CN103657518B - A kind of Nonionic organosilicon surfactant and preparation method thereof - Google Patents
A kind of Nonionic organosilicon surfactant and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of Nonionic organosilicon surfactant, this surfactant has elongated the spacing of siloxanes and hydrophilic radical, effectively can improve the hydrolytic resistance of siloxanes.Nonionic organosilicon surfactant of the present invention, it has the structure of following structural formula I:
in structural formula I: the value of m is 1 ~ 100; The value of n is 0 ~ 20.R is for having following structure single functionality polyether ester
in single functionality polyether ester structure, R
1for CH
3, CH
3cH
2, CH
3cH
2cH
2, CH (CH
3)
2or CH
3cH
2cH
2cH
2structure; R
2it is the moieties of alpha-olefine acid or unrighted acid; The value of x is 20 ~ 120; The value of y is 0 ~ 75.
Description
Technical field
The present invention relates to a kind of surfactant and preparation method thereof, more specifically to a kind of Nonionic organosilicon surfactant and preparation method thereof.
Background technology
Surfactant is so a kind of material, it can reduce the surface tension (or interfacial tension) of solvent widely when addition is little, change interface state, thus produce a series of effects such as wetting, emulsification, foaming and solubilising, to reach the requirement of practical application.The organic silicon surfactant with special performance is the up-and-coming youngster of surfactant field.The hydrophobic grouping of organosilicone surfactant material is made up of alkylsiloxane main chain, and its hydrophobic performance is more excellent than carbochain, in the solution of comparable sodium, has lower surface tension, has the surface-active stronger than carbochain hydrocarbon-surfactant.At present, along with the deep exploitation to such material, and application constantly expands, the purposes of organic silicon surfactant has covered the industrial circles such as coating, weaving, fiber, plastics, machinery, daily use chemicals, agricultural chemicals, oil, and its status in surface active material also shows especially day by day.
The hydrophobic part structural formula of Nonionic organosilicon surfactant is Me
3siO (Me
2siO)
m, its low surface tension and weak intermolecular force are all relevant with its structure.Main chain is similar to SiO
2inorganic structure, therefore have excellent high-and low-temperature resistance and stability.Silicon atom is in tetrahedral center in compound, in this tetrahedral structure, in two methyl plane perpendicular to silicon oxygen bond place, Si – O key bond distance is larger, to such an extent as to three hydrogen atoms on two nonpolar methyl can strut and make it to have good hydrophobicity as umbrella, methyl and with hydrogen in rotating freely, need larger space, also adjacent large intermolecular distance is just added, reduce the active force between them, siloxanes is made to be easy to sprawl on interface, the Another reason that dimethicone easily spreads in polar surfaces is that the oxygen atom on main chain can form hydrogen bond structure with polar molecule or atomic group, add the active force of main chain and polar surfaces, make it spread and become monolayer, present the configuration of distinctive " extended chain ".
The hydrophilic segment of organic silicon surfactant is made up of the polyethers of good hydrophilic property, and representative configurations formula is:
–RO(C
2H
4O)
x(C
3H
6O)
yR’。
With most of nonionic surfactants seemingly, there is general Poisson distribution scope, be made up of multiple hydrophilic ethyoxyl (EO) unit, its hydrophily can by embedding, polarity be little, propoxyl group (PO) unit of oleophylic regulates, and surfactant HLB value is then controlled by total substitution value.Prior art is all adopt anion open-loop method addition ethylene oxide or propylene oxide with unsaturated monohydric alcohol, then adopts Si―H addition reaction method synthesizing polyether modified organic silicon copolymer.Typical technology path, as Chinese patent ZL200710025596.0 and ZL200710025597.5, is all to obtain polyether-modified Nonionic organosilicon surfactant after allyl alcohol polyether and silicon oil of low hydrogen content Si―H addition reaction.Wherein allyl alcohol polyether end is hydroxyl, for a change the hydrophily of polyether structure, provides the surface-active that some is special, needs to carry out end-blocking to hydroxyl, replaces hydrogen atom with alkyl such as methyl.Such as Chinese patent ZL200710025596.0 describes a kind of end-sealed type organic silicon modified by polyether surfactant, and Chinese patent ZL200810021953.0 then describes a kind of method of polyethers end-blocking.But all in all, the closed-end technology of polyethers is complicated, and primary hydroxyl ending ratio is higher, and secondary hydroxyl ending ratio is lower.
Summary of the invention
The object of the invention is to solve the above-mentioned existing deficiency that exists in the art and problem, provide a kind of Nonionic organosilicon surfactant, this surfactant has elongated the spacing of siloxanes and hydrophilic radical, effectively can improve the hydrolytic resistance of siloxanes.
Another object of the present invention is to provide a kind of preparation method of this Nonionic organosilicon surfactant.
The present invention is achieved through the following technical solutions:
Nonionic organosilicon surfactant of the present invention, it has the structure of following structural formula I:
Wherein in structural formula I: the value of m is 1 ~ 100; The value of n is 0 ~ 20.
R is for having following structure single functionality polyether ester
In single functionality polyether ester structure, R
1for CH
3, CH
3cH
2, CH
3cH
2cH
2, CH (CH
3)
2or CH
3cH
2cH
2cH
2structure; R
2it is the moieties of alpha-olefine acid or unrighted acid; The value of x is 20 ~ 120; The value of y is 0 ~ 75; Double bond wherein in alpha-olefine acid or unrighted acid and the hydrogen atom of polysiloxanes carry out Si―H addition reaction, the hydrophilic structure of hydrosilylation is double bond containing polyether ester, unsaturated polyetherester can be obtained by unsaturated carboxylic acid and single functionality polyethers esterification, also can be obtained by ester exchange reaction with unsaturated carboxylic methyl ester and single functionality polyethers, unsaturated carboxylic acid is the derivative unrighted acid of alpha-olefine acid or crude vegetal.
The preparation method of Nonionic organosilicon surfactant of the present invention, it comprises the following steps:
Take monohydric alcohol as initiator, add oxirane and expoxy propane in the reactor, under catalyst a exists, Stress control at≤0.4MPa, react 4 ~ 6 hours under 100 ~ 130 DEG C of conditions, obtain single functionality polyethers;
Alpha-olefine acid or unrighted acid and single functionality polyethers are added reactor, under catalyst b exists, reacts 4 ~ 6 hours under 160 ~ 220 DEG C of conditions, obtain double bond containing polyether ester; Or the methyl esters of alpha-olefine acid or the methyl esters of unrighted acid and single functionality polyethers are added reactor, and under catalyst b exists, react 1 ~ 3 hour under 170 ~ 200 DEG C of conditions, methanol removal, obtains double bond containing polyether ester;
With octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and HMDO or tetramethyl disiloxane for raw material is under catalyst c effect, react 5 ~ 7 hours under reaction temperature is 60 ~ 90 DEG C of conditions, obtain polysiloxanes;
Adding reactor by reacting the double bond containing polyether ester of acquisition, polysiloxanes, Pt catalyst and solvent above, under normal pressure, being heated to 60 ~ 120 DEG C of reactions 2 ~ 10 hours, open reflux condensing tube cooling water while adding thermal response to ensure solvent refluxing; After reaction terminates, first carry out air-distillation and carry out decompression distillation again, lower the temperature after solvent has been steamed, obtain Nonionic organosilicon surfactant.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme is described alpha-olefine acid is acrylic acid, 3-butenoic acid, 4-penetenoic acid, 5-hexenoic acid, 6-heptenoic acid, 7-octenoic acid, 8-nonenoic acid, 9-decylenic acid or 10 hendecenoic acid; Described unrighted acid is oleic acid, erucic acid, linoleic acid or leukotrienes.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be the methyl esters of described alpha-olefine acid is methyl acrylate, 3-butenoic acid methyl esters, 4-amylene-4 acid methyl ester, 5-hexenoic acid methyl ester, 6-heptenoic acid methyl esters, 7-octenoic acid methyl esters, 8-nonenoic acid methyl esters, 9-decenoate or 10 hendecenoic acid methyl esters; The methyl esters of described unrighted acid is methyl oleate, methyl erucate, methyl linoleate or methyl linolenate.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be described monohydric alcohol is methyl alcohol, ethanol, normal propyl alcohol, isopropyl alcohol or n-butanol.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be described catalyst a is base catalyst, and its consumption is 0.1 ~ 0.5% of oxirane and expoxy propane gross mass; Preferred KOH or NaOH of base catalyst.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be described catalyst b is inorganic acid or organotin, and consumption is 0.03 ~ 0.5% of reactant quality; Inorganic acid is preferably sulfuric acid, and organotin is preferably stannous oxalate, Mono-n-butyltin and derivative thereof or Dibutyltin oxide and derivative thereof.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be described catalyst c is lewis acid, and consumption is 0.1 ~ 3% of quality of material used; Lewis acid is preferably sulfuric acid.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be 3 ~ 50ppm and 30 ~ 90% that described Pt catalyst and solvent load are respectively material gross mass, and described solvent is toluene or dimethylbenzene.
The preparation method of Nonionic organosilicon surfactant of the present invention, its further technical scheme can also be that in described containing hydrogen silicone oil, the mass fraction of hydrogen is 1.55 ~ 1.66%.
The hydrophilic structure of hydrosilylation of the present invention is double bond containing polyether ester.Unsaturated polyetherester can be obtained by unsaturated carboxylic acid and single functionality polyethers esterification, also can obtain with unsaturated carboxylic methyl ester and single functionality polyether ester exchange reaction.Unsaturated carboxylic acid can select alpha-olefine acid, also can select the derivative unrighted acid of crude vegetal.
Compared with prior art the invention has the beneficial effects as follows:
The present invention has expanded the raw material of hydrosilylation, and alpha-olefine acid or vegetable oil derivatives unrighted acid can be used to prepare organic silicon surfactant.The end of polyethers is by alkyl-blocked, and ending ratio 100%.Preparation method's reaction condition is gentle, and raw material is easy to get.
Detailed description of the invention
Embodiment 1
A) add methyl alcohol 8.0g, oxirane 165g and expoxy propane 58g in the reactor, 1.1gKOH catalyst exist under, pressure≤0.4MPa, reaction temperature be 110 DEG C of conditions under reaction 4 hours, obtain single functionality polyethers (I);
B) by 8.0g acrylic acid and the above-mentioned single functionality polyethers (I) of 103g under 0.1% sulfuric acid catalyst condition, in 210 DEG C of reactions 3 hours, obtain double bond containing polyether ester (II);
C) octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and tetramethyl disiloxane are reacted 5 hours in 80 DEG C under effect of sulfuric acid, obtain polysiloxanes (III), wherein octamethylcy-clotetrasiloxane, mol ratio between containing hydrogen silicone oil (hydrogen content 1.58%) and tetramethyl disiloxane are 10:0.11:1;
D) polyether ester (II) 120g obtained by above two-step reaction, polysiloxanes (III) 67g add reactor, under normal pressure, be heated to 60 ~ 120 DEG C of reactions 7 hours at 30ppmPt catalyst and 80g toluene solvant, open reflux condensing tube cooling water while adding thermal response to ensure solvent refluxing.After reaction terminates, first carry out air-distillation and carry out decompression distillation again, lower the temperature after solvent has been steamed, obtain polyether ester modified polyorganosiloxane surfactant, its structural formula is:
Wherein R is:
Embodiment 2
A) add ethanol 46g, oxirane 792g in the reactor, 4.0gKOH catalyst exist under, pressure≤0.4MPa, reaction temperature be 110 DEG C of conditions under reaction 4 hours, obtain single functionality polyethers (I);
B) by 40.0g oleic acid and the above-mentioned single functionality polyethers (I) of 120g under 0.1% Mono-n-butyltin catalysts conditions, in 210 DEG C of reactions 3 hours, obtain double bond containing polyether ester (II);
C) octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and HMDO are reacted 5 hours in 80 DEG C under effect of sulfuric acid, obtain polysiloxanes (III), wherein octamethylcy-clotetrasiloxane, mol ratio between containing hydrogen silicone oil (hydrogen content 1.59%) and HMDO are 8:0.11:1;
D) polyether ester (II) 112g obtained by above two-step reaction, polysiloxanes (III) 68g add reactor, under normal pressure, be heated to 60 ~ 120 DEG C of reactions 7 hours at 20ppmPt catalyst and 80g toluene solvant, open reflux condensing tube cooling water while adding thermal response to ensure solvent refluxing.After reaction terminates, first carry out air-distillation and carry out decompression distillation again, lower the temperature after solvent has been steamed, obtain polyether ester modified polyorganosiloxane surfactant, its structural formula is:
Wherein R is:
Embodiment 3
A) add n-butanol 9.8g, oxirane 330g, expoxy propane 96g in the reactor, 1.5gKOH catalyst exist under, pressure≤0.4MPa, reaction temperature be 110 DEG C of conditions under reaction 4 hours, obtain single functionality polyethers (I);
B) by 20.0g10-methyl undecylenate and the above-mentioned single functionality polyethers (I) of 265g under 0.1% Dibutyltin oxide catalysts conditions, in 200 DEG C of reactions 3 hours, obtain double bond containing polyether ester (II);
C) octamethylcy-clotetrasiloxane and tetramethyl disiloxane are reacted 5 hours in 80 DEG C under effect of sulfuric acid, obtain polysiloxanes (III), the mol ratio wherein between octamethylcy-clotetrasiloxane and tetramethyl disiloxane is 5:1;
D) polyether ester (II) 282g obtained by above two-step reaction, polysiloxanes (III) 80g add reactor, under normal pressure, be heated to 60 ~ 120 DEG C of reactions 7 hours at 20ppmPt catalyst and 70g toluene solvant, open reflux condensing tube cooling water while adding thermal response to ensure solvent refluxing.After reaction terminates, first carry out air-distillation and carry out decompression distillation again, lower the temperature after solvent has been steamed, obtain polyether ester modified polyorganosiloxane surfactant, its structural formula is:
Wherein R is:
Embodiment 4
A) add methyl alcohol 4.0g, oxirane 550g, expoxy propane 7.3g in the reactor, 3.5gKOH catalyst exist under, pressure≤0.4MPa, reaction temperature be 110 DEG C of conditions under reaction 5 hours, obtain single functionality polyethers (I);
B) by 5.0g3-M Cr and the above-mentioned single functionality polyethers (I) of 310g under 0.1% Mono-n-butyltin catalysts conditions, in 200 DEG C of reactions 3 hours, obtain double bond containing polyether ester (II);
C) octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and HMDO are reacted 5 hours in 80 DEG C under effect of sulfuric acid, obtain polysiloxanes (III), wherein octamethylcy-clotetrasiloxane, mol ratio between containing hydrogen silicone oil (hydrogen content 1.59%) and HMDO are 18:0.09:1;
D) polyether ester (II) 63g obtained by above two-step reaction, polysiloxanes (III) 18g add reactor, under normal pressure, be heated to 60 ~ 120 DEG C of reactions 6 hours at 20ppmPt catalyst and 50g toluene solvant, open reflux condensing tube cooling water while adding thermal response to ensure solvent refluxing.After reaction terminates, first carry out air-distillation and carry out decompression distillation again, lower the temperature after solvent has been steamed, obtain polyether ester modified polyorganosiloxane surfactant, its structural formula is:
Wherein R is:
Claims (9)
1. a preparation method for Nonionic organosilicon surfactant, is characterized in that comprising the following steps:
Take monohydric alcohol as initiator, add oxirane and expoxy propane in the reactor, under catalyst a exists, Stress control at≤0.4MPa, react 4 ~ 6 hours under 100 ~ 130 DEG C of conditions, obtain single functionality polyethers;
Alpha-olefine acid or unrighted acid and single functionality polyethers are added reactor, under catalyst b exists, reacts 4 ~ 6 hours under 160 ~ 220 DEG C of conditions, obtain double bond containing polyether ester; Or the methyl esters of alpha-olefine acid or the methyl esters of unrighted acid and single functionality polyethers are added reactor, and under catalyst b exists, react 1 ~ 3 hour under 170 ~ 200 DEG C of conditions, methanol removal, obtains double bond containing polyether ester;
With octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and HMDO or tetramethyl disiloxane for raw material is under catalyst c effect, react 5 ~ 7 hours under reaction temperature is 60 ~ 90 DEG C of conditions, obtain polysiloxanes;
Adding reactor by reacting the double bond containing polyether ester of acquisition, polysiloxanes, Pt catalyst and solvent above, under normal pressure, being heated to 60 ~ 120 DEG C of reactions 2 ~ 10 hours, open reflux condensing tube cooling water while adding thermal response to ensure solvent refluxing; After reaction terminates, first carry out air-distillation and carry out decompression distillation again, lower the temperature after solvent has been steamed, obtain Nonionic organosilicon surfactant.
2. the preparation method of Nonionic organosilicon surfactant according to claim 1, is characterized in that described alpha-olefine acid is acrylic acid, 3-butenoic acid, 4-penetenoic acid, 5-hexenoic acid, 6-heptenoic acid, 7-octenoic acid, 8-nonenoic acid, 9-decylenic acid or 10 hendecenoic acid; Described unrighted acid is oleic acid, erucic acid, linoleic acid or leukotrienes.
3. the preparation method of Nonionic organosilicon surfactant according to claim 1, is characterized in that the methyl esters of described alpha-olefine acid is methyl acrylate, 3-butenoic acid methyl esters, 4-amylene-4 acid methyl ester, 5-hexenoic acid methyl ester, 6-heptenoic acid methyl esters, 7-octenoic acid methyl esters, 8-nonenoic acid methyl esters, 9-decenoate or 10 hendecenoic acid methyl esters; The methyl esters of described unrighted acid is methyl oleate, methyl erucate, methyl linoleate or methyl linolenate.
4. the preparation method of Nonionic organosilicon surfactant according to claim 1, is characterized in that described monohydric alcohol is methyl alcohol, ethanol, normal propyl alcohol, isopropyl alcohol or n-butanol.
5. the preparation method of Nonionic organosilicon surfactant according to claim 1, is characterized in that described catalyst a is base catalyst, and its consumption is 0.1 ~ 0.5% of oxirane and expoxy propane gross mass.
6. the preparation method of Nonionic organosilicon surfactant according to claim 1, it is characterized in that described catalyst b is inorganic acid or organotin, consumption is 0.03 ~ 0.5% of reactant quality.
7. the preparation method of Nonionic organosilicon surfactant according to claim 1, it is characterized in that described catalyst c is lewis acid, consumption is 0.1 ~ 3% of quality of material used.
8. the preparation method of Nonionic organosilicon surfactant according to claim 1, it is characterized in that described Pt catalyst and solvent load are respectively the 3 ~ 50ppm and 30 ~ 90% of material gross mass, described solvent is toluene or dimethylbenzene.
9. the preparation method of Nonionic organosilicon surfactant according to claim 1, is characterized in that the mass fraction of hydrogen in described containing hydrogen silicone oil is 1.55 ~ 1.66%.
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