CN109439056A - A kind of non-ionic associative type aqueous polyurethane thickener and preparation method thereof - Google Patents
A kind of non-ionic associative type aqueous polyurethane thickener and preparation method thereof Download PDFInfo
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- CN109439056A CN109439056A CN201811132419.7A CN201811132419A CN109439056A CN 109439056 A CN109439056 A CN 109439056A CN 201811132419 A CN201811132419 A CN 201811132419A CN 109439056 A CN109439056 A CN 109439056A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- Engineering & Computer Science (AREA)
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Abstract
The invention discloses a kind of non-ionic associative type aqueous polyurethane thickeners and preparation method thereof, and preparation method is as follows: (1) handling PEG vacuum dehydration；(2) 250-500 parts of PEG and 18-25 parts of HDI are mixed at 60-70 DEG C, and catalyst is added, in 105 DEG C of ± 5 DEG C of reactions under inert gas shielding；(3) 10-20 parts of GMO and 5-10 parts of C12 alcohol-C14 alcohol are added and add catalyst in 105 DEG C ± 5 DEG C under inert gas shielding, be warming up to 110 DEG C of -120 DEG C of reactions；(4) 90-100 DEG C is cooled to, hydrogen peroxide is added and keeps reaction；(5) cool down, solvent is added, stir 20-30min, then plus water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.It is suitable that thickener prepared by the present invention compares thickening effect with foreign brand name, excellent water resistance, and storage stability is good.
Description
Technical field
The present invention relates to coating additive fields, in particular it relates to which a kind of non-ionic associative type aqueous polyurethane increases
Thick dose and preparation method thereof.
Background technique
With the development of society, environment is faced with severe tests, and requirement of the people to living environment is also higher and higher,
Coating mainly develops toward directions such as large arch dam, low VOC, powdered, Water-borne modification and photocurings at present, and wherein powdery paints is to painting
Dress technology and film thickness have higher requirements, and are promoting and application above has a certain limitation, and water paint due to its with
For water as decentralized medium, Environmental Safety is easy for construction, is just gradually accepted by people, fast-growth.Water-based thickener is water
Indispensable a part in property Design of Coatings Formulation, market are increasing to its demand.
Thickener is broadly divided into inorganic and organic currently on the market.Organic thickener divides alkali soluble swollen association thickener
(ASE-60, TT-935 etc.) cellulose family macromolecule thickener (hydroxyethyl cellulose etc.) and non-ionic associative type aqueous polyurethane
Thickener.However, non-ion aqueous polyurethane thickener is mainly occupied an leading position with external product on domestic market now,
Cost 10 yuan/kilogram or so product, to coatings enterprises hand in price reach 60 yuan/kilogram unexpectedly, have sieve door currently on the market
8W, 12W of Haas, 1290 series of products and Japanese firm's SN-612 series of products of BASF etc..Although now domestic
Have a corresponding non-ionic associative type aqueous polyurethane thickener, only a small number of producers' productions, but domestic manufacturer's production it is non-from
Much there is the problems such as partially yellow appearance, layering, thickening efficiency is low in sub- association type aqueous polyurethane thickener.
Summary of the invention
Based on this, the invention reside in overcoming the deficiencies of existing technologies, a kind of non-ionic associative type aqueous polyurethane increasing is provided
Thick dose and preparation method thereof, it is suitable that prepared thickener compares thickening effect with foreign brand name, excellent water resistance, and stores
Stability is good.
Its technical solution is as follows:
A kind of preparation method of non-ionic associative type aqueous polyurethane thickener, includes the following steps:
(1) polyethylene glycol vacuum dehydration is handled；
(2) at 60-70 DEG C that 250-500 parts of polyethylene glycol (PEG) and 18-25 parts of hexa-methylenes two are different in the reactor
Cyanate (HDI) mixing, and organotin catalysts are added, stirred under inert gas shielding and are warming up to 105 DEG C ± 5 DEG C, so
After react 2-3h；
(3) 10-20 parts of Monooleins (GMO) and 5-10 parts of C12 alcohol-C14 alcohol are added, are protected under inert gas shielding
105 DEG C ± 5 DEG C are held, 0.5h-1h is reacted, adds 1-2 parts of organic bismuth catalysts, is warming up to 110 DEG C -120 DEG C, keeps temperature not
Become, reacts 3-4h；
(4) 90-100 DEG C is cooled to, 20-40 parts of hydrogen peroxide are added and keep 0.5-1.5h；
(5) 70 DEG C are cooled to hereinafter, 200-450 parts of dipropylene glycol monomethyl ethers are added, then stirring 20-30min is added
200-400 parts of water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.
The non-ionic associative type aqueous polyurethane thickener of the application preparation is mainly first reacted with HDI with polyethylene glycol
To polyurethane, then using HDI as linking point, the Monoolein with hydrophobic grouping is introduced into molecule, side chain is had
Hydrophobic group, and the isocyano of strand is sealed by the 12 alcohol-C14 alcohol of hydrophobicity long-chain substance C of monohydroxy
End control molecular size range, so that obtaining strand both ends and side chain is the macromolecular chain of hydrophobic chain.Initial reaction stage will gather
Ethylene glycol reacts to obtain polyurethane with HDI, and for HDI as linking point, HDI is excessive, and the strand of synthesis there remains isocyano；And
GMO is introduced into strand afterwards, and using HDI segment as linking point, then isocyano is sealed with C12 alcohol-C14 alcohol
End, one side C12 alcohol-C14 alcohol can control polyurethane molecular chain, and another aspect C12 alcohol-C14 alcohol alkyl segment can be improved
The hydrophobicity of system；Hydrogen peroxide is added to post-process isocyano, be eventually adding water emulsification have excellent performance to obtain the final product it is non-
Ionic aqueous polyurethane thickener.Only needing that a small amount of thickener is added in Design of Coatings Formulation can reach well
Thickening efficiency, thickening power mainly pass through the inside that the hydrophobic end of the chain stretches to latex particle, and polyethanol hydrophilic segment is then staying
In water phase, so that particle is together in series, the mobility reflected under shearing force.
The polyethylene glycol is PEG-6000, PEG-7000, PEG-8000 or PEG- in one of the embodiments,
10000.If PEG molecular weight is lower, the strand synthesized is short, and thickening efficiency does not have the good of high molecular weight, if but molecular weight mistake
Height, then the chain molecular weight synthesized is larger, reacts easy gel and is not easily controlled.Further, comprehensive from cost and in performance
It closes and considers, preferred polyethylene glycol is PEG-6000.
The polyethylene glycol vacuum dehydration processing in one of the embodiments, are as follows: 250-550 parts of polyethylene glycol heat up
To 70-80 DEG C, 1-2 parts of antioxidant are added after polyethylene glycol is completely dissolved, temperature maintains 100-105 DEG C, the pumpdown time
3-4 hours.Due to containing water impurity in polyethylene glycol, there is large effect to later period synthesis and emulsion appearance, therefore first
It to clean to Macrogol 6000, vacuumize and remove extra moisture.
The organotin catalysts are T-12 or tin octoate in one of the embodiments,.
The organic bismuth catalyst is DY-20 in one of the embodiments,.
The non-ionic associative type aqueous polyurethane thickener that the preparation method is prepared.
The beneficial effects of the present invention are: the present invention is using polyethylene glycol as hydrophilic segment, and HDI is as linking point, band
Having the Monoolein of hydrophobic grouping to be introduced into molecule makes side chain have hydrophobic group, and passes through the hydrophobic of monohydroxy
Property long-chain substance sealing end control molecular size range is carried out to strand, to obtain strand both ends and side chain is hydrophobic chain
Macromolecular chain, its inside that latex particle is stretched to by the hydrophobic end of the chain, hydrophilic section are then staying in water phase in coating system, from
And particle can be together in series, the mobility reflected under shearing force.
Specific embodiment
To make the objectives, technical solutions, and advantages of the present invention more comprehensible, below in conjunction with specific embodiment, to this
Invention is described in further detail.It should be understood that the specific embodiments described herein are only to explain this hair
It is bright, and the scope of protection of the present invention is not limited.
Embodiment 1
A kind of non-ionic associative type aqueous polyurethane thickener, preparation process are as follows:
(1) 400 parts of polyethylene glycol PEG-6000 are warming up to 70-80 DEG C, 2 parts is added after polyethylene glycol is completely dissolved and resists
Oxygen agent, temperature maintain 100-105 DEG C, pumpdown time 3-4 hour；
(2) polyethylene glycol (PEG-6000) and 26 part of six Asia after purifying 360 parts at 60-70 DEG C in four-hole boiling flask
Methyl diisocyanate (HDI) mixing, and 1.5g organotin catalysts T-12 is added, it is displaced in four-hole boiling flask by argon gas
Air stirs under inert gas argon gas shielded and is warming up to 105 DEG C ± 5 DEG C, then proceedes to reaction 2-3h；
(3) gas in four-hole boiling flask is exhausted, 18.5 parts of Monooleins and 8.5 parts of 14 alcohol of carbon are added, in indifferent gas
Body protection is lower to be kept for 105 DEG C ± 5 DEG C, is reacted 0.5h-1h, is added 1.5 parts of organic bismuth catalysts, be warming up to 110 DEG C -120 DEG C,
It keeps temperature-resistant, reacts 3-4h；
(4) 90-100 DEG C is cooled to, 25 parts of hydrogen peroxide are added and keep 0.5-1.5h；
(5) 70 DEG C are cooled to hereinafter, 324 parts of dipropylene glycol monomethyl ethers are added, then stirring 20-30min is added 300 parts
Water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.
Embodiment 2
A kind of non-ionic associative type aqueous polyurethane thickener, preparation process are as follows:
(1) 550 parts of polyethylene glycol PEG-10000 are warming up to 70-80 DEG C, 2 parts is added after polyethylene glycol is completely dissolved
Antioxidant, temperature maintain 100-105 DEG C, pumpdown time 3-4 hour；
(2) in four-hole boiling flask at 60-70 DEG C by 500 parts purification after polyethylene glycol (PEG-10000) and 22.3 parts
Hexamethylene diisocyanate mixing, and 2g organotin catalysts T-12 is added, the sky in four-hole boiling flask is displaced by argon gas
Gas stirs under inert gas argon gas shielded and is warming up to 105 DEG C ± 5 DEG C, then proceedes to reaction 2-3h；
(3) gas in four-hole boiling flask is exhausted, 15.9 parts of Monooleins and 7.3 parts of 14 alcohol of carbon are added, in indifferent gas
Body protection is lower to be kept for 105 DEG C ± 5 DEG C, is reacted 0.5h-1h, is added 1.5 parts of organic bismuth catalysts, be warming up to 110 DEG C -120 DEG C,
It keeps temperature-resistant, reacts 3-4h；
(4) 90-100 DEG C is cooled to, 30 parts of hydrogen peroxide are added and keep 0.5-1.5h；
(5) 70 DEG C are cooled to hereinafter, 420 parts of dipropylene glycol monomethyl ethers are added, then stirring 20-30min is added 400 parts
Water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.
Embodiment 3
A kind of non-ionic associative type aqueous polyurethane thickener, preparation process are as follows:
(1) 300 parts of polyethylene glycol PEG-10000 are warming up to 70-80 DEG C, 1 part is added after polyethylene glycol is completely dissolved
Antioxidant, temperature maintain 100-105 DEG C, pumpdown time 3-4 hour；
(2) in four-hole boiling flask at 60-70 DEG C by 250 parts purification after polyethylene glycol (PEG-6000) and 18.6 part six
Methylene diisocyanate mixing, and 1g organotin catalysts T-12 is added, the air in four-hole boiling flask is displaced by argon gas,
It is stirred under inert gas argon gas shielded and is warming up to 105 DEG C ± 5 DEG C, then proceed to reaction 2-3h；
(3) gas in four-hole boiling flask is exhausted, 13.3 parts of Monooleins and 6 parts of 14 alcohol of carbon are added, in inert gas
Protection is lower to be kept for 105 DEG C ± 5 DEG C, is reacted 0.5h-1h, is added 1 part of organic bismuth catalyst, be warming up to 110 DEG C -120 DEG C, keeps
It is temperature-resistant, react 3-4h；
(4) 90-100 DEG C is cooled to, 20 parts of hydrogen peroxide are added and keep 0.5-1.5h；
(5) 70 DEG C are cooled to hereinafter, 200 parts of dipropylene glycol monomethyl ethers are added, then stirring 20-30min is added 235 parts
Water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.
Embodiment 4
A kind of non-ionic associative type aqueous polyurethane thickener, preparation process are as follows:
(1) 500 parts of polyethylene glycol PEG-8000 are warming up to 70-80 DEG C, 2 parts is added after polyethylene glycol is completely dissolved and resists
Oxygen agent, temperature maintain 100-105 DEG C, pumpdown time 3-4 hour；
(2) in four-hole boiling flask at 60-70 DEG C by 400 parts purification after polyethylene glycol (PEG-8000) and 22.3 part six
Methylene diisocyanate mixing, and 2g organotin catalysts T-12 is added, the air in four-hole boiling flask is displaced by argon gas,
It is stirred under inert gas argon gas shielded and is warming up to 105 DEG C ± 5 DEG C, then proceed to reaction 2-3h；
(3) gas in four-hole boiling flask is exhausted, 15.9 parts of Monooleins and 6.34 parts of 12 alcohol of carbon are added, in indifferent gas
Body protection is lower to be kept for 105 DEG C ± 5 DEG C, is reacted 0.5h-1h, is added 2 parts of organic bismuth catalysts, be warming up to 110 DEG C -120 DEG C, protects
Hold temperature-resistant, reaction 3-4h；
(4) 90-100 DEG C is cooled to, 40 parts of hydrogen peroxide are added and keep 0.5-1.5h；
(5) 70 DEG C are cooled to hereinafter, 370 parts of dipropylene glycol monomethyl ethers are added, then stirring 20-30min is added 300 parts
Water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.
Comparative example 1
A kind of thickener, preparation process is substantially the same manner as Example 1, and difference is, with 9.06 part 1,2- in step (3)
Monoolein in decanediol alternate embodiment 1.
Comparative example 2
A kind of thickener, preparation process is substantially the same manner as Example 1, and difference is, with 4.65 part of three hydroxyl in step (3)
Monoolein in methylpropane alternate embodiment 1.
Non-ionic associative type aqueous polyurethane thickener and comparative example 1 preparation for taking 5g embodiment 1-4 to be prepared respectively
Thickener, be added separately in 500g styrene-acrylic emulsion (BASF 296-DS), the viscosity of measurement system, measurement result such as table 1
It is shown.
Table 1
The formula for selecting wood lacquer emulsion (2695 hydroxyl dispersion of Bayer) adds this experiment according to 0.5% amount and closes
At non-ionic associative type aqueous polyurethane thickener into formula, then prepare paint film on a glass, be put into drying box
In 50 DEG C of baking 8h, from drying box take out be cooled to room temperature, then glass plate is put into water, so that paint film one third
It sentences down and is immersed in the water, observe paint film water resistance.Test result is shown in Table 2.
Table 2
| Test item | 24h | 48h | 96h |
| Embodiment 1 | Do not whiten not blistering | Do not whiten not blistering | Do not whiten not blistering |
| Embodiment 2 | Do not whiten not blistering | Do not whiten not blistering | Do not whiten not blistering |
| Embodiment 3 | Do not whiten not blistering | Do not whiten not blistering | Do not whiten not blistering |
| Embodiment 4 | Do not whiten not blistering | Do not whiten not blistering | Do not whiten not blistering |
| Comparative example 1 | Do not whiten not blistering | Do not whiten not blistering | Whiten not blistering |
| Comparative example 2 | Do not whiten not blistering | Do not whiten not blistering | Whiten not blistering |
The thickener for taking 100g embodiment 1-4, comparative example 1, comparative example 2 to prepare is placed in the reagent bottle of 200mL, static,
The appearance of observation thickener judges its storage stability.It the results are shown in Table 3.
Table 3
9 yuan of cost price of the non-ionic associative type aqueous polyurethane thickener per kilogram of the present embodiment 1-4 preparation, produces than foreign countries
Product have significant price advantage.
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (6)
1. a kind of preparation method of non-ionic associative type aqueous polyurethane thickener, which comprises the steps of:
(1) polyethylene glycol vacuum dehydration is handled；
(2) 250-500 parts of polyethylene glycol and 18-25 parts of hexamethylene diisocyanates are mixed at 60-70 DEG C in the reactor
It closes, and organotin catalysts is added, stirred under inert gas shielding and be warming up to 105 DEG C ± 5 DEG C, then react 2-3h；
(3) 10-20 part Monooleins and 5-10 parts of C12 alcohol-C14 alcohol are added, under inert gas shielding 105 DEG C of holding ±
5 DEG C, 0.5h-1h is reacted, 1-2 parts of organic bismuth catalysts are added, be warming up to 110 DEG C -120 DEG C, kept temperature-resistant, react 3-
4h；
(4) 90-100 DEG C is cooled to, 20-40 parts of hydrogen peroxide are added and keep 0.5-1.5h；
(5) 70 DEG C are cooled to hereinafter, 200-450 parts of dipropylene glycol monomethyl ethers are added, then 200- is added in stirring 20-30min
400 parts of water, filtering obtain the thickening of non-ionic associative type aqueous polyurethane.
2. preparation method according to claim 1, which is characterized in that the polyethylene glycol be PEG-6000, PEG-7000,
PEG-8000 or PEG-10000.
3. preparation method according to claim 1, which is characterized in that the polyethylene glycol vacuum dehydration processing are as follows: will
250-550 parts of polyethylene glycol are warming up to 70-80 DEG C, and 1-2 parts of antioxidant are added after polyethylene glycol is completely dissolved, and temperature maintains
100-105 DEG C, pumpdown time 3-4 hour.
4. preparation method according to claim 1, which is characterized in that the organotin catalysts are T-12 or tin octoate.
5. preparation method according to claim 1, which is characterized in that the organic bismuth catalyst is DY-20.
6. the non-ionic associative type aqueous polyurethane that preparation method described in claim 1-5 any claim is prepared increases
Thick dose.
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| CN112708095A (en) * | 2020-12-28 | 2021-04-27 | 华南理工大学 | Branched hydrophobic end modified association type water-based urethane thickener and preparation method and application thereof |
| CN115652660A (en) * | 2022-11-10 | 2023-01-31 | 广东传化富联精细化工有限公司 | Reactive dye printing thickener and preparation method thereof |
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