CN103030811B - Amino modified polysiloxane copolymer and application thereof - Google Patents
Amino modified polysiloxane copolymer and application thereof Download PDFInfo
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Abstract
The invention relates to an amino modified polysiloxane copolymer with a modified group amino on a polysiloxane copolymer backbone and a application thereof. The amino modified polysiloxane copolymer comprises a polyamine chain segment, a polyether chain segment and a polysiloxane chain segment, wherein the viscosity of the amino modified polysiloxane copolymer is 38, 591-10, 272 cp (25 DEG C). The amino modified polysiloxane copolymer provided by the invention can be used as organic pigment (in particular heterocyclic or azo organic pigments) dispersants.
Description
Technical field
The present invention relates to a kind of amino modified polysiloxane multipolymer and uses thereof, particularly relate to amino amino modified polysiloxane multipolymer being positioned at polysiloxane copolymer main chain of a kind of modified group and uses thereof.
Background technology
Because the thermo-sensitivity of pigment, tinting strength are good, so be widely used in coating, plastics, ink and other daily necessities.Different from dyestuff, pigment is a kind of trickle saccharoid, and in the media such as coating, its particle is in suspended state, and form solid-liquid dispersion, this dispersion system is thermodynamically unstable.Form larger particle because the existence of Intermolecular Forces easily flocks together between granules of pigments, therefore in actual applications, effectively must disperse pigment.
The main chain of organosilicon macromolecule is made up of the siloxane bond of softness; can fully stretch in media as well; can ensure to form enough thick protective layer at pigment particle surface; on its chain, introduce some anchoring groups simultaneously, by reactive forces such as ionic linkage, covalent linkage, hydrogen bond and Van der Waals forces, be tightly adsorbed on granules of pigments; prevent dispersion agent desorption; simultaneously due to Existential Space obstacle between adsorption layer, particle can be made mutually to flick, thus realize the stable dispersion of particle in non-aqueous media.In addition, silicoorganic compound also have lower surface tension, when organosilicon is adsorbed on pigment particle surface, can reduce the surface tension of particle and medium key, thus make pigment have better wettability and mobility.
It is amino modified silicoorganic compound that GB1088207A discloses a kind of side chain, although this compound can play good dissemination to pigment, to the color and luster decrease to some degree of pigment, therefore its application receives and limit significantly.
Given this, develop a kind of can dispersing organic pigment and there is good dispersion effect, the pigment dyestuff dispersion agent of the coloured light and tinting strength that do not affect again pigment dyestuff becomes this area technical problem in the urgent need to address.
Summary of the invention
The present inventor is through extensive and deep research, design and prepare the amino modified polysiloxane multipolymer that a kind of modified group amino is positioned at polysiloxane copolymer main chain, after tested, this amino modified polysiloxane multipolymer can dispersing organic pigment and have good dispersion effect, does not affect again coloured light and the tinting strength of pigment dyestuff.
Therefore, one object of the present invention is, provides a kind of modified group amino to be positioned at the amino modified polysiloxane multipolymer of polysiloxane copolymer main chain.
Amino modified polysiloxane multipolymer of the present invention, is obtained by the preparation method comprised the steps:
(1) having under platinum catalyst and rare gas element existent condition, in 100 DEG C ~ 120 DEG C reactions, intermediate A is obtained by hydrogen containing siloxane (shown in formula I compound), allyl polyether compound (shown in formula II compound) and allyl group epoxy compounds (formula III or formula IV shown in compound);
(2) under rare gas element existence condition, reacted in 75 DEG C ~ 90 DEG C by intermediate A and secondary amine (shown in formula V compound), obtain target compound (amino modified polysiloxane multipolymer of the present invention), the viscosity of the target product obtained is 38,591cp ~ 10,272cp(25 DEG C);
Wherein, n is the integer of 1 ~ 12,000, and a is the integer of 2 ~ 200, and b is the integer of 0 ~ 100, R
1and R
2independently be selected from: C
1~ C
20straight or branched alkyl or the C replaced by group shown in hydroxyl or formula VI
1~ C
4straight or branched alkyl,
In formula VI, R
3and R
4independently be selected from: hydrogen (H) or C
1~ C
4straight or branched alkyl.
Another object of the present invention is, discloses a kind of purposes of above-mentioned amino modified polysiloxane multipolymer, that is, described amino modified polysiloxane multipolymer is as the application of pigment dyestuff (particularly heterocycle or azo pigment dyestuff) dispersion agent.
In described amino modified polysiloxane multipolymer provided by the invention: polyamine segment makes pigment anchoring section, interact be adsorbed on pigment dyestuff by hydrogen bond, coordinate bond, soda acid; And polyether segment is as solvent chain, pigment flocculation and precipitation (length that can adjust polyether segment as required makes silicoorganic compound and matrix have good consistency) in storage process can be prevented; Polysiloxane segment not only can make described organosilicon polymer have good wettability, greatly can also improve degree of mobilization and the tinting strength (especially Be very effective in the dispersion of pigment dyestuff) of pigment dyestuff.
Embodiment
In the present invention's preferred technical scheme, the mol ratio of hydrogen containing siloxane (shown in formula I compound), allyl polyether compound (shown in formula II compound) and allyl group epoxy compounds (formula III or formula IV shown in compound) is 1:(0.6 ~ 1.2): (1.0 ~ 1.6), secondary amine compound (shown in formula V compound) is 1:(0.8 ~ 1.6 with the mol ratio of intermediate product A);
Best technical scheme is: shown in compound shown in compound shown in formula I, formula II and formula III or formula IV, compound mole ratio is 1:0.8:1.4, and the mol ratio of compound and intermediate product A shown in formula V is 1:0.8.
In another preferred technical scheme of the present invention, R
1and R
2independently be selected from: C
2~ C
18straight or branched alkyl or the C replaced by group shown in hydroxyl or formula VI
1~ C
4straight or branched alkyl,
In formula VI, R
3and R
4independently be selected from: H or C
1~ C
4straight or branched alkyl;
Preferred technical scheme is further: R
1and R
2independently be selected from: ethyl (CH
3cH
2-), 2-hydroxy-ethyl (OHCH
2cH
2-), Octadecane base (CH
3(CH
2)
16cH
2-) or 3-N, N-dimethylammo-propyl (CH
3)
2n (CH
2)
2cH
2-) middle a kind of.
In another optimal technical scheme of the present invention, platinum catalyst used is Platinic chloride (H
2ptCl
66H
2o).
In addition, the method for the described amino modified polysiloxane multipolymer of preparation provided by the present invention, specifically comprises the steps:
(1) by hydrogen containing siloxane (shown in formula I compound), allyl polyether compound (shown in formula II compound), allyl group epoxy compounds (formula III or formula IV shown in compound) and organic solvent (as benzene or alkyl substituted benzene (as toluene or dimethylbenzene etc.)) are placed in ratio as described in above and answer bottle, under rare gas element (as nitrogen etc.) protection, stir and be heated to 100 DEG C ~ 120 DEG C, add the aqueous isopropanol (consumption is preferably the 0.05wt% ~ 0.10wt% of raw material total mass) that concentration is the Platinic chloride of 1.0wt% again, react 6 ~ 8 hours, underpressure distillation, steaming desolventizes and unreacted raw material, residue is intermediate A,
(2) intermediate A, secondary amine compound (shown in formula V compound) and organic solvent are placed in another reactor, under rare gas element (as nitrogen etc.) protection, stir and be heated to 75 DEG C ~ 90 DEG C, and keep 10 little of 24 hours in this state, cooling, steam except organic solvent, residue is target product (amino modified polysiloxane multipolymer of the present invention);
Wherein, described organic solvent is that aliphatic alcohol is or/and the compound of ether.Preferred organic solvent is selected from: one or two or more kinds mixture (containing two kinds) in Virahol, isopropylcarbinol, propyl carbinol, ethylene glycol monobutyl ether or butyl.
Amino modified polysiloxane multipolymer provided by the invention has the following advantages:
(1) there is good consistency, can well be dissolved in dispersion medium, and energy quick humidification organic pigment particles, pigment dyestuff milling time can be shortened;
(2) there is good bonding force, the lipophilicity of pigment dyestuff, gloss and flocculation resistance can be improved;
(3) (can directly use close to colourless) of light color and the tinting strength of raw material itself can not be reduced.
Below by embodiment, the present invention is further illustrated, and its object is only better understand content of the present invention but not limit the scope of the invention.
Embodiment 1
120g is held containing hydrogen silicone oil (n=8000), 12.5g allyl polyether (a=200, b=100), 190g toluene adds in there-necked flask, stirring heating is warming up to 100 DEG C, dropwise add the aqueous isopropanol (massfraction is 1.0%) of Platinic chloride, react and add 1.4g glycidyl allyl ether after 3 hours, continuation reaction is reduced pressure after 5 hours and is steamed solvent and low-boiling-point substance, adds proper amount of methanol washing, leave standstill removing impurity phase, obtain intermediate A-1.Gel chromatography (GPC) test data of intermediate A-1 is as shown in table 1 below.
IR (pressed disc method): 3449.59 (s, υ-OH), 2869.86 (s, υ CH
2-O), 1457.30 (w, δ-CH
2-), 1109.32 (s, υ-CH
2-O-CH
2-), 1101.94,1020.47 (s ， υ – Si-O-Si-), 1260.95,803.95 (s, δ Si-CH
3), 855.17 (w, δ-CH
2oCH
2-).
Table 1
Embodiment 2
120g is held containing hydrogen silicone oil (n=12; 000), 8.4g allyl polyether (a=200; b=100), 160g toluene adds in there-necked flask; under nitrogen protection, stirring heating is warming up to 100 DEG C, adds the aqueous isopropanol (massfraction is 1.0%) of Platinic chloride; react and to add 2.8g methyl propenoic acid glycidyl ether after 3 hours and continue reaction and reduce pressure after 5 hours and steam solvent and low-boiling-point substance; add proper amount of methanol washing, leave standstill removing impurity phase, obtain intermediate A-2.The GPC test data of intermediate A-2 is as shown in table 2 below
IR (pressed disc method): 3449.59 (s, υ-OH), 2889.06 (s, υ CH
2-O), 1790.03 (s, υ-C=O), 1453.70 (w, δ-CH
2-), 1102.39 (s, υ-CH
2-O-CH
2-), 1101.91,1021.21 (s, υ-Si-O-Si-), 1262.42,803.95 (s, δ Si-CH
3), 855.73 (w, δ-CH
2oCH
2-).
Table 2
Embodiment 3
120g is held containing hydrogen silicone oil (n=12,000), 8g allyl polyether (a=150, b=0), 120g toluene adds in there-necked flask, stirring heating is warming up to 100 DEG C, adds the aqueous isopropanol (massfraction is 1.0%) of Platinic chloride, reacts and add 1.4g glycidyl allyl ether after 3 hours, continuation reaction is reduced pressure after 5 hours and is steamed solvent and low-boiling-point substance, add proper amount of methanol washing, leave standstill removing impurity phase, obtain intermediate A-3.The GPC test data of intermediate A-3 is as shown in table 3 below
IR (pressed disc method): 3450.41 (s, υ-OH), 2867.80 (s, υ CH
2-O), 1458.55 (w, δ-CH
2-), 1109.72 (s, υ-CH
2-O-CH
2-), 1020.29 (s ， υ – Si-O-Si-), 1261.25,804.16 (s, δ Si-CH
3), 856.38 (w, δ-CH
2oCH
2-)
GPC test data is as shown in the table
Table 3
Embodiment 4
80g intermediate A-1 and 35g Virahol are joined in there-necked flask, drips 12.9gN under nitrogen protection, N-dimethyl-1,3-propylene diamine, control temperature of reaction at 65 DEG C, react 10 hours, obtain amino modified polysiloxane copolymer A.
IR (pressed disc method): 3449.59 (s, υ-OH), 3200.16 (s, υ-NH-), 2968.83 (s, υ-CH
2-), 2870.37 (s, υ C-H), 2786.32 (s, υ N-CH3), 1453.46 (w, δ-CH
2-), 1101.94,1020.47 (s ， υ – Si-O-Si-), 1260.95,803.95 (s, δ Si-CH
3).
Embodiment 5
80g intermediate A-1 and 35g Virahol are joined in there-necked flask, drips 4.2g diethylamine under nitrogen protection, control temperature of reaction at 65 DEG C, react 10 hours, obtain amino modified polysiloxane multipolymer B.
IR (pressed disc method): 3450.41 (s, υ-OH), 2968.28 (s, υ-CH
2-), 2871.42 (s, υ C-H), 2784.83 (s, υ N-CH3), 1454.95 (w, δ-CH
2-), 1101.36,1020.29 (s, υ-Si-O-Si-), 1261.25,804.16 (s, δ Si-CH
3).
Embodiment 6
80g intermediate A-1 and 50g Virahol are joined in there-necked flask, drips the two stearylamine of 28.6g under nitrogen protection, control temperature of reaction at 65 DEG C, react 24 hours, obtain amino modified polysiloxane multipolymer C.
IR (pressed disc method): 3449.93 (s, υ-OH), 2969.14 (s, υ-CH
2-), 2870.86 (s, υ C-H), 2843.54 (s, δ-CH3), 1455.13 (w, δ-CH
2-), 1102.28,1021.36 (s, υ-Si-O-Si-), 1261.87,803.96 (s, δ Si-CH
3).
Embodiment 7
80g intermediate A-1 and 40g Virahol are joined in there-necked flask, drips 16.4gN under nitrogen protection, N-tetramethyl-dipropylenetriamine, control temperature of reaction at 65 DEG C, react 12 hours, obtain amino modified polysiloxane multipolymer D.
IR (pressed disc method): 3450.11 (s, υ-OH), 3202.18 (s, υ-NH-), 2969.86 (s, υ-CH
2-), 2871.36 (s, υ C-H), 1455.99 (w, δ-CH
2-), 1102.58,1021.30 (s ， υ – Si-O-Si-), 1262.30,803.92 (s, δ Si-CH
3).
Embodiment 8
80g intermediate A-2 and 50g Virahol are joined in there-necked flask, drips the two stearylamine of 20.1g under nitrogen protection, control temperature of reaction at 65 DEG C, react 24 hours, obtain amino modified polysiloxane multipolymer E.
IR (pressed disc method): 3451.13 (s, υ-OH), 2969.26 (s, υ-CH2-), 2871.96 (s, υ C-H), 2874.03 (s, δ-CH3), 1790.03 (s, υ-C=O), 1454.99 (w, δ-CH2-), 1102.69,1021.39 (s ， υ – Si-O-Si-), 1263.47,803.92 (s, δ Si-CH3)
Embodiment 9
80g intermediate A-3 and 50g Virahol are joined in there-necked flask, drips the two stearylamine of 25.0g under nitrogen protection, control temperature of reaction at 65 DEG C, react 12 hours, obtain amino modified polysiloxane multipolymer F.
IR (pressed disc method): 3451.13 (s, υ-OH), 2969.26 (s, υ-CH2-), 2871.96 (s, υ C-H), 2874.03 (s, δ-CH3), 1454.99 (w, δ-CH2-), 1102.69,1021.39 (s υ – Si-O-Si-), 1263.47,803.92 (s, δ Si-CH3)
Embodiment 10
The performance test of amino modified polysiloxane copolymer A ~ F:
(1) dispersion stabilization test:
0.1 part of amino modified polysiloxane copolymer A ~ F and sample dispersion agent W-252 is dissolved in 10 parts of ethanol respectively, under violent stirring, add 0.1 part of PR122(technical grade respectively, Zhejiang lily chemical industry is controlled interest group) dry powder, ultrasonic 30 minutes, leave standstill 24 hours, 1cm place below respective liquid level, draw 0.5ml liquid respectively, be diluted to 5ml respectively, with UV755B spectrophotometric determination transmitance T, with the transmitance numerical evaluation dispersion stabilization (DE% of maximum absorption wave strong point, DE%=(1-T) × 100%), result is shown in table 4
Table 4
* in table 4, W-525 provides commodity silicone oil dispersion agent sample (lower with) for Zhejiang flower of Greenish Lily company
(2) dispersion particle diameters test:
0.1 part of amino modified polysiloxane copolymer A ~ F and sample dispersion agent W-252 is dissolved in 10 parts of ethanol respectively, under violent stirring, add 0.1 part of PR122(technical grade respectively, Zhejiang lily chemical industry is controlled interest group) dry powder, after ultrasonic 30min, dispersion particle diameters Mastersizer2000 particle size analyzer measures.Result is as shown in table 5:
Table 5
(3) pigment coloured light detects:
On seven blocks of sheet glass, respectively take standard chalk 2g respectively, then take the mill base of 50mg amino modified polysiloxane copolymer A ~ F and W-252 as dispersion agent respectively, fully mix well with inking cutter respectively, scrape sample.Aberration evaluation is carried out with color measurement instrument.Result is as shown in table 6:
Table 6
Data declaration in table 6: painted dynamics represents the size of sample relative to standard tinting strength; DH
*=H
sample-H
standard specimen, represent the aberration of color, represent the hue difference of sample and standard specimen, judge that conclusion is as follows qualitatively:
Red pigment DH
*> 0 sample is more yellow than standard specimen
DH
*< 0 sample is more blue than standard specimen
Yellow ultramarine DH
*> 0 sample is greener than standard specimen
DH
*< 0 sample is redder than standard specimen
Veridian DH
*> 0 sample is more blue than standard specimen
DH
*< 0 sample is more yellow than standard specimen
Blue pigments DH
*> 0 sample is redder than standard specimen
DH
*< 0 sample is greener than standard specimen
DL
*=L
sample-L
standard specimen, represent the depth or deep or light of color
DL
*> 0 sample is than standard specimen look lighter
DL
*< 0 sample is than standard specimen look denseer
DC
*=C
sample-C
standard specimen, represent that the saturation ratio of color is poor
DC
*> 0 sample is higher than standard specimen saturation ratio, bright-coloured
DC
*< 0 sample is lower than standard specimen saturation ratio, not bright-coloured
From test result, through the pigment of amino modified polysiloxane copolymer A ~ F process, its tinting strength is respectively 106.33%, 109.3%, 105.49%, 103.62%, 104.21%, 103.6%, be all improved to some extent (untreated pigment dynamics is 100%) than undressed pigment; And select the pigment of commodity W-252 process, its tinting strength declines to some extent, and fall is 5.31%.
In addition, through the DC of the pigment of amino modified polysiloxane multipolymer process
*value be all greater than zero, illustrate that pigment vividness all increases, and through the pigment of W-252 process vividness decline (DC
*value be less than zero).
Claims (9)
1. an amino modified polysiloxane multipolymer, is obtained by the preparation method comprised the steps:
(1) having under platinum catalyst and rare gas element existent condition, by compound shown in compound shown in compound shown in formula I, formula II and formula III or formula IV in 100 DEG C ~ 120 DEG C reactions, obtaining intermediate A;
(2) under rare gas element existence condition, reacted in 75 DEG C ~ 90 DEG C by compound shown in intermediate A and formula V, obtain target compound;
When 25 DEG C, the viscosity of the target product obtained is 38,591cp ~ 10,272cp;
Wherein, n is the integer of 1 ~ 12,000, and a is the integer of 2 ~ 200, and b is the integer of 0 ~ 100, R
1and R
2independently be selected from: C
1~ C
20straight or branched alkyl or the C replaced by group shown in hydroxyl or formula VI
1~ C
4straight or branched alkyl,
In formula VI, R
3and R
4independently be selected from: H or C
1~ C
4straight or branched alkyl.
2. amino modified polysiloxane multipolymer as claimed in claim 1, is characterized in that, wherein R
1and R
2independently be selected from: C
2~ C
18straight or branched alkyl or the C replaced by group shown in hydroxyl or formula VI
1~ C
4straight or branched alkyl.
3. amino modified polysiloxane multipolymer as claimed in claim 2, is characterized in that, wherein R
1and R
2independently be selected from: ethyl, 2-hydroxy-ethyl, a kind of in Octadecane base or 3-N, N-dimethylammo-propyl.
4. amino modified polysiloxane multipolymer as claimed in claim 1, it is characterized in that, wherein said platinum catalyst is H
2ptCl
66H
2o.
5. as the amino modified polysiloxane multipolymer in Claims 1 to 4 as described in any one, it is characterized in that, shown in compound shown in compound, formula II shown in its Chinese style I and formula III or formula IV, compound mole ratio is 1:(0.6 ~ 1.2): (1.6 ~ 1.0), formula V is 1:(0.8 ~ 1.6 with the mol ratio of intermediate product A).
6. amino modified polysiloxane multipolymer as claimed in claim 5, is characterized in that, wherein little of 8 hours in 100 DEG C ~ 120 DEG C reactions 6 by compound shown in compound shown in compound shown in formula I, formula II and formula III or formula IV, obtains intermediate A.
7. amino modified polysiloxane multipolymer as claimed in claim 5, is characterized in that, wherein reacts 10 little of 24 hours by compound shown in intermediate A and formula V in 75 DEG C ~ 90 DEG C.
8. if the amino modified polysiloxane multipolymer in claim 1 ~ 7 as described in any one is as the application of pigment dyestuff dispersion agent.
9. apply as claimed in claim 8, it is characterized in that, wherein said pigment dyestuff is heterocycle or azo pigment dyestuff.
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| 氨基聚醚改性有机硅表面活性剂的合成研究;张鹏等;《吉林化工学院学报》;20110115;第28卷(第1期);1-4 * |
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Address after: 311222 Linjiang Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Applicant after: Lily Group Co., Ltd. Applicant after: East China University of Science and Technology Address before: 311222 Linjiang Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Applicant before: Lily Group Co., Ltd. Applicant before: East China University of Science and Technology |
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