JP6427171B2 - 硫酸化オリゴヒドロキシカルボン酸エステル、及びその使用 - Google Patents
硫酸化オリゴヒドロキシカルボン酸エステル、及びその使用 Download PDFInfo
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- JP6427171B2 JP6427171B2 JP2016517241A JP2016517241A JP6427171B2 JP 6427171 B2 JP6427171 B2 JP 6427171B2 JP 2016517241 A JP2016517241 A JP 2016517241A JP 2016517241 A JP2016517241 A JP 2016517241A JP 6427171 B2 JP6427171 B2 JP 6427171B2
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- 239000002253 acid Substances 0.000 title description 17
- 150000002148 esters Chemical class 0.000 title description 9
- -1 2-ethylhexyl Chemical group 0.000 claims description 156
- 239000000203 mixture Substances 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 73
- 239000002537 cosmetic Substances 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 238000005886 esterification reaction Methods 0.000 claims description 33
- 239000004094 surface-active agent Substances 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 230000032050 esterification Effects 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 17
- 239000000344 soap Substances 0.000 claims description 16
- 239000003945 anionic surfactant Substances 0.000 claims description 14
- 239000003599 detergent Substances 0.000 claims description 14
- 239000000499 gel Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001768 cations Chemical group 0.000 claims description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 239000002453 shampoo Substances 0.000 claims description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000006260 foam Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
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- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000004310 lactic acid Substances 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 5
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000012459 cleaning agent Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000005644 linolenyl group Chemical group 0.000 claims description 3
- 125000005645 linoleyl group Chemical group 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000271 synthetic detergent Substances 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 28
- 239000000194 fatty acid Substances 0.000 description 28
- 229930195729 fatty acid Natural products 0.000 description 28
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 23
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002562 thickening agent Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000002191 fatty alcohols Chemical class 0.000 description 17
- 150000004665 fatty acids Chemical class 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002671 adjuvant Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920002125 Sokalan® Polymers 0.000 description 8
- 238000006384 oligomerization reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000005670 sulfation reaction Methods 0.000 description 7
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
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- 230000019635 sulfation Effects 0.000 description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 5
- 239000004166 Lanolin Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- QQQMUBLXDAFBRH-UHFFFAOYSA-N dodecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)O QQQMUBLXDAFBRH-UHFFFAOYSA-N 0.000 description 5
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- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- 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
- A61Q19/007—Preparations for dry skin
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- 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
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
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Description
基R2は互いに独立して、水素、メチル、エチル、−OA、−COOR4、−CH2−OA及び−CH2−COOR4から選択され、前記基R4は水素又は1〜30個の炭素原子及び0、1、2若しくは3個の二重結合を有する直鎖若しくは分枝脂肪族炭化水素基であり、
基R3は互いに独立して、水素、メチル、エチル、−OA、−COOR5、−CH2−OA及び−CH2−COOR5から選択され、前記基R5は水素又は1〜30個の炭素原子及び0、1、2若しくは3個の二重結合を有する直鎖若しくは分枝脂肪族炭化水素基であり、
AはH又は−SO3Bであり、Bは水素又はカチオン等価物であり、
nは平均で少なくとも0.1の値であり、
m1及びm2は互いに独立して0又は1であり、
但し、少なくとも1つの基Aは−SO3Bであり、
但し、少なくとも1つの基R1、基R4又は基R5は1〜30個の炭素原子及び0、1、2若しくは3個の二重結合を有する直鎖若しくは分枝脂肪族炭化水素基である)
Bは水素又はカチオン等価物であり、
nは平均で少なくとも0.1の値である)
a)一般式(I.A)で表される少なくとも1つのヒドロキシカルボン酸
(式中、R2、R3及びm1は請求項1〜8のいずれかに定義されるものと同じである)
をエステル化反応により反応させ、ここで、前記エステル化は少なくとも1つのアルコールR1−OH(式中、R1は請求項1〜8のいずれかに定義されるものと同じである)の存在下で行う、又はヒドロキシカルボン酸(I.A)のエステル化による生成物を次いで少なくとも1つのアルコールR1−OHと反応させる、
b)工程a)による反応生成物を硫化剤と反応させ、
c)必要に応じて、工程b)による反応生成物を少なくとも部分的に塩基で中和させる、方法を提供する。
工程a)のエステル化反応をいくつかの段階で行うことができ、この場合にはまず、少なくとも1つのヒドロキシカルボン酸(I.A)をオリゴマー化を含むエステル化に供し、次いで得られた反応混合物を、必要に応じて分離及び/又は精製後、少なくとも1つのアルコールR1−OHと共にさらにエステル化反応させる。
界面活性アルコールの硫酸化反応は、当業者に公知であり、例えば、WO93/24453、DE4003096A1及び「Ullmann's Encyclopedia of Industrial Chemistry」、第5版、第A25(1994年)巻、779−783頁に記載され、この文献は本明細書で参照される。
使用され得る中和のための塩基は、アルカリ金属塩(例えば、水酸化ナトリウム溶液、水酸化カリウム溶液、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム又は炭酸水素カリウム)、及びアルカリ土類金属塩(例えば、水酸化カルシウム、酸化カルシウム、水酸化マグネシウム又は炭酸マグネシウム)、及びアミンである。適当なアミンは例えば、C1−C6−アルキルアミン、好ましくはn−プロピルアミン及びn−ブチルアミン、ジアルキルアミン、好ましくはジエチルプロピルアミン及びジプロピルメチルアミン、トリアルキルアミン、好ましくはトリエチルアミン及びトリイソプロピルアミンである。アミノアルコール、例えば、トリアルカノールアミン、例えば、トリエタノールアミン、アルキルジアルカノールアミン、例えば、メチル又はエチルジエタノールアミン及びジアルキルアルカノールアミン、例えば、ジメチルエタノールアミン、また2−アミノ−2−メチル−1−プロパノールアミンが好適である。酸性基の中和は、2以上の塩基の混合物によっても行うことができる。塩基は部分的に、好ましくはNaOH、KOH、2−アミノ−2−メチル−1−プロパノール、トリエチルアミン、ジエチルアミノプロピルアミン、ジエタノールアミン、トリエタノールアミン、トリイソプロパノールアミン及びそれらの混合物である。中和は部分的又は全体的に、意図される使用に応じて行うことができる。部分的な中和について、例えば、50〜100%未満の酸性基を中和できる。完全な中和が好適である。
一般式(I)又は一般式(I.A)で表される本発明による化合物は、界面活性剤含有組成物を調製するのに特に有利に適している。特に、これらは水性界面活性剤含有組成物である。化合物(I)及び(I.A)は、そのような組成物において、それらの良好な水溶性、化粧品に使用される活性成分及び補助剤の多くと良好な相容性、良好な起泡力及び良好なレオロジー的挙動により特徴づけられる。
(式中、COR7は、6〜22個の炭素原子及び0、1、2又は3つの二重結合を有する直鎖又は分枝アシル基であり、Xは水素、アルカリ金属、1価のアルカリ土類金属、アンモニウム、アルキルアンモニウム、アルカノールアンモニウム又はグルカモニウムである。)
・脂肪アルコールポリオキシアルキレンエステル、例えば、ラウリルアルコールポリオキ
シエチレンアセテート、
・低分子量C1−C6アルコール又はC7−C30脂肪アルコールから生じるアルキルポリ
オキシアルキレンエーテル。ここで、エーテル成分はエチレンオキシド単位、プロ
ピレンオキシド単位、1,2−ブチレンオキシド単位、1,4−ブチレンオキシド単位及
びそれらのランダムコポリマー及びブロックコポリマーに由来する。これらは特に、脂
肪アルコールアルコキシレート及びオキソアルコールアルコキシレート、とりわけ型RO
−(R8O)r(R9O)SR10(式中、R8及びR9は互いに独立して、C2H4、C3
H6、C4H8、及びR10はH又はC1−C12−アルキル、RはC3−C30−アルキル又
はC6−C30−アルケニルを含み、r及びsは互いに独立して、0〜50、ここで両方は
0ではない)、例えば、イソトリデシルアルコール及びオレイルアルコールポリオキシエ
チレンエーテル、
・アルキルアリルアルコールポリオキシエチレンエーテル、例えば、オクチルフェノール
ポリオキシエチレンエーテル、
・アルコキシ化された動物性及び/又は植物性の脂肪及び/又は油、例えば、トウモロコ
シ油エトキシレート、ヒマシ油エトキシレート、獣脂肪エトキシレート、
・グリセロールエステル、例えば、グリセロールモノステアレートなど、
・アルキルフェノールアルコキシレート、例えば、エトキシ化イソオクチル−、オクチル
−又はノニルフェノール、トリブチルフェノールポリオキシエチレンエーテルなど、
・脂肪アミンアルコキシレート、脂肪酸アミドアルコキシレート及び脂肪酸ジエタノール
アミドアルコキシレート、特にそれらのエトキシレート、
・糖界面活性剤、ソルビトールエステル、例えば、ソルビタン脂肪酸エステル(ソルビタ
ンモノオレエート、ソルビタントリステアレート)、ポリオキシエチレンソルビタン脂肪
酸エステル、アルキルポリグリコシド、N−アルキルグルコンアミドなど、
・アルキルメチルスルホキシド、
・アルキルジメチルホスフィンオキシド、例えば、テトラデシルジメチルホスフィンオキ
シドなどを含む。
一般式(I)及び一般式(I.1)で表される化合物は、好ましくは化粧品及び医薬品、特に水性化粧品及び水性医薬品を調製するのに適する。
a)上記に記載の少なくとも1つの一般式(I)で表される化合物
b)少なくとも1つの化粧品用活性成分又は医薬品用活性成分、及び
c)必要に応じて、成分a)及び成分b)とは異なる少なくとも1つの化粧品用助剤又は医薬品用助剤を含む。
i) 水
ii) 水混和性有機溶媒、好ましくはC2−C4アルカノール、特にエタノール
iii) 油、脂肪、ワックス、
iv) iii)とは異なる、C6−C30−モノカルボン酸と、1価、2価又は3価アルコールとのエステル
v) 飽和非環式炭化水素及び環式炭化水素、
vi) 脂肪酸、
vii) 脂肪アルコール、
viii) 噴射ガス
及びそれらの混合物から選択される。
式(I)及び式(I.1)で表される本発明による化合物は、例えば、繊維及び/又は硬表面を洗浄するための洗剤及び洗浄剤の製造にも適する。この種類の洗浄剤は、手洗い又は機械的食器洗浄用洗浄剤、非繊維表面のための(例えば、金属、塗装木材又はプラスチック製の)多目的洗剤、又はセラミック物品(例えば、磁器、スラブ、タイル)のための洗浄剤の形態であり得る。好ましくは本発明による洗剤又は洗浄剤は、液体繊維洗浄剤の形態である。望ましくは、これらはまた、ペースト状で処方され得る。
多目的洗浄剤、霧務洗浄剤、家庭、工業及び企業における洗浄用の手洗用食器洗浄剤;
保湿剤;
印刷業における印刷用ロールクリーナー及び印刷版クリーナー;
ペイント剤及びカラー剤;
コーティング剤(例えば紙用コーディング剤);
接着剤;
スプレー用途、例えばインクジェットインク用の製剤;
革処理組成物;
金属処理用組成物、例えば腐食防止剤;
切断、研磨又は穿孔助剤及び潤滑剤;
繊維業における製剤、例えば、平滑化剤又は糸洗浄用製剤:
浮遊助剤及び発泡助剤
である。
ジャケット冷却及びSO3ガス供給部を備えた連続的流下薄膜式反応器において、工業グレードのラウリルオリゴラクテート(68%のモノエステル)600gを40℃で三酸化硫黄と反応させた。モル比は、ラウリルオリゴラクテート1モルに対して1.2モルのSO3であった。三酸化硫黄を、65重量%濃度の発煙硫酸に相当する量から加熱により排斥し、5体積%の濃度に窒素で希釈し、ノズルを介してラウリルラクテートと接触させた。その後、50重量%の濃度の水酸化ナトリウム溶液と共に、1重量%濃度のリン酸二水素カリウム溶液中で撹拌し、pH5.5〜7.5に中和した。
アニオン性界面活性剤含量 14.5%(MW=374.4g/mol)
不飽和: 2.47%
カール・フィッシャー滴定法による水 83.9%
Na2SO4: 1.7%
ジャケット冷却及びSO3ガス供給部を備えた連続的流下薄膜式反応器において、ラウリルラクテート(87%のモノエステル)600gを40℃で三酸化硫黄と反応させた。モル比は、ラウリルラクテート1モルに対して1.2モルのSO3であった。三酸化硫黄は、65重量%濃度の発煙硫酸に相当する量から加熱により排斥し、5体積%の濃度に窒素で希釈し、ノズルを通じてラウリルラクテートと接触させた。その後、50重量%濃度の水酸化ナトリウム溶液と共に、1重量%濃度のリン酸二水素カリウム溶液中で撹拌し、pH5.5〜7.5に中和した。
アニオン性界面活性剤: 15.4%(MW=368.5g/mol)
不飽和: 1.3%
カール・フィッシャー滴定法による水 82.8%
Na2SO4: 1.72%
実施例1で得られた物質及び比較例の物質を、12%の濃度に調整し、NaClの量を増加させつつ添加した。溶液の粘度は粘度計(測定温度22℃で、ブルックフィールドDII+pro)を用いて測定した。
Claims (15)
- 一般式(I)
基R2は互いに独立して、水素、メチル、エチル、−OA、−COOR4、−CH2−OA及び−CH2−COOR4から選択され、前記基R4は水素又は1〜30個の炭素原子及び0、1、2若しくは3個の二重結合を有する直鎖若しくは分枝脂肪族炭化水素基であり、
基R3は互いに独立して、水素、メチル、エチル、−OA、−COOR5、−CH2−OA及び−CH2−COOR5から選択され、前記基R5は水素又は1〜30個の炭素原子及び0、1、2又は3個の二重結合を有する直鎖又は分枝脂肪族炭化水素基であり、
AはH又は−SO3Bであり、Bは水素又はカチオン等価物であり、
nは平均で少なくとも0.1の値であり、
m1及びm2は互いに独立して0又は1であり、
但し、少なくとも1つの基Aは−SO3Bであり、
但し、少なくとも1つの基R1、基R4又は基R5は1〜30個の炭素原子及び0、1、2又は3個の二重結合を有する直鎖又は分枝脂肪族炭化水素基である]
で表される化合物。 - m1及びm2は同じ意味を有する、請求項1に記載の化合物(I)。
- 乳酸、グリコール酸、リンゴ酸、酒石酸又はそれらの混合物に由来する、請求項1又は2に記載の化合物(I)。
- nは、0.1〜100、好ましくは0.15〜50、特に0.2〜20の値である、請求項1〜4のいずれかに記載の化合物(I)。
- 少なくとも1つの基R1、基R4及び基R5は、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、sec−ブチル、tert−ブチル、n−ペンチル、イソアミル、n−ヘキシル、2−エチルヘキシル、n−ヘプチル、n−オクチル、n−ノニル、n−デシル、2−プロピルヘプチル、n−ウンデシル、n−ドデシル、n−トリデシル、n−テトラデシル、n−ペンタデシル、n−ヘキサデシル、n−ヘプタデシル、n−オクタデシル、n−ノナデシル、アラキニル、ベヘニル、リグノセリニル、メリッシニル、イソトリデシル、イソステアリル、オレイル、リノレイル、リノレニル又は少なくとも2つのこれらの基の組み合わせである、請求項1〜5のいずれかに記載の化合物(I)。
- 少なくとも1つの基R1、基R4及び基R5は、8〜18個の炭素原子を有する直鎖飽和アルコールに由来する、請求項1〜6のいずれかに記載の化合物(I)。
- 少なくとも1つの基R1、基R4及び基R5は、直鎖飽和C12−/C14−アルコールの混合物に由来する、請求項1〜7のいずれかに記載の化合物(I)。
- 一般式(I)で表される化合物を製造する方法であって、
a)一般式(I.A)
で表される少なくとも1つのヒドロキシカルボン酸をエステル化反応により反応させ、ここで、前記エステル化は少なくとも1つのアルコールR1−OH[式中、R1は、請求項1〜8のいずれかに記載のものと同じである(ただし、水素ではない)]の存在下で行う、又はヒドロキシカルボン酸(I.A)のエステル化による生成物を次いで少なくとも1つのアルコールR1−OHと反応させる、
b)工程a)による反応生成物を硫酸化剤と反応させ、
c)必要に応じて、工程b)による反応生成物を、少なくとも部分的に塩基で中和させる、方法。 - 工程b)で使用する硫酸化剤は、SO3を含む、又はSO3からなる、請求項9に記載の方法。
- a)請求項1〜8のいずれかに記載の一般式(I)で表される少なくとも1つの化合物、
b)少なくとも1つの化粧品用活性成分又は医薬品用活性成分、及び
c)必要に応じて、構成要素a)及びb)とは異なる少なくとも1つの化粧品用助剤又は医薬品用助剤
を含む、化粧品組成物又は医薬品組成物。 - ヘアシャンプー、シャワーゲル、石鹸、合成洗剤、洗浄用糊、洗浄用ローション、スクラブ剤、バス用フォーム剤、バス用オイル、シャワーバス、ひげ剃り用フォーム、ひげ剃り用ローション又はひげ剃り用クリームの形態である、請求項11に記載の化粧品組成物。
- 請求項1〜8のいずれかに記載の一般式(I)で表される少なくとも1つの化合物を含む、洗剤又は洗浄剤。
- 請求項1〜8のいずれかに記載の一般式(I)で表される少なくとも1つの化合物の、界面活性剤としての使用。
- 請求項1〜8のいずれかに記載の一般式(I)で表される少なくとも1つの化合物の、化粧品組成物、医薬品組成物、洗剤又は洗浄剤のためのアニオン性界面活性剤としての使用。
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EP13170255.7 | 2013-06-03 | ||
EP13170255.7A EP2810935B1 (de) | 2013-06-03 | 2013-06-03 | Sulfatierte Ester von Oligohydroxycarbonsäuren und deren Verwendung |
PCT/EP2014/061086 WO2014195210A1 (de) | 2013-06-03 | 2014-05-28 | Sulfatierte ester von oligohydroxycarbonsäuren und deren verwendung |
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EP3199204A1 (de) * | 2016-01-29 | 2017-08-02 | Basf Se | Wässrige tensid-zusammensetzungen |
DE102018127180A1 (de) * | 2018-10-31 | 2020-04-30 | Henkel Ag & Co. Kgaa | Wirkstoffzusammensetzung zur Pflege von Humanhaaren |
DE102019206912A1 (de) * | 2019-05-13 | 2020-11-19 | Henkel Ag & Co. Kgaa | Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, einer farbgebenden Verbindung, eines modifizierten Fettsäureesters und eines filmbildenden Polymers I |
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FR2110268B1 (ja) | 1970-10-07 | 1976-06-04 | Minnesota Mining & Mfg | |
US4237253A (en) | 1977-04-21 | 1980-12-02 | L'oreal | Copolymers, their process of preparation, and cosmetic compounds containing them |
DE3708451A1 (de) | 1987-03-16 | 1988-10-06 | Henkel Kgaa | Zwitterionische polymere und deren verwendung in haarbehandlungsmitteln |
DE3929973A1 (de) | 1989-09-08 | 1991-03-14 | Henkel Kgaa | Haarpflegemittel |
DE4003096A1 (de) * | 1990-02-02 | 1991-08-08 | Henkel Kgaa | Sulfierte hydroxycarbonsaeureester |
US5366665A (en) * | 1991-07-30 | 1994-11-22 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising alkyl sulfooxyalkanoate compounds containing a beneficial reagent component |
EP0530866A1 (en) | 1991-07-30 | 1993-03-10 | Unilever N.V. | Alkyl sulphooxyalkanoate compounds and compositions |
DE4218075A1 (de) | 1992-06-01 | 1993-12-02 | Henkel Kgaa | Verfahren zur Herstellung geruchsarmer Fettalkoholethersulfat-Salze |
US5429773A (en) * | 1993-02-05 | 1995-07-04 | The Procter & Gamble Company | Process to improve alkyl ester sulfonate surfactant compositions |
DE4333238A1 (de) | 1993-09-30 | 1995-04-06 | Basf Ag | Pyrrolidongruppenhaltige Polyester und Polyamide |
DE4340042A1 (de) | 1993-11-24 | 1995-06-01 | Henkel Kgaa | Verwendung von sulfierten Hydroxycarbonsäureestern als Tenside zum Reinigen und Spülen harter Oberflächen |
MX2008013861A (es) * | 2006-05-02 | 2009-01-26 | Huntsman Spec Chem Corp | Composiciones y produccion de proceso de composiciones de alquilisetionato de acilo. |
US8501972B2 (en) * | 2007-10-22 | 2013-08-06 | Lion Corporation | Solid fatty alkyl ester sulfonate metal salt and method for producing powder thereof with sharp particle size distribution |
EP2810640A1 (de) | 2013-06-03 | 2014-12-10 | Basf Se | Ester von Oligohydroxycarbonsäuren und deren Verwendung |
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CN105263904B (zh) | 2017-08-08 |
EP2810935A1 (de) | 2014-12-10 |
KR20160016934A (ko) | 2016-02-15 |
CN105263904A (zh) | 2016-01-20 |
RU2015156750A (ru) | 2017-07-17 |
PL2810935T3 (pl) | 2016-11-30 |
BR112015030129A2 (pt) | 2017-07-25 |
RU2015156750A3 (ja) | 2018-03-29 |
US20160102050A1 (en) | 2016-04-14 |
EP2810935B1 (de) | 2016-05-25 |
KR102204483B1 (ko) | 2021-01-18 |
MX2015016490A (es) | 2016-06-10 |
RU2674984C2 (ru) | 2018-12-14 |
JP2016520631A (ja) | 2016-07-14 |
ES2588382T3 (es) | 2016-11-02 |
US9790172B2 (en) | 2017-10-17 |
BR112015030129B1 (pt) | 2020-09-29 |
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