CN108409968A - A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant - Google Patents
A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant Download PDFInfo
- Publication number
- CN108409968A CN108409968A CN201810271391.9A CN201810271391A CN108409968A CN 108409968 A CN108409968 A CN 108409968A CN 201810271391 A CN201810271391 A CN 201810271391A CN 108409968 A CN108409968 A CN 108409968A
- Authority
- CN
- China
- Prior art keywords
- glucoheptose
- sugar
- organosilicon
- combed
- grafting rate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- YPZMPEPLWKRVLD-PJEQPVAWSA-N D-Glycero-D-gulo-Heptose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O YPZMPEPLWKRVLD-PJEQPVAWSA-N 0.000 title claims abstract description 71
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 34
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- -1 cyclosiloxane Chemical compound 0.000 claims abstract description 26
- 150000001408 amides Chemical class 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000002779 inactivation Effects 0.000 claims abstract description 11
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910000077 silane Inorganic materials 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims abstract description 9
- UNYNVICDCJHOPO-UHFFFAOYSA-N quabalactone III Natural products CC1OC(=O)C(O)=C1C UNYNVICDCJHOPO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 9
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical group [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- NTSNXSJENBZFSF-UHFFFAOYSA-N [Na+].[SiH3][O-] Chemical group [Na+].[SiH3][O-] NTSNXSJENBZFSF-UHFFFAOYSA-N 0.000 claims description 2
- YAGNBBKTVGENKK-UHFFFAOYSA-N azane methoxy(trimethyl)silane Chemical group CO[Si](C)(C)C.N YAGNBBKTVGENKK-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 238000005265 energy consumption Methods 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 7
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 6
- 239000000693 micelle Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 description 5
- 229960005179 primaquine Drugs 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical class CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 125000003147 glycosyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- GOCRPOKWZIVUQG-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propan-1-amine Chemical class CCOC(OCC)[SiH2]CCCN GOCRPOKWZIVUQG-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003845 household chemical Substances 0.000 description 1
- XFFPIAQRIDTSIZ-UHFFFAOYSA-N n'-[3-(dimethoxymethylsilyl)propyl]ethane-1,2-diamine Chemical class COC(OC)[SiH2]CCCNCCN XFFPIAQRIDTSIZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/008—Polymeric surface-active agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/82—Compounds containing silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Silicon Polymers (AREA)
- Detergent Compositions (AREA)
Abstract
A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant is using low-boiling point alcohol as solvent, and glucoheptose sugar lactone, amino silane are raw material;14 h are reacted under the conditions of 50 150 DEG C;Low boiling point solvent is steamed after reaction, obtains glucoheptose sugar amide silane;With glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, 25 h of reaction make catalyst inactivation after reaction under the conditions of 70 150 DEG C, obtain high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant.The present invention has the advantages that preparation is simple, low energy consumption, grafting rate agent is high, good water solubility.
Description
Technical field
The invention belongs to synthesis of surfactant field, a kind of washing is related generally to, high grafting rate combed used for cosmetic has
The preparation method of machine silicon glucoheptose sugar acidamide surfactant.
Technical background
The existing preparation method hydrosilation method and bulk polymerization-Graft Method for preparing organosilicon sugar amide.
It is relatively more for the relevant report of hydrosilation method, as Wagner R report a kind of system of organosilicon glucamide
Preparation Method is that epoxy-modified polysiloxane is prepared using containing hydrogen silicone oil and allyl glycidyl ether as raw material, then and mistake
The reacting ethylenediamine of amount obtains amino modified polysiloxane, and organosilicon glucamide is finally obtained by the reaction with sugar lactone, in addition, also
Some are then to carry out hydrosilation method by containing hydrogen silicone oil and allyl ammonia to obtain amido silicon oil, subsequent amino silane in sugar
Organosilicon glucamide is obtained by the reaction in ester.However, in these synthetic methods, there are hydrosilation method, reaction used catalyst more
It is expensive for chloroplatinic acid, and the reaction time is longer.
And CN101942097B reports a kind of preparation method of organosilicon glucamide, first passes through cyclosiloxane, amino
Silane, hexamethyl siloxane are that raw material carries out bulk polymerization, then carry out glycosyl and be modified to obtain organosilicon glucamide, the method without
It is malicious, at low cost, but since glycosyl grafting rate is relatively low, the water solubility of product is poor, influences its application range.
Invention content
The purpose of the present invention is overcome existing technological deficiency with it is insufficient, provide and a kind of prepare that simple, low energy consumption, grafting rate
The preparation method of high, good water solubility high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant.
The preparation path of the present invention is as follows:
(1) glucoheptose sugar lactones is reacted with amino silane, prepares glucoheptose sugar amide silane:
Wherein, R1For CH3Or C2H5;N is the integer of 1-6.
(2) it with glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, prepares
High grafting rate combed organosilicon glucoheptose sugar acidamide surfactant:
Wherein, X is the integer of 5-10;P is the integer of 4-60;M is the integer of 10-200.
A kind of preparation method of high grafting rate organosilicon glucoheptose sugar acidamide surfactant of the present invention, including walk as follows
Suddenly:
(1) using low-boiling point alcohol as solvent, glucoheptose sugar lactone, amino silane are raw material;It is reacted under the conditions of 50-150 DEG C
1-4h;Low boiling point solvent is steamed after reaction, obtains glucoheptose sugar amide silane;
(2) with glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, in
2-5h is reacted under the conditions of 70-150 DEG C, after reaction, makes catalyst inactivation, obtains high grafting rate combed organosilicon glucoheptose sugar
Acidamide surfactant.
Glucoheptose sugar lactones is as described above:
Amino silane is as described above:
Wherein R1For CH3Or C2H5, n is the integer of 1-6.
Cyclosiloxane is as described above:
Wherein, X is the integer of 5-10.
As described above, low boiling point solvent used is one kind of the low boiling point solvents such as methanol, ethyl alcohol, isopropanol in step (1)
Or it is several.Solvent usage amount is 5-10 times of glucoheptose sugar lactone quality.
As described above, the molar ratio of glucoheptose sugar lactone and amino silane is 1 in step (1):6-1:1, preferably 1:4-1:
1;Preferred 60-100 DEG C of reaction temperature;Reaction time preferred 1.5-3.5h.
As described above, the molar ratio of glucoheptose sugar amide silane in step (2), cyclosiloxane, hexamethyldisiloxane is
1-40:0.5-20:1, preferably 2-30:1-10:1;Preferred 80-120 DEG C of reaction temperature;Reaction time preferred 2-4h.
As described above, step (2) catalyst be alkali metal hydroxide such as sodium hydroxide etc., silicon alkoxide such as sodium silanolate etc.,
Quaternary ammonium base such as tetramethylammonium hydroxide etc., silanol quaternary ammonium salt such as tetramethyl silanol ammonium etc..Catalyst amount is cyclosiloxane quality
0.01%-2%, preferably 0.1%-2%.
As described above, there are mainly two types of modes for step (2) catalyst inactivation:When catalyst is alkali metal hydroxide, silicon
When alkoxide, acid, which is added, makes it lose catalytic activity, and is removed through filtering;When catalyst is quaternary ammonium base, silanol quaternary ammonium salt, heating
It is set to decompose inactivation.
The present invention compared with having technology the same as having the following advantages that:
1, high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant prepared by the present invention, grafting rate are up to
95%-98% has larger dissolubility (solubility is 1-30g/100g water) in aqueous solution, and the surface tension of aqueous solution is
21.0-29.0mN·m-1;Critical micelle concentration is 25-1000mgL-1.It is easy to prepare in household chemicals, in daily use chemicals etc.
Field has potential application.
2, grafting time used in preparation process of the present invention is shorter, more energy saving, and grafting rate higher is more advantageous to industrialization.
Description of the drawings
Fig. 1 is the infrared spectrogram of organosilicon glucoheptose sugar acidamide surfactant.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of organosilicon glucoheptose sugar acidamide surfactant.
Specific implementation mode
It enumerates specific example below to illustrate patent of the present invention, but the present invention is not limited in following embodiment.
Embodiment 1:
17.80g glucoheptose sugar lactones are added in flask, 100mL is added in 19.10g aminopropyl diethoxymethylsilanes
Methanol makees solvent, at 80 DEG C, reacts 2h, distillation removal methanol obtains glucamide diethoxymethylsilane.Add in flask
Enter 19.10g glucoheptose sugar amides diethoxymethylsilane, decamethylcyclopentaandoxane 20.00g, hexamethyl siloxane
3.70g, addition 0.08g tetramethylammonium hydroxide are catalyst, react 4h at 90 DEG C;After reaction, being heated to 134 DEG C makes
Catalyst inactivation, you can obtain organosilicon glucoheptose sugar acidamide surfactant.Primaquine value, meter are measured by non-hyperbolic curve
It is 95% to calculate grafting rate;The surface tension of products therefrom is 24.3mNm-1, critical micelle concentration 52mgL-1, solubility
For 5g/100g water.
Embodiment 2:
15.00g glucoheptose sugar lactones are added in flask, 140mL is added in 19.10g aminopropyl dimethoxy methyl-monosilanes
Ethyl alcohol makees solvent, at 90 DEG C, reacts 3h, distillation removal ethyl alcohol obtains glucoheptose sugar amide dimethoxymethylsilane.In flask
Middle addition 32.10g glucoheptose sugar amides dimethoxymethylsilane, ten pregnancy basic rings, eight siloxanes 100.00g, hexamethyl silica
Alkane 3.20g, it is catalyst 8.10g that the trimethyl silicane potassium alcoholate that mass fraction is 1.5%, which is added, reacts 3h at 85 DEG C;Reaction knot
Shu Hou, being heated to 134 DEG C makes catalyst inactivation, you can obtains organosilicon glucoheptose sugar acidamide surfactant.Pass through non-water power
Position titration determination primaquine value, it is 98% to calculate grafting rate;The surface tension of products therefrom is 22.4mNm-1, critical micelle concentration
For 390mgL-1, solubility is 9g/100g water.
Embodiment 3:
20.7g glucoheptose sugar lactones are added in flask, 30.6g aminoethylaminopropyl dimethoxymethylsilanes are added
200mL isopropanols make solvent, at 95 DEG C, react 1.5h, distillation removal isopropanol obtains glucoheptose sugar amide dimethoxy-methyl
Silane.It is added 92.10g glucoheptose sugar amides dimethoxymethylsilanes, ten prestox rings nine siloxanes 180g in flask, six
Methylsiloxane 1.60g, addition 1.8g potassium hydroxide are catalyst, react 4h at 110 DEG C;After reaction, acetic acid is added to make
Catalyst inactivation, filtering can be obtained organosilicon glucoheptose sugar acidamide surfactant.Primaquine is measured by non-hyperbolic curve
Value, it is 97.5% to calculate grafting rate;The surface tension of products therefrom is 26.4mNm-1, critical micelle concentration 740mgL-1, solubility is 15g/100g water.
Embodiment 4:
9.58g glucoheptose sugar lactones are added in flask, 90mL first is added in 26.40g aminopropyl dimethoxy methyl-monosilanes
Alcohol makees solvent, at 90 DEG C, reacts 3.5h, distillation removal methanol obtains glucoheptose sugar amide dimethoxymethylsilane.In flask
Middle addition 24.10g glucoheptose sugar amides dimethoxymethylsilane, ten diformazan basic rings, six siloxanes 89.10g, hexamethyl silica
Alkane 3.20g, addition 0.40g sodium hydroxides are catalyst, react 2.5h at 90 DEG C;After reaction, acetic acid is added to make catalyst
Inactivation, filtering can be obtained organosilicon glucoheptose sugar acidamide surfactant.Primaquine value is measured by non-hyperbolic curve, is calculated
Grafting rate is 98%;The surface tension of products therefrom is 24.3mNm-1, critical micelle concentration 980mgL-1, solubility is
26g/100g water.
Embodiment 5:
12.30g glucoheptose sugar lactones are added in flask, 95mL is added in 32.10g aminopropyl dimethoxy methyl-monosilanes
Methanol makees solvent, at 95 DEG C, reacts 3h, distillation removal methanol obtains glucoheptose sugar amide dimethoxymethylsilane.In flask
Middle addition 53.34g glucoheptose sugar amides dimethoxymethylsilane, ten diformazan basic rings, six siloxanes 79.10g, hexamethyl silica
Alkane 3.20g, addition 0.35g sodium hydroxides are catalyst, react 3h at 85 DEG C;After reaction, add acetic acid that catalyst is made to lose
Living, filtering can be obtained organosilicon glucoheptose sugar acidamide surfactant.Primaquine value is measured by non-hyperbolic curve, calculating connects
Branch rate is 98.5%;The surface tension of products therefrom is 26.4mNm-1, critical micelle concentration 894mgL-1, solubility is
32g/100g water.
Claims (17)
1. a kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant, it is characterised in that including such as
Lower step:
(1) using low-boiling point alcohol as solvent, glucoheptose sugar lactone, amino silane are raw material;1-4h is reacted under the conditions of 50-150 DEG C;
Low boiling point solvent is steamed after reaction, obtains glucoheptose sugar amide silane;
(2) with glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, in 70-150
2-5h is reacted under the conditions of DEG C, after reaction, makes catalyst inactivation, obtains high grafting rate combed organosilicon glucoheptose sugar amide table
Face activating agent.
2. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that the glucoheptose sugar lactones is:
3. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that amino silane is:
Wherein R1For CH3Or C2H5, n is the integer of 1-6.
4. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that cyclosiloxane is:
Wherein, X is the integer of 5-10.
5. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that low boiling point solvent used is one or more of methanol, ethyl alcohol, isopropanol, solvent in the step (1)
Usage amount is 5-10 times of glucoheptose sugar lactone quality.
6. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that the molar ratio of glucoheptose sugar lactone and amino silane is 1 in the step (1):6-1:1.
7. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 6
Method, it is characterised in that the molar ratio of glucoheptose sugar lactone and amino silane is 1 in the step (1):4-1:1.
8. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that reaction temperature is 60-100 DEG C in the step (1);Reaction time is 1.5-3.5h.
9. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that glucoheptose sugar amide silane in the step (2), cyclosiloxane, hexamethyldisiloxane molar ratio be
1-40:0.5-20:1。
10. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 9
Method, it is characterised in that glucoheptose sugar amide silane in the step (2), cyclosiloxane, hexamethyldisiloxane molar ratio be
2-30:1-10:1。
11. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that reaction temperature is 80-120 DEG C in the step (2);Reaction time is 2-4h.
12. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that step (2) catalyst is alkali metal hydroxide, silicon alkoxide, quaternary ammonium base or silanol quaternary ammonium salt.
13. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 12
Method, it is characterised in that alkali metal hydroxide is sodium hydroxide, and silicon alkoxide is sodium silanolate, and quaternary ammonium base is tetramethylammonium hydroxide,
Silanol quaternary ammonium salt is tetramethyl silanol ammonium.
14. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that step (2) catalyst amount is the 0.01%-2% of cyclosiloxane quality.
15. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 14
Method, it is characterised in that step (2) catalyst amount is the 0.1%-2% of cyclosiloxane quality.
16. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that there are two types of modes for step (2) catalyst inactivation:When catalyst is alkali metal hydroxide, silicon alkoxide
When, acid, which is added, makes it lose catalytic activity, and is removed through filtering;When catalyst is quaternary ammonium base, silanol quaternary ammonium salt, heating makes it
Decompose inactivation.
17. the high grafting rate combed organosilicon glucoheptose sugar amide surface as prepared by any one of claim 1-16 the methods is lived
Property agent, it is characterised in that
Wherein;P is the integer of 4-60;M is the integer of 10-200.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810271391.9A CN108409968A (en) | 2018-03-29 | 2018-03-29 | A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810271391.9A CN108409968A (en) | 2018-03-29 | 2018-03-29 | A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant |
Publications (1)
Publication Number | Publication Date |
---|---|
CN108409968A true CN108409968A (en) | 2018-08-17 |
Family
ID=63132666
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810271391.9A Pending CN108409968A (en) | 2018-03-29 | 2018-03-29 | A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108409968A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109106608A (en) * | 2018-09-18 | 2019-01-01 | 中国日用化学研究院有限公司 | A kind of cleaning skin solid particle and the facial cleanser and preparation method thereof for preventing skin deposits solid particle |
CN110437272A (en) * | 2019-08-05 | 2019-11-12 | 中国日用化学研究院有限公司 | A kind of preparation method of ABA type organosilicon glucoheptonic acid acidamide surfactant |
CN111449993A (en) * | 2020-04-27 | 2020-07-28 | 中国日用化学研究院有限公司 | Foam type low-carbon alcohol system hand disinfectant and preparation method thereof |
CN113024816A (en) * | 2021-03-30 | 2021-06-25 | 中国日用化学研究院有限公司 | Comb-type aminosiloxane-allyl polydimethylsiloxane co-modified organic silicon and preparation method thereof |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5100991A (en) * | 1988-05-17 | 1992-03-31 | Dow Corning Limited | Organosilicon compounds |
JP2002173664A (en) * | 2000-12-04 | 2002-06-21 | Nec Corp | Surface preparation agent, surface preparation agent composition, head for ink-jet printer and ink-jet printer |
CN1357022A (en) * | 1999-06-18 | 2002-07-03 | 全球财富(Bvi)有限公司 | Multifunctional nonionic siloxane copolymer for modification of synthetic materials |
CN101641396A (en) * | 2007-03-30 | 2010-02-03 | 日油株式会社 | Sugar alcohol-modified organopolysiloxane compound and method for producing the same |
CN101942096A (en) * | 2010-09-09 | 2011-01-12 | 浙江温州轻工研究院 | Modified amino silicone oil and preparation method thereof |
CN101942097A (en) * | 2010-09-20 | 2011-01-12 | 中国日用化学工业研究院 | Method for preparing glycosyl amide modified polysiloxane |
WO2012027143A1 (en) * | 2010-08-23 | 2012-03-01 | Dow Corning Corporation | Saccharide siloxane copolymers and methods for their preparation and use |
CN102558561A (en) * | 2010-10-25 | 2012-07-11 | 赢创高施米特有限公司 | Polysiloxanes with groups containing nitrogen |
CN104130415A (en) * | 2014-07-15 | 2014-11-05 | 北京工商大学 | Organosilicon quaternary ammonium salt containing alkyl group and glycosylamide group, and preparation method thereof |
CN107599096A (en) * | 2017-09-20 | 2018-01-19 | 安徽三和工艺品有限公司 | A kind of processing method for improving wood surface wearability |
-
2018
- 2018-03-29 CN CN201810271391.9A patent/CN108409968A/en active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5100991A (en) * | 1988-05-17 | 1992-03-31 | Dow Corning Limited | Organosilicon compounds |
CN1357022A (en) * | 1999-06-18 | 2002-07-03 | 全球财富(Bvi)有限公司 | Multifunctional nonionic siloxane copolymer for modification of synthetic materials |
JP2002173664A (en) * | 2000-12-04 | 2002-06-21 | Nec Corp | Surface preparation agent, surface preparation agent composition, head for ink-jet printer and ink-jet printer |
CN101641396A (en) * | 2007-03-30 | 2010-02-03 | 日油株式会社 | Sugar alcohol-modified organopolysiloxane compound and method for producing the same |
WO2012027143A1 (en) * | 2010-08-23 | 2012-03-01 | Dow Corning Corporation | Saccharide siloxane copolymers and methods for their preparation and use |
CN101942096A (en) * | 2010-09-09 | 2011-01-12 | 浙江温州轻工研究院 | Modified amino silicone oil and preparation method thereof |
CN101942097A (en) * | 2010-09-20 | 2011-01-12 | 中国日用化学工业研究院 | Method for preparing glycosyl amide modified polysiloxane |
CN102558561A (en) * | 2010-10-25 | 2012-07-11 | 赢创高施米特有限公司 | Polysiloxanes with groups containing nitrogen |
CN104130415A (en) * | 2014-07-15 | 2014-11-05 | 北京工商大学 | Organosilicon quaternary ammonium salt containing alkyl group and glycosylamide group, and preparation method thereof |
CN107599096A (en) * | 2017-09-20 | 2018-01-19 | 安徽三和工艺品有限公司 | A kind of processing method for improving wood surface wearability |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109106608A (en) * | 2018-09-18 | 2019-01-01 | 中国日用化学研究院有限公司 | A kind of cleaning skin solid particle and the facial cleanser and preparation method thereof for preventing skin deposits solid particle |
CN110437272A (en) * | 2019-08-05 | 2019-11-12 | 中国日用化学研究院有限公司 | A kind of preparation method of ABA type organosilicon glucoheptonic acid acidamide surfactant |
CN110437272B (en) * | 2019-08-05 | 2022-10-11 | 中国日用化学研究院有限公司 | Preparation method of ABA type organosilicon glucoheptonamide surfactant |
CN111449993A (en) * | 2020-04-27 | 2020-07-28 | 中国日用化学研究院有限公司 | Foam type low-carbon alcohol system hand disinfectant and preparation method thereof |
CN113024816A (en) * | 2021-03-30 | 2021-06-25 | 中国日用化学研究院有限公司 | Comb-type aminosiloxane-allyl polydimethylsiloxane co-modified organic silicon and preparation method thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108409968A (en) | A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant | |
CN101805996A (en) | Hydrophilic amino-polysiloxane softener and preparation method thereof | |
CN102675652B (en) | Preparation method of crosslinking-modified pectinate polyether amino-silicone oil | |
CN104479133A (en) | Preparation method of long-chain alkyl modified silicone oil | |
CN106632839B (en) | A kind of organic-silicon-modified amphipathic polymer type heavy crude thinner of easy breaking emulsion and dewatering and preparation method thereof | |
CN104672460B (en) | Polyether block piperazine silicone oil, preparation method and its application in Cotton Fabric | |
CN102558561A (en) | Polysiloxanes with groups containing nitrogen | |
CN105297427B (en) | A kind of compound for improving amino-modified silicone oil based carbon fiber finish heat resistance and its preparation and application | |
CN102775613B (en) | Method for preparing alpha, omega-bis(aminopropyl)polydimethylsiloxane | |
CN104307570B (en) | A kind of platinum allyl polyether composition catalyst and its preparation method and application | |
CN109824900A (en) | Deep silicone oil of the amino modified increasing of one kind and preparation method thereof | |
CN105694046A (en) | Preparation method of highly-branched block polyether-aminosiloxane finishing agent | |
CN101648123A (en) | Nonionic aqueous POSS-based polymer surfactant | |
CN116713033B (en) | Supported platinum catalyst, preparation method and preparation method of gemini quaternary ammonium salt | |
CN112409598B (en) | Bola type organosilicon quaternary ammonium salt, preparation method and application thereof | |
CN103408759A (en) | Preparation method of methyl phenyl silicone oil with high refractive index | |
CN103304818B (en) | A kind of preparation method of methyl phenyl silicone oil | |
CN103103765B (en) | Self-emulsifying wet rubbing resistant leather top layer coating agent and preparation method thereof | |
CN105461929B (en) | A kind of synthetic method of high-quality phenyl hydrogen-containing silicon oil for LED encapsulation | |
CN104945628B (en) | A kind of polyglycerol-modified organosilicon and preparation method thereof | |
CN103804690B (en) | Method for preparing double amino-terminated linear polydimethylsiloxane | |
CN105601934A (en) | Aminoalkyl side chain modified double-end amino polydimethylsiloxane and preparation method thereof | |
US20220332899A1 (en) | Processes for making polysiloxazanes and using same for producing amino-functional polyorganosiloxanes | |
CN101463134A (en) | Modified amino alkyl polysiloxane, method for synthesizing the same and microemulsion composed thereof | |
CN103588974B (en) | The synthetic method of epoxy-modified polysiloxane flax soft finishing agent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180817 |
|
RJ01 | Rejection of invention patent application after publication |