Nothing Special   »   [go: up one dir, main page]

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 PDF

Info

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
Application number
CN201810271391.9A
Other languages
Chinese (zh)
Inventor
白艳云
王国永
台秀梅
刘晓英
马晓原
王万绪
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China Daily Chemical Research Institute Co Ltd
Original Assignee
China Daily Chemical Research Institute Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by China Daily Chemical Research Institute Co Ltd filed Critical China Daily Chemical Research Institute Co Ltd
Priority to CN201810271391.9A priority Critical patent/CN108409968A/en
Publication of CN108409968A publication Critical patent/CN108409968A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898Polysiloxanes 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/008Polymeric surface-active agents
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/82Compounds 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

A kind of preparation of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant Method
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.
CN201810271391.9A 2018-03-29 2018-03-29 A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant Pending CN108409968A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (10)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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