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(11) | EP 1 154 068 B1 |
| (12) | EUROPEAN PATENT SPECIFICATION |
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| (54) |
SOFTENER COMPOSITION WEICHMACHERZUSAMMENSETZUNG COMPOSITION D'ADOUCISSANT |
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| Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). |
Technical Field
Background Art
Disclosure of Invention
(a) 3 to 50 % by weight of a quaternary ammonium compound represented by the formula
(1) :
wherein R1 and R2 independently represent a C12-22 alkyl or alkenyl group, X and Y are independently -COO-, -CONR7-, -OCO- or - NR7CO-, preferably provided that at least one of X and Y is -COO- or -OCO-. R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group. R3 and R4 independently represent a C1-5 alkylene group, R5 and R6 represent a C1-3 alkyl or hydroxyalkyl group or R1-X-R3-, and Z- is an anionic group,
(b) a quaternary ammonium compound represented by formula (2) :
wherein R8 represents a C12-22 alkyl or alkenyl group, W is a group selected from -COO-, -CONR7-, -OCO- and -NR7CO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom, R9 represents a C1-5 alkylene group, R10 and R11 represent a C1-3 alkyl or hydroxyalkyl group, R12 represents a C1-3 alkyl group or -R26-OH, R26 is a C1-5 alkylene group and Z- is an anionic group, and a compound selected from the following component (c) or
(d):
(c) 0.1 to 15 % by weight of a compound represented by formula (3) and/or formula
(4):
wherein R13 and R18 independently represent a C5-19 alkyl or alkenyl group, R14 and R15 independently represent a C1-3 alkyl or hydroxyalkyl group, and T is -COO-, -OCO-, -CONH-, -NHCO-,
or a linkage; R16 represents a C1-3 alkylene group, R17 represents a C1-6 alkylene group or -(O-R19)n, R19 is ethylene group or propylene group and n is a number of 1 to 10 and W- is an anionic group, and
(d) 0.01 to 15 % by weight, preferably 0.1 to 15 % by weight of a compound represented
by formula (5):
wherein 2 or 3 groups of R20, R21, R22 and R23 represent a C8-12 alkyl group while the remainder(s) represents a C1-3 alky group, C1-3 hydroxyalkyl group or C7-15 arylalkyl group, and Z- is an anionic group, wherein the weight ratio of (c)/(a) is in the range of 1/30
to 1/1.
Best Mode for Carrying Out the Invention
(Softener composition)
Examples
<Compounding ingredients>
(a-1)
R: a mixed C18 and C16 saturated alkyl group (ratio by weight of C18 group/C16 group = 60/40)
(a-2)
R: a mixed C18 and C16 saturated alkyl group (ratio by weight of C18 group/C16 group = 60/40)
(a-3)
R: a mixed C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
(a-4)
R: a mixted C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
(a-5) Di(oleoyl xyethyl) dimethyl ammonium methyl sulfate.
(a-6)
R: a mixed C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
(a'-1) Dioleyl dimethyl ammonium chloride.
(b-1)
R: a mixed C18 and C16 saturated alkyl group (ratio by weight of C18 group/C16 group = 60/40)
(b-2)
R: a mixed C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
(c-1)
(c-2)
(c-3)
(d-1) Didecyl dimethyl ammonium chloride.
(e-1) An addition product of a saturated alcohol containing 12 carbon atoms to which 21 moles on the average of ethylene oxide have been added.
(e-2) An addition product of lauric acid diethanolamide to which 20 moles on the average of ethylene oxide have been added.
(f-1) Lunack™ S-50 (stearic acid produced by Kao Corporation).
(f-2) Lauric acid.
(f-3) Myristic acid.
(f-4) Palmitic acid.
(g-1) Excel™ 150 [a mixture of stearic mono-, di- and triglycerides (mono : di : tri = 60 : 35 : 5) produced by Kao Corporation].
(g-2) Calcium chloride.
(g-3) Ethylene glycol.
(h-1) Coloring matter (Acid blue 9).
(h-2) Perfume [a mixture of hexyl cinnamic aldehyde (18), nerolin yarayara (4), tricyclodecenyl acetate (4), benzyl acetate (10), musk ketone (5), anisyl acetone (2), sandal mysolcore (2), aldehyde C14 peach (1), linalool (18), dihydroxy myrcenol (8), borneol (4), cedrol (4), mugoal (5), benzyl alcohol (5) and dipropylene glycol (10), the figures shown in the parentheses meaning a percent by weight in the perfume mixture.].
(h-3) Silicone (TSA730 produced by Toshiba Silicone Co., Ltd.).
Example 1
(Evaluation of smell)
Example 2
| Perfume Ingredient (wt%) | Perfume 1 | Perfume 2 | Perfume 3 | Perfume 4 | Perfume 5 |
| hexyl cinnamic aldehyde | 0 | 0 | 13 | 0 | 0 |
| Nerolin yarayara | 0 | 0 | 3 | 0 | 0 |
| tricyclodecenyl acetate | 0 | 0 | 3 | 0 | 0 |
| benzyl acetate | 0 | 0 | 7 | 0 | 0 |
| musk ketone | 0 | 0 | 3 | 0 | 0 |
| anisyl acetone | 0 | 0 | 1 | 0 | 0 |
| Sandalmysore core | 0 | 0 | 1 | 0 | 0 |
| Aldehyde C14 peach | 0 | 0 | 1 | 0 | 0 |
| Metyl ionone- γ | 7 | 0 | 0 | 3 | 0 |
| Iso E Super | 7 | 0 | 0 | 3 | 0 |
| Tentarome | 14 | 0 | 0 | 7 | 0 |
| 4-t-butylcyclohexylacetate | 14 | 0 | 0 | 7 | 0 |
| Lilial | 20 | 0 | 0 | 10 | 0 |
| Herional | 3 | 0 | 0 | 2 | 0 |
| coumarin | 3 | 0 | 0 | 1 | 0 |
| Ambroxan | 1 | 0 | 0 | 0 | 0 |
| α-Terpinyl acetate | 0 | 12 | 0 | 0 | 20 |
| cedryl acetate | 0 | 8 | 0 | 0 | 13 |
| Lyral | 0 | 8 | 0 | 0 | 13 |
| Pearlide | 0 | 4 | 0 | 0 | 7 |
| Sandal synth | 0 | 4 | 0 | 0 | 7 |
| phenylacetoaldehyde 50% PEA | 0 | 0 | 0 | 0 | 1 |
| aldehyde C12MNA | 0 | 0 | 0 | 0 | 1 |
| cinnamyl cinnamate | 0 | 2 | 0 | 0 | 3 |
| benzyl isoeugenol | 0 | 2 | 0 | 0 | 3 |
| linalool | 0 | 0 | 0 | 0 | 13 |
| dihydromyrcenol | 0 | 0 | 0 | 0 | 7 |
| borneol | 0 | 0 | 0 | 0 | 3 |
| cedrol | 0 | 0 | 0 | 0 | 3 |
| Muguol | 0 | 0 | 0 | 0 | 3 |
| benzyl alcohol | 0 | 0 | 0 | 0 | 3 |
| phenylethyl alcohol | 12 | 0 | 29 | 0 | 0 |
| citronellol | 6 | 0 | 13 | 0 | 0 |
| terpineol | 6 | 0 | 13 | 0 | 0 |
| phenylethyldimethyl carbinol | 3 | 0 | 7 | 0 | 0 |
| styrallyl alcohol | 2 | 0 | 3 | 0 | 0 |
| cinnamic alcohol | 2 | 0 | 3 | 0 | 0 |
| 1-menthol | 0 | 24 | 0 | 27 | 0 |
| geraniol | 0 | 12 | 0 | 13 | 0 |
| dihydromyrcenol | 0 | 12 | 0 | 13 | 0 |
| Phenyl hexanol | 0 | 6 | 0 | 7 | 0 |
| dimethylbenzyl carbinol | 0 | 6 | 0 | 7 | 0 |
| Total (wt%) | 100 | 100 | 100 | 100 | 100 |
Example 3
(Evaluation of deodorizing effect)
(Evaluation of softness)
(a) 3 to 50 % by weight of a quaternary ammonium compound represented by the formula
(1) :
wherein R1 and R2 independently represent a C12-22 alkyl or alkenyl group, X and Y are independently -COO-, -CONR7-, -OCO- or-NR7CO-, provided that at least one of X and Y is -COO- or - OCO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, R3 and R4 independently represent a C1-5 alkylene group, R5 and R6 represent a C1-3 alkyl or hydroxyalkyl group or R1-X-R3- and Z- is an anionic group,
(b) a quaternary ammonium compound represented by the formula (2):
wherein R8 represents a C12-22 alkyl or alkenyl group, W is a group selected from -COO-, -CONR7-, -OCO- and -NR7CO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom, R9 represents a C1-5 alkylene group, R10 and R11 represent a C1-3 alkyl or hydroxyalkyl group, R12 represents a C1-3 alkyl group or -R26-OH, R26 is a C1-5 alkylene group and Z- is an anionic group, and a compound selected from the following component (c) or
(d):
(c) 0.1 to 15 % by weight of a compound represented by formula (3) and/or formula
(4):
wherein R13 and R18 independently represent a C5-19 alkyl or alkenyl group, R14 and R15 independently represent a C1-3 alkyl or hydroxyalkyl group, and T is -COO-, -OCO-, -CONH-, -NHCO-,
or a linkage, R16 represents a C1-3 alkylene group, R17 represents a C1-6 alkylene group or -(O-R19)n-, R19 is ethylene group or propylene group and n is a number of 1 to 10 and W- is an anionic group, and
(d) 0.01 to 15 % by weight of a compound represented by formula (5) :
wherein 2 or 3 groups out of R20, R21, R22 and R23 represent a C8-12 alkyl group, the remainder of them represent a C1-3 alkyl group, a C1-3 hydroxyalkyl group or a C7-15 arylalkyl group and Z- is an anionic group, wherein the weight ratio of (c)/(a) is in the range of 1/30
to 1/1.
(a) 3 bis 50 Gew.% einer quaternären Ammoniumverbindung, die durch die Formel (1)
dargestellt wird:
wobei R1 und R2 unabhängig voneinander eine C12-22-Alkyl- oder -Alkenylgruppe darstellen, X und Y unabhängig voneinander -COO-, -CONR7-, -OCO- oder -NR7CO- darstellen, unter der Massgabe, dass mindestens ein Vertreter von X und Y -COO-
oder -OCOist, R7 ein Wasserstoffatom oder eine C1-3-Alkyl- oder -Hydroxyalkylgruppe darstellt, R3 und R4 unabhängig voneinander eine C1-5-Alkylengruppe darstellen, R5 und R6 eine C1-3-Alkyl- oder -Hydroxyalkylgruppe oder R1-X-R3- darstellen und Zeine anionische Gruppe ist,
(b) eine quaternäre Ammoniumverbindung, dargestellt durch die Formel (2):
wobei R8 eine C12-22-Alkyl- oder -Alkenylgruppe darstellt, W eine Gruppe, ausgewählt aus -COO-, -CONR7-, -OCO- und -NR7CO-, ist, R7 ein Wasserstoffatom oder eine C1-3-Alkyl- oder -Hydroxyalkylgruppe, vorzugsweise ein Wasserstoffatom, darstellt, R9 eine C1-5-Alkylengruppe darstellt, R10 und R11 eine C1-3-Alkyl- oder -Hydroxygruppe darstellen, R12 eine C1-3-Alkylgruppe oder -R26-OH darstellt, R26 eine C1-5-Alkylengruppe ist und Z- eine anionische Gruppe ist, und
eine Verbindung, ausgewählt aus den folgenden Komponenten (c) oder (d):
(c) 0,1 bis 15 Gew.% einer Verbindung, die durch die Formeln (3) und/oder (4) dargestellt
wird:
wobei R13 und R18 unabhängig voneinander eine C5-19-Alkyl- oder -Alkenylgruppe darstellen, R14 und R15 unabhängig voneinander eine C1-3-Alkyl- oder -Hydroxyalkylgruppe darstellen, und T -COO-, -OCO-, -CONH-, -NHCO-,
oder eine Bindung ist, R16 eine C1-3-Alkylengruppe darstellt, R17 eine C1-6-Alkylengruppe oder -(O-R19)n- darstellt, R19 eine Ethylengruppe oder Propylengruppe ist, n eine Zahl von 1 bis 10 ist und W- eine anionische Gruppe ist, und
(d) 0,01 bis 15 Gew.% einer Verbindung, dargestellt durch die Formel (5):
wobei 2 oder 3 Gruppen von R20, R21, R22 und R23 eine C8-12-Alkylgruppe darstellen und der Rest eine C1-3-Alkylgruppe, eine C1-3-Hydroxyalkylgruppe oder eine C7-15-Arylalkylgruppe darstellt, und W- eine anionische Gruppe ist, wobei das Gewichtsverhältnis
von (c)/(a) im Bereich von 1:30 bis 1:1 liegt.
(a) 3 à 50 % en poids d'un composé d'ammonium quaternaire représenté par la formule
(1) :
dans laquelle R1 et R2 représentent indépendamment un groupe alkyle ou alcényle en C12-22, X et Y sont indépendamment -COO-, -CONR7-, -OCO- ou - NR7CO-, à condition que au moins l'un de X et Y soit -COO- ou -OCO-, R7 représente un atome d'hydrogène ou un groupe alkyle ou hydroxyalkyle en C1-3, R3 et R4 représentent indépendamment un groupe alkylène en C1-5, R5 et R6 représentent un groupe alkyle ou hydroxyalkyle en C1-3 ou R1-X-R3- et Z- est un groupe anionique,
(b) un composé d'ammonium quaternaire représenté par la formule (2) :
dans laquelle R8 représente un groupe alkyle ou alcényle en C12-22, , W est un groupe choisi parmi -COO-, -CONR7-, -OCO- et -NR7CO-, R7 représente un atome d'hydrogène ou un groupe alkyle ou hydroxyalkyle en C1-3, de préférence un atome d'hydrogène, R9 représente un groupe alkylène en C1-5, R10 et R11 représentent un groupe alkyle ou hydroxyalkyle en C1-3, R12 représente un groupe alkyle en C1-3 ou -R26-OH, R26 est un groupe alkylène en C1-5 et Z- est un groupe anionique, et un composé choisi parmi le composant (c) ou (d) suivant
:
(c) 0,1 à 15 % en poids d'un composé représenté par la formule (3) et/ou la formule
(4) :
dans lesquelles R13 et R18 représentent indépendamment un groupe alkyle ou alcényle en C5-19, R14 et R15 représentent indépendamment un groupe alkyle ou hydroxyalkyle en C1-3, et T est -COO-, -OCO-, -CONH-, -NHCO-,
ou une liaison, R16 représente un groupe alkylène en C1-3, R17 représente un groupe alkylène en C1-6 ou (O-R19)n-, R19 est un groupe éthylène ou un groupe propylène et n est un nombre de 1 à 10 et W- est un groupe anionique, et
(d) 0,01 à 15 % en poids d'un composé représenté par la formule (5) :
dans laquelle 2 ou 3 groupes parmi R20, R21, R22 et R23 représentent un groupe alkyle en C8-12, ceux qui restent de ceux-ci représentent un groupe alkyle en C1-3, un groupe hydroxyalkyle en C1-3 ou un groupe arylalkyle en C7-15 et Z- est un groupe anionique, dans laquelle le rapport en poids de (c)/(a) est dans la
gamme de 1/30 à 1/1.