EP0845523A2 - Ingredient preventing the viscosity problem encountered in a perfumed concentrated fabric softener - Google Patents

Ingredient preventing the viscosity problem encountered in a perfumed concentrated fabric softener Download PDF

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Publication number
EP0845523A2
EP0845523A2 EP97120431A EP97120431A EP0845523A2 EP 0845523 A2 EP0845523 A2 EP 0845523A2 EP 97120431 A EP97120431 A EP 97120431A EP 97120431 A EP97120431 A EP 97120431A EP 0845523 A2 EP0845523 A2 EP 0845523A2
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EP
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Prior art keywords
ingredient
group
fabric softener
perfumed
coor
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EP97120431A
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German (de)
French (fr)
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EP0845523A3 (en
Inventor
Philippe Blondeau
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Givaudan SA
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Givaudan Roure International SA
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Priority to EP97120431A priority Critical patent/EP0845523A3/en
Publication of EP0845523A2 publication Critical patent/EP0845523A2/en
Publication of EP0845523A3 publication Critical patent/EP0845523A3/en
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/667Neutral esters, e.g. sorbitan esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes

Definitions

  • the present invention is concerned with an ingredient preventing viscosity problems encountered in a perfumed concentrated fabric softener in liquid form.
  • the invention is further related to a process for prevention of viscosity problems in a perfumed concentrated fabric softener, a softener produced according to the process and the use of the ingredient.
  • Fabric softeners in liquid form to be added in the rinse step of a laundry cycle are well known. It is, since long, common practice that the fabric softeners are perfumed by fragrances incorporated in the softener composition.
  • softener compositions comprise at least a dispersion of cationic surfactants in water, see, e.g. happi, March 1995, 95 - 97.
  • other usual components can be present, e.g. non ionic surfactants, anti-foaming agents, fluorescents, colourants, optical brightening agents and the like.
  • a common composition of a concentrated fabric softener which is about 3 or 4 times higher in concentration than a normal fabric softener, contains about
  • the cationic surfactant can be dihardened tallow dimethyl ammonium chloride (available from Akzo as Arquad ® 2HT), the ionic surfactant can be a tallow alcohol with 15 mole ethylene oxide (available as Genapol T ® from Hoechst) and the fragrance can be any of the fragrances usually used in this connection, e.g. any mixture of odorant materials of natural and/or synthetic origin suitable for perfuming fabric softeners, e.g. a floral fragance (Perfume A) or a lavender fragrance (Perfume B) or a mixture of fragrances.
  • a floral fragance Perfume A
  • Perfume B lavender fragrance
  • the object of the invention is to find an ingredient to be added to the fragrance used for perfuming a concentrated fabric softener or directly to the perfumed concentrated fabric softener in liquid form in order to avoid or at least to reduce the instability and to stabilize the viscosity, respectively, to such an extent that the softener can be handled without restrictions, i.e. the concentrated fabric softener in liquid form should be stable with respect to viscosity within a shelf life time of about two months at 37 o C after the production date. It was found that the two months stability at 37 o C is equivalent to about four months at room temperature (20-25 o C).
  • the active component(s) either should not be cleaved by the lipase or if the lipase is able to cleave the active component(s) the resultant reaction products should not negatively influence the smell of the perfume added to the concentrated fabric softener, i.e. the reaction products should not have a deleterious odoriferous effect after enzymatic cleavage.
  • R is a radical of a monohydric aliphatic alcohol or a group (CH 2 ) n COOR 1 or a group CH 2 -CH(OCOR 4 )-CH 2 (OCOR 5 ) and Y is R' which is a saturated or unsaturated straight or branched C 6 -C 24 alkyl group, preferably a C 7 -C 24 alkyl group, a group (CH 2 ) n COOR 1 or a group CH 2 -C(OH) (COOR 2 )-CH 2 (COOR 3 ), wherein n is 1 to 6, and R1 - R5 are each a radical of a monohydric aliphatic alcohol, the afore mentioned instability and viscosity problem, respectively, is prevented.
  • R' is saturated or unsaturated straight or branched C 12 - C 16 alkyl.
  • ester I is a diester (Ia) or a triester (Ib, Ic) of one of the general formulae: , wherein R, R2, R3 and R', R4, R5, respectively, are identical.
  • ester I is at least one of the group consisting of propylene glycol dicaprylate/dicaprate, trioctyl citrate, dioctyl adipate, triheptanoin and octyl octanoate.
  • the concentrated fabric softener comprises the ester I in an amount of about 0,05 to 5%, preferably of about 0,15 to 0,5%.
  • ester I is at least one of the group consisting of propylene glycol dicaprylate/dicaprate, triheptanoin and trioctyl citrate, because after enzymatic cleavage the reaction products of propylene glycol dicaprylate/dicaprate and triheptanoin are non-odoriferous and trioctyl citrate is not cleaved at all.
  • Propylene glycol dicaprylate/dicaprate is a mixture of the propylene glycol diesters of caprylic and capric acids.
  • the ingredient is added in an amount of up to 30%, most preferably of about 16%, of the fragrance used to perfume the concentrated fabric softener.
  • Rewoquat WE 18 supplied by Rewo company, is di-(tallow carboxyethyl)hydroxy ethyl methylammonium methosulfate.
  • test temperature of 37 o C is preferred because it reduces the testing time. In all further described experiments therefore the test temperature is 37 o C.
  • composition II a fabric softener with the same composition except that the fragrance was substituted by the same amount of water
  • composition III a fabric softener with the same composition except that the fragrance was substituted by the same amount of water
  • fragrance storage time at 37 o C production date after 1 week after 2 weeks Perfume A 15 mPa 200 mPa >500 mPa Perfume B 15 mPa 152 mPa solid
  • the solution of the problem can be solved simply by adding an ingredient comprising at least one compound of formula I to the perfume used to perfume the concentrated fabric softener or to the already perfumed concentrated fabric softener.
  • the performance is divided roughly in three categories with respect to the viscosity values after 2 months, viz. very efficient ⁇ 20 mPa, efficient 21 ⁇ 40 mPa, still reasonable efficient 41 ⁇ 150 mPa.
  • R is a radical of a monohydric aliphatic alcohol or a group (CH 2 ) n COOR 1 or a group CH 2 -CH(OCOR 4 )-CH 2 (OCOR 5 ) and Y is R' which is a saturated or unsaturated straight or branched C 6 -C 24 alkyl group, preferably a C 7 -C 24 alkyl group, a group (CH 2 ) n COOR 1 or a group CH 2 -C(OH) (COOR 2 )-CH 2 (COOR 3 ) , wherein n is 1 to 6, and R1 - R5 are each a radical of a monohydric aliphatic alcohol, overcomes the afore mentioned problem.
  • Prefered R' is a C 12 - C 16 alkyl.
  • the ingredient is also effective if it contains more than one ester, especially more than one of those mentioned in column 1 and /or 2 of Table III.
  • the lipase works during the drying cycle, i.e. after the wet fabric from the washing cycle, in which a lipase containing powder detergent is used, has been handled in the following rinse step with the fabric softener. So, in case of the use of a fabric softener containing the ingredient as described before the lipase contained in the water remaining in the fabric, even if the fabric has been centrifuged between the washing cycle and rinse step, may attack the esters in the fabric softener, especially the ester of the fragrance.
  • the ester(s) of the general formula I with the restrictions as specified above comprised in the ingredient preventing the viscosity problem encountered in a perfumed concentrated fabric softener might as well be attacked by the lipase to yield an alcohol. As said before this alcohol should not negatively influence the smell of the fabric softener.
  • the esters can be cut by the lipase by the following reaction to yield an alcohol according to the general reaction:
  • the other three tested esters are not cleaved or are enzymatically cleaved but are producing non odoriferous alcohols according to the following reactions:
  • R in the general formula I is a radical of a non-odoriferous alcohol of formula ROH.
  • a process for prevention of viscosity problems in a perfumed concentrated fabric softener is performed in that the ingredient as described before is added to said softener.
  • the addition of the ingredient may be done during the production of the softener or after the softener has already been produced.
  • Addition of the ingredient to the fragrance which is used to perfume the concentrated fabric softener is the prefered method.
  • As the afore described experiments signify it is advisable to incorporate the ingredient into the complete softener soon after the production date or, what is more recommended, immediately after the production.

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  • 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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Ingredient preventing viscosity problems encountered in a perfumed concentrated fabric softener comprising at least an ester of the general formula
Figure 80000001
   ,wherein R is a radical of a monohydric aliphatic alcohol or a group (CH2)nCOOR1 or a group CH2-CH(OCOR4)-CH2(OCOR5) and Y is R' which is a saturated or unsaturated straight or branched C6-C24 alkyl group, a group (CH2)n COOR1 or a group CH2-C(OH) (COOR2)-CH2(COOR3), wherein n is 1 to 6, and R1 - R5 are each a radical of a monohydric aliphatic alcohol.

Description

The present invention is concerned with an ingredient preventing viscosity problems encountered in a perfumed concentrated fabric softener in liquid form. The invention is further related to a process for prevention of viscosity problems in a perfumed concentrated fabric softener, a softener produced according to the process and the use of the ingredient.
Fabric softeners in liquid form to be added in the rinse step of a laundry cycle are well known. It is, since long, common practice that the fabric softeners are perfumed by fragrances incorporated in the softener composition. In general softener compositions comprise at least a dispersion of cationic surfactants in water, see, e.g. happi, March 1995, 95 - 97. Of course, also other usual components can be present, e.g. non ionic surfactants, anti-foaming agents, fluorescents, colourants, optical brightening agents and the like. For example in general a common composition of a concentrated fabric softener, which is about 3 or 4 times higher in concentration than a normal fabric softener, contains about
  • 14 - 20% commonly used cationic surfactant,
  • 0,75 - 1,2% fragrance,
  • optionally 0,5 - 1,5% commonly used nonionic surfactant,
  • balance to 100% water.
  • Here and in furtherance all percent values are weight percent values and the terms fragrance and perfume are interchangeably used within the following text.
    For example the cationic surfactant can be dihardened tallow dimethyl ammonium chloride (available from Akzo as Arquad ® 2HT), the ionic surfactant can be a tallow alcohol with 15 mole ethylene oxide (available as Genapol T ® from Hoechst) and the fragrance can be any of the fragrances usually used in this connection, e.g. any mixture of odorant materials of natural and/or synthetic origin suitable for perfuming fabric softeners, e.g. a floral fragance (Perfume A) or a lavender fragrance (Perfume B) or a mixture of fragrances.
    It now turned out that a viscosity problem has been encountered in connection with concentrated fabric softeners, especially with those of the type of the above mentioned kind. More particularly, the problem has emerged in connection with the fragrance used to perfume the concentrated liquid fabric softener. If a fragrance is present - and it is since long common practice to add perfume materials to a fabric softener - the viscosity of the concentrated liquid fabric softener becomes higher and even gelification occurs within two months of storage time, in some cases already within some days as outlined below. A product is gelified when its viscosity is 500mPa or higher. On the other hand experiments with the same basic compositions but without a fragrance revealed no upgrading in viscosity. Thus, this situation represents a serious drawback in modern concentrated fabric softener composition distribution and handling by the end user, respectively.
    Hence, the object of the invention is to find an ingredient to be added to the fragrance used for perfuming a concentrated fabric softener or directly to the perfumed concentrated fabric softener in liquid form in order to avoid or at least to reduce the instability and to stabilize the viscosity, respectively, to such an extent that the softener can be handled without restrictions, i.e. the concentrated fabric softener in liquid form should be stable with respect to viscosity within a shelf life time of about two months at 37oC after the production date. It was found that the two months stability at 37oC is equivalent to about four months at room temperature (20-25oC).
    Further, as a positive characteristic of the ingredient in case a lipase (see below) is contacted with the active component(s) of the ingredient added to the perfume in order to overcome the viscosity problem the active component(s) either should not be cleaved by the lipase or if the lipase is able to cleave the active component(s) the resultant reaction products should not negatively influence the smell of the perfume added to the concentrated fabric softener, i.e. the reaction products should not have a deleterious odoriferous effect after enzymatic cleavage.
    It has now surprisingly been found that when adding an ingredient to the fragrance used for perfuming a concentrated fabric softener or directly to a perfumed concentrated fabric softener in liquid form comprising at least one ester of the general formula
    Figure 00030001
       ,wherein R is a radical of a monohydric aliphatic alcohol or a group (CH2)nCOOR1 or a group CH2-CH(OCOR4)-CH2(OCOR5) and Y is R' which is a saturated or unsaturated straight or branched C6-C24 alkyl group, preferably a C7-C24 alkyl group, a group (CH2)nCOOR1 or a group CH2-C(OH) (COOR2)-CH2(COOR3), wherein n is 1 to 6, and R1 - R5 are each a radical of a monohydric aliphatic alcohol, the afore mentioned instability and viscosity problem, respectively, is prevented. Preferably R' is saturated or unsaturated straight or branched C12 - C16 alkyl. Further, preferably the ester I is a diester (Ia) or a triester (Ib, Ic) of one of the general formulae:
    Figure 00030002
       , wherein R, R2, R3 and R', R4, R5, respectively, are identical.
    Most preferably the ester I is at least one of the group consisting of propylene glycol dicaprylate/dicaprate, trioctyl citrate, dioctyl adipate, triheptanoin and octyl octanoate.
    Preferably the concentrated fabric softener comprises the ester I in an amount of about 0,05 to 5%, preferably of about 0,15 to 0,5%.
    If a lipase is contacted with or is part of the composition of the concentrated fabric softener preferably the ester I is at least one of the group consisting of propylene glycol dicaprylate/dicaprate, triheptanoin and trioctyl citrate, because after enzymatic cleavage the reaction products of propylene glycol dicaprylate/dicaprate and triheptanoin are non-odoriferous and trioctyl citrate is not cleaved at all.
    Propylene glycol dicaprylate/dicaprate is a mixture of the propylene glycol diesters of caprylic and capric acids.
    The other above mentioned specific esters conform to the following formulas.
  • trioctyl citrate:
    Figure 00040001
       (tri-2-ethylhexyl citrate)
  • dioctyl adipate:
    Figure 00040002
       (ethyl-2-hexyl adipate)
  • triheptanoin:
    Figure 00040003
       (glycerol triheptanoate)
  • octyl octanoate:
    Figure 00050001
       (2-ethylhexyl-2-ethylhexanoate)
  • Preferably the ingredient is added in an amount of up to 30%, most preferably of about 16%, of the fragrance used to perfume the concentrated fabric softener.
    All afore mentioned results have been derived from tests performed at 37oC using each time a batch of 100g of a concentrated fabric softener in liquid form comprising:
    Figure 00050002
    Rewoquat WE 18, supplied by Rewo company, is di-(tallow carboxyethyl)hydroxy ethyl methylammonium methosulfate.
    The measurement of viscosity were performed using a Hacke VT 501 viscosimeter with NV spindle at a speed of 64 rounds per minute.
    As described previously the effect at 37oC is double that at room-temperature. The test temperature of 37oC is preferred because it reduces the testing time. In all further described experiments therefore the test temperature is 37oC.
    Measurements of the viscosity of the fabric softener with the above composition I but containing 0,9% of Perfume A and no ingredient (composition II) compared with a fabric softener with the same composition except that the fragrance was substituted by the same amount of water (composition III) yield the following results.
    storage time at 37oC
    production date after 1 week after 2 weeks after 2 months
    composition II 15 mPa 200 mPa >500mPa solid
    composition III 15 mPa 15 mPa 15 mPa 15 mPa
    (1 mPa = 1cps)
    This shows that the unperfumed composition III is stable, i.e. the viscosity does not increase whereas the perfumed composition under the same storage conditions is instable and becomes a gel within two weeks (>500mPa) and even a solid after two months.
    Further, tests have been made under the same conditions as above with composition II but using other fragrances. The results are presented in Table II.
    fragrance storage time at 37oC
    production date after 1 week after 2 weeks
    Perfume A 15 mPa 200 mPa >500 mPa
    Perfume B 15 mPa 152 mPa solid
    The results show that some key components of the perfumes may be responsible for the viscosity increase. Therefore, to reduce the instability of the perfumed concentrated softener some components of the perfume have to be reduced and/or rebalanced by other odoriferous ingredients.
    According to the invention the solution of the problem can be solved simply by adding an ingredient comprising at least one compound of formula I to the perfume used to perfume the concentrated fabric softener or to the already perfumed concentrated fabric softener.
    With the knowledge of all these results a further test series was performed with numerous esters. This gave the best results leading to the ingredient as claimed. The test series was performed in the same way as above with the same concentrated fabric softener by adding 0,15% of the ingredient. Results are presented in the following Table III.
    Performance
    1 very efficient 2 efficient 3 still reasonable efficient
    propylene glycol dicaprylate /dicaprate triheptanoin isopropyl myristate
    trioctyl citrate octyl octonoate isopropyl palmitate
    dioctyl adipate
    The performance is divided roughly in three categories with respect to the viscosity values after 2 months, viz.
    very efficient ≤ 20 mPa,
    efficient 21 ≤ 40 mPa,
    still reasonable efficient 41 ≤ 150 mPa.
    So it turned out, as already said before, that an ingredient comprising an ester of the general formula
    Figure 00070001
       ,wherein R is a radical of a monohydric aliphatic alcohol or a group (CH2)nCOOR1 or a group CH2-CH(OCOR4)-CH2(OCOR5) and Y is R' which is a saturated or unsaturated straight or branched C6-C24 alkyl group, preferably a C7-C24 alkyl group, a group (CH2)nCOOR1 or a group CH2-C(OH) (COOR2)-CH2(COOR3) , wherein n is 1 to 6, and R1 - R5 are each a radical of a monohydric aliphatic alcohol, overcomes the afore mentioned problem. Prefered R' is a C12 - C16 alkyl.
    The ingredient is also effective if it contains more than one ester, especially more than one of those mentioned in column 1 and /or 2 of Table III.
    In addition, the interaction between these esters and a lipase was tested because lipases may be used in a washing cycle, especially to remove greasy stains.
    The lipase works during the drying cycle, i.e. after the wet fabric from the washing cycle, in which a lipase containing powder detergent is used, has been handled in the following rinse step with the fabric softener. So, in case of the use of a fabric softener containing the ingredient as described before the lipase contained in the water remaining in the fabric, even if the fabric has been centrifuged between the washing cycle and rinse step, may attack the esters in the fabric softener, especially the ester of the fragrance. The ester(s) of the general formula I with the restrictions as specified above comprised in the ingredient preventing the viscosity problem encountered in a perfumed concentrated fabric softener might as well be attacked by the lipase to yield an alcohol. As said before this alcohol should not negatively influence the smell of the fabric softener. The esters can be cut by the lipase by the following reaction to yield an alcohol according to the general reaction:
    Figure 00080001
    Therefore, the interactions of a lipase with the ester(s) of the general formula I with the restrictions as specified have been tested with the help of the linitest method.
    A piece of fabric has been washed during 30 minutes at a temperature of 40oC with 2g of a commercial powder detergent containing a lipase and was then rinsed with a fabric softener containing an ingredient to be tested in an amount of 0,3%. The olfactive evaluation has been done as well on the damp as an the dry fabric to evaluate the smell of the released alcohol. The results are presented in Table IV.
    ester released alcohol olfactive aspect of released alcohol
    dioctyl adipate ethyl-2 hexanol odoriferous
    octyl octanoate ethyl-2 hexanol odoriferous
    trioctyl citrate none
    propylene glycol dicaprylate/dicaprate propylene glycol non odoriferous
    triheptanoin glycerol non odoriferous
    The reactions are as follows.
  • dioctyl adipate:
    Figure 00090001
  • octyl octanoate:
    Figure 00090002
  • The other three tested esters are not cleaved or are enzymatically cleaved but are producing non odoriferous alcohols according to the following reactions:
  • propylene glycol dicaprylate/dicaprate:
    Figure 00100001
  • triheptanoin:
    Figure 00100002
  • Due to the enzymatic cleavage dioctyl adipate and octyl octanoate are each producing ethyl-2 hexanol, an odoriferous alcohol having a green metallic smell.
    Propylene glycol dicaprylate/dicaprate, trioctyl citrate and triheptanoin do not affect the strength and the character of the fabric softener when a lipase is present. Added to the fragrance of a concentrated fabric softener the olfactive behavior of these esters is neutral and olfactively acceptable for an expert panel. So, preferably R in the general formula I is a radical of a non-odoriferous alcohol of formula ROH.
    A process for prevention of viscosity problems in a perfumed concentrated fabric softener is performed in that the ingredient as described before is added to said softener. The addition of the ingredient may be done during the production of the softener or after the softener has already been produced. Addition of the ingredient to the fragrance which is used to perfume the concentrated fabric softener is the prefered method. As the afore described experiments signify it is advisable to incorporate the ingredient into the complete softener soon after the production date or, what is more recommended, immediately after the production.

    Claims (10)

    1. Ingredient preventing viscosity problems encountered in a perfumed concentrated fabric softener comprising at least one ester of the general formula
      Figure 00120001
         ,wherein R is a radical of a monohydric aliphatic alcohol or a group (CH2)nCOOR1 or a group CH2-CH(OCOR4)-CH2(OCOR5) and Y is R' which is a saturated or unsaturated straight or branched C6-C24 alkyl group, preferably a C7-C24 alkyl group, a group (CH2)nCOOR1 or a group CH2-C(OH) (COOR2)-CH2 (COOR3), wherein n is 1 to 6, and R1 - R5 are each a radical of a monohydric aliphatic alcohol.
    2. Ingredient of claim 1 characterized in that the ester is a monoester, a diester or a triester.
    3. Ingredient of claim 1 or 2 characterized in that the diester has the general formula
      Figure 00120002
         , especially
      Figure 00120003
    4. Ingredient of claim 1 or 2 characterized in that the triester has the general formula
      Figure 00130001
         ,wherein R, R2, R3, and R', R4, R5, respectively, are identical.
    5. Ingredient of claim 1 characterized in that the ester is at least one of the group consisting of propylene glycol dicaprylate/dicaprate, trioctyl citrate, dioctyl adipate, triheptanoin and octyl octanoate.
    6. Ingredient of claim 5 characterized in that the ester is at least one of the group consisting of propylene glycol dicaprylate/dicaprate, trioctyl citrate, triheptanoin.
    7. Ingredient of claim 6 characterized in that the ester is propylene glycol dicaprylate/dicaprate.
    8. Process for prevention of viscosity problems in a perfumed concentrated fabric softener comprising adding the ingredient of any one of the claims 1 to 7 to said softener.
    9. Softener having a viscosity stability of at least 2 months storage time at 37°C and having incorporated the ingredient of any one of the claims 1 to 7.
    10. Use of the ingredient of any one of the claims 1 to 7 for prevention of viscosity problems in a perfumed concentrated fabric softener.
    EP97120431A 1996-11-28 1997-11-21 Ingredient preventing the viscosity problem encountered in a perfumed concentrated fabric softener Withdrawn EP0845523A3 (en)

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    EP96119072 1996-11-28
    EP96119072 1996-11-28
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    WO2001013875A1 (en) * 1999-08-26 2001-03-01 Lvmh Recherche Non-ethanol composition comprising hydrofluoroether
    WO2001046360A1 (en) * 1999-12-22 2001-06-28 Unilever Plc A method of stabilising fabric softening compositions
    WO2006007911A1 (en) * 2004-07-20 2006-01-26 Unilever Plc Laundry product
    US7691801B2 (en) 2006-05-31 2010-04-06 The Sun Products Corporation Laundry product
    US7763579B2 (en) 2004-10-29 2010-07-27 The Sun Products Corporation Method of preparing a laundry product
    EP2646533B1 (en) 2010-12-03 2015-07-29 Unilever PLC Fabric conditioners
    WO2018019593A1 (en) * 2016-07-25 2018-02-01 Henkel Ag & Co. Kgaa Propylene glycol ester as fabric care constituents
    EP3489337A1 (en) 2017-11-28 2019-05-29 The Procter & Gamble Company Fabric softener composition having improved viscosity stability

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    JPS63282372A (en) * 1987-05-08 1988-11-18 花王株式会社 Softening finish agent
    EP0637625A1 (en) * 1993-08-02 1995-02-08 The Procter & Gamble Company Super concentrate emulsions with fabric actives
    GB9403242D0 (en) * 1994-02-21 1994-04-13 Unilever Plc Fabric softening composition
    US5562847A (en) * 1995-11-03 1996-10-08 The Procter & Gamble Company Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity
    WO1997017419A1 (en) * 1995-11-07 1997-05-15 Quest International Fabric conditioning composition

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    Publication number Priority date Publication date Assignee Title
    US7425529B1 (en) 1999-08-26 2008-09-16 Lvmh Recherche Non-ethanol perfume compositions comprising hydrofluoroether
    FR2797764A1 (en) * 1999-08-26 2001-03-02 Lvmh Rech NON-ETHANOLIC COMPOSITION COMPRISING A PERFLUOROUS HYDROFLUOROETHER AND AT LEAST ONE CO-SOLVENT OTHER THAN WATER AND ETHANOL COMPRISING AN ESTER OF A POLYACID AND ITS USE IN FRAGRANCE COMPOSITIONS
    WO2001013875A1 (en) * 1999-08-26 2001-03-01 Lvmh Recherche Non-ethanol composition comprising hydrofluoroether
    WO2001046360A1 (en) * 1999-12-22 2001-06-28 Unilever Plc A method of stabilising fabric softening compositions
    US7718596B2 (en) 2004-07-20 2010-05-18 The Sun Products Corporation Unit dose laundry products containing fatty acid esters
    WO2006007911A1 (en) * 2004-07-20 2006-01-26 Unilever Plc Laundry product
    US7763579B2 (en) 2004-10-29 2010-07-27 The Sun Products Corporation Method of preparing a laundry product
    US7691801B2 (en) 2006-05-31 2010-04-06 The Sun Products Corporation Laundry product
    EP2646533B1 (en) 2010-12-03 2015-07-29 Unilever PLC Fabric conditioners
    EP2646533B2 (en) 2010-12-03 2023-07-05 Unilever IP Holdings B.V. Fabric conditioners
    WO2018019593A1 (en) * 2016-07-25 2018-02-01 Henkel Ag & Co. Kgaa Propylene glycol ester as fabric care constituents
    EP3489337A1 (en) 2017-11-28 2019-05-29 The Procter & Gamble Company Fabric softener composition having improved viscosity stability
    WO2019108342A1 (en) 2017-11-28 2019-06-06 The Procter & Gamble Company Fabric softener composition having improved viscosity stability
    US10815450B2 (en) 2017-11-28 2020-10-27 The Procter & Gamble Company Fabric softener composition having improved viscosity stability

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