CN107345261A - The carboxyl silsesquioxane tanning agent of water solubility eight and its method prepared based on mercaptan alkene clicking chemistry method - Google Patents
The carboxyl silsesquioxane tanning agent of water solubility eight and its method prepared based on mercaptan alkene clicking chemistry method Download PDFInfo
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- CN107345261A CN107345261A CN201710666235.8A CN201710666235A CN107345261A CN 107345261 A CN107345261 A CN 107345261A CN 201710666235 A CN201710666235 A CN 201710666235A CN 107345261 A CN107345261 A CN 107345261A
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- silsesquioxane
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- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
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Abstract
The present invention relates to the carboxyl silsesquioxane tanning agent of water solubility eight and its method prepared based on mercaptan alkene clicking chemistry method, the vinyl silsesquioxane of cage modle eight is prepared for using vinyltrimethoxy silane by hydrolytic condensation method first, then under the conditions of light trigger and ultra violet lamp, reacted with TGA, produce water-soluble eight carboxyl silsesquioxane tanning agents.Yield of the present invention is high, and purity is high, the easily controllable operation of course of reaction, and the reaction time is short;And the tanning agent has certain tanning effect, 2% chromium powder is coordinated to be applied to goat acid skin process for tanning, the shrinkage temperature of crust leather lifts 35 DEG C after tanning, thickens rate up to 67% or so.
Description
Technical field
The present invention relates to leather retanning agent synthesis technical field, and in particular to one kind is prepared based on mercaptan-alkene clicking chemistry method
The carboxyl silsesquioxane tanning agent of water solubility eight and its method.
Background technology
As the improvement of people's living standards, leather and fur products be increasingly becoming in current life it is indispensable required
Product.It can be used in leather processing procedure and arrive hundreds of leather chemicals, these materials are for obtaining the leather of excellent properties extremely
Close important, wherein tanning agent is chemical action to occur with rawhide collagenous fibres, and make rawhide that qualitative change occur turns into leather, and has leather
There are flexibility, high intensity, chemical material that is water-fast, heat-resisting, corrosion-resistant, having chemical stability.The tanning agent used at present in process hides
Based on chrome tanning agent, the combination property of chrome tanning agent tanning is that other inorganic tanning agents, syntans and vegetable tanning agent can not compare
Intend.But recently as chrome tanning environmental problem increasingly uprush and strategic consideration to chromium resource, chrome tanning agent and chrome tanning
It has been faced with stern challenge.At present, process hides worker has begun to primary study Chrome-free or few chrome tanning agent, to adapt to environment
Need, ensure the sustainable development of leather industry.
Polyhedral oligomeric silsesquioxane(POSS)It is that a kind of oxygen ratio occurred in recent years is higher to stand with space
The novel organic-inorganic nano particle of body yardstick.Synthesized first by D.W. etc. in nineteen forty-six.General molecular formula is(RSO1.5)n, n mono-
As be 6,8,10,12 etc., wherein with the most typically of n=8.POSS is considered as form stable and the nano silicon particles of minimum, and diameter is about
1nm or so, POSS are in hollow rigid cagelike structure, because the molecular structure of its fixation and easily modified surface turn into research
Focus.Multiple different functional groups can be introduced on POSS surfaces, such as vinyl, hydroxyl, methacryloxy, alcoxyl
Base, epoxy radicals, amino etc., with different functionalities or the function nano particle of reactivity.
Click chemistry is the Americanized scholar Sharpless of Nobel chemistry Prize winner in 2001 [Kolb H C, Finn
M G, Sharpless K B. Click chemistry: diverse chemical function from a few
good reactions[J]. Angewandte Chemie International Edition, 2001, 40(11):
2004-2021] propose a kind of a large amount of compounds of Fast back-projection algorithm new method.Such reaction raw materials and reagent are easy to get, and use model
Enclose extensively, reaction condition is simply gentle, is hardly affected by the external environment, and without using heavy metal catalyst, yield is high, and product easily divides
From purifying, it is not necessary to the advantages that solvent or the solvent used are easily isolated.And mercaptan-alkene clicking chemistry is that development derives in recent years
A kind of new click chemistry out, it is using Light lnduced Free Radicals reaction as catalytic media, fully by the excellent of light-initiated process
The characteristics of point and traditional click-reaction, is combined, and is reacted between specific region and functional group, has the selectivity of height, into
For the important channel of synthetic material.
The content of the invention
It is an object of the invention to provide a kind of carboxyl silsesquioxane of water solubility eight prepared based on mercaptan-alkene clicking chemistry method
Alkane tanning agent and its method, the use of the tanning agent can improve leather heat endurance, fillibility, can reduce chromium in tannery again
The use of powder, Cr in waste liquid after reduction tanning3+Content.
The technical solution adopted in the present invention is:
The method that water-soluble eight carboxyl silsesquioxane tanning agents are prepared based on mercaptan-alkene clicking chemistry method, it is characterised in that:
Realized by following steps:
Step 1:The synthesis of the vinyl silsesquioxane of cage modle eight:
Vinyltrimethoxy silane 33-66mL is added in 1000mL three-necked flask, adds 337-675mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer, 97-125mL, 6mol/L watery hydrochloric acid is slowly dropped in flask,
The return stirring at 30-45 DEG C;
Reaction washs product after terminating, dry the vinyl silsesquioxane of white powder cage modle eight;
Then the vinyl silsesquioxane of cage modle eight is dissolved with enough dichloromethane, treats that solvent volatilizees to form homogeneous saturated solution knot
Crystalline substance goes out white solid;
Step 2:The preparation of water-soluble eight carboxyl silsesquioxanes:
By the vinyl silsesquioxane of cage modle eight and TGA that are obtained in step 1 in molar ratio 1:(8-10)It is dissolved in enough
In dichloromethane;
Then the vinyl silsesquioxane of cage modle eight and TGA quality 1%-2% light trigger dimethoxybenzoin are added,
It is placed in conical flask, is then irradiated under uviol lamp, reaction obtains light yellow viscous liquid after terminating;
By the liquid with water washing is distilled 2-3 times, solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary;
Product is placed on thermostatic mixer with distillation aqueous mixtures and heated, is creamy white, treats with the volatilization system of dichloromethane
Solvent volatilization is complete, then is filtered after standing, and is volatilized naturally in culture dish, produces the carboxyl of water solubility eight of the sticky shape of water white transparency
Silsesquioxane tanning agent.
In step 1:
Washing step is:Product is washed 1-3 times with 66-132mL absolute ethyl alcohols;
Drying steps are:Dried in 45-55 DEG C of vacuum drying chamber.
In step 2, the condition irradiated under uviol lamp is λ=365nm, time 5-20min.
Water-soluble eight carboxyl silsesquioxane tanning agents made from method as mentioned.
The present invention has advantages below:
The present invention is prepared for eight carboxyl cage-type silsesquioxane tanning agents using mercaptan-alkene clicking chemistry, and this method, which has, applies model
Many advantages, such as wide, reaction condition is simple, speed is fast, yield is high is enclosed, is especially had to leather retanning agent synthesis technical field important
Reference value.The tanning agent is a kind of nano-hybrid material formed by Covalently attached interaction, water-soluble good, is coordinated
2% chromium powder tanning, 35 DEG C of the shrinkage temperature raising of crust leather after tan can be made, thicken rate up to 67% or so.
Embodiment
With reference to embodiment, the present invention will be described in detail.
It is of the present invention based on mercaptan-alkene clicking chemistry method prepare the carboxyl silsesquioxane tanning agent of water solubility eight and its
Method, the vinyl silsesquioxane of cage modle eight is prepared for first with hydrolytic condensation method, is then shone in light trigger and uviol lamp
Under the conditions of penetrating, reacted with TGA, produce water-soluble eight carboxyl silsesquioxane tanning agents, reaction scheme is as follows:
The present invention prepares water-soluble eight carboxyl silsesquioxane tanning agents, eight carboxyl silsesquioxanes using mercaptan-alkene clicking chemistry method
Alkane, which contains eight carboxyls, to be interacted with the amino in materials with hide glue fibril, multiple spot combination is advantageously formed, so as to play tan
Make and use;Carboxyl can coordinate tanning with a small amount of chromium powder simultaneously, realize Chrome-free or less chrome tannage, reduce pollution in leather industry, realize clear
Clean production.
Concretely comprise the following steps:
Step 1:The synthesis of the vinyl silsesquioxane of cage modle eight:
Vinyltrimethoxy silane 33-66mL is added in 1000mL three-necked flask, adds 337-675mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer, 97-125mL, 6mol/L watery hydrochloric acid is slowly dropped in flask,
The return stirring at 30-45 DEG C;
Reaction washs product after terminating, dry the vinyl silsesquioxane of white powder cage modle eight;
Then the vinyl silsesquioxane of cage modle eight is dissolved with enough dichloromethane, treats that solvent volatilizees to form homogeneous saturated solution knot
Crystalline substance goes out white solid;
Step 2:The preparation of water-soluble eight carboxyl silsesquioxanes:
By the vinyl silsesquioxane of cage modle eight and TGA that are obtained in step 1 in molar ratio 1:(8-10)It is dissolved in enough
In dichloromethane;
Then the vinyl silsesquioxane of cage modle eight and TGA quality 1%-2% light trigger dimethoxybenzoin are added,
It is placed in conical flask, is then irradiated under uviol lamp, reaction obtains light yellow viscous liquid after terminating;
By the liquid with water washing is distilled 2-3 times, solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary;
Product is placed on thermostatic mixer with distillation aqueous mixtures and heated, is creamy white, treats with the volatilization system of dichloromethane
Solvent volatilization is complete, then is filtered after standing, and is volatilized naturally in culture dish, produces the carboxyl of water solubility eight of the sticky shape of water white transparency
Silsesquioxane tanning agent.
In step 1:
Washing step is:Product is washed 1-3 times with 66-132mL absolute ethyl alcohols;
Drying steps are:Dried in 45-55 DEG C of vacuum drying chamber.
In step 2, the condition irradiated under uviol lamp is λ=365nm, time 5-20min.
Embodiment 1:
Vinyltrimethoxy silane 33mL is added in 1000mL three-necked flask at 35 DEG C, adds 337mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer.The hydrochloric acid diluted is slowly dropped in flask, at 35 DEG C next time
Product is washed 3 times, is then dried in vacuo 48h at 45 DEG C, obtains white by stream stirring 40h, reaction after terminating with 66mL absolute ethyl alcohols
The powdered vinyl silsesquioxane of cage modle eight of color;Then the vinyl silsesquioxane of cage modle eight is dissolved with q. s. methylene chloride,
Treat that solvent evaporate into certain time and forms homogeneous saturated solution and crystallize out white solid.
The vinyl silsesquioxane of cage modle eight and 0.2764g TGAs for weighing 0.2132g respectively are dissolved in dichloromethane
It is in water white transparency settled solution in alkane.Then 1wt% light trigger dimethoxybenzoin 0.0048g is added, is placed on taper
In bottle, 5min is irradiated under uviol lamp, reaction obtains light yellow viscous liquid after terminating.The liquid is used into distillation water washing 3 times,
Solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary.Product is placed in into constant temperature with distillation aqueous mixtures to stir
Mix and heated on device, is creamy white with the volatilization system of dichloromethane, treat that solvent volatilization is complete, filtered after standing, in culture dish
Naturally volatilize, produce eight carboxyl silsesquioxanes of the sticky shape of water white transparency.
Embodiment 2:
Vinyltrimethoxy silane 45mL is added in 1000mL three-necked flask at 45 DEG C, adds 337mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer.The hydrochloric acid diluted is slowly dropped in flask, at 45 DEG C next time
Product is washed 3 times, is then dried in vacuo 48h at 45 DEG C, obtains by stream stirring 40h, reaction after terminating with 66mL absolute ethyl alcohols
The vinyl silsesquioxane of white powder cage modle eight;Then the vinyl silsesquioxane of cage modle eight is dissolved with q. s. methylene chloride
Alkane, treat that solvent evaporate into certain time and forms homogeneous saturated solution and crystallize out white solid.
The vinyl silsesquioxane and 0.2764g TGAs for weighing 0.2132g respectively are dissolved in dichloromethane and are in
Water white transparency settled solution.Then 1wt% light trigger dimethoxybenzoin 0.0048g is added, is placed in conical flask,
5min is irradiated under uviol lamp, reaction obtains light yellow viscous liquid after terminating.By the liquid with water washing is distilled 3 times, fully
Solution is layered after standing, and aqueous phase has white product with oil phase boundary.Product and distillation aqueous mixtures are placed in thermostatic mixer
Upper heating, it is creamy white with the volatilization system of dichloromethane, treats that solvent volatilization is complete, filtered after standing, it is natural in culture dish
Volatilize, produce eight carboxyl silsesquioxanes of the sticky shape of water white transparency.
Embodiment 3:
Vinyltrimethoxy silane 33mL is added in 1000mL three-necked flask at 40 DEG C, adds 337mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer.The hydrochloric acid diluted is slowly dropped in flask, at 35 DEG C next time
Product is washed 3 times, is then dried in vacuo 48h at 45 DEG C, obtains by stream stirring 40h, reaction after terminating with 66mL absolute ethyl alcohols
The vinyl silsesquioxane of white powder cage modle eight;Then the vinyl silsesquioxane of cage modle eight is dissolved with q. s. methylene chloride
Alkane, treat that solvent evaporate into certain time and forms homogeneous saturated solution and crystallize out white solid.
The vinyl silsesquioxane of cage modle eight and 0.2764g TGAs for weighing 0.2132g respectively are dissolved in dichloromethane
It is in water white transparency settled solution in alkane.Then 1wt% light trigger dimethoxybenzoin 0.0048g is added, is placed on taper
In bottle, 5min is irradiated under uviol lamp, reaction obtains light yellow viscous liquid after terminating.The liquid is used into distillation water washing 3 times,
Solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary.Product is placed in into constant temperature with distillation aqueous mixtures to stir
Mix and heated on device, is creamy white with the volatilization system of dichloromethane, treat that solvent volatilization is complete, filtered after standing, in culture dish
Naturally volatilize, produce eight carboxyl silsesquioxanes of the sticky shape of water white transparency.
Embodiment 4:
Vinyltrimethoxy silane 66mL is added in 1000mL three-necked flask at 45 DEG C, adds 337mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer.The hydrochloric acid diluted is slowly dropped in flask, at 45 DEG C next time
Stream stirring 40h, reaction wash product 3 times with 120mL absolute ethyl alcohols after terminating, and are then dried in vacuo 48h at 45 DEG C,
Obtain the vinyl silsesquioxane of white powder cage modle eight;Then the vinyl times of cage modle eight is dissolved with q. s. methylene chloride
Half siloxanes, treat that solvent evaporate into certain time and forms homogeneous saturated solution and crystallize out white solid.
The vinyl silsesquioxane of cage modle eight and 0.1245g TGAs for weighing 0.2132g respectively are dissolved in dichloromethane
It is in water white transparency settled solution in alkane.Then 1wt% light trigger 2 is added, 2- dihydromethyl propionic acid 0.0048g, is placed on
In conical flask, 5min is irradiated under uviol lamp.Reaction obtains light yellow viscous liquid after terminating.By liquid distillation water washing
3 times, solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary.Product and distillation aqueous mixtures are placed in perseverance
Heat on warm agitator, be creamy white with the volatilization system of dichloromethane, treat that solvent volatilization is complete, filtered after standing, in culture
Volatilized naturally in ware, produce eight carboxyl silsesquioxanes of the sticky shape of water white transparency.
Embodiment 5:
Vinyltrimethoxy silane 66mL is added in 1000mL three-necked flask at 45 DEG C, adds 337mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer.The hydrochloric acid diluted is slowly dropped in flask, at 45 DEG C next time
Stream stirring 40h, reaction wash product 3 times with 120mL absolute ethyl alcohols after terminating, and are then dried in vacuo 48h at 45 DEG C,
Obtain the vinyl silsesquioxane of white powder cage modle eight;Then the vinyl sesquialter of cage modle eight is dissolved with q. s. methylene chloride
Siloxanes, treat that solvent evaporate into certain time and forms homogeneous saturated solution and crystallize out white solid.
The vinyl silsesquioxane of cage modle eight and 0.1245g TGAs for weighing 0.2132g respectively are dissolved in dichloromethane
It is in water white transparency settled solution in alkane.Then 2wt% light trigger dimethoxybenzoin 0.0068g is added, is placed on taper
In bottle, 5min is irradiated under uviol lamp.Reaction obtains light yellow viscous liquid after terminating.The liquid is used into distillation water washing 3 times,
Solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary.Product is placed in into constant temperature with distillation aqueous mixtures to stir
Mix and heated on device, is creamy white with the volatilization system of dichloromethane, treat that solvent volatilization is complete, filtered after standing, in culture dish
Naturally volatilize, produce eight carboxyl silsesquioxanes of the sticky shape of water white transparency.
Eight carboxyl silsesquioxane tanning agents prepared by the present invention coordinate 2% chromium powder tanning, can make the contraction temperature of crust leather after tan
35 DEG C of degree lifting, thickens rate up to 67% or so.
Present disclosure is not limited to cited by embodiment, and those of ordinary skill in the art are by reading description of the invention
And any equivalent conversion taken technical solution of the present invention, it is that claim of the invention is covered.
Claims (4)
1. the method for water-soluble eight carboxyl silsesquioxane tanning agents is prepared based on mercaptan-alkene clicking chemistry method, it is characterised in that:
Realized by following steps:
Step 1:The synthesis of the vinyl silsesquioxane of cage modle eight:
Vinyltrimethoxy silane 33-66mL is added in 1000mL three-necked flask, adds 337-675mL acetone,
It is placed in the water-bath equipped with condensation and heating stirrer, 97-125mL, 6mol/L watery hydrochloric acid is slowly dropped in flask,
The return stirring at 30-45 DEG C;
Reaction washs product after terminating, dry the vinyl silsesquioxane of white powder cage modle eight;
Then the vinyl silsesquioxane of cage modle eight is dissolved with enough dichloromethane, treats that solvent volatilizees to form homogeneous saturated solution knot
Crystalline substance goes out white solid;
Step 2:The preparation of water-soluble eight carboxyl silsesquioxanes:
By the vinyl silsesquioxane of cage modle eight and TGA that are obtained in step 1 in molar ratio 1:(8-10)It is dissolved in enough
In dichloromethane;
Then the vinyl silsesquioxane of cage modle eight and TGA quality 1%-2% light trigger dimethoxybenzoin are added,
It is placed in conical flask, is then irradiated under uviol lamp, reaction obtains light yellow viscous liquid after terminating;
By the liquid with water washing is distilled 2-3 times, solution is layered after sufficient standing, and aqueous phase has white product with oil phase boundary;
Product is placed on thermostatic mixer with distillation aqueous mixtures and heated, is creamy white, treats with the volatilization system of dichloromethane
Solvent volatilization is complete, then is filtered after standing, and is volatilized naturally in culture dish, produces the carboxyl of water solubility eight of the sticky shape of water white transparency
Silsesquioxane tanning agent.
2. according to claim 1 prepare water-soluble eight carboxyl silsesquioxane tanning agents based on mercaptan-alkene clicking chemistry method
Method, it is characterised in that:
In step 1:
Washing step is:Product is washed 1-3 times with 66-132mL absolute ethyl alcohols;
Drying steps are:Dried in 45-55 DEG C of vacuum drying chamber.
3. according to claim 1 prepare water-soluble eight carboxyl silsesquioxane tanning agents based on mercaptan-alkene clicking chemistry method
Method, it is characterised in that:
In step 2, the condition irradiated under uviol lamp is λ=365nm, time 5-20min.
4. water-soluble eight carboxyl silsesquioxane tanning agents made from the method as described in claim 1.
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CN108384013B (en) * | 2018-03-30 | 2021-05-25 | 常州大学 | Carboxy-functionalized hybrid silicon materials |
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CN115677249A (en) * | 2022-11-22 | 2023-02-03 | 河南建筑材料研究设计院有限责任公司 | Preparation method of hydrothermally synthesized fly ash silicate aggregate |
CN115677249B (en) * | 2022-11-22 | 2023-06-27 | 河南建筑材料研究设计院有限责任公司 | Preparation method of hydro-thermal synthesis fly ash silicate aggregate |
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