CN104130278A - Ethoxy-modified trisiloxane comprising glycosylamide, and preparation method thereof - Google Patents
Ethoxy-modified trisiloxane comprising glycosylamide, and preparation method thereof Download PDFInfo
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- CN104130278A CN104130278A CN201410336248.5A CN201410336248A CN104130278A CN 104130278 A CN104130278 A CN 104130278A CN 201410336248 A CN201410336248 A CN 201410336248A CN 104130278 A CN104130278 A CN 104130278A
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Abstract
The invention relates to ethoxy-modified trisiloxane comprising glycosylamide, and a preparation method thereof. The invention relates to the technical field of organic compound synthesis. The substance is a compound obtained by a bonding reaction with silicon and oxygen, nitrogen or carbon formed in molecules. The preparation method comprises the following steps: hexamethyl disiloxane and chloropropyl silane are subjected to acidic catalyst action, such that chloropropyl trisiloxane is prepared; and chloropropyl trisiloxane is subjected to a reaction with alkyldiamine, such that N-beta-aminoalkyl-gamma-aminopropyl trisiloxane is prepared; and the material is subjected to a reaction with sugar acid or sugar acid lactone in a lower alcohol solvent; and diol methyl ether glycidyl ether is added, such that the ethoxy-modified trisiloxane comprising glycosylamide is obtained. The minimal surface tension of the water solution of the ethoxy-modified trisiloxane comprising glycosylamide is 20-21mN/m. The product is widely applied in fields such as cosmetics.
Description
Technical field
The present invention relates to silicoorganic compound preparation method field, especially relate to trisiloxanes of a kind of sugary amide group of oxyethyl group modification and preparation method thereof.
Background technology
Trisiloxane surfactant is except having the character of conventional surfactants, also have than the more superiority of conventional surfactants, can be applied to non-aqueous system, there is lower surface tension, extremely low physiology toxicity, especially there is good wetting and spreadability etc.
Han Fu (Chinese patent 200410092453.8) has reported a kind of method of preparing glucosyacylamino modification trisiloxane surfactant, react with hexamethyldisiloxane by aminosilane and generate amino trisiloxanes, react with Gluconolactone again, generate glucosyacylamino trisiloxane surfactant.Chinese patent 200410092454.2 has been reported a kind of method of preparing glucosyacylamino trisiloxanes Gemini surface active agent, reacts with diglycidylether by glucosyacylamino trisiloxanes, generates glucosyacylamino trisiloxanes Gemini surface active agent.
In the trisiloxane surfactant of these sugary amide group, carbon chain linker group between trisiloxanes and glucose amide is very short, in the emulsion system of the Application Areass such as makeup, sometimes needing increases its oil soluble compared with long carbochain, sometimes needing again increases its wetting ability by oxyethyl group, regulate hydrophilic-lipophilic balance with this, change the absorption property on oil/water interface.
Summary of the invention
The object of the invention is the high biological degradability of the low surface tension of trisiloxane surfactant and sugar surfactants to combine, and between trisiloxanes and sugared acid amides, introduce longer carbochain, introduce oxyethyl chain simultaneously, provide that a kind of surface tension is low, biological degradability good, the preparation method of the trisiloxanes of the sugary amide group of oil soluble/water-soluble adjustable oxyethyl group modification.
The molecular structural formula of the trisiloxanes of the sugary amide group of oxyethyl group modification of the present invention is as follows:
Wherein, R
1for
R
2for
R
3for
R
4for
X is 3～6 integer, the integer that n is 1～10.
The preparation method of the trisiloxanes of the sugary amide group of oxyethyl group modification of the present invention comprises the following steps:
1. by hexamethyldisiloxane, chloropropyl silane and an acidic catalyst, be 40～100 DEG C in temperature of reaction, preferably in the situation of 50～80 DEG C, react; Wherein mole proportioning of hexamethyldisiloxane and chloropropyl silane is (1～20): 1, and preferably (2～10): 1, the mole dosage of an acidic catalyst is 0.3%～25% of hexamethyldisiloxane and chloropropyl silane mole sum; After having reacted, make an acidic catalyst inactivation, elimination solid, underpressure distillation, obtains chloropropyl trisiloxanes;
2. alkyl diamine and chloropropyl trisiloxanes, is 60～150 DEG C in temperature of reaction, preferably in the situation of 80～120 DEG C, reacts; Wherein mole proportioning of alkyl diamine and chloropropyl trisiloxanes is (1～20): 1, and preferably (6～15): 1; After having reacted, mixture stratification, upper strata underpressure distillation, obtains N-β-aminoalkyl-γ-aminopropyl trisiloxane;
3.N-β-aminoalkyl-γ-aminopropyl trisiloxane and saccharic acid or saccharic acid lactone, make solvent in low-carbon alcohol, and temperature of reaction is 60～150 DEG C, preferably 60～100 DEG C of reactions; Wherein mole proportioning of N-β-aminoalkyl-γ-aminopropyl trisiloxane and saccharic acid or saccharic acid lactone is 1～2: 1, preferably 1: 1; After having reacted, steaming desolventizes, and obtains the trisiloxanes of sugary amide group;
4. the trisiloxanes of sugary amide group and dibasic alcohol methyl ether glycidyl ether, make solvent in low-carbon alcohol, and temperature of reaction is 60～150 DEG C, preferably 60～100 DEG C of reactions; Wherein mole proportioning of the trisiloxanes of sugary amide group and dibasic alcohol methyl ether glycidyl ether is 1～2: 1, preferably 1: 1; After having reacted, steaming desolventizes, and obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.
Chloropropyl silane as above can comprise: chloropropyl dimethoxy-methyl silane, chloropropyl diethoxymethyl silane etc.
An acidic catalyst as above can comprise: the vitriol oil, acidic white earth etc.
An acidic catalyst inactivation that makes as above is in the time that an acidic catalyst is the vitriol oil, adds alkali catalyst neutralisation, makes it inactivation; In the time that an acidic catalyst is acidic white earth, filter, make it to remove.
Alkyl diamine as above can comprise: 1,3-propylene diamine, Putriscine, 1,5-pentamethylene diamine, 1,6-hexanediamine etc.
Saccharic acid as above or saccharic acid lactone can comprise: gluconic acid or Gluconolactone, lactobionic acid or lactobionic acid lactone, mannonic acid or mannonic acid lactone etc.
Low-carbon alcohol as above can comprise: methyl alcohol, ethanol, n-propyl alcohol, Virahol etc.
Dibasic alcohol methyl ether glycidyl ether as above can comprise: ethylene glycol monomethyl ether glycidyl ether, diethylene glycol dimethyl ether glycidyl ether, triethylene glycol methyl ether glycidyl ether, TEG methyl ether glycidyl ether, five ethylene glycol methyl ether glycidyl ether, six ethylene glycol monomethyl ether glycidyl ethers, seven ethylene glycol monomethyl ether glycidyl ethers, eight ethylene glycol monomethyl ether glycidyl ethers, nine ethylene glycol monomethyl ether glycidyl ethers, ten ethylene glycol monomethyl ether glycidyl ethers etc.
The trisiloxanes of the sugary amide group of the prepared oxyethyl group modification of the present invention, its advantage is that the high biological degradability of the low surface tension of organic silicon surfactant and sugar surfactants is combined, and between trisiloxanes and sugared acid amides, introduce longer carbochain, introduce oxyethyl chain simultaneously, hydrophilic-lipophilic balance is adjustable, and the absorption property on oil/water interface is good.Can be used as cosmetic composition for cosmetic formulations.Its using method and other cosmetic material are similar.
Embodiment
Below in conjunction with embodiment, the present invention is made an explanation.
Embodiment 1
In reactor 1, add hexamethyldisiloxane 1.62kg, chloropropyl dimethoxy-methyl silane 1.83kg, vitriol oil 0.006kg, at 40 DEG C of temperature, react 4 hours, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, 1,3-propylene diamine 0.74kg, is heated to 60 DEG C, react 4 hours, and mixture stratification, upper strata underpressure distillation, obtains N-β-aminopropyl-γ-aminopropyl trisiloxane.In reactor 3, add N-β-aminopropyl-γ-aminopropyl trisiloxane 3.36kg, Gluconolactone 1.78kg, makes solvent with methyl alcohol, is heated to 60 DEG C, reacts 8 hours.Add again ethylene glycol monomethyl ether glycidyl ether 1.32kg, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 20.5mN/m.
Embodiment 2
In reactor 1, add hexamethyldisiloxane 8.12kg, chloropropyl dimethoxy-methyl silane 1.83kg, acidic white earth 0.10kg reacts 4 hours under temperature 50 C, removes by filter catalyzer, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, Putriscine 2.64kg, is heated to 80 DEG C, react 3 hours, and mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia butyl-γ-aminopropyl trisiloxane.In reactor 3, add N-β-ammonia butyl-γ-aminopropyl trisiloxane 3.50kg, gluconic acid 1.96kg, makes solvent with ethanol, is heated to 70 DEG C, reacts 8 hours.Add again diethylene glycol dimethyl ether glycidyl ether 1.76kg, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 20.5mN/m.
Embodiment 3
In reactor 1, add hexamethyldisiloxane 16.24kg, chloropropyl dimethoxy-methyl silane 1.83kg, vitriol oil 0.54kg, under temperature 60 C, react 4 hours, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, 1,5-pentamethylene diamine 6.12kg, is heated to 90 DEG C, react 2 hours, and mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia amyl group-γ-aminopropyl trisiloxane.In reactor 3, add N-β-ammonia amyl group-γ-aminopropyl trisiloxane 3.64kg, mannonic acid lactone 1.78kg, makes solvent with methyl alcohol, is heated to 80 DEG C, reacts 10 hours.Add again triethylene glycol methyl ether glycidyl ether 2.20kg, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 20.6mN/m.
Embodiment 4
In reactor 1, add hexamethyldisiloxane 32.48kg, chloropropyl dimethoxy-methyl silane 1.83kg, acidic white earth 5.59kg reacts 4 hours under temperature 70 C, removes by filter catalyzer, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, 1,6-hexanediamine 11.6kg, is heated to 100 DEG C, react 1 hour, and mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia hexyl-γ-aminopropyl trisiloxane.In reactor 3, add N-β-ammonia hexyl-γ-aminopropyl trisiloxane 3.78kg, mannonic acid 1.96kg, makes solvent with ethanol, is heated to 90 DEG C, reacts 10 hours.Add again TEG methyl ether glycidyl ether 2.64kg, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 20.7mN/m.
Embodiment 5
In reactor 1, add hexamethyldisiloxane 1.62kg, chloropropyl diethoxymethyl silane 2.11kg, vitriol oil 0.20kg, at 80 DEG C of temperature, react 3 hours, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, 1,3-propylene diamine 8.88kg, is heated to 110 DEG C, react 4 hours, and mixture stratification, upper strata underpressure distillation, obtains N-β-aminopropyl-γ-aminopropyl trisiloxane.In reactor 3, add N-β-aminopropyl-γ-aminopropyl trisiloxane 3.36kg, lactobionic acid lactone 3.40kg, makes solvent with methyl alcohol, is heated to 100 DEG C, reacts 8 hours.Add again five ethylene glycol methyl ether glycidyl ether 3.08kg, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 20.8mN/m.
Embodiment 6
In reactor 1, add hexamethyldisiloxane 8.12kg, chloropropyl diethoxymethyl silane 2.11kg, acidic white earth 3.19kg reacts 3 hours at 80 DEG C of temperature, removes by filter catalyzer, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, Putriscine 13.2kg, is heated to 120 DEG C, react 3 hours, and mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia butyl-γ-aminopropyl trisiloxane.In reactor 3, add N-β-ammonia butyl-γ-aminopropyl trisiloxane 3.50kg, lactobionic acid 3.58kg, makes solvent with ethanol, is heated to 120 DEG C, reacts 8 hours.Add again six ethylene glycol monomethyl ether glycidyl ether 3.52kg, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 21.0mN/m.
Embodiment 7
In reactor 1, add hexamethyldisiloxane 16.24kg, chloropropyl diethoxymethyl silane 2.11kg, vitriol oil 2.70kg, at 90 DEG C of temperature, react 3 hours, hydro-oxidation sodium makes catalyst deactivation, solids removed by filtration, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, 1,5-pentamethylene diamine 18.36kg, is heated to 130 DEG C, react 2 hours, and mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia amyl group-γ-aminopropyl trisiloxane.In reactor 3, add N-β-ammonia amyl group-γ-aminopropyl trisiloxane 3.64kg, lactobionic acid lactone 3.40kg, makes solvent with methyl alcohol, is heated to 140 DEG C, reacts 9 hours.Add again seven ethylene glycol monomethyl ether glycidyl ether 3.96kg, continue reaction 12 hours.Steaming desolventizes methyl alcohol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 20.9mN/m.
Embodiment 8
In reactor 1, add hexamethyldisiloxane 32.48kg, chloropropyl diethoxymethyl silane 2.11kg, acidic white earth 27.93kg reacts 2 hours at 100 DEG C of temperature, removes by filter catalyzer, and underpressure distillation obtains chloropropyl trisiloxanes.In reactor 2, add chloropropyl trisiloxanes 2.99kg, 1,6-hexanediamine 23.2kg, is heated to 150 DEG C, react 1 hour, and mixture stratification, upper strata underpressure distillation, obtains N-β-ammonia hexyl-γ-aminopropyl trisiloxane.In reactor 3, add N-β-ammonia hexyl-γ-aminopropyl trisiloxane 3.78kg, lactobionic acid 3.58kg, makes solvent with ethanol, is heated to 150 DEG C, reacts 9 hours.Add again eight ethylene glycol monomethyl ether glycidyl ether 4.40kg, continue reaction 12 hours.Steaming desolventizes ethanol, obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.The lowest surface tension that records its aqueous solution is 21.2mN/m.
Claims (9)
1. a trisiloxanes for the sugary amide group of oxyethyl group modification, is characterized in that the molecular structural formula of trisiloxanes of the sugary amide group of oxyethyl group modification is as follows:
Wherein, R
1for
R
2for
R
3for
R
4for
X is 3～6 integer, the integer that n is 1～10.
2. a preparation method for the trisiloxanes of the sugary amide group of oxyethyl group modification, is characterized in that comprising the steps:
(1), by hexamethyldisiloxane, chloropropyl silane and an acidic catalyst, in the situation that being 40～100 DEG C, temperature of reaction reacts; Wherein mole proportioning of hexamethyldisiloxane and chloropropyl silane is (1～20): 1, and the mole dosage of an acidic catalyst is 0.3%～25% of hexamethyldisiloxane and chloropropyl silane mole sum; After having reacted, make an acidic catalyst inactivation, elimination solid, underpressure distillation, obtains chloropropyl trisiloxanes;
(2) alkyl diamine and chloropropyl trisiloxanes react in the situation that temperature of reaction is 60～150 DEG C; Wherein mole proportioning of alkyl diamine and chloropropyl trisiloxanes is (1～20): 1; After having reacted, mixture stratification, upper strata underpressure distillation, obtains N-β-aminoalkyl-γ-aminopropyl trisiloxane;
(3) N-β-aminoalkyl-γ-aminopropyl trisiloxane and saccharic acid or saccharic acid lactone, make solvent in low-carbon alcohol, and temperature of reaction is 60～150 DEG C of reactions; Wherein mole proportioning of N-β-aminoalkyl-γ-aminopropyl trisiloxane and saccharic acid or saccharic acid lactone is 1～2: 1; After having reacted, steaming desolventizes, and obtains the trisiloxanes of sugary amide group;
(4) trisiloxanes of sugary amide group and dibasic alcohol methyl ether glycidyl ether, make solvent in low-carbon alcohol, and temperature of reaction is 60～150 DEG C of reactions; Wherein mole proportioning of the trisiloxanes of sugary amide group and dibasic alcohol methyl ether glycidyl ether is 1～2: 1; After having reacted, steaming desolventizes, and obtains the trisiloxanes of the sugary amide group of oxyethyl group modification.
3. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that described chloropropyl silane is chloropropyl dimethoxy-methyl silane, chloropropyl diethoxymethyl silane.
4. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that described an acidic catalyst is the vitriol oil, acidic white earth.
5. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that the described an acidic catalyst inactivation that makes is in the time that an acidic catalyst is the vitriol oil, adds alkali catalyst neutralisation, makes it inactivation; In the time that an acidic catalyst is acidic white earth, filter, make it to remove.
6. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that described alkyl diamine is 1,3-propylene diamine, Putriscine, 1,5-pentamethylene diamine, 1,6-hexanediamine.
7. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that described saccharic acid or saccharic acid lactone are gluconic acid or Gluconolactone, lactobionic acid or lactobionic acid lactone, mannonic acid or mannonic acid lactone.
8. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that described low-carbon alcohol is methyl alcohol, ethanol, n-propyl alcohol, Virahol.
9. the preparation method of the trisiloxanes of the sugary amide group of a kind of oxyethyl group modification as claimed in claim 2, is characterized in that described dibasic alcohol methyl ether glycidyl ether is ethylene glycol monomethyl ether glycidyl ether, diethylene glycol dimethyl ether glycidyl ether, triethylene glycol methyl ether glycidyl ether, TEG methyl ether glycidyl ether, five ethylene glycol methyl ether glycidyl ether, six ethylene glycol monomethyl ether glycidyl ethers, seven ethylene glycol monomethyl ether glycidyl ethers, eight ethylene glycol monomethyl ether glycidyl ethers, nine ethylene glycol monomethyl ether glycidyl ethers, ten ethylene glycol monomethyl ether glycidyl ethers.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108867071A (en) * | 2018-07-12 | 2018-11-23 | 黄勇 | A kind of adjustable fabric and preparation method thereof |
| JP2021088670A (en) * | 2019-12-05 | 2021-06-10 | 信越化学工業株式会社 | Organopolysiloxane and fiber treating agent using the same |
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| CN1660883A (en) * | 2004-12-28 | 2005-08-31 | 中国日用化学工业研究院 | Polyglycol modified trisilicate containing glucose amide group and preparation method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108867071A (en) * | 2018-07-12 | 2018-11-23 | 黄勇 | A kind of adjustable fabric and preparation method thereof |
| JP2021088670A (en) * | 2019-12-05 | 2021-06-10 | 信越化学工業株式会社 | Organopolysiloxane and fiber treating agent using the same |
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Application publication date: 20141105 |