CN101818458A - Organosilicon modified polyurethane hyperchromic improver and preparation method thereof - Google Patents
Organosilicon modified polyurethane hyperchromic improver and preparation method thereof Download PDFInfo
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- CN101818458A CN101818458A CN200910188847A CN200910188847A CN101818458A CN 101818458 A CN101818458 A CN 101818458A CN 200910188847 A CN200910188847 A CN 200910188847A CN 200910188847 A CN200910188847 A CN 200910188847A CN 101818458 A CN101818458 A CN 101818458A
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Abstract
The invention discloses an organosilicon modified polyurethane hyperchromic improver and a preparation method thereof. The organosilicon modified polyurethane hyperchromic improver is an aqueous emulsion of which the solid content is 20 to 45 percent and the viscosity range is between 800 and 30,000 cp. The organosilicon modified polyurethane forming the emulsion comprises polyether, diisocyanate and siloxane structural units, wherein the mole ratio of a diisocyanate structure to a polyether structure is 2-4:1; and the mole ratio of the diisocyanate structure to a siloxane structure is 5-25:1. The flow path of the preparation method of the hyperchromic improver is as shown in the figure. Compared with the conventional color fixing agent, the hyperchromic improver is safer and more environment-friendly, and makes fabrics have firmer dye fastness and softer handfeel.
Description
Technical field
The present invention relates to a kind of organosilicon modified polyurethane hyperchromic improver, relate in particular to the aqueous polyurethane hyperchromic improver that contains polyethers, isocyanates and siloxane structure unit in a kind of emulsion.This hyperchromic improver is compared with traditional color-fixing agent, and safer, more environmental protection makes fabric possess more firm dyefastness and softer feel.
Background technology
Color-fixing agent can be directly as finishing agent or add in other auxiliary agents, improve the COLOR FASTNESS of textiles after dyeing is handled effectively, therefore be to solve one of requisite auxiliary agents such as COLOR FASTNESS problem that in the dope dyeing production process, occur.
Come out beginning at color-fixing agent, the dicyandiamide class color fixing agent Y of always continuing to use dicyandiamide and formaldehyde condensation dyes the color-fixing agent of cotton and silk as direct dyes, ACID DYES, but since color fixing agent Y after arrangement, have very high free formaldehyde content (＞200mg/kg), can cause chafing with after its fixation treatment, even generation ulcer, thereby causing people's attention, nowadays strict restriction is used.
The appearance of environment-friendly type aldehyde-free colour stabilizer has solved this type of pollution problem.This series products has obvious effects to cotton, the activity of polyester-cotton blend, the COLOR FASTNESS of direct dyeing, but to poor effect behind the acid dyeings such as the dark fabric of spy and silk, polyamide fibre, nylon.
Direct dyes, ACID DYES and REACTIVE DYES can reduce the affinity between dyestuff and cellulose fibre because of containing hydrophilic radical when meeting water.Adopt cationic compound to make color-fixing agent, can form insoluble salt, can prevent that like this dyestuff from coming off and hydrolysis from fabric because of ionization, thereby improve COLOR FASTNESS with fiber and dyestuff.The colloid dielectric that also can regard water-soluble dye as a kind of anion active is met water generation dissociation, generates the anion of high molecular, and it can carry out ion-exchange with cationic surfactant on fiber, generate slightly soluble or water-fast salt:
D-SO
3 -·Na
++(F-NH
3)
+·Cl-→D-SO
3 -·NH
3 ++NaCl
If the design color-fixing agent is a high polymer, can make it in the fabric face film forming after the heat-treated, cover caducous dyestuff; Can also be the polymer that contains active group or cross-linked structure according to structure of cotton fiber characteristics design color-fixing agent simultaneously, make color-fixing agent be adsorbed on fabric face firmly together with dyestuff; Thereby improve the dye fastness index of each side effectively.
Therefore, prior art awaits improving and development.
Summary of the invention
Problem to be solved by this invention is to provide a kind of organosilicon modified polyurethane hyperchromic improver and preparation method thereof, to obtain a kind of dyefastness that does not have the aldehyde environmental protection, can improve dyestuff simultaneously again, improves the hyperchromic improver of fabric property.
In order to solve the problems of the technologies described above, technical scheme of the present invention is as follows:
A kind of organosilicon modified polyurethane hyperchromic improver, it is the water-based emulsion of solid content 20%～45%, range of viscosities 800～30000cp; Constitute in the organic silicon modified polyurethane of emulsion, contain polyethers, vulcabond and siloxane structure unit, the mol ratio of described vulcabond structure and polyether structure is 2～4: 1; The mol ratio of described vulcabond structure and siloxane structure is 5～25: 1.
The preparation method of described organosilicon modified polyurethane hyperchromic improver, it may further comprise the steps:
A, be 1000 to 2000 polyether compound blend with two or more molecular weight, add the excess diisocyanate compounds, the mol ratio that makes isocyano and hydroxyl is 2～4: 1, reaction generation end group is-and the performed polymer of NCO;
B, add 5%～25% of weight with diisocyanate compound described in the step a and add the siloxanes coupling agent and carry out organic-silicon-modified;
C, add the hydrophily chain extender with 8%～10% of reinforced gross weight among step a, the b and carry out chain extending reaction;
D, measure remaining isocyano, add end-capping reagent, carry out end capping reaction according to the equimolar amounts of measured value;
The equimolar epoxychloropropane of e, adding and chain extender carries out quaternized;
Described step a-e carries out in water-less environment;
F, with organic acid for adjusting pH value to 6～7, add deionized water and carry out emulsification and obtain emulsion.
Described preparation method, wherein, described step a-e also carries out under nitrogen protection.Also can be at other inert gases, as carrying out under the protection of argon gas.
Described preparation method, wherein, described polyether compound is the blend of polyethylene glycol and polypropylene glycol, and the weight ratio of preferred polyethylene glycol and polypropylene glycol is 1: 20～20: 1, and especially preferred its weight ratio is 1: 1～20: 1.But be not limited to these 2 kinds, can also use for example polytetramethylene glycol, ethylene glycol propylene glycol copolymers etc.Also can use polyol ethers such as polyether-tribasic alcohol as required.
Described preparation method, wherein, described diisocyanate compound is toluene di-isocyanate(TDI), isophorone diisocyanate or hexamethylene diisocyanate.
Described preparation method, wherein, described siloxanes coupling agent is gamma-aminopropyl-triethoxy-silane or γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane or N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane also can be the siloxanes coupling agents of other band amino or epoxy radicals.
Described preparation method, wherein, described hydrophily chain extender is N methyldiethanol amine, diethylenetriamine.Also can use other hydrophily chain extenders, diglycol for example, anhydrous ethylenediamine waits the micromolecular compound that contains two hydroxyls or two amino.
Described preparation method, wherein, the remaining isocyano of described measurement can use the di-n-butylamine method.
Described preparation method, wherein, described end-capping reagent is preferably a kind of in diethyl malonate, antifebrin, the sodium hydrogensulfite, also can use other end-capping reagents such as ethyl acetoacetate, phenol to stop polymerisation.The deblocking temperature of these end-capping reagents is lower, can increase the deblocking degree at a certain temperature, promptly increase can with fiber-reactive-NCO, thereby strengthen COLOR FASTNESS.
Described preparation method, wherein, epoxychloropropane is used for quaternized, to form quaternary ammonium salt cationic.
Described preparation method, wherein, described organic acid is trichloroacetic acid or acetate.Also can be other organic acids such as formic acid, propionic acid.
Contain a large amount of cation groups in the organosilicon modified polyurethane hyperchromic improver of employing method for preparing, can form insoluble color lake with the anionic group reaction in the dyestuff, thereby improve the WASHING COLOR FASTNESS of fabric; Also contain hydroxyl, epoxy radicals isoreactivity group can react with fiber, forms cross-linked structure; Molecular weight is bigger, can form fine and close film in fabric surface and cover dye coatings, has further strengthened the combine fastness of dyestuff with fiber; In addition, the siloxane structure of introducing, its silicon oxygen bond can form cross-linking system at the cloth surface hydrolysis, thereby improves aqueous polyurethane at the film forming on the cloth surface, can give fabric softer feel, and the water proofing property of fabric is also made moderate progress.
The present invention can increase substantially the washing fastness of fabric by the organosilicon modified polyurethane hyperchromic improver of such scheme preparation, crock fastness, and soaping fastnesses etc. reach colour fixation, provide fabric softer feel simultaneously.And it is a medium with water, no hazardous solvent volatilization in the process of film-forming on fabric, and composite green chemical standard and auxiliary chemicals environmental requirement are compared with traditional color-fixing agent, safer, more environmental protection.
Description of drawings
Fig. 1 is an organosilicon modified polyurethane hyperchromic improver preparation method's of the present invention flow chart;
Fig. 2 is the infrared spectrogram of the organosilicon modified polyurethane hyperchromic improver of the embodiment of the invention 1 preparation;
Fig. 3 is the infrared spectrogram of the organosilicon modified polyurethane hyperchromic improver of the embodiment of the invention 2 preparations;
Fig. 4 is the infrared spectrogram of the organosilicon modified polyurethane hyperchromic improver of the embodiment of the invention 3 preparations.
The specific embodiment
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is described in further detail.
The invention provides a kind of organosilicon modified polyurethane hyperchromic improver and preparation method thereof, being prepared according to flow process as shown in Figure 1, is that polyethylene glycol and polypropylene glycol, diisocyanate compound are that the situation of isophorone diisocyanate (IPDI) is that example describes below with the polyethers:
(1) prepolymerization reaction of polyurethane
The blend that in the reaction vessel of drying, adds cetomacrogol 1000 (being PEG1000) and polypropylene glycol 1000 (being PPG1000), under 100 ℃～120 ℃ conditions, vacuumize decompression distillation 2～3 hours to remove moisture and small molecular weight impurity, be cooled to 60 ℃～70 ℃ then, (NCO): (OH)=2～4: 1 ratio adds isoflurane chalcone diisocyanate (IPDI) to n, and maintains the temperature at this interval reaction 3～4 hours with the mol ratio n of isocyano and hydroxyl.
(2) organic-silicon-modified reaction
The required siloxanes coupling agent of modification is dissolved in the acetone with respect to 5%～25% of diisocyanate cpd weight, be made into organosilicon-acetone soln of about 30%, under 30 ℃～40 ℃ conditions, be added drop-wise in the above-mentioned reaction system, and reacted 1～1.5 hour.
(3) chain extending reaction
The chain extender that will be equivalent to 5%～20% (can preferred 8%～10%) of above-mentioned reinforced gross mass dilutes with small amount of acetone, is added dropwise in above-mentioned (2) reaction system, and temperature is controlled between 40 ℃～60 ℃, reacts 1～2 hour.
(4) end capping reaction
Above-mentioned polymer temperature is controlled at 70 ℃～80 ℃, adopts the di-n-butylamine method to measure the residue isocyano, and the end-capping reagent-acetone soln of dropping and residue-NCO equimolar amounts, reacted 2 hours.
(5) quaterisation
Keep 60 ℃～75 ℃ of temperature in above-mentioned system, dropping was carried out quaterisation 3 hours with the epoxychloropropane of chain extender equimolar amounts then.
(6) emulsion reaction
Regulate pH to neutral (pH=6～7) with trichloroacetic acid, at room temperature add appropriate amount of deionized water and be emulsified into emulsion.
(7) desolventize
Under the decompression distillation condition, remove the residual acetone in the above-mentioned emulsion, obtain organosilicon modified polyurethane hyperchromic improver.
All carry out under nitrogen protection above-mentioned steps (1)～(5), and corresponding steps in an embodiment has nitrogen protection too.
The blend ratio of poly-ethanol and poly-propyl alcohol can be regulated on demand, as poly-ethanol only being arranged or only having poly-propyl alcohol also can obtain organosilicon modified polyurethane hyperchromic improver emulsion of the present invention, the weight ratio of preferred polyethylene glycol and polypropylene glycol is 1: 20～20: 1, and especially preferred its weight ratio is 1: 1～20: 1.
Operable end-capping reagent and chain extender are as previously mentioned.
The emulsion solid content 20%～45% that obtains, range of viscosities 800～30000cp.Emulsion is dry at a lower temperature, measure its infrared spectrum, can determine functional group in the product according to the infrared signature peak in the spectrogram.
Below among each embodiment, the commodity in use name is represented the title of each raw material, described commodity are all on sale in market, concrete trade name contrasts as follows with standard name:
PEG: polyethylene glycol
PPG: polypropylene glycol
HDI: hexamethylene diisocyanate
TDI: toluene di-isocyanate(TDI)
IPDI: isophorone diisocyanate
The MDEA:N-methyl diethanolamine
KH550: gamma-aminopropyl-triethoxy-silane
KH560: γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane
HD121:N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane
The preparation of organosilicon modified polyurethane hyperchromic improver
(1) prepolymerization reaction of polyurethane
In the reaction vessel of drying, add 20g PEG1000 (cetomacrogol 1000) and 5g PPG 1000 (polypropylene glycol 1000), under 100 ℃～120 ℃ conditions, vacuumized decompression distillation 2～3 hours, to remove moisture and small molecular weight impurity wherein, be cooled to 60 ℃～70 ℃ then, add 16.7g IPDI (isoflurane chalcone diisocyanate), and maintain the temperature at this interval reaction 3～4 hours.
(2) organic-silicon-modified reaction
2.8g KH550 (gamma-aminopropyl-triethoxy-silane) is dissolved in the acetone, is made into organosilicon-acetone soln of about 30%, under 30 ℃～40 ℃ conditions, be added drop-wise in the reaction system of above-mentioned (1) insulation reaction 1～1.5 hour.
(3) chain extending reaction
2.4g MDEA is diluted with small amount of acetone, be added drop-wise in the reaction system of above-mentioned (2), temperature is controlled between 40 ℃～60 ℃, reacts 1～2 hour.Too fast as the viscosity increase, then add acetone in right amount and reduce viscosity.
(4) end capping reaction
Above-mentioned polymer temperature is reduced to 40 ℃～50 ℃, adopt the di-n-butylamine method to measure the residue isocyano, and drip the 2g diethyl malonate, reacted 2 hours.
(5) quaterisation
In the reaction system of above-mentioned (4), drip the 1.8g epoxychloropropane, be warming up to 60 ℃～70 ℃ reactions 3 hours.
(6) emulsion reaction
Regulate pH value to 5～6 with trichloroacetic acid, at room temperature add the 60g deionized water and be emulsified into emulsion.
(7) desolventize
Under the decompression distillation condition, remove the residual acetone in the above-mentioned emulsion, obtain organosilicon modified polyurethane hyperchromic improver.
Emulsion is placed 105 ℃ of baking ovens,, measure its infrared spectrum, obtain infrared spectrum as shown in Figure 2: at 3459cm through oven dry in 4 hours
-1Place's part is the stretching vibration absworption peak of the association OH of C-OH; 1715cm
-1The place is the stretching vibration peak of C=O in the ester group; 2916cm
-1Near be the stretching vibration peak of saturated C-H, illustrate to contain in the polymer on the long carbochain-CH
2-,-CH
31108cm
-1Near be the characteristic absorption peak of Si-O-Si, illustrate and contain the siloxanes segment in the polymer.
The preparation of organosilicon modified polyurethane hyperchromic improver
(1) prepolymerization reaction of polyurethane
In the reaction vessel of drying, add 20g PEG1000 and 2.5g PPG1000, under 100 ℃～120 ℃ conditions, vacuumized decompression distillation 2～3 hours, to remove moisture and small molecular weight impurity, be cooled to 60 ℃～70 ℃ then, add 6.5g TDI, and maintain the temperature at this interval reaction 3～4 hours.
(2) organic-silicon-modified reaction
1.9g KH560 is dissolved in the acetone, is made into organosilicon-acetone soln of about 30%, under 30 ℃～40 ℃ conditions, be added drop-wise in the reaction system of above-mentioned (1) insulation reaction 1～1.5 hour.
(3) chain extending reaction
1.6g MDEA is diluted with small amount of acetone, be added drop-wise in the reaction system of above-mentioned (2), temperature is controlled between 40 ℃～60 ℃, reacts 1～2 hour.Too fast as the viscosity increase, then add acetone in right amount and reduce viscosity.
(4) end capping reaction
Above-mentioned polymer temperature is reduced to 40 ℃～50 ℃, adopt the di-n-butylamine method to measure the residue isocyano, and the 1.2g antifebrin is dissolved in the reaction system that proper amount of acetone adds above-mentioned (3), reacted 2 hours.
(5) quaterisation
In the reaction system of above-mentioned (4), drip the 1.2g epoxychloropropane, be warming up to 60 ℃～70 ℃ reactions 3 hours.
(6) emulsion reaction
Regulate pH value to 5～6 with trichloroacetic acid, at room temperature add the 50g deionized water and be emulsified into emulsion.
(7) desolventize
Under the decompression distillation condition, remove the residual acetone in the above-mentioned emulsion, obtain organosilicon modified polyurethane hyperchromic improver.
Emulsion is placed 105 ℃ of baking ovens,, measure its infrared spectrum, obtain infrared spectrum as shown in Figure 3: 1732cm through oven dry in 4 hours
-1The place is the stretching vibration peak of C=O in the ester group; 2959～2874cm
-1Near be the stretching vibration peak of saturated C-H, illustrate to contain in the polymer on the long carbochain-CH
2-,-CH
31117cm
-1Near be the characteristic absorption peak of Si-O-Si, illustrate and contain the siloxanes segment in the polymer; 1454cm
-1, 1398cm
-1, 702cm
-1Near absorption is arranged, illustrate and contain phenyl ring in the polymer.
Embodiment 3
The preparation of organosilicon modified polyurethane hyperchromic improver
(1) prepolymerization reaction of polyurethane
In the reaction vessel of drying, add 20gPEG1000 and 5gPPG1000, under 100 ℃～120 ℃ conditions, vacuumize decompression distillation 2～3 hours to remove moisture and small molecular weight impurity, be cooled to 60 ℃～70 ℃ then, add 12.6gHDI, and maintain the temperature at this interval reaction 3～4 hours.
(2) organic-silicon-modified reaction
2.48gHD121 is dissolved in the acetone, is made into organosilicon-acetone soln of about 30%, under 30 ℃～40 ℃ conditions, be added drop-wise in the above-mentioned reaction system insulation reaction 1～1.5 hour.
(3) chain extending reaction
The 2.1g diethylenetriamine is diluted with small amount of acetone, be added dropwise in above-mentioned (2) reaction system, temperature is controlled between 40 ℃～60 ℃, reacts 1～2 hour.Too fast as the viscosity increase, then add the acetone viscosity reduction in right amount.
(4) end capping reaction
Above-mentioned polymer temperature is reduced to 40 ℃～50 ℃, adopt the di-n-butylamine method to measure the residue isocyano, and 2.0g sodium hydrogensulfite and the blend of 0.2g sodium sulfite are dissolved in the double solvents of isopropyl alcohol and water, add above-mentioned (3) system, reacted 2 hours.
(5) quaterisation
In above-mentioned (4) reaction system, drip the 1.8g epoxychloropropane, be warming up to 60 ℃～70 ℃ reactions 3 hours.
(6) emulsion reaction
Regulate pH to 5～6 with trichloroacetic acid, at room temperature add the 60g deionized water and be emulsified into emulsion.
(7) desolventize
Under the decompression distillation condition, remove the residual acetone in the above-mentioned emulsion, obtain organosilicon modified polyurethane hyperchromic improver.
Emulsion is placed 105 ℃ of baking ovens,, measure its infrared spectrum, obtain infrared spectrum as shown in Figure 4: 3332cm through oven dry in 4 hours
-1Place's part is the stretching vibration absworption peak of the association OH of C-OH; 1717cm
-1The place is the stretching vibration peak of C=O in the ester group; 2928cm
-1Near the stretching vibration peak of very strong saturated C-H is arranged, illustrate to contain in the polymer on the long carbochain-CH
2-,-CH
31107cm
-1Near be the characteristic absorption peak of Si-O-Si, illustrate and contain the siloxanes segment in the polymer.
Embodiment 4
The contrast of organosilicon modified polyurethane hyperchromic improver of the present invention and other color-fixing agent colour fixations
Hyperchromic improver emulsion of the present invention is used for dye fixing, with other two kinds of commercially available color-fixing agent (sample A: color fixing agent Y; Sample B is available from Zhejiang company) compare, obtain result such as following table 1.
As shown in table 1, by more every index as seen, sample A has formaldehyde residual, the organosilicon modified polyurethane hyperchromic improver that do, fastness to wet rubbing and soap staining fastness and feel all prepares not as the embodiment of the invention 1～3; Though sample B is formaldehydeless residual, fastness to wet rubbing is slightly poor, and feel is also harder; Compare with sample A, B, the hyperchromic improver of the embodiment of the invention 1～3 preparation has more superior performance.
The contrast of table 1 color-fixing agent effect
* annotate: 1, dried fastness to wet rubbing test: GB/T3920-1997
2, soaping fastness test: GB/T3921.1-1997
Should be understood that, for those of ordinary skills, can be improved according to the above description or conversion, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Claims (10)
1. an organosilicon modified polyurethane hyperchromic improver is characterized in that, it is the water-based emulsion of solid content 20%～45%, range of viscosities 800～30000cp; Constitute in the organic silicon modified polyurethane of emulsion, contain polyethers, vulcabond and siloxane structure unit, the mol ratio of described vulcabond structure and polyether structure is 2～4: 1; The mol ratio of described vulcabond structure and siloxane structure is 5～25: 1.
2. the preparation method of the organosilicon modified polyurethane hyperchromic improver of a claim 1, it may further comprise the steps:
A, be to add the excess diisocyanate compounds in 1000 to 2000 the polyether compound to one or more molecular weight, the mol ratio that makes isocyano and hydroxyl is 2～4: 1, reaction generation end group is-and the performed polymer of NCO;
B, add 5%～25% of weight with diisocyanate compound described in the step a and add the siloxanes coupling agent and carry out organic-silicon-modified;
C, add the hydrophily chain extender with reinforced gross weight 8%～10% among step a, the b and carry out chain extending reaction;
D, measure remaining isocyano, add end-capping reagent, carry out end capping reaction according to the equimolar amounts of measured value;
The equimolar epoxychloropropane of e, adding and chain extender carries out quaternized;
Described step a-e carries out in water-less environment;
F, with organic acid for adjusting pH value to 6～7, add deionized water and carry out emulsification and obtain emulsion.
3. preparation method as claimed in claim 2, wherein, described step a-e also carries out under nitrogen protection.
4. preparation method as claimed in claim 2, wherein, described polyether compound is a polyether Glycols.
5. preparation method as claimed in claim 4, wherein, described polyether Glycols is the blend of polyethylene glycol and polypropylene glycol.
6. preparation method as claimed in claim 2, wherein, described diisocyanate compound is toluene di-isocyanate(TDI), isophorone diisocyanate or hexamethylene diisocyanate.
7. preparation method as claimed in claim 2, wherein, described siloxanes coupling agent is gamma-aminopropyl-triethoxy-silane or γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane or N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane.
8. preparation method as claimed in claim 2, wherein, described hydrophily chain extender is N methyldiethanol amine or diethylenetriamine.
9. preparation method as claimed in claim 2, wherein, described end-capping reagent is to be selected from a kind of in diethyl malonate, antifebrin, the sodium hydrogensulfite.
10. preparation method as claimed in claim 2, wherein, described organic acid is trichloroacetic acid or acetate.
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