JP2012500342A - ポリグリセロールエステルを含む有益組成物 - Google Patents
ポリグリセロールエステルを含む有益組成物 Download PDFInfo
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- JP2012500342A JP2012500342A JP2011523154A JP2011523154A JP2012500342A JP 2012500342 A JP2012500342 A JP 2012500342A JP 2011523154 A JP2011523154 A JP 2011523154A JP 2011523154 A JP2011523154 A JP 2011523154A JP 2012500342 A JP2012500342 A JP 2012500342A
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- polyglycerol ester
- esterification rate
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- 239000000203 mixture Substances 0.000 title claims abstract description 159
- 150000002148 esters Chemical class 0.000 title claims abstract description 38
- 229920000223 polyglycerol Polymers 0.000 title claims abstract description 36
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- 238000000034 method Methods 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 24
- -1 brighteners Substances 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 45
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 44
- 230000032050 esterification Effects 0.000 claims description 40
- 238000005886 esterification reaction Methods 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 21
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- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 18
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
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- 125000005313 fatty acid group Chemical group 0.000 claims 1
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- 125000002091 cationic group Chemical group 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
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- 239000000047 product Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
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- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 5
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- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 3
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- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
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- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 1
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- 229940057874 phenyl trimethicone Drugs 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
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- 229920000712 poly(acrylamide-co-diallyldimethylammonium chloride) Polymers 0.000 description 1
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000013514 silicone foam Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl 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])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical group OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 108010038851 tannase Proteins 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- LINXHFKHZLOLEI-UHFFFAOYSA-N trimethyl-[phenyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=CC=CC=C1 LINXHFKHZLOLEI-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3707—Polyethers, e.g. polyalkyleneoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
本明細書で使用するとき、「a」及び「an」を包含する冠詞は、特許請求の範囲で使用されるときには、請求又は記載されるものの1つ以上を意味するものと理解される。
a)nが約1.5〜約6であってもよいとき、PGEの平均エステル化率(%)は約20%〜約100%であってもよく、
b)nが約1.5〜約5であってもよいとき、平均エステル化率(%)は約20%〜約90%であってもよく、
c)nが約1.5〜約4であってもよいとき、平均エステル化率(%)は約20%〜約80%であってもよく、
PGE混合物の約50%超が少なくとも2つのエステル結合を有する、PGEを含んでもよい。
脂肪酸部分の炭素鎖が、約10〜約22炭素原子の平均炭素鎖長を有し、
PGEが約0〜約145のヨウ素価を有し、
a)nが約3〜約6であってもよいとき、エステル化率(%)は約20%〜約100%であってもよく、
b)nが約3〜約6であってもよいとき、エステル化率(%)は約25%〜約90%であってもよく、
c)nが約3〜約6であってもよいとき、エステル化率(%)は約35%〜約90%であってもよい、PGEを含んでもよい。
PGEが約0〜約20のヨウ素価を有し、
a)nが約1.5〜約3.5であってもよいとき、エステル化率(%)は約20%〜約60%であってもよく、
b)nが約1.5〜約4.5であってもよいとき、エステル化率(%)は約20%〜約70%であってもよく、
c)nが約1.5〜約6であってもよいとき、エステル化率(%)は約20%〜約80%であってもよい、PGEを含んでもよい。
脂肪酸部分の炭素鎖が、約16〜約18炭素原子の平均炭素鎖長を有し、
PGEが約45〜約135のヨウ素価を有し、
a)nが約1.5〜約3であってもよいとき、エステル化率(%)は約70%〜約100%であってもよく、
b)nが約1.5〜約4.5であってもよいとき、エステル化率(%)は約50%〜100%であってもよく、
c)nが約1.5〜約6であってもよいとき、エステル化率(%)は約25%〜60%であってもよい、PGEを含んでもよい。
a)nが約3〜約6であってもよいとき、エステル化率(%)は約15%〜約100%であってもよく、
b)nが約3〜約6であってもよいとき、エステル化率(%)は約25%〜約90%であってもよく、
c)nが約3〜約6であってもよいとき、エステル化率(%)は約35%〜約90%であってもよいPGEを含んでもよい。
[R1R2R3SiO1/2]n[R4R4SiO2/2]m[R4SiO3/2]j (式I)
式中、
i)各R1、R2、R3及びR4は、H、−OH、C1〜C20アルキル、C1〜C20置換アルキル、C6〜C20アリール、C6〜C20置換アリール、アルキルアリール、及び/又はC1〜C20アルコキシ、部分から成る群から独立して選択されてもよく、
ii)nは、n=j+2であるように、約2〜約10、又は約2〜約6、又は2の整数であってもよく、
iii)mは、約5〜約8,000、約7〜約8,000、又は約15〜約4,000の整数であってもよく、
iv)jは、約0〜約10、又は約0〜約4、又は0の整数であってもよく、
1つの態様では、R2、R3及びR4は、メチル、エチル、プロピル、C4〜C20アルキル、及び/又はC6〜C20アリール部分を含んでもよい。1つの態様では、R2、R3及びR4は、それぞれメチルであってもよい。シリコーン鎖の末端をブロックする各R1部分は、水素、メチル、メトキシ、エトキシ、ヒドロキシ、プロポキシ、及び/又はアリールオキシから成る群から選択される部分を含んでもよい。
[R1R2R3SiO1/2]n[(R4Si(X−Z)O2/2]k[R4R4SiO2/2]m[R4SiO3/2]j (式II)
式中、
i.各R1、R2、R3及びR4は、H、−OH、C1〜C20アルキル、C1〜C20置換アルキル、C6〜C20アリール、C6〜C20置換アリール、アルキルアリール、及び/又はC1〜C20アルコキシから独立して選択されてもよく、
ii.各Xは、2〜12炭素原子を含む二価アルキレンラジカル、−(CH2)s−(式中、sは約2〜約10の整数であってもよい)、−CH2−CH(OH)−CH2−、及び/又は
iv.kは、約3〜約20、又は約5〜約18超、又は約5〜約10の整数であってもよく、
v.mは、約100〜約2,000、又は約150〜約1,000の整数であってもよく、
vi.nは、n=j+2であるように、約2〜約10、又は約2〜約6、又は2の整数であってもよく、
vii.jは、約0〜約10、又は約0〜約4、又は0の整数であってもよく、
1つの態様では、R1は−OHを含んでもよい。この態様では、有機シリコーンは、アモジメチコンであってもよい。
1つの態様では、PGEを含有するサンプルの特性を決定する方法であって、
a.PGEを含むサンプルをイオン化助剤と組み合わせる工程であって、前記イオン化助剤が溶媒に可溶性であり、イオン化したサンプルを生成させることができる工程と、
b.フーリエ変換質量分析器を使用してイオン化したサンプルのデータを得る工程と、 c.未処理のデータの質量マッピングを正規化する工程であって、前記正規化が、前記PGEの繰り返し単位である部分に基づいてもよい工程と、
d.所望により、前記マップを用いて前記PGEの特性を決定する工程と、を含んでもよい方法を開示する。
先ず、10mMのアセタートアンモニウムを含有する50/50イソプロパノール−メタノール(v/v)溶液に、1mg/mLでPGEを溶解させることにより、分析されるサンプルを調製することができる。溶液が曇っている場合、透明になるまでクロロホルムを滴加してもよい。同じ手順を用いて、100〜500ng/マイクロリットルに最終希釈を行う。
先ずPGE材料を乳化して、PGE 25%、セチルトリメチルアンモニウムクロリド(CTMAC)5%、及びTMN−6(Dow Corningから入手可能な非イオン性界面活性剤)3.2%の最終濃度を得る。次いで、PGE原材料を融点よりも少し高い温度まで加熱し、次いでTMN−6と混合して、均質に混合されるまで撹拌してもよい。次いで、CTMACを収容する(PGEの融点に)加熱した容器にこの混合物をゆっくりと添加し、すべてのPGE/TMN−6が添加され、クリーム状の白色エマルションが得られるまで1500rpmでオーバーヘッドミキサ(IKA Lobartechnik、型番RWZODZM−N)により混合する。1500rpmで撹拌しながら脱イオン水を混合物にゆっくりと添加して、所望の最終濃度を得る。混合物を氷浴中で室温まで冷却する。
12.89g(0.054mol)のトリグリセロール(Fluka≧80%)を、機械的撹拌器、温度計、凝縮器、及び陽性(positive)N2を備える、乾燥した500mLの3つ口丸底フラスコに入れる。無水THFのサンプル76mLを、カニューレによりフラスコに移す。次いで、フラスコを油浴に入れ、48℃に加熱する。加熱後、0.79g(0.006mol)の4−(ジメチルアミノ)ピリジン(Alfa Aesar 99%)及び10.88g(0.107mol)のトリエチルアミン(Aldrich)をフラスコに添加し、続いて27mLのテトラヒドロフラン(オキサシクロペンタン)を添加して、Et3N中ですすぐ。次いで、14.98g(0.054mol)のパルミトイル酸塩化物(Aldrich,98.5%)及び16.43g(0.054mol)のステアロイル酸塩化物(TCI,99%)を、125mLの添加漏斗中で、53mLのTHFと混合する。次いで、酸塩化物の溶液を、透明な48℃のトリグリセロール溶液に滴下し、滴下速度により制御可能な発熱が同時に生じる。Et3N・HClが形成されると、混合物は白色になる。次いで、14mLのTHFサンプルを用いて、すべての酸塩化物をすすぐ。反応混合物を2時間混合する。次いで、油浴を取り除き、混合物を室温にする。冷却された混合物をロータリーエバポレータ(Rotavap)により濃縮して固体にし、次いで塩化メチレンに溶解させ、Whatman #1濾紙及びCeliteを通して濾過する。次いで、濾液を1Lの分液漏斗に入れ、NaClの飽和溶液で2回、H2Oで1回洗浄する。CH2Cl2層をNa2SO4で乾燥させる。得られた溶液からNa2SO4を濾し取り、次いで残りの溶液をロータリーエバポレータで蒸発させて、CH2Cl2を除去する。ワックス状の白色固体のサンプル36.5gを、91%の収率で回収することができる。
ヘキサグリセロールC16/C18トリエステル(Grindsted PGE 215、Danisco A/S,Denmarkから入手可能)のサンプル10.50g(0.009mol)を、機械的撹拌器、温度計、凝縮器、及び陽性N2を備える、乾燥した250mLの3つ口丸底フラスコに入れる。35mLの無水THFをカニューレにより移す。次いで、以下を添加する:0.13g(0.001mol)の4−(ジメチルアミノ)ピリジン(Alfa Aesar 99%)及び4.36g(0.043mol)のトリエチルアミン(Aldrich)、少量のTHFを用いてEt3N中ですすぐ。次いで、フラスコを油浴に入れ、48℃にする。次いで、6.00g(0.022mol)のパルミトイル酸塩化物(Aldrich,98.5%)及び6.58g(0.022mol)のステアロイル酸塩化物(TCI,99%)を、125mLの添加漏斗中で、30mLのTHFと混合する。次いで、酸塩化物の溶液を、48℃のヘキサグリセロールトリエステル溶液に滴下すると、滴下速度により制御可能な発熱が同時に生じる。Et3N・HClが形成されると、混合物は白色になる。少量のTHFを用いてすべての酸塩化物をすすぐ。得られた混合物を約4.5時間混合した後、油浴を取り除き、溶液を混合し、室温に冷却する。冷却された混合物をロータリーエバポレータで濃縮させて固体にする。得られた固体をエーテルに入れ、Celiteを備えるWhatman #4濾紙で濾過する。次いで、濾液を分液漏斗に入れ、NaClの飽和溶液で2回、H2Oで1回洗浄する。エーテル層をNa2SO4で乾燥させる。Na2SO4を濾し取り、次いでロータリーエバポレータで蒸発させてエーテルを除去する。脆性の白色固体のサンプル21.09gを99%の収率で得た。
bPGE−2=平均グリセロール鎖長4.5及び平均エステル化度6のポリグリセロールエステル
cCTMAC=セチルトリメチルアンモニウムクロライド
dシリコーン−1=Wacker Silicones製SLM−21200
eシリコーン−2=Shin−Etsu Silicones製KF−873
fエチレンオキシドを用いて2,6,8−トリメチル−4−ノナノールから誘導された非イオン性界面活性剤
gNational Starch製のカタトニー的(Catatonically)化工デンプン
hBASF製のポリビニルアミン(PVAm)
iBASF製のポリエチレンイミン(Polytheylenimine)(PEI)
jNALCO製のポリアクリルアミドメタクリレートアミドプロピル/トリメチルアンモニウムクロリド(PAM/MAPTAC)
kProxel=1,2ベンズイソチオゾリン−3−オン
lDantoguard=ジメチロール−5,5−ジメチルヒダノトイン
mTMBA=トリメトキシ安息香酸
nDTPA=NALCO製のナトリウムジエチレントリアミンペンタアセテート
mDTDMAC=ジタロージメチルアンモニウムクロリド
nDEEDMAC=ジタロイルエタノールエステルジメチルアンモニウムクロリド
oTEA QUAT 1=N,N−ジ(カノリル−オキシ−エチル)−N−メチル−N−(2−ヒドロキシエチル)アンモニウムメチルサルフェート
pHCL=塩酸
qDC2310=Dow Corning製のシリコーン泡抑制剤
rCaCl2=塩化カルシウム
sKathon=5−クロロ−2−メチル−4−イソチアゾリン−3−オン及び2−メチル−4−イソチアゾリン−3−オンの混合物
sNI 45−8=約C14、C15の平均鎖長及び平均8個のエトキシレートを有するアルコールエトキシレート
tAES=アルキルエトキシレートサルフェート
uHLAS=H直鎖アルキルベンゼンスルホネート
vTPK FA=縦長(Tall)パーム核脂肪酸
w国際公開第01/62882号及び6,444,633号に記載されている(四級化トランス硫酸化ヘキサメチレンジアミン)
xDTPMP=ジエチレントリアミンペンタ(メチルホスホン)酸
Claims (15)
- 式Iの構造を有するポリグリセロールエステルと処理剤及び/又はケア剤とを含む組成物であって、
a)nが1.5〜6であるとき、前記ポリグリセロールエステルの平均エステル化率(%)が20%〜100%であり、
b)nが1.5〜5であるとき、平均エステル化率(%)が20%〜90%であり、
c)nが1.5〜4であるとき、平均エステル化率(%)が20%〜80%であり、
前記組成物中の前記ポリグリセロールエステルの50%超が少なくとも2つのエステル結合を有する、組成物。 - 式Iのポリグリセロールエステルを含む、請求項1に記載の組成物であって、
前記脂肪酸部分の炭素鎖が、10〜22炭素原子の平均鎖長を有し、
前記ポリグリセロールエステルが0〜145のヨウ素価を有し、
a)nが3〜6であるとき、平均エステル化率(%)が20%〜100%であり、
b)nが3〜6であるとき、平均エステル化率(%)が25%〜90%であり、
c)nが3〜6であるとき、平均エステル化率(%)が35%〜90%である、組成物。 - 式Iのポリグリセロールエステルを含む、請求項1に記載の組成物であって、前記脂肪酸部分の炭素鎖が、16〜18炭素原子の平均炭素鎖長を有し、
前記ポリグリセロールエステルが0〜20のヨウ素価を有し、
a)nが1.5〜3.5であるとき、平均エステル化率(%)が20%〜60%であり、
b)nが1.5〜4.5であるとき、平均エステル化率(%)が20%〜70%であり、
c)nが1.5〜6であるとき、平均エステル化率(%)が20%〜80%である、組成物。 - 式Iのポリグリセロールエステルを含む、請求項1に記載の組成物であって、前記脂肪酸が、16〜18炭素原子の平均炭素鎖長を有し、
前記ポリグリセロールエステルが45〜135のヨウ素価を有し、
a)nが1.5〜3であるとき、平均エステル化率(%)が70%〜100%であり、
b)nが1.5〜4.5であるとき、平均エステル化率(%)が50%〜100%であり、
c)nが1.5〜6であるとき、平均エステル化率(%)が25%〜60%である、組成物。 - 式Iのポリグリセロールエステルを含む、請求項1に記載の組成物であって、
a)nが3〜6であるとき、平均エステル化率(%)が15%〜100%であり、
b)nが3〜6であるとき、平均エステル化率(%)が25%〜90%であり、
c)nが3〜6であるとき、平均エステル化率(%)が35%〜90%である、組成物。 - 式Iのポリグリセロールエステルを含む、請求項1に記載の組成物であって、前記脂肪酸基が、12〜18炭素原子の平均鎖長を有し、nが1.5〜6であるとき、平均エステル化率(%)が20%〜80%である、組成物。
- ジエステル又は更に高級なエステルを50%〜100%含み、好ましくは、前記ポリグリセロールエステルが50%未満のモノエステルを含む、請求項1〜6のいずれか一項に記載の組成物。
- 前記処理剤及び/又はケア剤が、ポリマー、界面活性剤、ビルダー、キレート剤、移染防止剤、分散剤、酵素、及び酵素安定剤、触媒物質、漂白活性化剤、ポリマー分散剤、泥汚れ除去/再付着防止剤、増白剤、抑泡剤、染料、香料、香料送達系、構造伸縮性付与剤、布地柔軟剤、担体、ヒドロトロープ、加工助剤、及び/又は色素から成る群から選択される材料を含み、好ましくは、非イオン性又はアニオン性界面活性剤、付着助剤ポリマー、香料、シリコーン、第四級アンモニウム化合物、及びこれらの組み合わせから成る群から選択される材料を含み、更により好ましくは、第四級アンモニウム化合物、(a)非官能化シロキサンポリマー、(b)官能化シロキサンポリマー、及びこれらの組み合わせから成る群から選択される有機シリコーン、並びにこれらの組み合わせから成る群から選択される材料を含む、請求項1〜7のいずれか一項に記載の組成物。
- 前記組成物が、10:1〜1:5の比でポリグリセロールエステルと第四級アンモニウム化合物とを含む、請求項8に記載の組成物。
- 物品が、バー、スティック、乾燥機に添加するシート、乾燥及び湿潤拭き取り用品並びにパッド、不織布基材、スポンジ、スプレー及び/又はミストを送達することができる容器等の基材を含む製品、並びにこれらの組み合わせから成る群から選択される、請求項1〜9のいずれか一項に記載の組成物を含む物品。
- ある部位を処理及び/又は洗浄する方法であって、a)所望により前記部位を洗浄及び/又はすすぐ工程と、b)前記部位を請求項1に記載の組成物と接触させる工程と、c)所望により前記部位を洗浄及び/又はすすぐ工程と、を含む、方法。
- ポリグリセロールエステルを含有するサンプルの特性を決定する方法であって、
a.ポリグリセロールエステルを含むサンプルをイオン化助剤と組み合わせる工程であって、前記イオン化助剤が溶媒に可溶性であり、イオン化したサンプルを生成させる工程と、
b.フーリエ変換質量分析器を使用してイオン化したサンプルのデータを得る工程と、
c.未処理のデータを質量マッピングにより正規化する工程であって、前記正規化が、前記ポリグリセロールエステルの繰り返し単位である部分に基づく工程と、
d.所望により、前記マップを使用して前記ポリグリセロールエステルの特性を決定する工程と、を含む、方法。 - 前記繰り返し単位が、グリセロール単位である、請求項12に記載の方法。
- 前記イオン化助剤が、カチオン及びアニオンを含む化合物であって、前記カチオンが、分析されるポリグリセロールエステルに対して親和性を有する化合物である、請求項12に記載の方法。
- 前記イオン化助剤が、ナトリウム、カリウム、アンモニウム、リチウム、及びこれらの混合物から成る群から選択されるカチオンと、フッ化物、塩化物、臭化物、ヨウ化物、ホルマート、アセタート、プロピオナート、及びこれらの混合物から成る群から選択されるアニオンと、を含む、請求項12に記載の方法。
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JP5368561B2 (ja) | 2013-12-18 |
US7998915B2 (en) | 2011-08-16 |
WO2010019727A1 (en) | 2010-02-18 |
US20100041583A1 (en) | 2010-02-18 |
US20110260052A1 (en) | 2011-10-27 |
MX2011001697A (es) | 2011-03-04 |
ZA201100829B (en) | 2015-12-23 |
CN102124092B (zh) | 2014-06-18 |
US8466100B2 (en) | 2013-06-18 |
US20120216353A1 (en) | 2012-08-30 |
EP2310482A1 (en) | 2011-04-20 |
RU2011103101A (ru) | 2012-09-20 |
CA2731106A1 (en) | 2010-02-18 |
CN102124092A (zh) | 2011-07-13 |
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