CN101735163B - Hyperbranched compound used as water repellent and synthetic method thereof - Google Patents
Hyperbranched compound used as water repellent and synthetic method thereof Download PDFInfo
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Abstract
The invention discloses a hyperbranched compound used as a water repellent and a synthetic method thereof. The hyperbranched compound has a tripolycyanamide nucleus as shown in the figure, wherein, R1 is an alkane group with 1-16 carbon atoms, and R2 is an alkane group with 12-16 carbon atoms; N is 2 or 3; and A is as specified in a specification. The hyperbranched compound is synthesized from cyanuric chloride through two or three steps. The hyperbranched compound has favorable water-repellent effect, and can be used as a fabric waterproof finishing agent. Since no formaldehyde exists in a synthetic reaction process and products, the hyperbranched compound has great advantages in environmental protection.
Description
Technical field
The present invention relates to a kind of hyperbranched compound and compound method thereof as water-resisting agent, relate in particular to a kind of hyperbranched compound and compound method thereof with trimeric cyanamide nuclear, this hyperbranched compound can be used as the waterproofing that water-resisting agent is applied to fabric.
Background technology
At present, both at home and abroad fabric waterproofing agent mainly contains silicone based, organic fluorine class, senior aliphatic hydrocarbon modified aminoresin class etc.With respect to silicone based and organic fluorine class, senior aliphatic hydrocarbon modified aminoresin class has excellent washing fastness and lower price, and therefore bigger advantage is arranged.This type of water-resisting agent is applied to textile industry already, like the Phobotex FTC series of Switzerland Ciba-Geigy company.Domesticly also get many achievements aspect such water-resisting agent development, just developing NB-501, SGF, DFT type water-resisting agent in the nineties in last century.They are to carry out two kinds of components of modification synthetic by hexamethylolmelamine ethyl etherate and Triple Pressed Stearic Acid, stearyl alcohol and trolamine etc. with the differing mol ratio; Piece together mixed forming with paraffin and emulsifying agent; Its water resistance has reached the level of Phobotex FTC, part index number even higher.Wherein, the industriallization of DFT type water-resisting agent is applied to wash, the WATER REPELLENT of fabric such as cotton.But owing to there is formaldehyde to produce in the building-up process of these series product, the meeting removing residue formaldehyde is unfavorable to HUMAN HEALTH in the fabric after the arrangement.The continuous reinforcement of Along with people's environmental consciousness, its market outlook are not expected.
Therefore, prior art awaits improving and development.
Summary of the invention
Problem to be solved by this invention is to provide a kind of hyperbranched compound and compound method thereof as water-resisting agent, to solve the formaldehyde residue problem of existing fabric waterproofing agent.
In order to solve the problems of the technologies described above, technical scheme of the present invention is following:
A kind of hyperbranched compound as water-resisting agent, it has following structure:
Wherein, R
1Alkyl, R for carbonatoms 1-16
2Alkyl for carbonatoms 12-16;
Described hyperbranched compound is characterized in that, said R
1=CH
3, C
2H
5, C
12H
25, C
14H
29Or C
16H
33Said R
2=C
12H
25, C
14H
29Or C
16H
33
Described hyperbranched compound is characterized in that, said R
1And R
2Be the straight-chain paraffin base.
A kind of compound method that is used as the hyperbranched compound of water-resisting agent, it may further comprise the steps:
A1: 1 part of cyanuric chloride, 2 parts of secondary amine and salt of wormwood are mixed in polar aprotic solvent, and after reacting 1-4 hour respectively under-20 ℃~0 ℃, 0 ℃~40 ℃, refluxing makes its sufficient reacting successively;
B1: in reaction solution, add 1/2 part of quadrol or 1 again, 4-tetramethylenediamine or 1, any in 6-hexanediamine or the piperazine 90-100 ℃ of fully reaction, removes and desolvates, and washing is filtered to neutral;
Wherein, said umber is mol ratio;
At least the alkyl that connects a carbonatoms 12-16 on the amido of said secondary amine.
The said compound method that comprises step a1, b1, wherein, the temperature of reacting successively described in the said step a1 is respectively 0 ℃, 25 ℃.
The said compound method that comprises step a1, b1, wherein, said polar aprotic solvent is an acetonitrile.
A kind of compound method that is used as the hyperbranched compound of water-resisting agent may further comprise the steps:
A2: 1 part of cyanuric chloride, 2 parts of secondary amine and salt of wormwood are mixed in polar aprotic solvent, successively-20 ℃~0 ℃, 0 ℃~40 ℃ react 1-4 hour respectively after, refluxing makes its sufficient reacting; B2: in reaction solution, add excessive quadrol again, and, remove and desolvate and excessive quadrol 90-100 ℃ of fully reaction; C2: in remaining solid, add 1/3 part of cyanuric chloride, salt of wormwood and polar aprotic solvent, successively-20 ℃~0 ℃, 0 ℃~40 ℃ react 1-4 hour respectively after, be back to raw material and disappear, remove and desolvate, washing is to neutral and filter; Wherein, said umber is mol ratio; At least the alkyl that connects a carbonatoms 12-16 on the amido of said secondary amine.
The said compound method that comprises step a2-c2, wherein, the temperature of reacting successively described in said step a2 and the c2 is respectively 0 ℃, 25 ℃.
The said compound method that comprises step a2-c2, wherein, said polar aprotic solvent is an acetonitrile.
Adopt such scheme, the present invention is through simple synthetic a kind of hyperbranched compound that can be used as water-resisting agent that prepared.Because the compound method of this hyperbranched compound does not all have formaldehyde in its reaction raw materials, solvent, centre and the final product, therefore, when this hyperbranched compound is used for the fabric waterproof arrangement, compare with existing common water-resisting agent, have the huge advantage in the environmental protection.
Description of drawings
Fig. 1 is the proton nmr spectra of the embodiment of the invention 1 synthetic compound;
Fig. 2 is the carbon-13 nmr spectra of the embodiment of the invention 1 synthetic compound;
Fig. 3 is the proton nmr spectra of the embodiment of the invention 2 synthetic compounds;
Fig. 4 is the carbon-13 nmr spectra of the embodiment of the invention 2 synthetic compounds;
Fig. 5 is the proton nmr spectra of the embodiment of the invention 3 synthetic compounds;
Fig. 6 is the carbon-13 nmr spectra of the embodiment of the invention 3 synthetic compounds;
Fig. 7 is the proton nmr spectra of the embodiment of the invention 4 synthetic compounds;
Fig. 8 is the carbon-13 nmr spectra of the embodiment of the invention 4 synthetic compounds;
Embodiment
Through embodiment, hyperbranched compound and the compound method thereof as water-resisting agent of the present invention done further explain below.
Hyperbranched compound of the present invention has 2-4 trimeric cyanamide nuclear, and structure is following:
Wherein, R
1Alkyl, R for carbonatoms 1-16
2Alkyl for carbonatoms 12-16; Said alkyl can be a straight chain, also can have side chain, preferred straight-chain paraffin; Preferred R
1Be CH
3, C
2H
5, C
12H
25, C
14H
29, C
16H
33R
2Be C
12H
25, C
14H
29, C
16H
33
Because this compound has the alkane chain of at least 4 carbonatoms 12-16, therefore have excellent hydrophobic property, can be used as water-resisting agent, like fabric waterproofing agent, waterproofing agent for leather, waterproof agent for building etc.In the present invention preferably with it as fabric waterproofing agent.
Synthetic above-mentioned hyperbranched compound, solvent is a polar aprotic solvent, for example acetonitrile, acetone, methyl-sulphoxide etc. preferably use acetonitrile.
When synthesizing this hyperbranched compound; At first; Cyanuric chloride and secondary amine are mixed in polar aprotic solvent with salt of wormwood with 1: 2 mol ratio, at first-20 ℃~0 ℃ (preferred 0 ℃) reaction 1-4 hour, then 0 ℃~40 ℃ (preferred room temperatures; Promptly about 25 ℃) reacted 1-4 hour, fully reflux.This step is step a.In step a, amido has replaced 2 chlorine on the cyanuric chloride.
Wherein, connect the alkyl of a carbonatoms 12-16 on the amido of said secondary amine at least, preferred said alkyl is the straight-chain paraffin base.Said secondary amine can be R
1NHR
2Return time can be 2 days.
After step a, if directly control ratio, like 1/2 mol ratio with former cyanuric chloride, add 1 or 1,4-tetramethylenediamine or 1,6-hexanediamine or piperazine are again in 90 ℃-100 ℃ fully reactions (for example 3 days).Remove through ways such as decompressions afterwards and desolvate, with the residue washing to neutral (pH=7) and filter, the compound in the time of can obtaining n=2 of the present invention.Referring to formula (I).
Formula (I)
Wherein, R
1And R
2As previously mentioned,
If after step a, add excessive quadrol, and fully react (for example 1 day) at 90-100 ℃, remove through methods such as decompressions and desolvate and excessive quadrol; Afterwards, add again a certain amount of cyanuric chloride (as former cyanuric chloride 1/3), salt of wormwood and polar aprotic solvent, at first-20 ℃~0 ℃ (preferred 0 ℃) reaction 1-4 hour; Then 0 ℃-40 ℃ (preferred room temperatures; Promptly about 25 ℃) reacted 1-4 hour down, be back to raw material and disappear, remove and desolvate; Washing is to neutral and filter, the compound in the time of then can obtaining n=3 of the present invention.Referring to formula (II).
Formula (II)
Wherein, R
1And R
2As previously mentioned,
According to above-mentioned compound method, obtain white solid product at last.In order further to understand the character of institute's synthetic compound, measure its fusing point through melting point detector, and utilize thin layer chromatography in ETHYLE ACETATE and sherwood oil blended developping agent, to measure its polarity, confirm the ratio of developping agent with this, thus purified product.For the structural formula of definite product, the proton nmr spectra of measurement purified product (
1H NMR, measuring condition are CDCl
3, 400MHz, 25 ℃) and the carbon spectrum (
13C NMR, measuring condition are CDCl
3, 125MHz, 25 ℃), can confirm to have synthesized compound thus with structure according to the invention.
Make water-resisting agent in order to verify that whether this compound is suitable for, this compound is carried out composite, reference standard AATCC22-2001: its water repellency is tested in spray test (Spray Test).Test result shows that compound of the present invention has good water repellency, can use water-resisting agent as textile finishing.
Below, be example during with embodiment 1,2 respectively to n=2, the situation of m=1 and m=3 is described; With embodiment 3 is example during to n=2,
Situation describe; With embodiment 4 is that example is described the situation of n=3; Among the said embodiment, R
1And R
2Be C
16H
33(palmityl/hexadecyl).
Embodiment 1
N, N '-two-(four-(hexadecyl)-melamine-based)-quadrol and compound method thereof
Step a1-1: 18.4g cyanuric chloride, 93.1g hexadecyl secondary amine and 41.4g salt of wormwood are added in the flask, add the 500ml acetonitrile again, stirring reaction 1 hour under 0 ℃, room temperature respectively successively, refluxed 2 days in the back;
Step b1-1: in flask, add the 3.0g anhydrous ethylenediamine, mixed solution is heated to about 100 ℃ reacted 3 days, the solvent of reaction solution is removed in decompression, and washing is extremely neutral, filtration;
Dry afterwards, obtain white solid 91.1g.Productive rate is 88%.
Measure the character of this compound.Its fusing point (mp) is 38~40 ℃.Measure its polarity, in the developping agent of ethyl acetate/petroleum ether=1: 50, climb plate, obtain the value of relatively moving R
f=0.3, thus product is separated purification.
The proton nmr spectra of measurement purified product (
1H NMR, CDCl
3, 400MHz, 25 ℃), obtain the spectrogram shown in accompanying drawing 1.Wherein, δ (ppm): 5.11 (br s, 2H), 3.43 (br s, 20H), 1.57 (br s, 16H), 1.27 (br s, 208H), 0.88 (t, 24H, J=6.8Hz).The carbon-13 nmr spectra of measurement product (
13C NMR, CDCl
3, 125MHz, 25 ℃), obtain the spectrogram shown in accompanying drawing 2.Wherein, δ (ppm): 166.38,164.90,47.16,41.30,32.65,31.91,29.72,29.66,29.36,28.88,28.23,26.88,22.66,14.06.Through analyzing carbon spectrum and hydrogen spectrum, can confirm that product has aforesaid structural formula, promptly successfully synthesize N, N '-two-(four-(hexadecyl)-melamine-based)-quadrol.
In following examples, if no special instructions, the measuring condition of proton nmr spectra/carbon spectrum is identical with present embodiment.
Whether be suitable for and make water-resisting agent for detecting it, the hyperbranched compound that present embodiment is obtained, reference standard AATCC22-2001: its water repellency is tested in spray test (Spray Test) if carrying out composite.Detected result reaches 100 fens.
Embodiment 2
N, N '-two-(four-(hexadecyl)-melamine-based)-1,6-hexanediamine and compound method thereof
Step a1-2: 18.4g cyanuric chloride, 93.1g hexadecyl secondary amine and 41.4g salt of wormwood are added in the flask, add the 500ml acetonitrile again, stirring reaction 4 hours under 0 ℃, room temperature successively, refluxed 2 days in the back;
Step b1-2: in flask, add 1 of 5.8g, the 6-hexanediamine was heated to about 100 ℃ reaction 3 days with mixed solution, and the solvent of reaction solution is removed in decompression, and washing is filtered to neutral;
Dry afterwards, obtain white solid 85.2g.Productive rate is 82%.
Measure the character of this compound.Measure its fusing point (mp), be 41-43 ℃.Measure the polarity of product, in the developping agent of ethyl acetate/petroleum ether=1: 50, climb plate, plate than upper/lower positions and hangover, the value of relatively moving R
f=0.3; Ethyl acetate/petroleum ether=1: 20, add 1% volume ratio ammoniacal liquor (NH simultaneously
3H
2O) climb plate in the developping agent, measure the value of relatively moving R
f=0.5, thus product is separated purification.
The proton nmr spectra of measurement product (
1H NMR), obtain spectrogram shown in accompanying drawing 3.Wherein, δ (ppm): 4.61 (t, 2H, J=5.6Hz), 3.43 (br s, 16H), 3.30 (q, 4H, J=6.4Hz), 1.74 (m, 4H), 1.56 (br s, 20H), 1.27 (br s, 208H), 0.88 (t, 24H, J=6.6Hz).The carbon-13 nmr spectra of measurement product (
13C NMR), obtain spectrogram shown in accompanying drawing 4.Wherein, δ (ppm): 166.25,164.98,47.12,40.75,38.74,31.94,30.18,29.74,29.69,29.38,28.28,27.38,27.17,22.70,14.11.Through analyzing carbon spectrum and hydrogen spectrum, can confirm that product has aforesaid structural formula, promptly successfully synthesize N, N '-two-(four-(hexadecyl)-melamine-based)-1, the 6-hexanediamine.
Whether be suitable for and make water-resisting agent for detecting it, the hyperbranched compound that present embodiment is obtained, reference standard AATCC22-2001: its water repellency is tested in spray test (Spray Test) if carrying out composite.Detected result reaches 100 fens.
Embodiment 3
N, N '-two-(four-(hexadecyl)-melamine-based)-piperazine and compound method thereof
Step a1-3: 18.4g cyanuric chloride, 93.1g hexadecyl secondary amine and 41.4g salt of wormwood are added in the flask, add the 500ml acetonitrile again, stirring reaction 3 hours under 0 ℃, room temperature successively, refluxed 2 days in the back;
Step b1-3: in flask, add the Piperazine anhydrous of 4.3g, mixed solution is heated to about 100 ℃ reacted 3 days, the solvent of reaction solution is removed in decompression, and washing is extremely neutral, filtration;
Dry afterwards, obtain white waxy solid 84.0g.Productive rate is 80%.
Measure the character of this compound.Measuring its fusing point (mp), is 52~54 ℃.Measure its polarity, in the developping agent of ethyl acetate/petroleum ether=1: 50, climb plate, need expansion cylinder is uncovered, and repeat to climb plate 2-3 time, measure the value of relatively moving R
f=0.3, thus product is separated purification.
The proton nmr spectra of measurement purified product (
1H NMR), obtain spectrogram shown in accompanying drawing 5.Wherein, δ (ppm): 3.78 (s, 8H), 3.48 (br s, 16H), 1.59 (br s, 16H), 1.29 (br s, 208H), 0.89 (t, 24H, J=6.8Hz).The carbon-13 nmr spectra of measurement product (
13C NMR), obtain spectrogram shown in accompanying drawing 6.Wherein, δ (ppm): 165.44,165.10,47.26,43.12,31.97,29.87,29.77,29.62,29.41,28.34,28.21,27.44,27.21,22.72,14.12.Through analyzing carbon spectrum and hydrogen spectrum, can confirm that product has aforesaid structural formula, promptly successfully synthesize N, N '-two-(four-(hexadecyl)-melamine-based)-piperazine.
Whether be suitable for and make water-resisting agent for detecting it, the hyperbranched compound that present embodiment is obtained, reference standard AATCC22-2001: its water repellency is tested in spray test (Spray Test) if carrying out composite.Detected result reaches 100 fens.
N, N ', N "-three-(four-(hexadecyl)-melamine-based ethyl)-trimeric cyanamide and compound method thereof
Step a2-1: 18.4g cyanuric chloride, 93.1g hexadecyl secondary amine and 41.4g salt of wormwood are added in the flask, add the 500ml acetonitrile again, under 0 ℃, room temperature stirring reaction 1-4 hour successively, refluxed 2 days in the back;
Step b2-1: in flask, add the 30.0g anhydrous ethylenediamine, mixed solution is heated to 90-100 ℃ of reaction 1 day, the solvent of reaction solution and excessive quadrol are removed in decompression;
Step c2-1: in remaining solid, add 6.2g cyanuric chloride, 13.8g salt of wormwood and 500ml acetonitrile, under 0 ℃, room temperature stirring reaction 1-4 hour successively, after be back to raw material and disappear, the reaction solution solvent is removed in decompression, washing is to neutral and filter;
Dry afterwards, obtain white powder 87.2g.Productive rate is 82%.
Measure the character of this compound.Measuring its fusing point (mp), is 38~40 ℃.Measure the polarity of product, ethyl acetate/petroleum ether=1: 15, add 1% volume ratio ammoniacal liquor (NH simultaneously
3H
2O) climb plate in the developping agent, measure the value of relatively moving R
f=0.3, thus product is separated purification.
The proton nmr spectra of measurement product (
1H NMR), obtain spectrogram shown in accompanying drawing 7.Wherein, δ (ppm): 5.06 (m, 6H), 3.53 (br s, 12H), 3.44 (br s, 24H), 1.57 (br s, 24H), 1.27 (br s, 312H), 0.88 (t, 36H, J=7.6Hz).The carbon-13 nmr spectra of measurement product (
13CNMR), obtain spectrogram shown in accompanying drawing 8.Wherein, δ (ppm): 164.84,47.28,31.94,29.87,29.75,29.69,29.38,28.30,27.43,27.21,22.69,14.09.Through analyzing carbon spectrum and hydrogen spectrum, can confirm that product has aforesaid structural formula, promptly successfully synthesize N, N ', N "-three-(four-(hexadecyl)-melamine-based ethyl)-trimeric cyanamide.
Whether be suitable for and make water-resisting agent for detecting it, the hyperbranched compound that present embodiment is obtained, reference standard AATCC22-2001: its water repellency is tested in spray test (Spray Test) if carrying out composite.Detected result reaches 100 fens.
Should be understood that, concerning those of ordinary skills, can improve or conversion, and all these improvement and conversion all should belong to the protection domain of accompanying claims of the present invention according to above-mentioned explanation.
Claims (2)
1. hyperbranched compound as water-resisting agent is characterized in that having following structure:
2. the compound method of the hyperbranched compound as water-resisting agent as claimed in claim 1 is characterized in that:
Step a2: 18.4g cyanuric chloride, 93.1g hexadecyl secondary amine and 41.4g salt of wormwood are added in the flask, add the 500ml acetonitrile again, under 0 ℃, room temperature stirring reaction 1-4 hour successively, refluxed 2 days in the back;
Step b2: in flask, add the 30.0g anhydrous ethylenediamine, mixed solution is heated to 90-100 ℃ of reaction 1 day, the solvent of reaction solution and excessive quadrol are removed in decompression;
Step c2: in remaining solid, add 6.2g cyanuric chloride, 13.8g salt of wormwood and 500ml acetonitrile, under 0 ℃, room temperature stirring reaction 1-4 hour successively, after be back to raw material and disappear, the reaction solution solvent is removed in decompression, washing is to neutral and filter;
Dry afterwards, obtain white powder 87.2g, productive rate is 82%.
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CN102965925A (en) * | 2012-11-20 | 2013-03-13 | 吴江市新丝源纺织有限公司 | Waterproof coating fabric |
CN102941721A (en) * | 2012-11-20 | 2013-02-27 | 吴江市新丝源纺织有限公司 | Waterproof antibiosis fabric |
CN102941716A (en) * | 2012-11-20 | 2013-02-27 | 吴江市新丝源纺织有限公司 | Water-proof wear-resistant coating fabric |
US10405543B2 (en) * | 2016-10-31 | 2019-09-10 | Rohm And Haas Company | Microcapsule compositions and the method of their release |
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