CN102421758A - Granular fabric softening compositions comprising a di-alkyl substituted imidazoline derivatives - Google Patents

Granular fabric softening compositions comprising a di-alkyl substituted imidazoline derivatives Download PDF

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Publication number
CN102421758A
CN102421758A CN2010800204719A CN201080020471A CN102421758A CN 102421758 A CN102421758 A CN 102421758A CN 2010800204719 A CN2010800204719 A CN 2010800204719A CN 201080020471 A CN201080020471 A CN 201080020471A CN 102421758 A CN102421758 A CN 102421758A
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fabric softening
softening compositions
substituted
independently
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胡戈·让·玛丽·德梅耶尔
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Procter and Gamble Ltd
Procter and Gamble Co
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Procter and Gamble Ltd
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    • 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
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • 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
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds

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

Abstract

The present invention describes a granular fabric softening composition comprising a di-alkyl substituted imidazoline derivative according to the formula : (I) wherein; X1 is a C2-3 alkylene group; X2 and X3 are independently C1-6 linear or branched alkylene or alkenylene groups; R1 and R2 are independently C8-22 linear or branched alkyl or alkenyl groups; characterized in that; A and B are independently O-(C=O)-.

Description

The particulate state fabric softening compositions that comprises the substituted imidazolidine derivatives of dialkyl group
Invention field
The present invention relates to the substituted imidazolidine derivatives of dialkyl group, wherein two alkyl are connected on the tetrahydroglyoxaline kernel through ester functional group.The substituted imidazolidine derivatives of dialkyl group of the present invention also can be used in the compsn, like Fabrid care composition and hair care composition.
Background of invention
In less developed country, logistical problem possibly appear in the supply of fabric softening compositions and their unique component and storage.Usually, the shipment distance of product is long, uses bad basic transportation loading and unloading facility, and is at high temperature.And because less developed country's resource-constrained, the preferred use is easy to biodegradable and to the minimum fabric-conditioning compositions of environmental influence.
Traditionally, fabric softening compositions adopts dialkyl group quaternary salt opsonic activity material.Yet the main drawback of these compounds is that they need add diluting solvent and store and transport.Consider with less developed country to store the logistical problem relevant, preferably do not use solvent with transportation.
The substituted imidazolinium compounds of dialkyl group is known in the art.Usually, they are as fabric-softening and hair-conditioning active substance.Yet other industrial application comprises as antistatic agent and corrosion inhibitor.Consider the fusing point that they are lower, the substituted imidazolidine derivatives of dialkyl group need not to add diluting solvent and stores and transport, thereby has saved a large amount of logistics costs.They still are noncorrosive, this means that the building material that can use low metallurgical grade is made, storage and transportation equipment.
Yet the substituted imidazolidine derivatives of dialkyl group is not easy to biological degradation, and this is the worthless characteristic of this compounds.EP 345, and 842A2 discloses the substituted imidazolidine derivatives of dialkyl group of the biodegradability that shows improvement; Yet find that after this these verivates form the obstinate substituted degradation production of monoalkyl.Therefore, only reach the part biological Degradation, this is worthless on environment.Yet JP05-105670 and JP06-228870 have described and have been easy to biodegradable dialkylimidazolium verivate.
This area need comprise the fabric softening compositions that is easy to the biological degradation activity material, and said active substance can not form the obstinate substituted degradation production of monoalkyl when degraded.Also need fabric softening compositions, wherein adopt bad basic transportation loading and unloading facility and at high temperature, the fabric-softening active substance can be easy to stored safely and long-distance transportation.What need be used for less developed country at last possesses all above-mentioned characteristics, can accept the fabric softening compositions of product form for the human consumer simultaneously.
Be surprisingly found out that the particulate state fabric softening compositions that comprises the substituted imdazole derivatives of dialkyl group that meets claim 1 chemical formula provides wherein softening active substance to be easy to biological degradation and can accept the fabric softening compositions of product form for the human consumer.And, but the transportation of said fabric-softening active substance safe ready under the situation that does not have diluting solvent.
Summary of the invention
First aspect of the present invention is the particulate state fabric softening compositions, and said compsn comprises the substituted imidazolidine derivatives of the dialkyl group that meets following formula:
Figure BDA0000107183860000021
Wherein:
X 1Be the C2-3 alkylidene group;
X 2And X 3Be C1-6 straight or branched alkylidene group or alkenylene independently;
R 1And R 2Be C8-22 straight or branched alkyl or alkenyl independently;
It is characterized in that:
A and B be independently O-(C=O)-.
Detailed Description Of The Invention
The present invention relates to the particulate state fabric softening compositions, said compsn comprises the substituted imidazolidine derivatives of the dialkyl group that meets following formula:
X wherein 1Be C2-3 alkylidene group, X 2And X 3Be C1-6 straight or branched alkylidene group or alkenylene independently, R 1And R 2Be C8-22 straight or branched alkyl or alkenyl independently, A and B be independently selected from comprise following group: O-(C=O)-,-(C=O)-O-or their mixture.Preferred A and B have independently of one another formula O-(C=O)-.In a preferred embodiment, X 1Be the C2 alkyl.In another preferred embodiment, X 2Be the C2-3 alkylidene group, more preferably the C2 alkylidene group.In another preferred embodiment, X 2Be sec.-propyl.In another preferred embodiment, X 3Be C1-4 alkylidene group, more preferably CH 2Group.In another preferred embodiment, R 1And R 2Be C12-18 alkyl or C12-18 thiazolinyl independently.Preferred R 1And R 2Be independently selected from and comprise following group: (hydrogenation) tallow fatty acid, PALM FATTY ACID, hydrogenated palm lipid acid, oleic acid, Semen Brassicae campestris lipid acid, winterized stearin vegetable seed lipid acid or their mixture.The substituted imidazolidine derivatives of these dialkyl group also can be called as the tetrahydroglyoxaline diester compound.
Group A and B all be independently O-(C=O)-, as the degraded point, guarantee that diester deriv does not form obstinate monoalkyl material.Through having two weak ester bonds, make formula I or II midbody in environment, to degrade and form III, avoided the formation of the obstinate substituted tetrahydroglyoxaline material of monoalkyl.
Structure I structure I I structure III
In particulate state fabric softening compositions of the present invention, A and B all have independently formula O-(C=O)-, institute is preferred because this structure is compound method as described herein.Yet those skilled in the art will identify other suitable ester and arrange.
The particulate state fabric softening compositions can be used as the additive in hand washing or the machine washing, or as other a kind of selection, can be used in the tumble drier application.Granular composition can be distributed in the water during use or before using.
The content of the substituted imidazolidine derivatives of dialkyl group is preferably 70% to 99% level by the weight of said particulate state fabric softening compositions.
The fabric softener composition that comprises the substituted imidazolidine derivatives of dialkyl group can be chosen wantonly and comprise other composition, and said other composition is preferably selected from and comprises following group: the spices that quaternary ammonium compound, silicone compounds, spices, capsule are sealed, dispersion agent, stablizer, pH regulator agent, tinting material, whitening agent, dyestuff, odor control agent, preceding spices, Schardinger dextrins, solvent, detergency polymkeric substance, sanitas, biocide, chlorine scavenger, nonshrink aqua, fabric even limit agent, spotting agent, inhibitor, anticorrosive agent, bodying agent, dangle and style control agent, along lubrication prescription, Electrostatic Control agent, wrinkle control agent, sanitising agent, sterilizing agent, germ control agent, mould control agent, mildew control agent, antiviral agent, biocide, siccative, stain control agent, washing agent, stench control agent, fabric refreshers, chlorine bleaching odor control agent, dye-fixing agent, dye transfer inhibitor, color retention agent, color restoration/shining new agent, anti-fading agent, whiteness toughener, anti-wear agent, anti-wear agent, fabric integrity agent, anti-agent, skimmer and anti-foaming agent, rinse aid, ultraviolet protecting agent, photobleaching suppressor factor, wormer, anti-allergic agent, enzyme, fire retardant, water-resisting agent, comfortable dose of fabric, water conditioner, the crease-resistant agent of contracting, anti-extension agent, thickening material, sequestrant, ionogen and their mixture wear.
Another aspect of the present invention is the method for the synthetic substituted imidazolidine derivatives of dialkyl group.
The preferred compound method of the substituted imidazolidine derivatives of preparation dialkyl group is as follows.
In the first step, make to have formula NH 2-X 1-NH-X 2The substituted polyalkylene diamines of the hydroxyl of-OH with have a formula OH-X 3The substituted fatty acid response of the hydroxyl of-COOH.In a preferred embodiment, the substituted polyalkylene diamines of hydroxyl is N-(2-hydroxyethyl)-1.In another preferred embodiment, the substituted polyalkylene diamines of hydroxyl is N-(2-hydroxyl sec.-propyl)-1.In another preferred embodiment, the substituted lipid acid of hydroxyl is oxyacetic acid.In this first step, the substituted polyalkylene diamines of hydroxyl mixes with fusion with the substituted lipid acid of hydroxyl mutually, and reaction mixture is kept stirring and remaining in the liquid phase.The mol ratio of substituted lipid acid of hydroxyl and the substituted polyalkylene diamines of hydroxyl is preferably between 0.8: 1 to 1.2: 1, more preferably between 0.9: 1 to 1: 1.Preferably reaction vessel is remained under the inert atmosphere, for example through using N 2Air-blowing is swept.
In second step, the reaction mixture of the first step is heated to 100 ℃ to 240 ℃, preferred 150 ℃ to 210 ℃, 180 ℃ to 200 ℃ temperature most preferably.Preferred then through using vacuum pump, from reaction vessel, remove reaction water.The gained reaction mixture will mainly comprise the substituted tetrahydroglyoxaline of the dihydroxyl with following formula this moment:
Figure BDA0000107183860000051
X wherein 1Be C2-3 alkylidene group, X 2Be C1-6 straight or branched alkylidene group or alkenylene, X 3Be C1-6 straight or branched alkylidene group or alkenylene, and C is OH, and D is OH.Preferably, X 1Be CH2-CH2, X 2Be CH2-CH2 or CH-(CH3)-CH2, X 3Be CH2, and C is OH, and D is OH.
In the 3rd step, make that the substituted tetrahydroglyoxaline of dihydroxyl further reacts with esterifying reagent in the step 2.Esterifying reagent is preferably selected from and comprises following group: the C1-4 short-chain ester and the glycerin fatty acid ester of lipid acid, lipid acid.The mol ratio of esterifying reagent and the substituted tetrahydroglyoxaline of dihydroxyl is 1.2: 1 to 2.2: 1, preferred 1.5: 1 to 2: 1.Reaction mixture is heated to 100 ℃ to 200 ℃, preferred 165 ℃ to 190 ℃ temperature.Then preferably through using vacuum pump from reaction vessel, to remove reaction water.Preferably make reaction remain on pressure, preferably under the inert atmosphere less than 250Pa less than 1500Pa.When esterifying reagent is fatty ester or glycerin fatty acid ester, preferably use esterifying catalyst.Esterifying catalyst is preferably selected from and comprises following group: metal alkoxide, metal halide, metal haloalkane, metal carboxylate, metal alkyl alkoxide and their mixture.In one embodiment, esterifying catalyst is a metal alkoxide, is preferably selected to comprise following group: Sn (OR) 4, Na (OR), K (OR) or Ti (OR) 4, and wherein R is the C1-6 alkyl, preferred C2-3 alkyl.In another embodiment, esterifying catalyst is a metal halide, is preferably selected to comprise following group: tin halide or transition metal halide, and preferred TiY4, wherein Y is Cl or Br.In another embodiment, esterifying catalyst is the metal haloalkane, preferred transition metal haloalkane.In another embodiment, esterifying catalyst is a metal carboxylate, is preferably selected to comprise following group: tin acetate or zinc acetate.In another embodiment, esterifying catalyst is the metal alkyl alkoxide, is preferably selected to comprise following group: transition-metal-alkyl alkoxide or tin alkynylene, like SnT4, wherein T is C1-8 alkyl or C1-8 hydroxyl independently.
Embodiment
The substituted imidazolidine derivatives of the preferred dialkyl group of the present invention comprises:
A) with fatty acid-esterified N-(2-hydroxyethyl)-1; The reaction product of 2-quadrol and oxyacetic acid, wherein lipid acid is (hydrogenation) tallow fatty acid, PALM FATTY ACID, hydrogenated palm lipid acid, oleic acid, Semen Brassicae campestris lipid acid, winterized stearin vegetable seed lipid acid or above-mentioned mixture.
B) with fatty acid-esterified N-(2-hydroxyl sec.-propyl)-1; The reaction product of 2-quadrol and oxyacetic acid, wherein lipid acid is hydrogenated tallow, PALM FATTY ACID, hydrogenated palm lipid acid, oleic acid, Semen Brassicae campestris lipid acid, winterized stearin vegetable seed lipid acid or above-mentioned mixture.
C) with N-(2-the hydroxyethyl)-1 of the methyl esters esterification of hydrogenated tallow, PALM FATTY ACID, hydrogenated palm lipid acid, oleic acid, Semen Brassicae campestris lipid acid, winterized stearin vegetable seed lipid acid or said mixture and the reaction product of oxyacetic acid.
D) with N-(2-hydroxyl the sec.-propyl)-1 of the methyl esters esterification of hydrogenated tallow, PALM FATTY ACID, hydrogenated palm lipid acid, oleic acid, Semen Brassicae campestris lipid acid, winterized stearin vegetable seed lipid acid or said mixture and the reaction product of oxyacetic acid.
E) triglyceride level or N-(2-the hydroxyethyl)-1 of partial glycerol ester esterification and the reaction product of oxyacetic acid of usefulness (hydrogenation) lipid acid such as tallow fatty acid, PALM FATTY ACID, Semen Brassicae campestris lipid acid etc.
F) triglyceride level or N-(2-hydroxyl the sec.-propyl)-1 of partial glycerol ester esterification and the reaction product of oxyacetic acid of usefulness (hydrogenation) lipid acid such as tallow fatty acid, PALM FATTY ACID, Semen Brassicae campestris lipid acid etc.
The preferred composition that comprises the dialkylimidazolium quinoline derivant comprises:
Figure BDA0000107183860000071
Per-cent is expressed as the per-cent by said composition weight meter.
aThe tetrahydroglyoxaline diester; With N-(2-the hydroxyethyl)-1 of subsclerotic tallow fatty acid esterification and the reaction product of oxyacetic acid.
bThe tetrahydroglyoxaline diester; With N-(2-the hydroxyethyl)-1 of the tallow fatty acid esterification of pansclerosis and the reaction product of oxyacetic acid.
cThe tetrahydroglyoxaline diester; With N-(2-hydroxyl the sec.-propyl)-1 of subsclerotic PALM FATTY ACID esterification and the reaction product of oxyacetic acid.
dNonionogenic tenside C12-14 alkyl 10 ethoxylates
eCitric Acid, usp, Anhydrous Powder
fPolyethylene glycol MW 4000
gDerive from the Liquitint Blue AF of Milliken company
Fused matter spray cooling through with imidazolinium compounds and nonionogenic tenside makes above-mentioned product.Make the fused matter cohesion of atomizing, and during condensing on it spray perfume (with last dye solution, Hydrocerol A and other minor component).
Should dimension disclosed herein and value be interpreted as the strictness restriction to quoting exact value.On the contrary, except as otherwise noted, each such dimension all is intended to represent the value of being quoted and centers on the scope that is equal on this value function.For example, disclosed dimension " 40mm " is intended to expression " about 40mm ".

Claims (6)

1. particulate state fabric softening compositions, said compsn comprises the substituted imidazolidine derivatives of the dialkyl group that meets following formula:
Figure FDA0000107183850000011
Wherein:
X 1Be the C2-3 alkylidene group;
X 2And X 3Be C1-6 straight or branched alkylidene group or alkenylene independently;
R 1And R 2Be C8-22 straight or branched alkyl or alkenyl independently;
Be characterised in that:
A and B be independently O-(C=O)-.
2. the described particulate state fabric softening compositions of claim 1, the X in the substituted imidazolidine derivatives of wherein said dialkyl group 1Be the C2 alkylidene group.
3. as the described particulate state fabric softening compositions of aforementioned each claim, the X in the substituted tetrahydroglyoxaline of wherein said dialkyl group 2Be the C2-3 alkylidene group, preferred C2 alkylidene group, more preferably sec.-propyl.
4. as the described particulate state fabric softening compositions of aforementioned each claim, the X in the substituted tetrahydroglyoxaline of wherein said dialkyl group 3Be the C1-4 alkylidene group, preferred CH 2Group.
5. as the described particulate state fabric softening compositions of aforementioned each claim, the R in the substituted tetrahydroglyoxaline of wherein said dialkyl group 1And R 2Be C12-18 alkyl or C12-18 thiazolinyl independently, more preferably be independently selected from and comprise following group: (hydrogenation) tallow fatty acid, PALM FATTY ACID, hydrogenated palm lipid acid, oleic acid, Semen Brassicae campestris lipid acid, winterized stearin vegetable seed lipid acid or their mixture.
6. like the described particulate state fabric softening compositions of aforementioned each claim, the content of the substituted imidazolidine derivatives of wherein said dialkyl group is counted 70% to 99% level by the weight of said granular composition.
CN2010800204719A 2009-05-14 2010-05-13 Granular fabric softening compositions comprising a di-alkyl substituted imidazoline derivatives Pending CN102421758A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP09160280.5 2009-05-14
EP09160280 2009-05-14
EP10159737A EP2264013A1 (en) 2009-05-14 2010-04-13 Granular fabric softening compositions comprising a di-alkyl substituted imidazoline derivatives
EP10159737.5 2010-04-13
PCT/US2010/034642 WO2010132629A1 (en) 2009-05-14 2010-05-13 Granular fabric softening compositions comprising a di-alkyl substituted imidazoline derivatives

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CN102421758A true CN102421758A (en) 2012-04-18

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EP (1) EP2264013A1 (en)
CN (1) CN102421758A (en)
BR (1) BRPI1010825A2 (en)
CA (1) CA2757177A1 (en)
MX (1) MX2011012132A (en)
WO (1) WO2010132629A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05105670A (en) * 1991-10-15 1993-04-27 Kao Corp New heterocyclic compound and its production

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0345842A3 (en) 1988-05-27 1990-04-11 The Procter & Gamble Company Fabric softening compositions containing mixtures of substituted imidazoline esters and quartenized ester-ammonium salts
JP3212175B2 (en) 1993-01-30 2001-09-25 ライオン株式会社 Softener composition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05105670A (en) * 1991-10-15 1993-04-27 Kao Corp New heterocyclic compound and its production

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WO2010132629A1 (en) 2010-11-18
CA2757177A1 (en) 2010-11-18
EP2264013A1 (en) 2010-12-22
MX2011012132A (en) 2011-12-06
BRPI1010825A2 (en) 2015-09-22

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Application publication date: 20120418