are the substances approved and suitable for cosmetic purposes, as are listed, for example in the publication “Kosmetician Anlagentrbesch” [Cosmetic Colorants] from the Farbstoffkommission der Deutschen Deutschen Deutschen Anlagensestesesterol] from the Farbstoffkommission der Deutschen Deutschen Deutschen Deutschen Anlagensestesesterol [Dyes Commission of the German Research Council], Verlag Chemie, Weinheim, 1984, pp. 81-106.
- the total proportion of auxiliaries and additives can be 1 to 10% by weight, preferably 2 to 5% by weight, based on the composition.
- compositions can be prepared in a manner known per se, i.e. for example by hot, hot-hot/cold or PIT emulsification.
- oligoesters in particular in O/W lotions and O/W creams, it is possible to obtain stable formulations which additionally impart a pleasant feel to the skin.
- polyesters were prepared in the manner described in the introduction.
- a POLYESTER 2 (Clariant) 1.00% Mineral oil, low-viscosity 8.00% Isopropyl palmitate 4.00% ® Eutanol G 4.00% B ® Aristoflex AVC (Clariant) 0.70% C Water 81.90% Preservative q.s. D Perfume 0.40% Preparation: as in Example 1
- a POLYESTER 1 (Clariant) 1.00% Mineral oil, high-viscosity 10.00% Isopropyl palmitate 5.00% B ® Neo - Heliopan E 1000 8.50% ® Neo - Heliopan BB 1.50% C ® Aristoflex AVC (Clariant) 0.60% D Glycerol 3.00% Water 70.10% Preservative q.s. E Perfume 0.30% Preparation:
- a POLYESTER 2 (Clariant) 1.00% Mineral oil, high-viscosity 10.00% Isopropyl palmitate 5.00% B ® Neo - Heliopan E 1000 8.50% ® Neo - Heliopan BB 1.50% C ® Aristoflex AVC (Clariant) 0.60% D Glycerol 3.00% Water 70.10% Preservative q.s. E Perfume 0.30% Preparation: as in Example 5
- a POLYESTER 3 (Clariant) 2.00% Mineral oil, high-viscosity 10.00% Isopropyl palmitate 5.00% B ® Neo - Heliopan E 1000 8.50% ® Neo - Heliopan BB 1.50% C ® Aristoflex AVC (Clariant) 0.60% D Glycerol 3.00% Water 69.10% Preservative q.s. E Perfume 0.30% Preparation: as Example 5
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Detergent Compositions (AREA)
Abstract
Emulsions are claimed which comprise oligoesters as emulsifiers. These oligoesters have hitherto only been used as soil release polymers.
Description
It is known that oligoesters are used as soil release polymers in detergents and cleaners. These oligoesters are condensation products of dimethyl terephthalate, ethylene glycol, propylene glycol and polyalkylene glycols. As a consequence of a molar excess of the alcohol component, these oligoesters contain terminal OH groups which may, wholly or in part, be terminated by alkoxy groups (endcaps). Compounds of this type are available commercially under the names ®Milease T, ®Permalose, ®Repel-O-Tex. For more details, reference may be made to the specifications EP 185 427, EP 241 984, EP 241 985, EP 272 033, EP 757 468, EP 201 124, EP 253 567, GB 2 304 727, U.S. Pat. No. 4,116,885, U.S. Pat. No. 4,210,417, U.S. Pat. No. 3,962,152 and WO 92/17 523.
We have now found, surprisingly, that such oligoesters are also highly suitable as emulsifiers for emulsions.
The invention thus provides emulsions comprising an oligoester.
These oligoesters are preferably obtained by polycondensation of one or more aromatic dicarboxylic acids or esters thereof and one or more polyhydric alcohols, such as, for example, ethylene glycol and/or propylene glycol. Where appropriate, these esters can also contain polyethylene glycol, polypropylene glycol, sulfoisophthalic acid, sulfobenzoic acid, isethionic acid, C1-C4-alcohols, oxalkylated C1-C24-alcohols, oxalkylated C6-C18-alkylphenols and/or oxalkylated C8-C24-alkylamines as monomers.
Particular preference is given to emulsions comprising those oligoesters which have been obtained by polycondensation of
-
- a) 40 to 52 mol %, preferably 45 to 50 mol %, of one or more dicarboxylic acids or esters thereof,
- b) 10 to 60 mol %, preferably 20 to 35 mol %, of ethylene glycol and/or propylene glycol,
- c) 0 to 20 mol %, preferably 10 to 15 mol %, of polyethylene glycol,
- d) 0 to 10 mol % of a water-soluble addition product of from 5 to 80 mol of an alkylene oxide with 1 mol of C1-C24-alcohols, C6-C18-alkylphenols or C8-C24-alkylamines and
- e) 0 to 10 mol % of one or more polyols having 3 to 6 hydroxyl groups.
Suitable as component a) for the preparation of the oligoesters are aromatic dicarboxylic acids, such as, for example, terephthalic acid, phthalic acid, isophthalic acid, and the mono- and dialkyl esters with C1- to C6-alcohols, such as dimethyl terephthalate, diethyl terephthalate and di-n-propyl terephthalate. Further examples of compounds which can be used as component a) for the preparation of the polyesters are oxalic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, itaconic acid, and the mono- and dialkyl esters of the carboxylic acids with C1-C6-alcohols, e.g. diethyl oxalate, diethyl succinate, diethyl glutarate, methyl adipate, diethyl adipate, di-n-butyl adipate, ethyl fumarate and dimethyl maleate. If the dicarboxylic acids which are suitable can form anhydrides, the anhydrides of the carboxylic acids having at least two carboxyl groups are also suitable as compound of component a) for the preparation of the oligoesters, e.g. maleic anhydride, phthalic anhydride or succinic anhydride. As compound of component a), particular preference is given to using terephthalic acid, phthalic acid, isophthalic acid, and the dimethyl, diethyl, dipropyl and dibutyl esters thereof. It is of course possible to use mixtures of different carboxylic acids or of different esters. Likewise, it is also possible to use, for example, mixtures of carboxylic acids and esters or mixtures of carboxylic acids and anhydrides in the condensation.
As component c), polyethylene glycols having molar masses of from 500 to 5000, preferably from 1000 to 3000, are used.
Suitable as component d) for the preparation of the oligoesters are water-soluble addition products of from 5 to 80 mol of at least one alkylene oxide with 1 mol of C1-C24-alcohols, C6-C18-alkylphenols or C8-C24-alkylamines. Preference is given to monomethyl ethers of polyethylene glycols. The alkylene oxides used for the preparation of the compounds of component d) are preferably ethylene oxide, and mixtures of ethylene oxide and propylene oxide. Also suitable are mixtures of ethylene oxide together with propylene oxide and/or butylene oxide, mixtures of ethylene oxide, propylene oxide and isobutylene oxide or mixtures of ethylene oxide and at least one butylene oxide. These water-soluble addition products of the alkylene oxide are surfactants. If mixtures of alkylene oxides are used for their preparation, then they may contain the alkylene oxides in blocks or else in random distribution.
Suitable alcohols which are alkoxylated are, for example, octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol or stearyl alcohol, but in particular methanol, and the alcohols having 8 to 24 carbon atoms obtainable by the Ziegler process, or the corresponding oxo alcohols. Of the alkylphenols, octylphenol, nonylphenol and dodecylphenol are of particular importance. The alkylamines used are, in particular, the C12-C18-monoalkylamines.
Suitable polyols (component e) are, for example, pentaerythritol, trimethylolethane, trimethylolpropane, 1,2,3-hexanetriol, sorbitol, mannitol and glycerol.
The oligoesters according to the invention are synthesized by processes known per se, by heating components a, b and c, and optionally d with the addition of a catalyst firstly at atmospheric pressure to temperatures of from 160 to about 220° C. The reaction is then continued under reduced pressure at temperatures of from 160 to about 240° C. with removal by distillation of excess glycols. The known transesterification and condensation catalysts of the prior art are suitable for the reaction, such as, for example, titanium tetraisopropoxide, dibutyltin oxide and/or antimony trioxide/calcium acetate. For further details on carrying out the process, reference is made to EP 442 101.
Also particularly suitable are the polyesters known from EP 241 985 which, in addition to oxyethylene groups and terephthalic acid units, contain 1,2-propylene, 1,2-butylene and/or 3-methoxy-1,2-propylene groups and glycerol units and are terminally capped with C1- to C4-alkyl groups; the soil release polymers, described in EP 253 567, having a molar mass of from 900 to 9000 g/mol of ethylene terephthalate and polyethylene oxide terephthalate, where the polyethylene glycol units have molecular weights of from 300 to 3000 g/mol and the molar ratio of the ethylene terephthalate to polyethylene oxide terephthalate is 0.6 to 0.95; and the polyesters, known from EP 272 033, containing polypropylene terephthalate and polyoxyethylene terephthalate units and being at least proportionately terminally capped by C1-C4-alkyl radicals.
Likewise preferred are oligoesters of ethylene terephthalate and polyethylene oxide terephthalate in which the polyethylene glycol units have molecular weights of from 750 to 5000 g/mol and the molar ratio of ethylene terephthalate to polyethylene oxide terephthalate is 50:50 to 90:10 and whose use in detergents is described in German Patent Specification DE 28 57 292, and oligoesters having molecular weights of from 15 000 to 50 000 g/mol of ethylene terephthalate and polyethylene oxide terephthalate, where the polyethylene glycol units have molecular weights of from 1000 to 10 000 g/mol and the molar ratio of ethylene terephthalate to polyethylene oxide terephthalate is 2:1 to 6:1, which, according to DE 33 24 258, can be used in detergents.
-
- R1 and R7 are linear or branched C1- to C18-alkyl,
- R2 and R6 are ethylene,
- R3 is 1,4-phenylene,
- R4 is ethylene,
- R5 is ethylene, 1,2-propylene or random mixtures of any composition of the two,
- x and y independently of one another are numbers between 1 and 500,
- z is a number between 10 and 140,
- a is a number between 1 and 12,
- b is a number between 7 and 40,
- where a+b is at least 11.
Preferably, independently of one another,
-
- R1 and R7 are linear or branched C1- to C4-alkyl,
- x and y are numbers between 3 and 45,
- z is a number between 18 and 70,
- a is a number between 2 and 5,
- b is a number between 8 and 12 and
- a+b is a number between 12 and 18 or between 25 and 35. The oligoesters described in DE 19 644 034 are obtained from dimethyl terephthalate, ethylene glycol and/or propylene glycol, polyethylene glycol and C1- to C18-alkylpolyethylene glycol with the addition of a catalyst firstly by transesterification at temperatures of from 160 to about 220° C. and distillative removal of the methanol at atmospheric pressure and subsequent distillative removal of the excess glycols at temperatures of from 160 to about 240° C.
The described oligoesters are usually present in the emulsions according to the invention in amounts of from 0.1 to 5% by weight, preferably 0.3 to 3% by weight, based on the finished emulsion. The emulsions may either be water-in-oil emulsions or oil-in-water emulsions.
The nonaqueous proportion of the emulsions, which is composed largely of the emulsifier and the oil substance and generally corresponds to the solids content, is usually 5 to 95% and preferably 15 to 75% by weight. This means that the emulsions may comprise 5 to 95% by weight and preferably 25 to 85% by weight of water, depending on whether the intention is to prepare lotions of comparatively low viscosity, or creams and ointments of high viscosity.
Examples of suitable oil substances are Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C6-C13-fatty acids with linear C6-C20-fatty alcohols, esters of branched C6-C13-carboxylic acids with linear C6-C20-fatty alcohols, esters of linear C6-C18-fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, dimerdiol or trimerdiol) and/or Guerbet alcohols, triglycerides based on C6-C10-fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates, dialkyl ethers and/or aliphatic or aromatic hydrocarbons.
The emulsions can be used as skin care compositions, such as, for example, day creams, night creams, care creams, nourishing creams, body lotions, ointments and the like, and can comprise, as further auxiliaries and additives, coemulsifiers, superfatting agents, fats, waxes, stabilizers, biogenic active ingredients, glycerol, preservatives, dyes and fragrances.
It is essential for the invention that the described oligoesters can also be used without the co-use of a nonionic surfactant as emulsifier. The co-use of emulsifiers is therefore not obligatory, but possible.
Suitable nonionogenic O/W coemulsifiers are addition products of from 2 to 30 mol of ethylene oxide and/or 0 to 5 mol of propylene oxide with linear fatty alcohols having 8 to 22 carbon atoms, with fatty acids having 12 to 22 carbon atoms and with alkylphenols having 8 to 15 carbon atoms in the alkyl group; C12-C18-fatty acid mono- and diesters of addition products of from 1 to 30 mol of ethylene oxide with glycerol; glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and the ethylene oxide addition products thereof; addition products of from 15 to 60 mol of ethylene oxide with castor oil and/or hydrogenated castor oil; polyol and, in particular, polyglycerol esters, such as e.g. polyglycerol polyricinoleate and polyglycerol poly-12-hydroxystearate. Also suitable are mixtures of compounds of two or more of these classes of substance. The addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. They are homolog mixtures whose average degree of alkoxylation corresponds to the ratio of the quantitative amounts of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out. C12-C18-fatty acid mono- and diesters of addition products of ethylene oxide with glycerol are known from DE 20 24 051 as refatting agents for cosmetic preparations.
Superfatting agents which can be used are substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter also serving as foam stabilizers. Typical examples of fats are glycerides, and suitable waxes are, inter alia, beeswax, paraffin wax or microcrystalline waxes, optionally in combination with hydrophilic waxes, e.g. cetyl stearyl alcohol. Stabilizers which can be used are metal salts of fatty acids, such as e.g. magnesium stearate, aluminum stearate and/or zinc stearate. Biogenic active ingredients means, for example, plant extracts and vitamin complexes. Examples of suitable preservatives are phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid. Suitable pearlizing agents are, for example, glycol distearic esters, such as ethylene glycol distearate, but also fatty acid monoglycol esters. Dyes which can be used are the substances approved and suitable for cosmetic purposes, as are listed, for example in the publication “Kosmetische Fätrbemittel” [Cosmetic Colorants] from the Farbstoffkommission der Deutschen Forschungsgemeinschaft [Dyes Commission of the German Research Council], Verlag Chemie, Weinheim, 1984, pp. 81-106.
The total proportion of auxiliaries and additives can be 1 to 10% by weight, preferably 2 to 5% by weight, based on the composition.
The compositions can be prepared in a manner known per se, i.e. for example by hot, hot-hot/cold or PIT emulsification.
Through the use according to the invention of the oligoesters in emulsions, in particular in O/W lotions and O/W creams, it is possible to obtain stable formulations which additionally impart a pleasant feel to the skin.
The examples below serve to illustrate the subject-matter of the invention in more detail, without limiting it thereto.
The following oligoesters according to the invention were used in the examples:
-
- Polyester 1: 40 mol % of terephthalic acid, 10 mol % of ethylene glycol, 10 mol % of propylene glycol, 20 mol % of polyethylene glycol, 10 mol % of fatty alcohol ethoxylate, 10 mol % of polyol
- Polyester 2: 50 mol % of terephthalic acid, 25 mol % of ethylene glycol, 20 mol % of polyethylene glycol, 5 mol % of fatty alcohol ethoxylate
- Polyester 3: 50 mol % of hexanedicarboxylic acid, 40 mol % of propylene glycol, 10 mol % of polyethylene glycol
These polyesters were prepared in the manner described in the introduction.
The following stability tests were carried out with the formulations described below:
-
- Storage at 40° C., 45° C. and 50° C. over a period of 90 days.
- Centrifugation at 20° C., 5000 rpm, 30 min
Under these conditions, all formulations exhibited good to very good stability.
O/W Cream
A | POLYESTER 1 (Clariant) | 1.00% | ||
® Cetiol V | 7.00% | |||
Jojoba oil | 5.00% | |||
Isopropyl palmitate | 6.00% | |||
B | ® Aristoflex AVC (Clariant) | 0.70% | ||
C | Glycerol | 3.00% | ||
Water | 76.90% | |||
Preservative | q.s. | |||
D | Perfume | 0.40% | ||
Preparation
-
- I B was stirred into A, then C was added and stirred well
- II D was added with stirring
- III The emulsion was homogenized.
O/W Cream
A | POLYESTER 2 (Clariant) | 1.00% | ||
® Cetiol V | 7.00% | |||
Jojoba oil | 5.00% | |||
Isopropyl palmitate | 6.00% | |||
B | ® Aristoflex AVC (Clariant) | 0.70% | ||
C | Glycerol | 3.00% | ||
Water | 76.90% | |||
Preservative | q.s. | |||
D | Perfume | 0.40% | ||
Preparation: as in Example 1
O/W Cream
A | POLYESTER 1 (Clariant) | 1.50% | ||
Mineral oil, low-viscosity | 8.00% | |||
Isopropyl palmitate | 4.00% | |||
® Eutanol G | 4.00% | |||
B | ® Aristoflex AVC (Clariant) | 0.70% | ||
C | Water | 81.40% | ||
Preservative | q.s. | |||
D | Perfume | 0.40% | ||
Preparation: as in Example 1
O/W Cream
A | POLYESTER 2 (Clariant) | 1.00% | ||
Mineral oil, low-viscosity | 8.00% | |||
Isopropyl palmitate | 4.00% | |||
® Eutanol G | 4.00% | |||
B | ® Aristoflex AVC (Clariant) | 0.70% | ||
C | Water | 81.90% | ||
Preservative | q.s. | |||
D | Perfume | 0.40% | ||
Preparation: as in Example 1
O/W Sun Protection Milk
A | POLYESTER 1 (Clariant) | 1.00% | ||
Mineral oil, high-viscosity | 10.00% | |||
Isopropyl palmitate | 5.00% | |||
B | ® Neo - Heliopan E 1000 | 8.50% | ||
® Neo - Heliopan BB | 1.50% | |||
C | ® Aristoflex AVC (Clariant) | 0.60% | ||
D | Glycerol | 3.00% | ||
Water | 70.10% | |||
Preservative | q.s. | |||
E | Perfume | 0.30% | ||
Preparation:
-
- I B was mixed with A, then C was added
- II D was added to the mixture I with stirring, then E was added.
- III The emulsion was homogenized
O/W Sun Protection Milk
A | POLYESTER 2 (Clariant) | 1.00% | ||
Mineral oil, high-viscosity | 10.00% | |||
Isopropyl palmitate | 5.00% | |||
B | ® Neo - Heliopan E 1000 | 8.50% | ||
® Neo - Heliopan BB | 1.50% | |||
C | ® Aristoflex AVC (Clariant) | 0.60% | ||
D | Glycerol | 3.00% | ||
Water | 70.10% | |||
Preservative | q.s. | |||
E | Perfume | 0.30% | ||
Preparation: as in Example 5
O/W Sun Protection Milk
A | POLYESTER 3 (Clariant) | 2.00% | ||
Mineral oil, high-viscosity | 10.00% | |||
Isopropyl palmitate | 5.00% | |||
B | ® Neo - Heliopan E 1000 | 8.50% | ||
® Neo - Heliopan BB | 1.50% | |||
C | ® Aristoflex AVC (Clariant) | 0.60% | ||
D | Glycerol | 3.00% | ||
Water | 69.10% | |||
Preservative | q.s. | |||
E | Perfume | 0.30% | ||
Preparation: as Example 5
-
- Chemical names of the commercial products used:
- Aristoflex AVC: Acrylamidopropylenesulfonic acid/vinylformamide copolymer
- Cetiol: Decyl oleate
- Eutanol G: Hexyldecanol
- Neo-Heliopan E 1000: Isoamyl p-methoxycinnamate
- Neo-Heliopan BB: Benzophenone-3
Claims (7)
1. A skin cosmetic emulsion comprising an emulsifier comprising oligoesters obtained by polycondensation of
a) 40 to 52 mol % of one or more aromatic dicarboxylic acids or esters thereof,
b) 10 to 60 mol % of ethylene glycol and/or propylene glycol,
c) 0 to 20 mol % of polyethylene glycol,
d) 0 to 10 mol % of a water-soluble addition product of from 5 to 80 mol of an alkylene oxide with 1 mol of a component selected from the group consisting of C1-C24-alcohols, C6-C18-alkylphenols, and C8-C24-alkylamines and
e) 0 to 10 mol % of one or more polyols having 3 to 6 hydroxyl groups wherein said cosmetic emulsion further comprises oils, superfatting agents, preservatives and fragrances.
2. The skin cosmetic emulsion as claimed in claim 1 , which comprises 0.1 to 5% by weight of said emulsifier.
3. The skin cosmetic emulsion as claimed in claim 1 wherein the oligoesters are obtained by polycondensation of 45 to 50 mol % of one or more aromatic dicarboxylic acids or esters thereof.
4. The skin cosmetic emulsion as claimed in claim 1 wherein the oligoesters are obtained by polycondensation of said aromatic dicarboxylic acids or esters thereof and 20 to 35 mol % of ethylene glycol and/or propylene glycol.
5. The skin cosmetic emulsion as claimed in claim 1 wherein the oligoesters are obtained by polycondensation of said aromatic dicarboxylic acids or esters thereof, said ethylene glycol and/or propylene glycol, and 10 to 15 mol % of polyethylene glycol.
6. A skin cosmetic emulsion comprising an emulsifier comprising oligoesters obtained by polycondensation of
a) 40 to 52 mol % of one or more aromatic dicarboxylic acids or esters thereof,
b) 10 to 60 mol % of ethylene glycol and/or propylene glycol,
c) 0 to 20 mol % of polyethylene glycol,
d) 0 to 10 mol % of a water-soluble addition product of from 5 to 80 mol of an alkylene oxide with 1 mol of a component selected from the group consisting of C1-C24-alcohols, C6-C18-alkylphenols, and C8-C24-alkylamines and
e) 0 to 10 mol % of one or more polyols having 3 to 6 hydroxyl groups
wherein said cosmetic emulsion further comprises superfatting agents, fats, waxes, stabilizers, biogenic active ingredients, glycerol, preservatives, dyes and fragrances.
7. The skin cosmetic emulsion of claim 6 wherein the aromatic dicarboxylic acids or esters thereof are selected from the group consisting of terephthalic acid, phthalic acid, isophthalic acid, and the dimethyl, diethyl, dipropyl and dibutyl esters thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US10/893,704 USRE39993E1 (en) | 1999-12-08 | 2004-07-16 | Emulsions |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19959119A DE19959119A1 (en) | 1999-12-08 | 1999-12-08 | Emulsions |
US09/733,201 US6489395B2 (en) | 1999-12-08 | 2000-12-08 | Emulsions |
US10/893,704 USRE39993E1 (en) | 1999-12-08 | 2004-07-16 | Emulsions |
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EP (1) | EP1106169B1 (en) |
JP (1) | JP2001226568A (en) |
DE (2) | DE19959119A1 (en) |
Families Citing this family (15)
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DE10003137A1 (en) * | 2000-01-26 | 2001-08-02 | Clariant Gmbh | Aqueous or aqueous-alcoholic body cleanser containing oligoester |
DE10059833A1 (en) * | 2000-12-01 | 2002-06-13 | Clariant Gmbh | Fluorine-modified comb polymers based on acryloyldimethylauric acid |
DE10065046A1 (en) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | O / W emulsions containing one or more ammonium acryloyldimethyltaurate / vinylpyrrolidone copolymers |
DE10065045A1 (en) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | W / O emulsions containing one or more ammonium acryloyldimethyltaurate / vinylpyrrolidone copolymers |
DE10065047A1 (en) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | Gelcèmes in the form of O / W emulsions containing one or more ammonium aryldimethyltaurate / vinylpyrrolidone copolymers |
DE10065044A1 (en) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | Yellow-based eyeshadow containing one or more ammonium acryloyldiamethyltaurate / vinylpyrrolidone copolymers |
DE102004029310A1 (en) * | 2004-06-17 | 2005-12-29 | Clariant Gmbh | Highly concentrated, aqueous formulations of oligoesters and polyesters |
US20060135383A1 (en) * | 2004-12-17 | 2006-06-22 | Cossa Anthony J | Cleansing compositions comprising polymeric emulsifiers and methods of using same |
US20060240144A1 (en) * | 2005-04-21 | 2006-10-26 | Shalaby Shalaby W | Biodegradable chewing gum bases |
US20070092458A1 (en) * | 2005-10-24 | 2007-04-26 | Librizzi Joseph J | Compositions comprising polymeric emulsifiers and methods of using the same |
US20070092457A1 (en) * | 2005-10-24 | 2007-04-26 | Librizzi Joseph J | Compositions comprising polymeric emulsifiers and methods of using the same |
US8425727B2 (en) * | 2010-01-22 | 2013-04-23 | Clariant Finance (Bvi) Limited | Method for increasing glueability of paper or paperboard |
EP3489340A1 (en) | 2017-11-28 | 2019-05-29 | Clariant International Ltd | Renewably sourced soil release polyesters |
EP3802765A1 (en) | 2018-05-24 | 2021-04-14 | Clariant International Ltd | Soil release polyesters for use in detergent compositions |
WO2021233987A1 (en) * | 2020-05-20 | 2021-11-25 | Clariant International Ltd | Soil release polyesters for use in detergent compositions |
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Also Published As
Publication number | Publication date |
---|---|
DE19959119A1 (en) | 2001-06-13 |
US20010005737A1 (en) | 2001-06-28 |
EP1106169B1 (en) | 2005-06-01 |
DE50010446D1 (en) | 2005-07-07 |
US6489395B2 (en) | 2002-12-03 |
EP1106169A2 (en) | 2001-06-13 |
JP2001226568A (en) | 2001-08-21 |
EP1106169A3 (en) | 2001-10-17 |
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