EP1806392A1 - Stable aqueous esterquat compositions - Google Patents

Stable aqueous esterquat compositions Download PDF

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Publication number
EP1806392A1
EP1806392A1 EP06013688A EP06013688A EP1806392A1 EP 1806392 A1 EP1806392 A1 EP 1806392A1 EP 06013688 A EP06013688 A EP 06013688A EP 06013688 A EP06013688 A EP 06013688A EP 1806392 A1 EP1806392 A1 EP 1806392A1
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Prior art keywords
formula
composition
metal salt
weight
esterquat
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EP06013688A
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German (de)
French (fr)
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EP1806392B1 (en
Inventor
Alexander Dr. Lerch
Hans Juergen Dr. Scholz
Manlio Gallotti
George Italo Pitombeira Nunes
Gustavo Kume
Claudia Barge
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Clariant Brazil SA
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Clariant Brazil SA
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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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts

Definitions

  • Quaternized fatty acid triethanolamine (TEA) esters and quaternized fatty acid methyldiethanolamine (MDEA) esters which are commonly called “esterquats", are widely known in detergent industry. They provide a softening effect to textile materials, especially for cotton. These compounds are made by esterification of triethanolamine (TEA) or methyldiethanolamine (MDEA) with a fatty acid and subsequent quaternisation by reacting with a short chain alkyl sulfate or alkyl chloride.
  • esterification of TEA esterquats one, two or three hydroxyl groups may react with the fatty acid and accordingly commercially available esterquat compositions contain quaternized mono-, di- and tri-esterquats. For the case of MDEA esterquats, only mono and di-esterquats are present.
  • a problem of aqueous compositions containing these Esterquats is that the Esterquats are not stable over prolonged storage since they undergo hydrolysis. In order to prevent hydrolysis it is known to add alkali metal salts ( JP 10-251 972 ).
  • the invention accordingly provides aqueous compositions containing an esterquat or mixtures thereof of the formula I wherein R is C 1 -C 4 -alkyl, preferably methyl, X has the same meaning as R or X is a group of the formula -C 2 H 4 OR 2 , R 1 and R 2 are independently hydrogen or a group -COR 3 , R 3 is C 7 -C 21 -alkyl or C 7 -C 21 -alkenyl and A is an anion, preferably chloride or methosulfate, and a metal salt, which composition is free of alkali or alkaline earth metal salt.
  • X in the formula (I) may be either an alkyl group R or a further hydroxyethyl group which may be esterified
  • the claimed compositions contain either TEA esterquats or MDEA esterquats of the following formulas II and III:
  • the group -COR 3 is preferably derived from natural occurring fatty acids such as capronic acid, caprylic acid, caprinic acid, lauric acid, myristiric acid, palmic acid, isostearic acid, stearic, oleic acid, eluidinic acid, arachinic acid, behenic acid and eruca acid.
  • Preferred acids containing the group -COR 3 are C 12 /C 18 coco fatty acids, tallow fatty acid, fully or partially hydrogenated tallow fatty acid, palm fatty acid, partially or fully hydrogenated palm fatty acid or stearic acid.
  • ester quats of formula II are present in the form of mixtures of the mono-, di- or triester of triethanolamine.
  • Preferred mixtures are those which have 10 to 38 % by weight of the monoester (R 1 and R 2 being hydrogen), 46 to 63 % by weight of the diester (R 1 being hydrogen and R 2 -COR 3 ) and 7 to 25 % by weight of the triester (R 1 and R 2 being -COR 3 ).
  • Especially preferred are also the following mixtures (all percentages are by weight):
  • esterquats of formula III are present in the form of mixtures of mono and di-ester of methyldiethanolamine.
  • Preferred mixtures are those which have from 1 to 70% by weight of monoester (R 1 being hydrogen), and from 30 to 99% by weight of the diester (R 1 being -COR 3 ).
  • Particular preferred are also the following mixtures (all percentages by weight): Monoester 2-60%; diester 35-98%, Monoester 2-40%; diester 60-98%.
  • the ester quat compositions accordingly to the present invention contain in general 0.5 to 30, preferable 2 to 24 and especially 4 to 22 % by weight of the ester quats of the formula II.
  • a salt is added which is not an alkali or alkaline earth metal salt.
  • the claimed compositions are free of such salts.
  • Preferred salts are transition metal salts, more preferably are zinc and aluminium salts such as ZnSO 4 , ZnCl 2 AlCl 3 or Al 2 (SO 4 ) 3 . These salts are present in an amount preferably from 0.002 to 10.0, preferably 0.03 to 5.0, and preferably 0.04 to 3.0 % by weight.
  • compositions according to the invention are also free of rare earth metal salts, metal salts of fatty acids, phthalocyanine metal complexes, phthalocyanine metal salts or chelating agents.
  • compositions according to the present invention can be made by mixing the aqueous solution of the ester quats of formulas II and III final softener formulations with the salt.
  • the salt can be added at any moment during the softeners process preparation and either in solid form or an aqueous solution. Heating and stirring is recommended for making the claimed compositions.
  • a concentrated pre-mix containing the same molar and/or mass ratio between the ester quats and the additives can be prepared in order to be diluted up to 45 times.
  • Other ingredients such as solvent, water or any ingredient that could be part of the final formulation may be added.
  • compositions according to the invention comprise, in addition to the mentioned compounds additives and auxiliaries which are customary and specific in each case such as for example others electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
  • additives and auxiliaries which are customary and specific in each case such as for example others electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
  • the composition may be composed only of water, one or more esterquat of formula (I) and a metal salt, which composition is free of an alkali or alkali earth metal salt.
  • the metal salt preferably is ZnSO 4 , ZnCl 2 , AlCl 3 or Al 2 (SO 4 ) 3 .
  • compositions according to the invention are notable for a good storage stability and can be used as such as fabric softener or can be further diluted with water either at around room temperature or under heating .
  • ester quat used in all examples was a mixture of the following compounds:
  • ester quat ZnCl 2 crossing point (days) 1 5 % active matter - 53 2 5 % active matter 0.13 63 3 5% active matter 0.61 79 ester quat AlCl 3 crossing point (days) 4 5 % active matter 0.08 65 5 5 % active matter 0.40 69
  • compositions based on MDEA esterquats (formula III):
  • the stability profile of the formulations was monitored through storage at 45°C.
  • the hydrolysis stability profile was analysed according to the amount of mono, di and triester analysed time to time.
  • MDEA esterquats it was analysed only the amount of mono and diesterquats.
  • As hydrolysis happens the amount of monoester increases while the amount of diester decreases for both, TEA and MDEA estequarts.
  • TEA esterquats there is also a decrease on the triester amount.
  • the amount of monoester is higher than the amount of diester for TEA and MDEA esterquats and for TEA esterquats the triester is presented in low levels.
  • the crossing point of the di and monoester curves was defined as the reference for comparison between the formulations. The later the crossing point, the lower the hydrolysis rate and, consequently, the more stable the formulation.

Abstract

Aqueous compositions are claimed which contain an esterquat or mixtures thereof of the formula I
Figure imga0001
 wherein R is C1-C4-alkyl, preferably methyl, X has the same meaning as R or X is a group of the formula -C2H4OR2, R1 and R2 are independently hydrogen or a group -COR3, R3 is C7-C21-alkyl or C7-C21-alkenyl and A is an anion, preferably chloride or methosulfate, and a metal salt, which composition is free of alkali or alkaline earth metal salt.
The addition of the metal salt, preferably zinc chloride, prevents hydrolysis of the esterquat.

Description

  • Quaternized fatty acid triethanolamine (TEA) esters and quaternized fatty acid methyldiethanolamine (MDEA) esters, which are commonly called "esterquats", are widely known in detergent industry. They provide a softening effect to textile materials, especially for cotton. These compounds are made by esterification of triethanolamine (TEA) or methyldiethanolamine (MDEA) with a fatty acid and subsequent quaternisation by reacting with a short chain alkyl sulfate or alkyl chloride. In the step of esterification of TEA esterquats, one, two or three hydroxyl groups may react with the fatty acid and accordingly commercially available esterquat compositions contain quaternized mono-, di- and tri-esterquats. For the case of MDEA esterquats, only mono and di-esterquats are present.
  • A problem of aqueous compositions containing these Esterquats is that the Esterquats are not stable over prolonged storage since they undergo hydrolysis. In order to prevent hydrolysis it is known to add alkali metal salts ( JP 10-251 972 ).
  • It has now been found that also other metal salts are capable of preventing hydrolysis of esterquats.
  • The invention accordingly provides aqueous compositions containing an esterquat or mixtures thereof of the formula I
    Figure imgb0001
     wherein R is C1-C4-alkyl, preferably methyl, X has the same meaning as R or X is a group of the formula -C2H4OR2, R1 and R2 are independently hydrogen or a group -COR3, R3 is C7-C21-alkyl or C7-C21-alkenyl and A is an anion, preferably chloride or methosulfate, and a metal salt, which composition is free of alkali or alkaline earth metal salt.
  • Since X in the formula (I) may be either an alkyl group R or a further hydroxyethyl group which may be esterified the claimed compositions contain either TEA esterquats or MDEA esterquats of the following formulas II and III:
    Figure imgb0002
  • The group -COR3 is preferably derived from natural occurring fatty acids such as capronic acid, caprylic acid, caprinic acid, lauric acid, myristiric acid, palmic acid, isostearic acid, stearic, oleic acid, eluidinic acid, arachinic acid, behenic acid and eruca acid. Preferred acids containing the group -COR3 are C12/C18 coco fatty acids, tallow fatty acid, fully or partially hydrogenated tallow fatty acid, palm fatty acid, partially or fully hydrogenated palm fatty acid or stearic acid.
  • As mentioned above the ester quats of formula II are present in the form of mixtures of the mono-, di- or triester of triethanolamine. Preferred mixtures are those which have 10 to 38 % by weight of the monoester (R1 and R2 being hydrogen), 46 to 63 % by weight of the diester (R1 being hydrogen and R2 -COR3) and 7 to 25 % by weight of the triester (R1 and R2 being -COR3). Especially preferred are also the following mixtures (all percentages are by weight):
    • Monoester: 18 - 22 %; diester 58 - 62 %; triester 18 - 22 %.
    • Monoester: 20 - 27 %; diester 53 - 60 %; triester 16 - 23 %.
    • Monoester: 29 - 37 %; diester 46 - 57; triester 7 - 14 %.
  • In the same way, the esterquats of formula III are present in the form of mixtures of mono and di-ester of methyldiethanolamine. Preferred mixtures are those which have from 1 to 70% by weight of monoester (R1 being hydrogen), and from 30 to 99% by weight of the diester (R1 being -COR3). Especially preferred are also the following mixtures (all percentages by weight): Monoester 2-60%; diester 35-98%, Monoester 2-40%; diester 60-98%.
  • The ester quat compositions accordingly to the present invention contain in general 0.5 to 30, preferable 2 to 24 and especially 4 to 22 % by weight of the ester quats of the formula II. In order to enhance the stability of these aqueous compositions a salt is added which is not an alkali or alkaline earth metal salt. The claimed compositions are free of such salts. Preferred salts are transition metal salts, more preferably are zinc and aluminium salts such as ZnSO4, ZnCl2 AlCl3 or Al2(SO4)3. These salts are present in an amount preferably from 0.002 to 10.0, preferably 0.03 to 5.0, and preferably 0.04 to 3.0 % by weight.
  • In a preferred aspect the compositions according to the invention are also free of rare earth metal salts, metal salts of fatty acids, phthalocyanine metal complexes, phthalocyanine metal salts or chelating agents.
  • The compositions according to the present invention can be made by mixing the aqueous solution of the ester quats of formulas II and III final softener formulations with the salt. The salt can be added at any moment during the softeners process preparation and either in solid form or an aqueous solution. Heating and stirring is recommended for making the claimed compositions.
    In order to make easier the preparation of the disclosed invention, a concentrated pre-mix containing the same molar and/or mass ratio between the ester quats and the additives can be prepared in order to be diluted up to 45 times. Other ingredients such as solvent, water or any ingredient that could be part of the final formulation may be added.
  • Depending on the intended use, the compositions according to the invention comprise, in addition to the mentioned compounds additives and auxiliaries which are customary and specific in each case such as for example others electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
  • In a second aspect of the invention the composition may be composed only of water, one or more esterquat of formula (I) and a metal salt, which composition is free of an alkali or alkali earth metal salt. The metal salt preferably is ZnSO4, ZnCl2, AlCl3 or Al2(SO4)3.
  • The compositions according to the invention are notable for a good storage stability and can be used as such as fabric softener or can be further diluted with water either at around room temperature or under heating .
    • Examples
  • All the following compositions based on formula (II) have been prepared in the following way:
    • I
    Water was heated to 85°C
    II
    addition of a varying amount of a 50 % solution of the salt as indicated and stirring for approximately 5 minutes with approximately 150 rpm
    III
    addition of the ester quat (5 % active content referred to the final composition)
    IV
    cooling under stirring within 30 minutes.
  • The ester quat used in all examples was a mixture of the following compounds:
    • 16 - 24 % of a compound of the formula
      Figure imgb0003
    • 58 - 64 % of a compound of the formula
      Figure imgb0004
    • 16- 24 % of a compound of the formula
      Figure imgb0005
    Examples
  • For compositions based on TEA esterquats (formula II):
    ester quat ZnCl2 crossing point (days)
    1 5 % active matter - 53
    2 5 % active matter 0.13 63
    3 5% active matter 0.61 79
    ester quat AlCl3 crossing point (days)
    4 5 % active matter 0.08 65
    5 5 % active matter 0.40 69
  • For compositions based on MDEA esterquats (formula III):
    • I.
    Water was heated to 45°C
    II.
    Addition of the esterquat at 50°C
    III.
    Cooling under stirring with approximately 150 rpm for 20 minutes
    IV.
    Fast cooling under stirring for 10 minutes
    V.
    Addition of a varying amount of a 50 % solution of the salt as indicated and stirring for approximately 5 minutes with approximately 150 rpm
    ester quat ZnCl2 crossing point (days)
    1 2% active matter - 28
    2 2% active matter 0.32 38
  • The stability profile of the formulations was monitored through storage at 45°C. The hydrolysis stability profile was analysed according to the amount of mono, di and triester analysed time to time. In the case of MDEA esterquats, it was analysed only the amount of mono and diesterquats. As hydrolysis happens the amount of monoester increases while the amount of diester decreases for both, TEA and MDEA estequarts. However, for TEA esterquats there is also a decrease on the triester amount. After a certain time the amount of monoester is higher than the amount of diester for TEA and MDEA esterquats and for TEA esterquats the triester is presented in low levels. The crossing point of the di and monoester curves was defined as the reference for comparison between the formulations. The later the crossing point, the lower the hydrolysis rate and, consequently, the more stable the formulation.
  • The results given above show that the addition of ZnCl2 or AlCl3 shifts the crossing point further as compared with the same formulation containing no salt. This indicates the positive effect on hydrolysis stability of these salts.

Claims (11)

  1. Aqueous compositions containing an esterquat or mixtures thereof of the formula I
    Figure imgb0006
     wherein R is C1-C4-alkyl, preferably methyl, X has the same meaning as R or X is a group of the formula -C2H4OR2, R1 and R2 are independently hydrogen or a group -COR3, R3 is C7-C21-alkyl or C7-C21alkenyl and A is an anion, preferably chloride or methosulfate, and a metal salt, which composition is free of alkali or alkaline earth metal salt.
  2. Aqueous compositions as claimed in claim 1 wherein the esterquat is of the formula
    Figure imgb0007
     wherein R, R1, R2, R3 and A are as defined in claim 1.
  3. Aqueous compositions as claimed in claim 1 wherein the esterquat is of the formula
    Figure imgb0008
     wherein R, R1, R3 and A are as defined in claim 1.
  4. A composition as claimed in claim 1 wherein the ester quat is of the formula II and is composed of 10 - 38 % by weight of monoester, 46 - 63 % by weight of diester and 7 - 25 % by weight of triester.
  5. A composition as claimed in claim 1 wherein the ester quat is of the formula III and is composed from 1-70% by weight of the monoester and from 30-99% by weight of diester.
  6. A composition as claimed in claim 1 wherein the total amount of ester quat of the formula II or of the formula III is from 0.5 to 30 % by weight.
  7. A composition as claimed in claim 1 containing ZnCl2, AlCl3, ZnSO4 or Al2(SO4)3 as metal salt.
  8. A composition as claimed in claim 1 containing 0.002 to 10 % by weight of the metal salt.
  9. A composition as claimed in claim 1 containing one or more additives or auxiliaries.
  10. A composition consisting of water, one or more esterquat of the formula I as defined in claim 1 and a metal salt, which composition is free of alkali or alkali earth metal salt.
  11. A composition as claimed in claim 1 which is a concentrated pre-mix of the esterquat and metal salt.
EP20060013688 2005-09-06 2006-07-01 Stable aqueous esterquat compositions Expired - Fee Related EP1806392B1 (en)

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EP05019277 2005-09-06
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Cited By (12)

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WO2012063055A1 (en) 2010-11-09 2012-05-18 Champion Technologies Ltd Method and composition for preventing corrosion of metal surfaces
WO2013113735A1 (en) * 2012-01-30 2013-08-08 Evonik Industries Ag Fabric softener active composition
US8883712B2 (en) 2010-04-28 2014-11-11 Evonik Degussa Gmbh Fabric softening composition
US9441187B2 (en) 2012-05-07 2016-09-13 Evonik Degussa Gmbh Fabric softener active composition and method for making it
EP3208314A1 (en) 2016-02-16 2017-08-23 Omya International AG Process for manufacturing white pigment containing products
EP3208315A1 (en) 2016-02-16 2017-08-23 Omya International AG Process for manufacturing white pigment containing products
US10011806B2 (en) 2013-11-05 2018-07-03 Evonik Degussa Gmbh Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester
US10113137B2 (en) 2014-10-08 2018-10-30 Evonik Degussa Gmbh Fabric softener active composition
CN109208328A (en) * 2017-07-07 2019-01-15 广州蓝月亮实业有限公司 Aqueous fabric soft compound
EP3444036A1 (en) 2017-08-16 2019-02-20 Omya International AG Indirect flotation process for manufacturing white pigment containing products
WO2020011876A1 (en) 2018-07-11 2020-01-16 Clariant International Ltd Preparation and use of high quality esterquats from rice bran fatty acids
WO2022148673A1 (en) 2021-01-11 2022-07-14 Clariant International Ltd Hydrogenated esterquats from rice bran fatty acids and their preparation

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EP0899325A2 (en) * 1997-08-15 1999-03-03 Ciba SC Holding AG Fabric softener composition
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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8883712B2 (en) 2010-04-28 2014-11-11 Evonik Degussa Gmbh Fabric softening composition
WO2012063055A1 (en) 2010-11-09 2012-05-18 Champion Technologies Ltd Method and composition for preventing corrosion of metal surfaces
CN104160008A (en) * 2012-01-30 2014-11-19 赢创工业集团股份有限公司 Fabric softener active composition
KR20140119709A (en) * 2012-01-30 2014-10-10 에보닉 인두스트리에스 아게 Fabric softener active composition
WO2013113453A1 (en) * 2012-01-30 2013-08-08 Evonik Industries Ag Fabric softener active composition
US8883713B2 (en) 2012-01-30 2014-11-11 Evonik Industries Ag Fabric softener active composition
AU2013214283B2 (en) * 2012-01-30 2015-08-20 Evonik Degussa Gmbh Fabric softener active composition
RU2612130C2 (en) * 2012-01-30 2017-03-02 Эвоник Дегусса Гмбх Fabric softener active composition
CN104160008B (en) * 2012-01-30 2017-05-03 赢创德固赛有限公司 Fabric softener active composition
KR102004012B1 (en) 2012-01-30 2019-07-25 에보니크 데구사 게엠베하 Fabric softener active composition
WO2013113735A1 (en) * 2012-01-30 2013-08-08 Evonik Industries Ag Fabric softener active composition
US9441187B2 (en) 2012-05-07 2016-09-13 Evonik Degussa Gmbh Fabric softener active composition and method for making it
US10011806B2 (en) 2013-11-05 2018-07-03 Evonik Degussa Gmbh Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester
US10113137B2 (en) 2014-10-08 2018-10-30 Evonik Degussa Gmbh Fabric softener active composition
EP3208315A1 (en) 2016-02-16 2017-08-23 Omya International AG Process for manufacturing white pigment containing products
WO2017140633A1 (en) 2016-02-16 2017-08-24 Omya International Ag Process for manufacturing white pigment containing products
WO2017140630A1 (en) 2016-02-16 2017-08-24 Omya International Ag Process for manufacturing white pigment containing products
EP3208314A1 (en) 2016-02-16 2017-08-23 Omya International AG Process for manufacturing white pigment containing products
US11168218B2 (en) 2016-02-16 2021-11-09 Omya International Ag Process for manufacturing white pigment containing products
CN109208328A (en) * 2017-07-07 2019-01-15 广州蓝月亮实业有限公司 Aqueous fabric soft compound
EP3444036A1 (en) 2017-08-16 2019-02-20 Omya International AG Indirect flotation process for manufacturing white pigment containing products
WO2019034491A1 (en) 2017-08-16 2019-02-21 Omya International Ag Indirect flotation process for manufacturing white pigment containing products
US11014096B2 (en) 2017-08-16 2021-05-25 Omya International Ag Indirect flotation process for manufacturing white pigment containing products
WO2020011876A1 (en) 2018-07-11 2020-01-16 Clariant International Ltd Preparation and use of high quality esterquats from rice bran fatty acids
US11773347B2 (en) 2018-07-11 2023-10-03 Clariant International Ltd Preparation and use of high quality esterquats from rice bran fatty acids
WO2022148673A1 (en) 2021-01-11 2022-07-14 Clariant International Ltd Hydrogenated esterquats from rice bran fatty acids and their preparation

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Publication number Publication date
ES2317370T3 (en) 2009-04-16
EP1806392B1 (en) 2008-12-24
DE602006004426D1 (en) 2009-02-05

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