CN102030778A - Siloxane with quaternary ammonium salt and quaternary phosphonium, preparation and application thereof - Google Patents
Siloxane with quaternary ammonium salt and quaternary phosphonium, preparation and application thereof Download PDFInfo
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- CN102030778A CN102030778A CN2010105519420A CN201010551942A CN102030778A CN 102030778 A CN102030778 A CN 102030778A CN 2010105519420 A CN2010105519420 A CN 2010105519420A CN 201010551942 A CN201010551942 A CN 201010551942A CN 102030778 A CN102030778 A CN 102030778A
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Abstract
The invention discloses siloxane with quaternary ammonium salt and quaternary phosphonium, which has a structure shown as follows. The invention also discloses a preparation method and an application method of the bactericide, wherein the preparation method comprises the following steps of: synthesizing amino silane quaternary phosphonium through the reaction of halogenated alkyl trialkyl phosphine and amine alkyl silane by taking silicone oxygroup as a carrier, and continuously subjecting the amino silane quaternary phosphonium and excessive halogenated alkyl to reaction to synthesize the siloxane with quaternary ammonium salt and quaternary phosphonium. The siloxane with quaternary ammonium salt and quaternary phosphonium can act as a reactive radical group to combine with inorganic materials (such as glass, cement, and metals), and realize the application and development in the aspects of bactericide synthesis and phase-transferred catalysis and the like.
Description
Technical field
The present invention relates to a kind of have can and inorganic materials (as: glass, cement, metal) siloxanes and preparation and the application that combine, a kind of specifically have quaternary ammonium with the preparation of the siloxanes of quaternary phosphine group and application.
Background technology
In order to link inorganic molecule and organic molecule, not to be difficult to form on compatible inorganics and the organism interface bridge having avidity mutually, the exploitation and the utilization of silane coupling agent are arisen at the historic moment.Silane coupling agent comes down to the silane that a class has organo-functional group, has energy and the chemically combined reactive group of inanimate matter material (as glass, silica sand, metal etc.) and and the chemically combined reactive group of organic material (synthetic resins etc.) in its molecule simultaneously.But because its special chain-like structure Y-R-Si-X
3(R: alkyl or aromatic base; X: methoxy or ethoxy etc.; Y: the organic reaction base, as vinyl, epoxy group(ing), amino, sulfenyl etc.), cause such coupling agent structural instability, rigidity is low, intensity is little.Therefore, have the stress retentivity, on the basis of silane coupling agent, developed and novel siloxanes instead in order to make silane coupling agent.
The present invention utilizes halogenated alkane and tertiary phosphine compounds to react the synthetic haloalkyl tertiary phosphine compounds that has the halogeno-group chain carrier, the tertiary phosphine compounds and the amine alkyl silane coupling agent that have the halogeno-group chain carrier carry out the quaternary phosphine reaction, thereby realize making amino quaternary phosphine silane with the C-P key.Because the amino quaternary phosphine silane of reaction product can continue reaction with the excess of halide substituted alkyl, generates by product tertiary amine quaternary alkylphosphonium salt even quaternized quaternary alkylphosphonium salt, therefore finally made the siloxanes that not only contains quaternary ammonium group but also contain the quaternary phosphine base.
Summary of the invention
In view of this, one of purpose of the present invention is to provide a kind of quaternary ammonium salt quaternary phosphine siloxanes, it is characterized in that having following structure:
Further, R
1Be aromatics group or C
1～C
8The alkyl of straight chain or branching, R
2Be C
2～C
10The alkyl of straight chain or branching, R
3Be methyl or methoxy, R
4Be methyl, n equals 2～10, and m equals 2～3;
Further, R
1Be aromatics group or C
1～C
8The alkyl of straight chain or branching, R
2Be C
2～C
6The alkyl of straight chain or branching, R
3Be oxyethyl group, R
4Be ethyl, n equals 2～10, and m equals 2～3.
Two of purpose of the present invention is to provide the preparation method of described quaternary ammonium salt quaternary phosphine siloxanes, can reach by following steps:
101: at nitrogen (N
2) as shielding gas, by weight with 1.2 parts of dimethylbenzene as solvent, add 1.0 parts of saturated dihalides, under stirring fast, drip 0.4～1.0 part tertiary phosphine compounds, in 2 hours, drip off.
102: with described mixed solution 60～140 ℃ of following heated and stirred and reacted 8～17 hours, reaction solution; With described reaction solution at room temperature the non-shock chilling after-filtration get colloid, wash colloid repeatedly to the reactant noresidue with anhydrous diethyl ether; With described colloid 50～90 ℃ of following vacuum-dryings to constant weight, the haloalkyl trialkyl phosphine.
103: by weight 5 parts of described haloalkyl trialkyl phosphines are dissolved in 5 parts of ethanol solutions, get solution;
104: 1.0 parts of amine alkyl silanes and 0.3 part of alkali, basic salt or organic amine are mixed, get mixed solution; 0.5 part of described solution is dropwise joined in the described mixing liquid,, get amino quaternary phosphine silane coupling agent 75～80 ℃ of reactions 6～8 hours;
105: 1: 1 in molar ratio, haloalkane is dropwise joined in the described amino quaternary phosphine silane coupling agent, 60～80 ℃ of reactions 2～3 hours, get reactant;
106: described reactant is obtained oily matter 60～90 ℃ of vacuum rotary steam to constant weights; Stir described oily matter to separating out solid with a large amount of anhydrous diethyl ethers, wash above-mentioned solid, after under 70～80 ℃ of vacuum conditions dry 5～10 hours, obtain quaternary ammonium salt quaternary phosphine siloxanes then by the methylene dichloride and the anhydrous diethyl ether of arbitrary proportion.
Further, saturated dihalide is the saturated dihalide of 2～10 C in step 101;
Further, tertiary phosphine compounds comprises in step 101: triphenyl phosphorus, tributylphosphine, tri octyl phosphine or three hexyl phosphines;
Further, the amine alkyl silane comprises in step 104: γ-An Bingjisanyiyangjiguiwan, N-aminoethyl-γ-An Bingjisanjiayangjiguiwan or N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane;
Further, alkali is NH in step 104
3H
2O; Basic salt comprises CH
3CH
2ONa or yellow soda ash; Organic amine comprises trolamine, thanomin, diethanolamine, Trimethylamine 99, methylamine or dimethylamine.
Quaternary ammonium salt quaternary phosphine siloxanes of the present invention can with inorganic materials (as glass, cement, metal etc.) bonded reactive group, can be applied and develop at aspects such as synthesizing fungicide and phase-transfer catalysiss.
Described quaternary ammonium salt quaternary phosphine siloxanes can combine with inorganic firmly, stability is high, have little, the nontoxic characteristics of environmental pollution, simultaneously, its polarized action of phosphorus atom ionic radius ambassador strengthens, electronegativity little (electron donation is strong) increases its positive polarity, behind synthesizing fungicide, the microorganisms electrostatic adsorption that the load phosphonium ion is easier and electronegative, easier kill microorganisms.Make with this coupling agent synthetic biocide have efficiently, bactericidal property, low dosage, the low toxicity of wide spectrum and the advantage that adapts to the pH value of broadness.
In addition, quaternary ammonium salt quaternary phosphine siloxanes has good prospect at the immobilized phase-transfer catalyst of gel-type, it is to concentrate the characteristics of inorganic silica gel carrier and a class new catalyst of phase-transfer catalyst advantage, can catalysis most of non-immobilized phase-transfer catalysts institute can catalytic reaction, has anti-dissolubility, advantage such as physical strength is good, nontoxic, free from environmental pollution.
Description of drawings
Below in conjunction with the drawings and specific embodiments the present invention is further described.
Fig. 1 is the synthetic route chart of the embodiment of the invention 1;
Fig. 2 is a process route chart of the present invention.
Embodiment
Fig. 1 is the synthetic route chart of the embodiment of the invention 1; Fig. 2 is a process route chart of the present invention.
Experimental procedure:
101: at nitrogen (N
2) as shielding gas, by weight with 1.2 parts of dimethylbenzene as solvent, add 1.0 parts of saturated dihalides, under stirring fast, drip 0.4～1.0 part tertiary phosphine compounds, in 2 hours, drip off.
102: with described mixed solution 60～140 ℃ of following heated and stirred and reacted 8～17 hours, reaction solution; With described reaction solution at room temperature the non-shock chilling after-filtration get colloid, wash colloid repeatedly to the reactant noresidue with anhydrous diethyl ether; With described colloid 50～90 ℃ of following vacuum-dryings to constant weight, the haloalkyl trialkyl phosphine.
103: by weight 5 parts of described haloalkyl trialkyl phosphines are dissolved in 5 parts of ethanol solutions, get solution;
104: 1.0 parts of amine alkyl silanes and 0.3 part of alkali, basic salt or organic amine are mixed, get mixed solution; 0.5 part of described solution is dropwise joined in the described mixing liquid,, get amino quaternary phosphine silane coupling agent 75～80 ℃ of reactions 6～8 hours;
105: 1: 1 in molar ratio, haloalkane is dropwise joined in the described amino quaternary phosphine silane coupling agent, 60～80 ℃ of reactions 2～3 hours, get reactant;
106: described reactant is obtained oily matter 60～90 ℃ of vacuum rotary steam to constant weights; Stir described oily matter to separating out solid with a large amount of anhydrous diethyl ethers, wash above-mentioned solid, after under 70～80 ℃ of vacuum conditions dry 5～10 hours, obtain quaternary ammonium salt quaternary phosphine siloxanes then by the methylene dichloride and the anhydrous diethyl ether of arbitrary proportion.
Embodiment 1:
Get that saturated dihalide is 1.4 dichlorobutane in the step 101, tertiary phosphine compounds is 0.4 part a tributylphosphine;
The heated and stirred temperature of getting mixed solution in the step 102 is 120 ℃, and the reaction times is 17 hours, and the colloid drying temperature is 50 ℃;
Get that the amine alkyl silane is γ-amine propyl group-triethoxyl silane in the step 104, getting alkali, basic salt or organic amine is NH
3H
2O, temperature of reaction is 75 ℃, the reaction times is 8 hours;
Get that haloalkane is a chlorobutane in the step 105, temperature of reaction is 70 ℃, and the reaction times is 2 hours;
Get that the vacuum rotary steam temperature is 90 ℃ in the step 106, the vacuum-drying temperature is 70 ℃, and the vacuum-drying time is 5 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Embodiment 2:
Get that saturated dihalide is 1.2 ethylene dichloride in the step 101, tertiary phosphine compounds is 0.6 part a triphenyl phosphorus;
The heated and stirred temperature of getting mixed solution in the step 102 is 100 ℃, and the reaction times is 14 hours, and the colloid drying temperature is 60 ℃;
Get that the amine alkyl silane is N-aminoethyl-γ-An Bingjisanjiayangjiguiwan in the step 104, getting alkali, basic salt or organic amine is CH
3CH
2ONa, temperature of reaction is 80 ℃, the reaction times is 7.5 hours;
Get that haloalkane is a chloropentane in the step 105, temperature of reaction is 60 ℃, and the reaction times is 2.5 hours;
Get that the vacuum rotary steam temperature is 80 ℃ in the step 106, the vacuum-drying temperature is 75 ℃, and the vacuum-drying time is 6 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Embodiment 3:
Get that saturated dihalide is 1.3 propylene dichlorides in the step 101, tertiary phosphine compounds is 0.8 part a tri octyl phosphine;
The heated and stirred temperature of getting mixed solution in the step 102 is 110 ℃, and the reaction times is 11 hours, and the colloid drying temperature is 70 ℃;
Get that the amine alkyl silane is N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane in the step 104, getting alkali, basic salt or organic amine is yellow soda ash, and temperature of reaction is 75 ℃, and the reaction times is 7 hours;
Get that haloalkane is a chlorohexane in the step 105, temperature of reaction is 75 ℃, and the reaction times is 3 hours;
Get that the vacuum rotary steam temperature is 70 ℃ in the step 106, the vacuum-drying temperature is 80 ℃, and the vacuum-drying time is 7 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Get that saturated dihalide is 1.5 dichloropentane in the step 101, tertiary phosphine compounds is 1 part three hexyl phosphines;
The heated and stirred temperature of getting mixed solution in the step 102 is 120 ℃, and the reaction times is 8 hours, and the colloid drying temperature is 80 ℃;
Get that the amine alkyl silane is γ-amine propyl group-triethoxyl silane in the step 104, getting alkali, basic salt or organic amine is trolamine, and temperature of reaction is 80 ℃, and the reaction times is 6.5 hours;
Get that haloalkane is a monochlorethane in the step 105, temperature of reaction is 80 ℃, and the reaction times is 8 hours;
Get that the vacuum rotary steam temperature is 60 ℃ in the step 106, the vacuum-drying temperature is 80 ℃, and the vacuum-drying time is 8 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Embodiment 5
Get that saturated dihalide is 1.6 dichloro hexanes in the step 101, tertiary phosphine compounds is 1 part a tributylphosphine;
The heated and stirred temperature of getting mixed solution in the step 102 is 140 ℃, and the reaction times is 17 hours, and the colloid drying temperature is 90 ℃;
Get that the amine alkyl silane is N-aminoethyl-γ-An Bingjisanjiayangjiguiwan in the step 104, getting alkali, basic salt or organic amine is thanomin, and temperature of reaction is 75 ℃, and the reaction times is 6 hours;
Get that haloalkane is a chloropropane in the step 105, temperature of reaction is 60 ℃, and the reaction times is 5 hours;
Get that the vacuum rotary steam temperature is 70 ℃ in the step 106, the vacuum-drying temperature is 70 ℃, and the vacuum-drying time is 8 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Embodiment 6
Get that saturated dihalide is 1.9 2 chlorononanes in the step 101, tertiary phosphine compounds is 0.4 part three hexyl phosphines;
The heated and stirred temperature of getting mixed solution in the step 102 is 140 ℃, and the reaction times is 8 hours, and the colloid drying temperature is 90 ℃;
Get that the amine alkyl silane is N-aminoethyl-γ-An Bingjisanjiayangjiguiwan in the step 104, getting alkali, basic salt or organic amine is methylamine, and temperature of reaction is 80 ℃, and the reaction times is 7.5 hours;
Get that haloalkane is a chlorohexane in the step 105, temperature of reaction is 80 ℃, and the reaction times is 2.5 hours;
Get that the vacuum rotary steam temperature is 80 ℃ in the step 106, the vacuum-drying temperature is 70 ℃, and the vacuum-drying time is 7 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Embodiment 7
Get that saturated dihalide is 1.10 two chlorodecanes in the step 101, tertiary phosphine compounds is 0.4 part a tributylphosphine;
The heated and stirred temperature of getting mixed solution in the step 102 is 100 ℃, and the reaction times is 17 hours, and the colloid drying temperature is 80 ℃;
Get that the amine alkyl silane is N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane in the step 104, getting alkali, basic salt or organic amine is dimethylamine, and temperature of reaction is 75 ℃, and the reaction times is 8.5 hours;
Get that haloalkane is a chloropropane in the step 105, temperature of reaction is 65 ℃, and the reaction times is 3 hours;
Get that the vacuum rotary steam temperature is 70 ℃ in the step 106, the vacuum-drying temperature is 75 ℃, and the vacuum-drying time is 10 hours.
Described quaternary ammonium salt quaternary phosphine siloxane structure is:
Embodiment 8～14
Among the embodiment 8～14, get that saturated dihalide is two bromoalkanes in the step 101, other experiment conditions are described according to embodiment 1～7.
Described quaternary ammonium salt quaternary phosphine siloxanes can be combined firmly with inorganic material, stability is high, have little, the nontoxic characteristics of environmental pollution, simultaneously, its polarization of phosphorus atomic ions radius ambassador strengthens, electronegativity little (electron donation is strong) increases its electropositive, behind synthesizing fungicide, easier and the electronegative microorganism of load phosphonium ion produces electrostatic adsorption, easier kill microorganisms. So that with the synthetic biocide of this coupling agent have efficiently, sterilization performance, low dosage, the low toxicity of wide spectrum and the advantage that adapts to the pH value of broadness.
Claims (9)
- One kind quaternary ammonium salt season the squama siloxanes, it is characterized in that having following structure:Or
- 2. quaternary ammonium salt season according to claim 1 the squama siloxanes, it is characterized in that: R 1Be aromatics group or C 1～C 8The alkyl of straight chain or branching, R 2Be C 2～C 10The alkyl of straight chain or branching, R 3Be methyl or methoxy, R 4Be methyl, n equals 2～10, and m equals 2～3.
- 3. quaternary ammonium salt season according to claim 1 the squama siloxanes, it is characterized in that: R 1Be aromatics group or C 1～C 8The alkyl of straight chain or branching, R 2Be C 2～C 6The alkyl of straight chain or branching, R 3Be oxyethyl group, R 4Be ethyl, n equals 2～10, and m equals 2～3.
- Described quaternary ammonium salt season of claim 1 the squama siloxanes the preparation method, it is characterized in that:101 at nitrogen (N 2) as shielding gas, get 1.2 parts of dimethylbenzene by weight and mix with 1.0 parts of saturated dihalides, under stirring fast, drip 0.4～1.0 part tertiary phosphine compounds, in 2 hours, drip off, get mixed solution;102 with described mixed solution 60～140 ℃ of following stirring reactions 8～17 hours, reaction solution; Described reaction solution is at room temperature left standstill cooled and filtered, get colloid, wash colloid repeatedly to the reactant noresidue with anhydrous diethyl ether; With described colloid 50～90 ℃ of following vacuum-dryings to constant weight, the haloalkyl trialkyl phosphine;103 are dissolved in 5 parts of described haloalkyl trialkyl phosphines in 5 parts of ethanol solutions by weight, get solution;104 mix 1.0 parts of amine alkyl silanes and 0.3 part of alkali, basic salt or organic amine, progressively drip 0.5 part of step 103 gained solution, again 75～80 ℃ of reactions 6～8 hours, amino season the squama silane coupling agent;105 1: 1 in molar ratio, haloalkane is dropwise joined in described amino season squama silane coupling agent, 60～80 ℃ of reactions 2～3 hours, reactant;106 obtain oily matter with step 105 gained reactant 60～90 ℃ of vacuum rotary steam to constant weights; Stir described oily matter to separating out solid with anhydrous diethyl ether, get methylene dichloride and/or anhydrous diethyl ether and wash above-mentioned solid, under 70～80 ℃ of vacuum conditions dry 5～10 hours then, quaternary ammonium salt season the squama siloxanes.
- 5. according to the preparation method of the described quaternary ammonium salt of claim 3 season squama siloxanes, it is characterized in that: saturated dihalide is C in step 101 2～C 10Saturated dihalide.
- 6. according to the preparation method of the described quaternary ammonium salt of claim 3 season squama siloxanes, it is characterized in that: tertiary phosphine compounds comprises in step 101: triphenyl phosphorus, tributylphosphine, tri octyl phosphine or three hexyl phosphines.
- 7. preparation method according to claim 3 is characterized in that: the amine alkyl silane comprises γ-An Bingjisanyiyangjiguiwan, N-aminoethyl-γ-An Bingjisanjiayangjiguiwan or N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane in step 104.
- 8. according to the preparation method of the described quaternary ammonium salt of claim 3 season squama siloxanes, it is characterized in that: alkali is NH in step 104 3H 2O; Basic salt comprises CH 3CH 2ONa or yellow soda ash; Organic amine comprises trolamine, thanomin, diethanolamine, Trimethylamine 99, methylamine or dimethylamine.
- 9. according to the preparation method of the described quaternary ammonium salt of claim 3 season squama siloxanes, it is characterized in that: haloalkane comprises C in step 105 2～C 6Halogenated alkane.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012782A (en) * | 2011-09-22 | 2013-04-03 | 中国石油化工股份有限公司 | Polyquaternary ammonium salt, and preparation method and application thereof |
| CN103012781A (en) * | 2011-09-22 | 2013-04-03 | 中国石油化工股份有限公司 | Polyquaternary ammonium salt, and preparation method and application thereof |
| JP2015529643A (en) * | 2012-08-01 | 2015-10-08 | 南京神奇科技▲開発▼有限公司Ｎｍｓ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｃｏ．， Ｌｔｄ． | Physical antimicrobial method |
| CN115073517A (en) * | 2022-06-01 | 2022-09-20 | 东营施普瑞石油工程技术有限公司 | Quaternary phosphonium quaternary ammonium salt bactericide and synthetic method thereof |
-
2010
- 2010-11-19 CN CN2010105519420A patent/CN102030778A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012782A (en) * | 2011-09-22 | 2013-04-03 | 中国石油化工股份有限公司 | Polyquaternary ammonium salt, and preparation method and application thereof |
| CN103012781A (en) * | 2011-09-22 | 2013-04-03 | 中国石油化工股份有限公司 | Polyquaternary ammonium salt, and preparation method and application thereof |
| JP2015529643A (en) * | 2012-08-01 | 2015-10-08 | 南京神奇科技▲開発▼有限公司Ｎｍｓ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｃｏ．， Ｌｔｄ． | Physical antimicrobial method |
| CN115073517A (en) * | 2022-06-01 | 2022-09-20 | 东营施普瑞石油工程技术有限公司 | Quaternary phosphonium quaternary ammonium salt bactericide and synthetic method thereof |
| CN115073517B (en) * | 2022-06-01 | 2023-12-12 | 东营施普瑞石油工程技术有限公司 | Quaternary phosphonium quaternary ammonium salt bactericide and synthesis method thereof |
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Application publication date: 20110427 |