CN101280515B - Fabric softener bisquaternary ammonium salt with ester group and preparation thereof - Google Patents
Fabric softener bisquaternary ammonium salt with ester group and preparation thereof Download PDFInfo
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- CN101280515B CN101280515B CN200710070954XA CN200710070954A CN101280515B CN 101280515 B CN101280515 B CN 101280515B CN 200710070954X A CN200710070954X A CN 200710070954XA CN 200710070954 A CN200710070954 A CN 200710070954A CN 101280515 B CN101280515 B CN 101280515B
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Abstract
The invention discloses an ester-containing bis-quaternary ammonium salt fabric softener and a preparation method thereof, aiming at the problem that the prior mono-quaternary ammonium salt softener, compared with the conventional amide type and imidazoliny type fabric softeners, has poor softness performance so that the use amount needs to be added for reaching same softness so as to increase the processing cost of fabric correspondingly. In the ester-containing Bis-quaternary ammonium salt fabric softener, fatty acid or fatty acid ester, triethanolamine, Antioxidant and catalyzer are used as raw materials, first, esterification or Interesterification are performed, and then the above production is added with Halogenated compounds containing two functional groups, quaternization is performed so as to obtain the ester-containing bis-quaternary ammonium salt. The ester-containing bis-quaternary ammonium salt fabric softener obtained by the invention has the advantages of excellent hand feeling, excellent yellowing, color change performance and friendly environment, so as to reach excellent softening effect and less usage amount, thereby reducing processing cost of cotton fabric.
Description
Technical field
The present invention relates to fabric softener, specifically a kind of fabric softener bisquaternary ammonium salt with ester group and preparation method thereof.
Background technology
COTTON FABRIC is in the dyeing and finishing process, and feel becomes coarse after repeatedly handling, and has smooth, soft hand feeling in order to make fabric, improves end product quality, often needs to carry out soft finish.At present after COTTON FABRIC the arrangement process in employed softener kind non-silicon kind fabric softener and amido silicon oil are arranged, wherein using more is the particularly cationic fabric softener of non-silicon kind fabric softener, and the fabric after arrangement has softness, plentiful, smooth, fluffy characteristics.
Existing cationic fabric softener mostly is acid amide type and imidazoline type softener.The amide type softener feel is general, and certain xanthochromia and look sex change are arranged; The imidazoline type feel is better, but cost is higher relatively and xanthochromia and look become bigger.For this reason, occurred stearate based quaternary ammonium salt type softener on the market, it has xanthochromia and look sex change energy, relatively low cost, excellent characteristics such as biological degradability preferably, but softness is unsatisfactory.Development along with dyeing, market is relatively low for cost, xanthochromia and look sex change energy, excellent feel and eco-friendly ester based quaternary ammonium salt type softener demand are urgent preferably, this type of softener is for improving quality of textile products and added value, and the market competitiveness that promotes textiles is significant.
Have a large amount of patent documentations to introduce the preparation method of ester based quaternary ammonium salt softener at present, mainly concentrate on Triethanolamine Esters of Stearic Acid and quaternary ammonium salt thereof preparation and and other component composite on, the structure of its main active matter mostly is mono-quaternaries.Though mono-quaternaries type softener has xanthochromia and look sex change energy, relatively low cost, excellent characteristics such as biological degradability preferably, but weak point is that to compare softness relatively poor with conventional acid amide type and imidazoline type fabric softener, reaching same soft effect need increase consumption, the corresponding increase of the processing cost of COTTON FABRIC.
Summary of the invention
Technical problem to be solved by this invention is to overcome the defective that above-mentioned prior art exists, and a kind of cost is relatively low, have excellent feel, excellence xanthochromia and look sex change energy and eco-friendly fabric softener bisquaternary ammonium salt with ester group and preparation method thereof are provided.
For this reason, the technical solution used in the present invention is as follows: fabric softener bisquaternary ammonium salt with ester group, it is characterized in that with LCFA or fatty acid ester, triethanolamine, antioxidant, catalyst is a raw material, carry out esterification or ester exchange earlier, in above-mentioned product, add the halogenated compound that contains dual-active functional group then, carry out quaterisation and obtain the ester group bi-quaternary ammonium salt, described LCFA or fatty acid ester and triethanolamine, the mol ratio of dual-active functional group halogenated compound is 1～4:2:1, and antioxidant and catalyst consumption are 0.1～0.5% of LCFA or fatty acid ester quality.Described fabric softener bisquaternary ammonium salt with ester group general structure is as follows:
Wherein: R is C
15～C
21Straight chained alkyl;
p＝1～3，q＝3-p；
Y is:
X is Cl
-Or Br
-
Concrete reaction equation is as follows:
(1) LCFA triethanolamine ester:
In the formula: R
1, R
2Be C
15～C
21Straight chained alkyl; R
3, R
4, R
5, R
6Be C
15～C
17Straight chained alkyl;
p＝1～3；q＝3-p.
(2) ester group bi-quaternary ammonium salt:
In the formula:
R
1, R
2Be C
15～C
21Straight chained alkyl; R
3, R
4, R
5Be C
15～C
17Straight chained alkyl;
R
6Be R
1, R
2, R
3, R
4Or R
5P=1～3; Q=3-p.
Described fabric softener bisquaternary ammonium salt with ester group, LCFA are palmitic acid, stearic acid or erucic acid, preferred palmitic acid or stearic acid; Described fatty acid ester is fatty acid methyl ester or triglyceride, and described fatty acid methyl ester is methyl hexadecanoate, methyl stearate or methyl erucate, preferred methyl stearate; Described triglyceride is hydrogenated palm oleic acid or hydrogenation cattle and sheep oleic acid, preferred hydrogenated palm oleic acid or hydrogenation cattle and sheep oleic acid.
Described fabric softener bisquaternary ammonium salt with ester group, the mol ratio of LCFA or fatty acid methyl ester and triethanolamine, dual-active functional group halogenated compound is 3～4: 2: 1; The mol ratio of triglyceride and triethanolamine, dual-active functional group halogenated compound is 1～1.5: 2: 1.
Described fabric softener bisquaternary ammonium salt with ester group, the esterification temperature of LCFA and triethanolamine are 160～210 ℃, preferred 170～190 ℃; The transesterification temperature of LCFA methyl esters and triethanolamine is 100～160 ℃, preferred 120～140 ℃; The transesterification temperature of triglyceride and triethanolamine is 160～210 ℃, preferred 170～190 ℃; Quaternized temperature is 60～100 ℃, preferred 80～100 ℃.
Described fabric softener bisquaternary ammonium salt with ester group, dual-active functional group halogenated compound is an epoxychloropropane, 1,2-Bromofume, monoxone diethylene glycol dilaurate, preferred epoxychloropropane or monoxone diethylene glycol dilaurate.
Described fabric softener bisquaternary ammonium salt with ester group, antioxidant are selected ortho phosphorous acid or potassium borohydride for use.
Described fabric softener bisquaternary ammonium salt with ester group, catalyst are selected ortho phosphorous acid, sodium methoxide or butyl titanate for use.
Novel fabric softener bisquaternary ammonium salt with ester group provided by the invention is that white is to light yellow solid, cost is low, have xanthochromia, look sex change energy and the friendly environment of excellent feel, excellence, the consumption that reaches excellent soft effect is few, has reduced the processing cost of COTTON FABRIC.
The specific embodiment
The invention will be further described below in conjunction with the specific embodiment.
One, the LCFA triethanolamine ester is synthetic
Embodiment 1
With 140.8g palmitic acid (mean molecule quantity is 258), the ortho phosphorous acid input one of 0.3g50% is equipped with thermometer, electronic stirring, condenser, constant pressure funnel, be connected with in the 500mL four-hole bottle of vacuum system and logical nitrogen system, heat with electric jacket, treat to start stirring after the material fusion, temperature control is about 80 ℃, with nitrogen four-hole bottle is replaced three times, logical nitrogen, the 45.5g triethanolamine is added in 10min by dropping funel, finish the back and heat up, temperature control to 190 ± 2 ℃, and under this temperature insulation dehydration 4h, sampling and measuring material acid number, after acid number is less than 5mgKOH/g, be cooled to 40 ℃, obtain the fatty acid triethanolamine ester A1 of above-mentioned a structure, 176.5g.
Embodiment 2
Replace the 140.8g palmitic acid with 146.8g stearic acid (mean molecule quantity is 267), other reagent and consumption and synthesis technique are constant, repeat the fatty acid triethanolamine ester A2 that embodiment 1 obtains a structure, 182.5g.
Embodiment 3
Replace the 140.8g palmitic acid with 176.0g erucic acid (mean molecule quantity is 330), other reagent and consumption and synthesis technique are constant, repeat the fatty acid triethanolamine ester A3 that embodiment 1 obtains a structure, 212.0g.
Embodiment 4
With 154.5g methyl stearate (mean molecule quantity is 281), 0.3g anhydrous boron hydrofining, 0.3g sodium methoxide input one is equipped with thermometer, electronic stirring, constant pressure funnel, be connected with in the 500mL four-hole bottle of vacuum system and logical nitrogen system, heat with electric jacket, treat to start stirring after the material fusion, temperature control is about 80 ℃, with nitrogen four-hole bottle is replaced three times, logical nitrogen, the 45.5g triethanolamine is added in 10min by dropping funel, finishing the back heats up, temperature control to 140 ± 2 ℃, and under this temperature, vacuumize 4h, be cooled to 40 ℃, obtain the fatty acid triethanolamine ester A4 of b structure, 182.7g.
Embodiment 5
With 153.8g HPO (mean molecule quantity is 839), 0.3g anhydrous boron hydrofining, 0.2g butyl titanate input one is equipped with thermometer, electronic stirring, constant pressure funnel, be connected with in the 500mL four-hole bottle of vacuum system and logical nitrogen system, heat with electric jacket, treat to start stirring after the material fusion, temperature control is about 80 ℃, with nitrogen four-hole bottle is replaced three times, logical nitrogen, the 45.5g triethanolamine is added in 10min by dropping funel, finishing the back heats up, temperature control to 190 ± 2 ℃, and, be cooled to 40 ℃ at this temperature insulation 4h, obtain the fatty acid triethanolamine ester A5 of c structure, 199.3g.
Embodiment 6
Replace the 153.8g HPO with 155.6g hydrogenation tallow oil (mean molecule quantity is 849), other reagent and consumption and synthesis technique are constant, repeat the fatty acid triethanolamine ester A6 that embodiment 5 obtains the c structure, 201.1g.
Two, ester group bi-quaternary ammonium salt softener is synthetic
Embodiment 7
160.5gA1 is dropped into one thermometer is housed, electronic stirring, condenser, constant pressure funnel, be connected with in the 500mL four-hole bottle of vacuum system and logical nitrogen system, heat with electric jacket, treat to start stirring after the material fusion, temperature control is about 80 ℃, with nitrogen four-hole bottle is replaced three times, logical nitrogen, the concentrated hydrochloric acid that slowly adds 14.5g36% by dropping funel, finish the back and add the 12.9g epoxychloropropane by the clean dropping funel of another in 30min, temperature control finishes the back at 80～100 ℃ of insulation 4～6h in 80～90 ℃, when amine value during less than 0.1mmol/g, vacuumize and take off most moisture and finish reaction, get the faint yellow solid C1 of d structure, 169.0g.
Embodiment 8
Replace 160.5gA1 with 166.0gA2, other reagent and consumption and synthesis technique are constant, repeat embodiment 7, get the faint yellow solid C2 of d structure, 174.5g.
Embodiment 9
Replace 160.5gA1 with 192.7gA3, other reagent and consumption and synthesis technique are constant, repeat embodiment 7, get the faint yellow solid C3 of d structure, 201.2g.
Embodiment 10
Replace 160.5gA1 with 160.0gA4, other reagent and consumption and synthesis technique are constant, repeat embodiment 7, get the faint yellow solid C4 of d structure, 174.3g.
Embodiment 11
Replace 160.5gA1 with 181.2gA5, other reagent and consumption and synthesis technique are constant, repeat embodiment 7, get the faint yellow solid C5 of d structure, 195.5g.
Embodiment 12
182.8gA6 is replaced 160.5gA1, and other reagent and consumption and synthesis technique are constant, repeat embodiment 7, get the faint yellow solid C6 of d structure, 197.1g.
Embodiment 13
166.0gA2 input one is equipped with thermometer, electronic stirring, condenser, constant pressure funnel, is connected with in the 500mL four-hole bottle of vacuum system and logical nitrogen system, heat with electric jacket, treat to start stirring after the material fusion, temperature control is about 80 ℃, with nitrogen four-hole bottle is replaced three times, logical nitrogen, the dropping funel clean by another adds the 26.1g Bromofume in 30min, temperature control is in 80～90 ℃, finish the back at 80～100 ℃ of insulation 6～8h, when the amine value finishes reaction during less than 0.1mmol/g, the faint yellow solid C7 of e structure, 192.0g.
Embodiment 14
160.5g embodiment 2 synthetic LCFA triethanolamine ester A2 are dropped into one thermometer is housed, electronic stirring, constant pressure funnel, be connected with in the 500mL four-hole bottle of vacuum system and logical nitrogen system, heat with electric jacket, treat to start stirring after the material fusion, temperature control is about 80 ℃, with nitrogen four-hole bottle is replaced three times, logical nitrogen, in 30min, add 29.1g monoxone diethylene glycol dilaurate by the four-hole bottleneck, temperature control is in 80～90 ℃, finish the back at 80～100 ℃ of insulation 6～8h, when the amine value finishes reaction during less than 0.1mmol/g, the faint yellow solid C8 of f structure, 189.5g.
The above-mentioned synthetic product that obtains adopts following method of testing:
1, characterizes the method for structure
Utilize the characteristic group in the determination of infrared spectroscopy molecular structure---the carbonyl of ester bond;
Utilize the position of each group in the nmr determination molecular structure;
Utilize mass spectrograph to measure the molecular weight of product.
2, the test of bi-quaternary ammonium salt content in the product
Adopt bromophenol blue to make the two-phase indicator, dichloroethanes is done to divide phase solvent, with bi-quaternary ammonium salt solution titration anion active agent to be measured (lauryl sodium sulfate) standard liquid, shows blue to lower floor's solvent layer, directly measures the content of bi-quaternary ammonium salt.
3, softness test
Fabric: all-cotton knitting TOWEL.
Impregnation technology: the preparation working solution (bath raio: 1:10) → 25 ℃ dipping 15min → dehydration → typing (160 ℃ * 120s) → the moisture regain evaluation.
Adopting traditional hand digital palpation for examination of trauma to estimate, is 1 grade with former cloth hand feel evaluation, and hand feel evaluation preferably is decided to be 5 grades.At least by the marking of 3 people's subjective assessments, average, numerical value is big more, and the expression feel is good more.
4, xanthochromia, look sex change can be tested
Fabric: the cotton bleaching machine is weaved cotton cloth; The woven cloth of light brown cotton.
Impregnation technology: the preparation working solution (bath raio: 1:10) → 25 ℃ dipping 15min → dehydration → typing (160 ℃ * 120s) → test with the Datacolor colour photometer.
With the cloth specimen before handling is standard specimen, and the cloth specimen after the processing is a test specimens, tests on the Datacolor colour photometer.The look that characterizes softener with GS, Δ Wi becomes and the xanthochromia performance, and GS represents the look variate, and its value is big more, and it is more little that look becomes, Δ Wi represent after the fabric treating with handle before the whiteness difference, its absolute value is big more, the whiteness variation be more greatly xanthochromia more greatly.
Fabric softener bisquaternary ammonium salt with ester group The performance test results of the present invention sees Table 1 and table 2.
Table 1 softener sample physicochemical property
Table 2 softener sample application performance
| Sequence number | The softener title | Feel | Xanthochromia value (Δ YI) | Look becomes grade (GS) |
| 1 | Softener 1 | 4 | 0.98 | 4.76 |
| 2 | Softener 2 | 5 | 3.82 | 4.23 |
| 3 | C1 | 4～5 | 0.94 | 4.77 |
| 4 | C2 | 5 | 0.99 | 4.75 |
| 5 | C3 | 5 | 1.01 | 4.67 |
| 6 | C4 | 5 | 0.97 | 4.75 |
| 7 | C5 | 5 | 0.96 | 4.76 |
| 8 | C6 | 5 | 1.05 | 4.63 |
| 9 | C7 | 5 | 0.97 | 4.76 |
| 10 | C8 | 5 | 0.99 | 4.77 |
[notes]: (1) softener 1 is Clariant ester based quaternary ammonium salt softener Praepagen TQ; Softener 2 is the acid amide type cationic softener CWS of Ciba; (2) feel is measured by general evaluation method, is divided into 5 grades, is preferably 5 grades; Xanthochromia, look sex change can be measured according to the AATCC standard.(3) Δ YI is the xanthochromia value in the table, and it is good more to be worth more little xanthochromia performance; GS is that look becomes grade, is preferably 5 grades, and being worth big more look sex change can be good more.
Can find out that from table 2 the novel fabric softener bisquaternary ammonium salt with ester group that is synthesized has excellent feel and excellent xanthochromia and look sex change energy.
The above only is preferred embodiment of the present invention.Every foundation technical spirit of the present invention all falls within the scope of protection of the present invention any simple modification, equivalent variations and modification that above embodiment did.
Claims (5)
1. fabric softener bisquaternary ammonium salt with ester group, it is characterized in that with LCFA or long-chain fatty acid ester, triethanolamine is a raw material, ortho phosphorous acid or potassium borohydride are antioxidant, ortho phosphorous acid or sodium methoxide or butyl titanate are catalyst, carry out esterification or ester exchange earlier, in above-mentioned product, add epoxychloropropane or 1 then, 2-Bromofume or monoxone diethylene glycol dilaurate, carry out quaterisation and obtain fabric softener bisquaternary ammonium salt with ester group, described LCFA or long-chain fatty acid ester and triethanolamine, epoxychloropropane or 1, the mol ratio of 2-Bromofume or monoxone diethylene glycol dilaurate is 1～4: 2: 1, antioxidant and catalyst consumption were 0.1～0.5% of LCFA or long-chain fatty acid ester quality;
Described LCFA is palmitic acid, stearic acid or erucic acid; Described long-chain fatty acid ester is LCFA methyl esters or LCFA triglyceride, and described LCFA methyl esters is methyl hexadecanoate, methyl stearate or methyl erucate, and described LCFA triglyceride is HPO or hydrogenation tallow oil.
2. fabric softener bisquaternary ammonium salt with ester group according to claim 1 is characterized in that described LCFA is palmitic acid or stearic acid; Described long-chain fatty acid ester is methyl stearate, HPO or hydrogenation tallow oil.
3. fabric softener bisquaternary ammonium salt with ester group according to claim 1 is characterized in that LCFA or LCFA methyl esters and triethanolamine, epoxychloropropane or 1, and the mol ratio of 2-Bromofume or monoxone diethylene glycol dilaurate is 3～4: 2: 1; LCFA triglyceride and triethanolamine, epoxychloropropane or 1, the mol ratio of 2-Bromofume or monoxone diethylene glycol dilaurate is 1～1.5: 2: 1.
4. fabric softener bisquaternary ammonium salt with ester group according to claim 1, the esterification temperature that it is characterized in that LCFA and triethanolamine is 160～210 ℃; The transesterification temperature of LCFA methyl esters and triethanolamine is 100～160 ℃; The transesterification temperature of LCFA triglyceride and triethanolamine is 160～210 ℃, and quaternized temperature is 60～100 ℃.
5. according to the preparation method of each described fabric softener bisquaternary ammonium salt with ester group of claim 1-4, it is characterized in that concrete steps are as follows: with LCFA or long-chain fatty acid ester and antioxidant, the catalyst input has in the reaction vessel of vacuum system and logical nitrogen system, heating, treat to stir after the material fusion, logical nitrogen, drip triethanolamine, finishing the back heats up, insulation then, sampling and measuring product acid number, behind acid number≤5mgKOH/g, lower the temperature, drip epoxychloropropane or 1 in the above-mentioned product that obtains, 2-Bromofume or monoxone diethylene glycol dilaurate finish the back at 60～100 ℃ of insulation 4～8h, when amine value≤0.1mmo l/g, finish reaction, vacuumize the faint yellow solid fabric softener bisquaternary ammonium salt with ester group.
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