CN106432661B - A kind of modified naphthalene series water-reducing agent and preparation method thereof - Google Patents
A kind of modified naphthalene series water-reducing agent and preparation method thereof Download PDFInfo
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- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/14—Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/16—Sulfur-containing compounds
- C04B24/20—Sulfonated aromatic compounds
- C04B24/22—Condensation or polymerisation products thereof
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/30—Water reducers, plasticisers, air-entrainers, flow improvers
- C04B2103/302—Water reducers
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Abstract
The present invention provides a kind of new modified naphthalene water reducer and preparation method thereof.New modified naphthalene water reducer of the present invention is that fused ring compound concentrated acid sulfonation is obtained sulfonated products.Fused ring compound is carried out to etherification modified, generation condensed ring polyethers.By sulfonated products, condensed ring polyethers and formaldehyde copolymer finally obtain the modified naphthalene series water-reducing agent with side chain.New modified naphthalene water reducer of the present invention has efficient water-reduction to concrete, and has preferable anti-clay and bleed, shows and the well adapting to property such as water-reducing agent, air entraining agent, retarder.
Description
Technical field
The present invention relates to a kind of new modified naphthalene water reducers and preparation method thereof, belong to concrete admixture field.
Background technique
Cement water reducing agent is the indispensable additive of high performance concrete, is referred to constant in concrete and cement consumption
In the case where, it can be reduced the additive of mixing water amount.It is that dosage is maximum, most widely used concrete admixture, at present city
Most commonly used on field is naphthalene water reducer, and there are also aliphatic, amido sulfoacid series and poly carboxylic acid series water reducers etc..
Naphthalene water reducer mixes in concrete, and a large amount of sulfonate ions can be attracted to cement surface, to make cement table
Face is negatively charged, since the repulsive interaction between negative electrical charge makes cement granules scatter, to reduce use when mixing and stirring
Water.103382092 A of Chinese patent CN provides a kind of preparation method of naphthalene water reducer, and first naphthalene and the concentrated sulfuric acid occur
Then sulfonating reaction the product after sulfonation is hydrolyzed, remove sulfonation byproduct, then add polyformaldehyde and water be condensed it is anti-
It answers, finally neutralizes condensation product, it is dry.This is the preparation method of typical naphthalene water reducer, wherein naphthalene and sulfuric acid reaction are raw
At naphthalene sulfonic acids, a large amount of sulfonate ions are provided, paraformaldehyde is aggregating it again, obtains naphthalene water reducer.
Summary of the invention
The water-reducing effect of naphthalene water reducer can not show a candle to polycarboxylic acid water reducing agent, from the mechanism of action, polyocarboxy acid type diminishing
There are polyethers branches for agent, it provides steric hindrance effect, so that cement granules is scatter, to achieve the effect that diminishing, for this purpose, right
Than the Electrostatic Absorption mechanism of existing naphthalene water reducer, reach water-reducing effect, polyether lateral chain is introduced into fused ring compound by the present invention
In, so as to provide steric hindrance, reach water-reducing effect.
The present invention provides a kind of new modified naphthalene water reducers and preparation method thereof.It is by the fused ring compound concentrated sulfuric acid
Sulfonation obtains sulfonating reaction product.Fused ring compound is carried out to etherification modified, generation condensed ring polyethers.By sulfonated products, condensed ring is poly-
Ether and formaldehyde copolymer finally obtain the modified naphthalene series water-reducing agent with side chain.
New modified naphthalene water reducer has efficient water-reduction to concrete, and have preferable anti-clay and
Bleed is shown and the well adapting to property such as water-reducing agent, air entraining agent, retarder.
Modified naphthalene series water-reducing agent of the present invention is by sulfonated products, condensed ring polyethers, formaldehyde according to molar ratio 1:(0.1
~10): compound made of (1.1~11) condensation.
It according to molar ratio is 1:(1.1~1.3 that the sulfonated products, which are by the first fused ring compound and the concentrated sulfuric acid) sulfonation is anti-
It should be made；
The condensed ring polyethers is general formula (A) compound represented,
R is 1- naphthalene, 2- naphthalene, 9- phenanthryl, 1- pyrenyl, and n=0~100 in general formula；M=0~100.
First fused ring compound is 1- naphthols, beta naphthal, 9- hydroxyl phenanthrene, 1- hydroxyl pyrene.
The condensed ring polyethers be by the second fused ring compound, catalyst and etherifying agent according to molar ratio be 1:(0.05~
0.1): (10~100) are made.
Second fused ring compound is 1- naphthols, beta naphthal, 9- hydroxyl phenanthrene, 1- hydroxyl pyrene；
The catalyst is potassium hydroxide, sodium hydroxide, potassium alcoholate, sodium alkoxide, metallic sodium；
The etherifying agent is one of ethylene oxide, propylene oxide or two kinds of mixture.
The preparation method of modified naphthalene series water-reducing agent of the present invention, specifically comprises the following steps:
(1) preparation of sulfonated products: the first fused ring compound is put into heat in reactor and is melted, is warming up to 140~150
DEG C, concentrated sulfuric acid 30min is slowly added dropwise, drips off and is warming up to 150~170 DEG C of 2~4h of sulfonation, reaction was completed, obtains sulfonated products；
(2) preparation of condensed ring polyethers: the second fused ring compound and catalyst are placed in reaction kettle, closed, are passed through nitrogen
Exchange 3~4 times to remove the air in kettle；120~160 DEG C are warming up to, under conditions of reaction pressure is less than 0.7Mpa, to anti-
It answers and is slowly introducing etherifying agent in kettle, cure 2~4h, then cooling degassing discharging, obtains condensed ring polyethers；
(3) preparation of modified naphthalene series water-reducing agent: condensed ring made from sulfonated products made from step (1) and step (2) is poly-
Ether is placed in reaction kettle, and the concentrated sulfuric acid and water are slowly added dropwise after mixing, and adjusting acidity is 26%~30%, is then heated to 90
~110 DEG C, formaldehyde 30min is slowly added dropwise, is added dropwise rear closed, is to slowly warm up to 120~140 DEG C of 4~6h of reaction.Reaction knot
Cooling after beam, with sodium hydroxide tune pH to 7~8, drying is crushed up to compound, the as described modified naphthalene series water-reducing agent.
The utility model has the advantages that
New modified naphthalene water reducer of the invention has the advantage that compared with traditional naphthalene water reducer
(1) polycondensation of raw materials of the new modified naphthalene water reducer of the present invention are relatively active compared with naphthalene sulfonic acids, therefore polycondensation is relatively held
Easily, more economical from the aspect of saving the energy.
(2) the new modified naphthalene water reducer of the present invention has polyether lateral chain, compared with conventional polycondensation type water-reducing agent, more skies
Between steric effect, better peptizaiton is played to cement granules.
Based on the difference in the above structure, therefore, the new modified naphthalene water reducer of the present invention is in addition to having height to concrete
Outside the water-reducing effect of effect, also there is preferable anti-clay and bleed.
Specific embodiment
Following embodiment has described in more detail the process of modified condensation polymer type water-reducing agent prepared according to the methods of the invention,
And these embodiments provide by way of illustration, of the invention its object is to which person skilled in the art can understand
Content is simultaneously implemented accordingly, but these embodiments are in no way intended to limit the scope of the present invention.Made by all Spirit Essences according to the present invention etc.
Changes or modifications are imitated, should be covered by the protection scope of the present invention.
In Application Example of the present invention, used cement is small open country II cement of field 52.5R.P., and sand is fineness modulus
For the middle sand of Mx=2.6, stone is the rubble that partial size is 5~20mm continuous grading.Concrete slump, water-reducing rate, air content
Test is executed referring to standard GB/T 8076-2008 " concrete admixture " relevant regulations.Raw material used in embodiment is all logical
Cross commercially available acquisition.
Synthetic example 1
(1) preparation of sulfonated products: 1mol beta naphthal is put into heat in reactor and is melted, is warming up to 140 DEG C, slowly
1.1mol concentrated sulfuric acid 30min is added dropwise, drips off and is warming up to 150 DEG C of sulfonation 2h, reaction was completed, obtains sulfonated products.
(2) preparation of condensed ring polyethers: 1mol beta naphthal and 0.05mol sodium methoxide are placed in reaction kettle, closed, are passed through
Nitrogen exchanges 3~4 times to remove the air in kettle.120 DEG C are warming up to, under conditions of reaction pressure is 0.5Mpa, Xiang Fanying
It is slowly introducing 10mol ethylene oxide in kettle, cures 2h, then cooling degassing discharging, obtains condensed ring polyethers.
(3) preparation of modified naphthalene series water-reducing agent: 1mol sulfonated products and 0.1mol condensed ring polyethers are placed in reaction kettle, are mixed
The a certain amount of concentrated sulfuric acid and water is slowly added dropwise after closing uniformly, Controlled acidity 26% is then heated to 90 DEG C, 1.1mol is slowly added dropwise
Formaldehyde 30min, is added dropwise rear closed, is to slowly warm up to 120 DEG C of reaction 4h.It cools down after reaction, with sodium hydroxide tune pH
To 7~8, it is the modified naphthalene series water-reducing agent that drying, which crushes up to condensation compound,.
Synthetic example 2
(1) preparation of sulfonated products: 1mol 1- naphthols is put into heat in reactor and is melted, is warming up to 150 DEG C, slowly
1.3mol concentrated sulfuric acid 30min is added dropwise, drips off and is warming up to 170 DEG C of sulfonation 4h, reaction was completed, obtains sulfonated products.
(2) preparation of condensed ring polyethers: 1mol beta naphthal and 0.1mol sodium hydroxide are placed in reaction kettle, closed, are passed through
Nitrogen exchanges 3~4 times to remove the air in kettle.140 DEG C are warming up to, under conditions of reaction pressure is 0.5Mpa, Xiang Fanying
It is slowly introducing 100mol ethylene oxide in kettle, cures 4h, then cooling degassing discharging, obtains condensed ring polyethers.
(3) preparation of modified naphthalene series water-reducing agent: 1mol sulfonated products and 10mol condensed ring polyethers are placed in reaction kettle, are mixed
The a certain amount of concentrated sulfuric acid and water is slowly added dropwise after closing uniformly, Controlled acidity 30% is then heated to 110 DEG C, 11mol is slowly added dropwise
Formaldehyde 30min, is added dropwise rear closed, is to slowly warm up to 140 DEG C of reaction 6h.It cools down after reaction, with sodium hydroxide tune pH
To 7~8, it is the modified naphthalene series water-reducing agent that drying, which crushes up to condensation compound,.
Synthetic example 3
(1) preparation of sulfonated products: 1mol beta naphthal is put into heat in reactor and is melted, is warming up to 150 DEG C, slowly
1.2mol concentrated sulfuric acid 30min is added dropwise, drips off and is warming up to 160 DEG C of sulfonation 3h, reaction was completed, obtains sulfonated products.
(2) preparation of condensed ring polyethers: 1mol beta naphthal and 0.05mol sodium methoxide are placed in reaction kettle, closed, are passed through
Nitrogen exchanges 3~4 times to remove the air in kettle.130 DEG C are warming up to, under conditions of reaction pressure is 0.5Mpa, Xiang Fanying
It is slowly introducing 50mol ethylene oxide in kettle, cures 3h, then cooling degassing discharging, obtains condensed ring polyethers.
(3) preparation of modified naphthalene series water-reducing agent: 1mol sulfonated products and 1mol condensed ring polyethers are placed in reaction kettle, mixing
The a certain amount of concentrated sulfuric acid and water is slowly added dropwise after uniformly, Controlled acidity 28% is then heated to 100 DEG C, and 2mol first is slowly added dropwise
Aldehyde 30min, is added dropwise rear closed, is to slowly warm up to 130 DEG C of reaction 5h.It cools down after reaction, with sodium hydroxide tune pH to 7
~8, it is the modified naphthalene series water-reducing agent that drying, which crushes up to condensation compound,.
Synthetic example 4
(1) preparation of sulfonated products: 1mol beta naphthal is put into heat in reactor and is melted, is warming up to 150 DEG C, slowly
1.2mol concentrated sulfuric acid 30min is added dropwise, drips off and is warming up to 160 DEG C of sulfonation 3h, reaction was completed, obtains sulfonated products.
(2) preparation of condensed ring polyethers: 1mol beta naphthal and 0.05mol sodium methoxide are placed in reaction kettle, closed, are passed through
Nitrogen exchanges 3~4 times to remove the air in kettle.130 DEG C are warming up to, under conditions of reaction pressure is 0.5Mpa, Xiang Fanying
It is slowly introducing 50mol ethylene oxide in kettle, cures 2h, then be slowly introducing 50mol propylene oxide, cures 2h, then cooling degassing
Discharging, obtains condensed ring polyethers.
(3) preparation of modified naphthalene series water-reducing agent: 1mol sulfonated products and 1mol condensed ring polyethers are placed in reaction kettle, mixing
The a certain amount of concentrated sulfuric acid and water is slowly added dropwise after uniformly, Controlled acidity 28% is then heated to 100 DEG C, and 2mol first is slowly added dropwise
Aldehyde 30min, is added dropwise rear closed, is to slowly warm up to 130 DEG C of reaction 5h.It cools down after reaction, with sodium hydroxide tune pH to 7
~8, it is the modified naphthalene series water-reducing agent that drying, which crushes up to condensation compound,.
Synthetic example 5
(1) preparation of sulfonated products: 1mol 9- hydroxyl phenanthrene is put into heat in reactor and is melted, 140 DEG C is warming up to, delays
It is slow that 1.1mol concentrated sulfuric acid 30min is added dropwise, it drips off and is warming up to 150 DEG C of sulfonation 2h, reaction was completed, obtains sulfonated products.
(2) preparation of condensed ring polyethers: 1mol beta naphthal and 0.05mol metallic sodium are placed in reaction kettle, closed, are passed through
Nitrogen exchanges 3~4 times to remove the air in kettle.120 DEG C are warming up to, under conditions of reaction pressure is 0.5Mpa, Xiang Fanying
It is slowly introducing 10mol ethylene oxide in kettle, cures 2h, then cooling degassing discharging, obtains condensed ring polyethers.
(3) preparation of modified naphthalene series water-reducing agent: 1mol sulfonated products and 0.1mol condensed ring polyethers are placed in reaction kettle, are mixed
The a certain amount of concentrated sulfuric acid and water is slowly added dropwise after closing uniformly, Controlled acidity 26% is then heated to 90 DEG C, 1.1mol is slowly added dropwise
Formaldehyde 30min after being added dropwise, is to slowly warm up to 120 DEG C of reaction 4h.Cool down after reaction, with sodium hydroxide tune pH to 7~
8, it is the modified naphthalene series water-reducing agent that drying, which crushes up to condensation compound,.
Synthetic example 6
(1) preparation of sulfonated products: 1mol 1- hydroxyl pyrene is put into heat in reactor and is melted, 140 DEG C is warming up to, delays
It is slow that 1.1mol concentrated sulfuric acid 30min is added dropwise, it drips off and is warming up to 150 DEG C of sulfonation 2h, reaction was completed, obtains sulfonated products.
(2) preparation of condensed ring polyethers: 1mol beta naphthal and 0.05mol metallic sodium are placed in reaction kettle, closed, are passed through
Nitrogen exchanges 3~4 times to remove the air in kettle.120 DEG C are warming up to, under conditions of reaction pressure is 0.5Mpa, Xiang Fanying
It is slowly introducing 10mol ethylene oxide in kettle, cures 2h, then cooling degassing discharging, obtains condensed ring polyethers.
(3) preparation of modified naphthalene series water-reducing agent: 1mol sulfonated products and 0.1mol condensed ring polyethers are placed in reaction kettle, are mixed
The a certain amount of concentrated sulfuric acid and water is slowly added dropwise after closing uniformly, Controlled acidity 28% is then heated to 90 DEG C, 1.1mol is slowly added dropwise
Formaldehyde 30min after being added dropwise, is to slowly warm up to 120 DEG C of reaction 4h.Cool down after reaction, with sodium hydroxide tune pH to 7~
8, it is the modified naphthalene series water-reducing agent that drying, which crushes up to condensation compound,.
Comparative example 1
Naphthalene series high-efficiency water-reducing agent；Jiangsu Subotexin Material Co., Ltd.
Comparative example 2
This comparative example is compared for synthetic example 1, without condensed ring polyethers in reaction raw materials,
(1) preparation of sulfonated products: 1mol beta naphthal is put into heat in reactor and is melted, is warming up to 140 DEG C, slowly
1.1mol concentrated sulfuric acid 30min is added dropwise, drips off and is warming up to 150 DEG C of sulfonation 2h, reaction was completed, obtains sulfonated products.
(2) preparation of water-reducing agent: 1.1mol sulfonated products are placed in reaction kettle, are slowly added dropwise after heating fusing a certain amount of
The concentrated sulfuric acid and water, Controlled acidity 26% are then heated to 90 DEG C, and 1.1mol formaldehyde 30min is slowly added dropwise, and are added dropwise rear close
It closes, is to slowly warm up to 120 DEG C of reaction 4h.It cools down after reaction, with sodium hydroxide tune pH to 7~8, drying is crushed up to contracting
Polymerisable compounds are the water-reducing agent.
Application examples
The present invention compares performance by concrete test, wherein concrete mix: cement 240kg, flyash 100kg,
Sand 750kg, great Shi 780kg, gravelstone 257kg, water 168kg.Test result is as follows shown in table 1.
The concrete performance of 1 water-reducing agent of table compares
As can be seen that new modified naphthalene water reducer is compared with traditional naphthalene water reducer from upper table 1, have to concrete
Higher water-reducing effect, and its air content is much larger than naphthalene series high-efficiency water-reducing agent.By comparative example 2 it can also be seen that not thickening the soup
Product water-reducing effect made of acyclic polyether is very poor, illustrates that water-reducing effect can be significantly when water-reducing agent space steric effect of the present invention is poor
It reduces.
The present invention investigates the anti-Property of Clay of water-reducing agent by Mortar'S Flowability.Wherein test uses iso standard with sand
Sand, cement-sand ratio 1:1.6, the montmorillonite of clay we selected typical, volume is in terms of the quality of sand, and water-reducing agent volume is with the quality of cement
Meter, test result is as follows shown in table 2.
The anti-Property of Clay of 2 water-reducing agent of table compares
Because 2 water-reducing effect of comparative example is poor, it is not involved in anti-stick soil nature contrast test.From the experimental result of upper table 2
As can be seen that traditional naphthalene water reducer performance is affected by clay, and the water-reducing agent prepared with the method for the present invention is by clay shadow
Sound is smaller, and far smaller than traditional naphthalene water reducer, it can be said that new modified naphthalene water reducer tool prepared by the present invention
There is excellent anti-Property of Clay.
Claims (4)
1. a kind of modified naphthalene series water-reducing agent, it is characterised in that: by sulfonated products, condensed ring polyethers, formaldehyde according to molar ratio 1:(0.1
~10): compound made of (1.1~11) condensation；
It according to molar ratio is 1:(1.1~1.3 that the sulfonated products, which are by the first fused ring compound and the concentrated sulfuric acid) sulfonating reaction system
?；
The condensed ring polyethers is general formula (A) compound represented,
R is 1- naphthalene, 2- naphthalene, 9- phenanthryl, 1- pyrenyl in general formula, and n=0~100, m=0~100, m, n are not 0 simultaneously；
First fused ring compound is 1- naphthols, beta naphthal, 9- hydroxyl phenanthrene, 1- hydroxyl pyrene.
2. a kind of modified naphthalene series water-reducing agent according to claim 1, which is characterized in that the condensed ring polyethers is thick by second
Cycle compound, catalyst and etherifying agent are 1:(0.05~0.1 according to molar ratio): (10~100) are made.
3. a kind of modified naphthalene series water-reducing agent according to claim 2, which is characterized in that second fused ring compound is 1-
Naphthols, beta naphthal, 9- hydroxyl phenanthrene, 1- hydroxyl pyrene；
The catalyst is potassium hydroxide, sodium hydroxide, potassium alcoholate, sodium alkoxide, metallic sodium；
The etherifying agent is one of ethylene oxide, propylene oxide or two kinds of mixture.
4. a kind of preparation method of modified naphthalene series water-reducing agent described in claim 2 or 3, which is characterized in that specifically include as follows
Step:
(1) preparation of sulfonated products: the first fused ring compound being put into heat in reactor and is melted, is warming up to 140~150 DEG C,
Concentrated sulfuric acid 30min is slowly added dropwise, drips off and is warming up to 150~170 DEG C of 2~4h of sulfonation, reaction was completed, obtains sulfonated products；
(2) preparation of condensed ring polyethers: the second fused ring compound and catalyst are placed in reaction kettle, closed, are passed through nitrogen exchange 3
~4 times to remove the air in kettle；120~160 DEG C are warming up to, under conditions of reaction pressure is less than 0.7MPa, to reaction kettle
In be slowly introducing etherifying agent, cure 2~4h, then cooling degassing discharging, obtains condensed ring polyethers；
(3) preparation of modified naphthalene series water-reducing agent: condensed ring polyethers made from sulfonated products made from step (1) and step (2) is set
In reaction kettle, it is slowly added dropwise the concentrated sulfuric acid and water after mixing, adjusting acidity is 26%~30%, it is then heated to 90~
110 DEG C, formaldehyde 30min is slowly added dropwise, is added dropwise rear closed, is to slowly warm up to 120~140 DEG C of 4~6h of reaction, reaction terminates
After cool down, with sodium hydroxide tune pH to 7~8, drying is crushed up to compound, the as described modified naphthalene series water-reducing agent.
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| CN107640922B (en) * | 2017-10-13 | 2020-05-22 | 浙江雄宇混凝土构件有限公司 | Additive for improving durability of concrete and preparation method thereof |
| CN107936208B (en) * | 2017-11-01 | 2020-05-26 | 江苏苏博特新材料股份有限公司 | Cationic monomer, modified naphthalene water reducer using same and preparation method |
| CN107973536A (en) * | 2017-11-16 | 2018-05-01 | 江苏苏博特新材料股份有限公司 | A kind of oligomeric-type concrete defoamer, its preparation method and application |
| CN108636284A (en) * | 2018-03-23 | 2018-10-12 | 上海师范大学 | Polyoxyethylene ether side chain naphthalene sulphonate formaldehyde is condensed surfactant and preparation method |
| CN110540639B (en) * | 2019-09-06 | 2021-10-15 | 武汉奥克特种化学有限公司 | Parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof |
| CN112812289A (en) * | 2021-01-21 | 2021-05-18 | 吉林瑞吉特殊化学品有限公司 | Anti-mud ethoxylated naphthalene aromatic ring derivative monomer and preparation method thereof |
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