CN1192083C - Stabilised quaternary ammonium compositions - Google Patents
Stabilised quaternary ammonium compositions Download PDFInfo
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- CN1192083C CN1192083C CNB998061689A CN99806168A CN1192083C CN 1192083 C CN1192083 C CN 1192083C CN B998061689 A CNB998061689 A CN B998061689A CN 99806168 A CN99806168 A CN 99806168A CN 1192083 C CN1192083 C CN 1192083C
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- Prior art keywords
- quaternary ammonium
- ammonium material
- stablizer
- weight
- described quaternary
- Prior art date
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- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 57
- 125000004185 ester group Chemical group 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims description 4
- 150000003140 primary amides Chemical class 0.000 claims description 4
- 150000003334 secondary amides Chemical class 0.000 claims description 4
- 238000005562 fading Methods 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 239000003381 stabilizer Substances 0.000 abstract description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- -1 alkoxy sulfate ion Chemical compound 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000014121 butter Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000370738 Chlorion Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 239000004667 Diesterquat Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003081 coactivator Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 229960000201 isosorbide dinitrate Drugs 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
- C11D3/323—Amides; Substituted amides urea or derivatives thereof
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2065—Polyhydric alcohols
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Abstract
Stabilised compositions comprising quaternary ammonium material containing at least one ester group characterised in that they further comprise one or more stabilising agents containing at least one ester group via the steps of adding at least one stabilising agent to the quaternary ammonium material, wherein the stabilising agent is a strong hydrogen bond donor is also provided.
Description
Technical field
The present invention relates to the quaternary ammonium Stability of Substance, specifically, the present invention relates to keep containing quaternary ammonium material the stablizing of at least one ester group in its raw material form or as the solution in the solvent that is fit to.
Background and prior art
All widespread uses in fabric softening compositions of quaternary ammonium material of solid or liquid.This composition generally contains water-insoluble quaternary ammonium fabric tenderizer, when described quaternary ammonium fabric tenderizer is dispersed in content in the water at the most under the situation of 8% (weight), described composition be considered to rare composition and when its content at the next enriched material that is considered to of 8 to 50% situation.
Follow the problem of the quaternary ammonium material that contains at least one ester group to be their storage unstable.
When the following time expand of temperature (over time) that changes when storing these materials this problem merit attention especially.
Fading of taking place in these solids and the liquid quaternary ammonium material storage process at various temperatures shows the unstable of these materials.Usually the table of degree that fades is understood the level of the decomposition that takes place in time expand.This decomposition will have very big stake when preserving under the quaternary ammonium material is being higher than their temperature of fusing point.
Past promptly is kept at far below improving its stability in the temperature below the fusing point of described compound by quaternary ammonium compound is preserved at low temperatures.Also adopt adding oxidation inhibitor to suppress its decomposition.
The soft finishing agent that contains the two long chain quaternaries with monoesters base and decyl dimethyl amine is disclosed in European patent 299 176 (Kao).
In United States Patent (USP) 4 937 008 (Kao), disclose and contained one or more quaternary ammonium salts and have the divalence of 2 to 3 carbon atoms or the concentrated fabric tenderizer of trivalent polyvalent alcohol.
We contain the solid of at least one ester group at unexpected discovery or the low temperature and the high-temperature stability of liquid quaternary ammonium compound can be improved by the stablizer that adds one or more selected groups, and described stablizer has stoped the decomposition of quaternary ammonium salt.
Definition of the present invention
Thus, provide the improved stable composition that contains the quaternary ammonium material with at least one ester group according to an aspect of the present invention, it is characterized in that they also contain one or more stablizers in addition, wherein said one or more stablizers are that strong hydrogen bonding is given body.
Provide by the step at least a stablizer adding quaternary ammonium material being stablized the method for the quaternary ammonium material that contains at least one ester group in a second aspect of the present invention, wherein said stablizer is that strong hydrogen bonding is given body.
In a third aspect of the present invention, defined composition is mixed in solid and/or the liquid rinse amendment.
The present invention also provides by adding stablizer as herein defined and has reduced the method for the level of fading of the quaternary ammonium material that contains at least one ester group of time expand.
" ester group " of terminology used here in the quaternary ammonium material comprises the ester group as the linking group on the molecule.Here the quaternary ammonium material of indication is meant that those have the quaternary ammonium material of at least one ester group on their structure.
We find to provide easily hydrogen bond to help to keep high-caliber quaternary ammonium material and avoid high-caliber degradation production to the compound of aforementioned quaternary ammonium material uncannily.
Detailed description of the present invention
Preferred described stablizer is selected from one or more following materials, comprising:
A) urea,
B) urea derivatives,
C) primary amide or secondary amide, and/or
D) polyvalent alcohol.
These compositions show improved stability under different temperature.
The quaternary ammonium compound that contains at least one ester group is meant the quaternary ammonium compound that ester connects here.
Preferred described quaternary ammonium compound contains two or more ester groups.Preferably the ester group in monoesters of the present invention and diester quat is the linking group between nitrogen-atoms and alkyl.Preferred ester group is connected on the described nitrogen-atoms by another alkyl.
The present invention is the most useful for the quaternary ammonium compound that contains at least one ester group, preferred two ester groups, wherein at least one contains the higher molecular weight group of at least one ester group and two or three lower molecular weight groups are connected on the common nitrogen-atoms to produce positively charged ion, and electrobalance negatively charged ion wherein is halogen root, acetate moiety or lower alkoxy sulfate ion, as chlorion or methoxyl group sulfate radical.Preferably the higher molecular weight substituting group on described nitrogen-atoms is for containing 12 to 28, preferred 12 to 22, senior alkyl as 12 to 20 carbon atoms, senior alkyl as cocounut oil alkyl, tallow alkyl, hydrogenated tallow alkyl or replacement, preferred described lower molecular weight substituting group is the low alkyl group of 1 to 4 carbon atom, as methyl or ethyl, the perhaps low alkyl group of Qu Daiing.One or more described lower molecular weight substituting groups can comprise aryl moiety or can be replaced as benzyl, phenyl or other substituting group that is fit to by aryl.
The preferred quaternary ammonium material that uses in the present invention is to have two C that are connected to the headgroup of quaternary ammonium by at least one ester bond, preferred two ester bonds
12-C
22Alkyl or alkenyl compound or contain mean chain length and be equal to or higher than C
20Single long-chain compound.
More preferably the present invention is used to contain and has two mean chain lengths and be equal to or higher than C
14Chain alkyl or the quaternary ammonium material of alkenyl chain in.Even more preferably each bar chain has the C of being equal to or higher than
16Mean chain length.Most preferably every of at least 50% chain alkyl or alkenyl have C
18Chain length.Preferred described chain alkyl or alkenyl are linear substantially.
We find that top indication problem often links together with the quaternary ammonium compound with ester bond, two or three electron-withdrawing groups of wherein said compound are by being connected on the quaternary nitrogen atoms at one or two carbon atom on the different substituents, and also have a methyl also to be connected on the described nitrogen-atoms.This being arranged in the following formula (A) represented.We find that these compounds with chlorine gegenion are in the present invention for stable particularly advantageous.
Do not want to be limited by theory, the applicant believe fade/problem of unstable containing that ester connects base, has the methyl that is connected on the nitrogen-atoms, is being the most general in the quaternary ammonium compound that chlorine gegenion and two or three are connected respectively to the electron-withdrawing group on the quaternary nitrogen atoms.
Fade and problem such as instability though the quaternary ammonium compound of following general formula (B) may have, we find these problems in the compound of following type (A), especially ubiquity in the compound of just having mentioned on those.
The quaternary ammonium material of the particularly preferred ester connection of using in the present invention thus, can be expressed from the next:
(A)
Each R wherein
1Group independently is selected from C
1-4Alkyl, hydroxyalkyl or C
2-4Alkenyl; Each R wherein
2Group independently is selected from C
8-28Alkyl or alkenyl; X
-Be any suitable gegenion, i.e. halogen ion, acetate moiety or lower alkoxy sulfate ion are as chlorion or methoxyl group sulfate radical.
T is-O-CO-or-CO-O-; Be the integer of 1-5 or be 0 with n.
Preferred especially each R
1Group is that methyl and each n are 2, and we find that such compound is subject to the influence of aforementioned stable problem especially.
Especially preferably derive from chlorination two (the butter oxygen ethyl) Dimethyl Ammonium of Hoechst, derive from chlorination two (the hardened tallow oxygen ethyl) Dimethyl Ammonium of Hoechst in addition.
The ester of spendable another preferred type connection quaternary ammonium material can be expressed from the next according to the present invention:
(B)
R wherein
1, n, R
2And x
-As above-mentioned definition.
Yet we find that these materials do not demonstrate the unstable as the compound in the formula of front, especially under as 60-70 ℃ of high temperature.
If described quaternary ammonium material is biodegradable, be quite favourable from environmental.
The material of preferred this type such as 1,2 pair of [hardened tallow oxygen base]-3-trimethyl ammonium propane of chlorination and their preparation method have description in as United States Patent (USP) 4 137 180 (Lever Brothers).Preferred these materials contain a spot of corresponding as monoesters described in United States Patent (USP) 4 137 180, as chlorination 1-hardened tallow oxygen base-2-hydroxyl-3-trimethyl ammonium propane.
Therefore, particularly preferred quaternary ammonium material contains at least one and is connected to methyl on the quaternary nitrogen atoms according to the present invention, and two or three nitrogen-atoms substituting groups contain electron withdrawing group and have the substituting group of chlorine gegenion.Especially preferably use the compound in the general formula A scope, even more preferably these compounds have two methyl substituents on described nitrogen-atoms, n is 1 or 2 in remaining group, R
2Be C
12-C
22, be in particular C
16-C
22, as butter.
The quaternary ammonium compound of Shi Yonging is substantially anhydrous also preferred in the present invention, and this is meant to contain at article of the present invention and is less than 10% water.
Described quaternary ammonium material can contain the optional other composition that is known in the art, in particular to low molecular weight solvent (for example Virahol and/or ethanol) and coactivator such as nonionic tenderizer, for example lipid acid or Isosorbide Dinitrate.
Spendable stabilizer types is that any strong hydrogen bonding is given body.
Described stablizer can be the urea or derivatives thereof, primary amide or secondary amide or polyvalent alcohol, perhaps their mixture.Can use two or more stablizers.
Preferably the level of described stablizer with 0.05 to 10% (weight with described quaternary ammonium material is calculated) added in the composition of the present invention.Yet, preferably than still less amount of this amount, more preferably add 0.1 to 7.5% (weight with described quaternary ammonium material is calculated), particularly 0.5 to 6.0%, even more preferably 0.5 to 4%.
Described stablizer is introduced wherein in the i.e. storage stage after can or producing in any stage in the described quaternary ammonium material production process.Described stablizer can add as directly adding with powder in the fused quaternary ammonium material or with the solution in the solvent (as Virahol) that is fit in any form.
Adding step can take place in the process of synthetic described quaternary ammonium material, preferably follows quaternized step and takes place.Can select or in the storage process of described quaternary ammonium material, carry out in addition described adding.
It is the most effective that any stage after the quaternized step of synthetic described quaternary ammonium material is introduced described stablizer.
The example of the acid amides that uses in the present invention is ethanamide (acetomide).Can use polyvalent alcohol such as glycerol as stablizer.Another preferred stablizer is a urea.The combination of the quaternary ammonium compound of preferred especially glycerol and general formula (A), particularly two R wherein
1Be CH
3, n is 2 and R
2Be butter.
Described stable composition can be liquid, melt or the semi-solid form that contains the water that is less than 10% (weight).
Also provide according to the present invention and to have contained the solid rinse amendment of stable composition as defined above, preferred composition is granular or powder-form.The rinse conditioner of other type provided by the invention is to contain the liquid rinse amendment of stable composition as defined above.
The present invention describes by following examples now.Other embodiment within the scope of the invention is conspicuous for those skilled in the art.
Embodiment
Add pulverous urea in the quaternary ammonium material and be heated to 82 ℃.The blended material was placed 3 days.
Under 82 ℃ through 3 days storage after, add at Datacolor International SpectraflashSF600 and to measure reflectivity in the reflexometer.
DEQ is the chlorination two that derives from Hoechst (2-[hardened tallow] oxygen base oxygen ethyl) Dimethyl Ammonium.It
| R540, under 82 ℃ through 3 days | |
| DEQ (contrast) | 19.8 |
| The DEQ+3.6% urea | 25.1 |
| The DEQ+7.3% urea | 27.4 |
Comprise the Virahol that about 10% monoesters and a spot of not quaternized amine/amine salt also have about 2% lipid acid and 14%.
These results' demonstrations add urea in the composition that contains quaternary ammonium compound and have suppressed its decomposition at high temperature.This very big raising by the R540 reflectance value that occurs in the quaternary ammonium compounds matter sample that has mixed urea and store together shows.
Claims (11)
1. the stable composition that contains the quaternary ammonium material, described quaternary ammonium material is expressed from the next:
Each R wherein
1Group independently is selected from C
1-4Alkyl, hydroxyalkyl or C
2-4Alkenyl; Each R wherein
2Group independently is selected from C
8-28Alkyl or alkenyl; X
-It is any suitable gegenion;
T is-O-CO-or-CO-O-; With
N is the integer of 1-5 or is 0,
It is characterized in that they contain one or more stablizers in addition, wherein said one or more stablizers exist with the level of the weight calculating 0.05 to 10% of described quaternary ammonium material, condition is that described composition is for containing liquid, melt, semisolid or the solid form of the water that is less than 10% (weight)
Wherein said stablizer is selected from one or more following materials, comprising:
A) urea,
B) urea derivatives,
C) primary amide or secondary amide, and/or
D) polyvalent alcohol.
2. the composition of claim 1, wherein said one or more stablizers calculate 0.5 to 6.0% level with the weight of described quaternary ammonium material and exist.
3. the composition of claim 2, wherein said one or more stablizers calculate 0.5 to 4% level with the weight of described quaternary ammonium material and exist.
4. by the step at least a stablizer adding quaternary ammonium material being stablized the method for quaternary ammonium material, described quaternary ammonium material is expressed from the next:
Each R wherein
1Group independently is selected from C
1-4Alkyl, hydroxyalkyl or C
2-4Alkenyl; Each R wherein
2Group independently is selected from C
8-28Alkyl or alkenyl; X
-It is any suitable gegenion;
T is-O-CO-,-CO-O-; With
N is the integer of 1-5 or is 0;
Wherein said stablizer exists with the level of the weight calculating 0.05 to 10% of described quaternary ammonium material, and condition is that described composition is liquid, melt or the semi-solid form that contains the water that is less than 10% (weight),
Wherein said stablizer is selected from one or more following materials, comprising:
A) urea,
B) urea derivatives,
C) primary amide or secondary amide, and/or
D) polyvalent alcohol.
5. the method for claim 4, wherein said one or more stablizers are calculated 0.5 to 6.0% level with the weight of described quaternary ammonium material and are existed.
6. the method for claim 5, wherein said one or more stablizers are calculated 0.5 to 4% level with the weight of described quaternary ammonium material and are existed.
7. according to each method among the claim 4-6, the step of at least a stablizer of wherein said adding takes place in the process of producing described quaternary ammonium material.
8. the method for claim 7, the quaternized step of the then synthetic described quaternary ammonium material of the step of at least a stablizer of wherein said adding takes place.
9. according to each method among the claim 4-6, the step of at least a stablizer of wherein said adding takes place after producing described quaternary ammonium material.
10. the method for claim 9, the step of at least a stablizer of wherein said adding takes place in the storage process of described quaternary ammonium material.
11. be used to reduce the level of fading of the quaternary ammonium material that contains at least one ester group as each defined stablizer in claim 1-3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9810655.2 | 1998-05-18 | ||
| GBGB9810655.2A GB9810655D0 (en) | 1998-05-18 | 1998-05-18 | Stable ammonium compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1301293A CN1301293A (en) | 2001-06-27 |
| CN1192083C true CN1192083C (en) | 2005-03-09 |
Family
ID=10832260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998061689A Expired - Fee Related CN1192083C (en) | 1998-05-18 | 1999-05-12 | Stabilised quaternary ammonium compositions |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1080171B1 (en) |
| JP (1) | JP2002515551A (en) |
| CN (1) | CN1192083C (en) |
| AR (1) | AR016032A1 (en) |
| AU (1) | AU732651B2 (en) |
| BR (1) | BR9910549B1 (en) |
| CA (1) | CA2325018C (en) |
| CZ (1) | CZ300743B6 (en) |
| DE (1) | DE69923175T2 (en) |
| ES (1) | ES2234259T3 (en) |
| GB (1) | GB9810655D0 (en) |
| HU (1) | HUP0101910A3 (en) |
| PL (1) | PL190329B1 (en) |
| RO (1) | RO121133B1 (en) |
| RU (1) | RU2220190C2 (en) |
| TR (1) | TR200003386T2 (en) |
| WO (1) | WO1999060081A1 (en) |
| ZA (1) | ZA200006734B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0207484D0 (en) * | 2002-03-28 | 2002-05-08 | Unilever Plc | Solid fabric conditioning compositions |
| US20090312428A1 (en) | 2008-06-13 | 2009-12-17 | Fernando Figueredo | Biocide Compositions Comprising Quaternary Ammonium and Urea and Methods for Their Use |
| UA106790C2 (en) * | 2010-04-01 | 2014-10-10 | Евонік Дегусса Гмбх | fabric softener active composition |
| EP2385099A1 (en) * | 2010-05-06 | 2011-11-09 | The Procter & Gamble Company | Process of making liquid fabric softening compositions |
| MY171472A (en) * | 2012-06-29 | 2019-10-15 | Lion Corp | Liquid softener composition |
| EP4043541B1 (en) | 2017-03-01 | 2024-02-21 | Ecolab USA Inc. | Mechanism of urea/solid acid interaction under storage conditions and method of making storage stable solid compositions comprising urea and acid |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2454465A1 (en) * | 1974-11-16 | 1976-05-20 | Hoechst Ag | Powdery germ inhibiting soft rinsing compsns for textiles - contg cationic soft rinse, cationic disinfectant, urea and non ionic dispersant |
| EP0258923B1 (en) * | 1986-09-02 | 1993-10-06 | Akzo Nobel N.V. | Fabric softening composition and detergent-composition comprising the same |
| US5282983A (en) * | 1990-08-22 | 1994-02-01 | Kao Corporation | Fabric softener composition and ammonium salt |
| US5259964A (en) * | 1991-12-18 | 1993-11-09 | Colgate-Palmolive Co. | Free-flowing powder fabric softening composition and process for its manufacture |
| US5543067A (en) * | 1992-10-27 | 1996-08-06 | The Procter & Gamble Company | Waterless self-emulsiviable biodegradable chemical softening composition useful in fibrous cellulosic materials |
| DE4307186A1 (en) * | 1993-03-08 | 1994-09-15 | Henkel Kgaa | Aqueous fabric softener composition |
| DE4308792C1 (en) * | 1993-03-18 | 1994-04-21 | Henkel Kgaa | Stabilised quaternised fatty acid tri:ethanolamine ester salt(s) prodn. - having stable colour and odour characteristics |
| WO1998002513A1 (en) * | 1996-07-11 | 1998-01-22 | The Procter & Gamble Company | Substantially odor-free polyhydroxyl solvents |
| DE19629666A1 (en) * | 1996-07-23 | 1998-01-29 | Henkel Kgaa | Process for the hydrophilic finishing of fibers or nonwovens |
-
1998
- 1998-05-18 GB GBGB9810655.2A patent/GB9810655D0/en not_active Ceased
-
1999
- 1999-05-12 BR BRPI9910549-7A patent/BR9910549B1/en not_active IP Right Cessation
- 1999-05-12 AU AU41438/99A patent/AU732651B2/en not_active Ceased
- 1999-05-12 HU HU0101910A patent/HUP0101910A3/en unknown
- 1999-05-12 RU RU2000131616/04A patent/RU2220190C2/en not_active IP Right Cessation
- 1999-05-12 ES ES99924984T patent/ES2234259T3/en not_active Expired - Lifetime
- 1999-05-12 PL PL99344240A patent/PL190329B1/en not_active IP Right Cessation
- 1999-05-12 RO ROA200001089A patent/RO121133B1/en unknown
- 1999-05-12 DE DE69923175T patent/DE69923175T2/en not_active Expired - Lifetime
- 1999-05-12 WO PCT/EP1999/003366 patent/WO1999060081A1/en active IP Right Grant
- 1999-05-12 JP JP2000549690A patent/JP2002515551A/en not_active Withdrawn
- 1999-05-12 TR TR2000/03386T patent/TR200003386T2/en unknown
- 1999-05-12 EP EP99924984A patent/EP1080171B1/en not_active Expired - Lifetime
- 1999-05-12 CZ CZ20004292A patent/CZ300743B6/en not_active IP Right Cessation
- 1999-05-12 CA CA2325018A patent/CA2325018C/en not_active Expired - Fee Related
- 1999-05-12 CN CNB998061689A patent/CN1192083C/en not_active Expired - Fee Related
- 1999-05-18 AR ARP990102345A patent/AR016032A1/en active IP Right Grant
-
2000
- 2000-11-17 ZA ZA200006734A patent/ZA200006734B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB9810655D0 (en) | 1998-07-15 |
| WO1999060081B1 (en) | 2000-01-20 |
| PL344240A1 (en) | 2001-10-08 |
| DE69923175D1 (en) | 2005-02-17 |
| CA2325018A1 (en) | 1999-11-25 |
| CN1301293A (en) | 2001-06-27 |
| ZA200006734B (en) | 2001-11-19 |
| EP1080171A1 (en) | 2001-03-07 |
| ES2234259T3 (en) | 2005-06-16 |
| JP2002515551A (en) | 2002-05-28 |
| PL190329B1 (en) | 2005-11-30 |
| EP1080171B1 (en) | 2005-01-12 |
| WO1999060081A8 (en) | 2001-03-22 |
| BR9910549B1 (en) | 2009-01-13 |
| RU2220190C2 (en) | 2003-12-27 |
| HUP0101910A3 (en) | 2002-08-28 |
| DE69923175T2 (en) | 2005-06-23 |
| WO1999060081A1 (en) | 1999-11-25 |
| BR9910549A (en) | 2001-01-30 |
| TR200003386T2 (en) | 2001-06-21 |
| AU4143899A (en) | 1999-12-06 |
| AR016032A1 (en) | 2001-05-30 |
| RO121133B1 (en) | 2006-12-29 |
| CZ20004292A3 (en) | 2001-12-12 |
| AU732651B2 (en) | 2001-04-26 |
| CZ300743B6 (en) | 2009-07-29 |
| CA2325018C (en) | 2010-07-13 |
| HUP0101910A2 (en) | 2001-11-28 |
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