CN107828049A - A kind of watersoluble closed polyisocyanate curing agent of aziridine type and preparation method thereof - Google Patents
A kind of watersoluble closed polyisocyanate curing agent of aziridine type and preparation method thereof Download PDFInfo
- Publication number
- CN107828049A CN107828049A CN201711116994.3A CN201711116994A CN107828049A CN 107828049 A CN107828049 A CN 107828049A CN 201711116994 A CN201711116994 A CN 201711116994A CN 107828049 A CN107828049 A CN 107828049A
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- China
- Prior art keywords
- curing agent
- polyisocyanate curing
- aziridine
- watersoluble closed
- aziridine type
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Classifications
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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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
-
- 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
- C08G18/08—Processes
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of watersoluble closed polyisocyanate curing agent of aziridine type and preparation method, it is comprised the following raw materials by weight percent：Aqueous polyisocyanate curing agent 65 70%, aziridine and/or its derivative 10 15%, Propylene Glycol Ether Ester Series Solvent 18 25%, auxiliary agent 0.5 0.8%；The polyisocyanate curing agent of the present invention is lacks with or without solvent, environment-protecting and non-poisonous, viscosity is low, is easily scattered in waterborne polymeric；The watersoluble closed polyisocyanate curing agent of aziridine type of the present invention has the characteristics that particle size is uniform, stability is good after pot-life length, emulsification, the baking deblocking of bottom temperature；It in addition, the present invention need not carry out any post processing, can be produced using in general prepolymer production equipment, without increasing new equipment, there is the characteristics of equipment cost is low, simple to operate, and energy consumption is small in processing procedure.
Description
Technical field
The present invention relates to a kind of polyurethane curing agent, specifically a kind of watersoluble closed polyisocyanate curing agent of aziridine type
And preparation method thereof.
Background technology
In recent years, because environmentally friendly pressure from public opinion is growing day by day and some developed country's fire codes and solvent regulation go out
Platform, limit the use of dissolvant type polyurethane curing agent, promote all over the world polyurethane material researcher actively carry out it is water-based
The exploitation and research of polyurethane curing agent, and then the curing agent of aqueous polyurethane also produces therewith and fast development.With the mankind
The increase of environmental consciousness, water-base polyurethane material substitute traditional solvent borne polyurethane material as inevitable trend and needs.
Watersoluble closed type polyurethane curing agent has few solvent or solvent-free, odorless, without dirt using water as decentralized medium
Dye, it is non-ignitable, easily with the blending of other emulsions, beneficial to it is modified the features such as, oneself is widely used in adhesive, coating, paper coating, skin
Remove from office in the products such as finishing agent.
The watersoluble closed polyisocyanate curing agent of aziridine type is introduced on the basis of aqueous polyisocyanate curing agent
Aziridine group carrys out blocked polyisocyanate, and to make it easier to the emulsion dispersion in water and keep certain stability, and can exists
Aziridine group is unsealed in the range of 105-120 DEG C；Its advantage is is free of or contained less solvent, environment-protecting and non-poisonous, viscosity is low, easily scattered
In waterborne polymeric.But at present, the watersoluble closed polyisocyanate curing agent largely produced is all that sealer is first and second
Ketoxime, imidazoles, phenol etc., such as patent document CN201110367434.1, CN201210397131.9, CN201410196585.9
Deng it is purely decomposable process that this type sealer unseals in the case of a high temperature.And it can both be decomposed as sealer with aziridine
Unlocking isocyano can be unsealed with aziridine ring-opening reaction again, wherein the maximum advantage of open loop deblocking be the amido generated and
Hydroxyl can react with isocyano, be formed more to close paint film.
The content of the invention
For overcome the deficiencies in the prior art, it is an object of the invention to provide a kind of watersoluble closed polyisocyanic acid of aziridine type
Ester curing agent and preparation method thereof.
The purpose of the present invention is achieved through the following technical solutions：
A kind of watersoluble closed polyisocyanate curing agent of aziridine type, including following raw material by weight percentage：
Aqueous polyisocyanate curing agent 64-75%；
Aziridine and/or its derivative 10-20%；
Propylene Glycol Ether Ester Series Solvent 14-25%
Auxiliary agent 0.2-1%.
Preferably, the watersoluble closed polyisocyanate curing agent of aziridine type includes following original by weight percentage
Material：
Aqueous polyisocyanate curing agent 65-70%；
Aziridine and/or its derivative 10-15%；
Propylene Glycol Ether Ester Series Solvent 18-24%
Other auxiliary agents 0.5-0.8%.
Further preferably, the aqueous polyisocyanate curing agent is the water that hexamethylene diisocyanate (HDI) is matrix synthesis
Property isocyanate curing agent and/or IPDI (IPDI) be matrix synthesis Water-borne modification cured with isocyanates
Agent.
It is highly preferred that the Water-borne modification isocyanate curing agent is selected from hexamethylene diisocyanate class addition product, oneself two isocyanic acids
Class tripolymer, hexamethylene diisocyanate (HDI) class polymer, hexamethylene diisocyanate (HDI) biuret and isophorone diisocyanate
At least one in esters addition product, IPDI class tripolymer and IPDI class polymer
Kind.
Preferably, the aziridine and/or its derivative be in aziridine, methylaziridine, ethylaziridine at least
It is a kind of.
Preferably, the Propylene Glycol Ether Ester Series Solvent is selected from propylene glycol monomethyl ether methyl esters, propylene-glycol ethyl ether acetate, propane diols
At least one of methyl ether acetate, propylene-glycol ethyl ether butyl ester, propylene-glycol methyl ether butyl ester, propandiol butyl ether acetate.
Preferably, the auxiliary agent is selected from 1-METHYLPYRROLIDONE, DMF, dibutyl tin laurate, pungent
Sour stannous, N, in N dimethyl cyclohexylamine, triethylenediamine, triethylamine, tripropylamine, diethanol amine, triethanolamine at least
It is a kind of.
The preparation method of the above-mentioned watersoluble closed polyisocyanate curing agent of aziridine type, comprises the following steps：
(1) by aqueous polyisocyanate curing agent and propylene glycol alcohols solvent input reactor, heat while stirring,
For temperature control in the range of 40-50 DEG C, mixing speed is about 60 revs/min；
(2) aziridine and/or its derivative are added in reactor, temperature control at 40-50 DEG C and constantly stirring thing material,
After fully reaction 2-6h, add auxiliary agent and illustrate anti-between 2.2-3.2 in 40-50 DEG C of insulation reaction 2-3h, test nco value stabilization
Should be own through completely, obtaining uniform solution；
(3) cool to 30-35 DEG C, filtering and discharging produces after stirring.
Beneficial effects of the present invention：
The present invention mainly improves water-based polyisocyanates by introducing aziridine and/or its derivatives group, makes it
The emulsion dispersion in water is can be easy to, and keeps certain stability.The advantages of polyisocyanate curing agent of the present invention is to contain less
Or without solvent, environment-protecting and non-poisonous, viscosity is low, is easily scattered in waterborne polymeric；And it can be unsealed at 105-120 DEG C more
Active group, make the film layer after film forming finer and close, physical property and patience all have a certain upgrade.The poly- ammonia of modification of the type
Ester can directly be dispersed in water to form stable polyaminoester emulsion.After the curing agent of gained of the invention has pot-life length, emulsification
The features such as particle size is uniform, stability is good.In addition, the present invention need not carry out any post processing, given birth to using in general prepolymer
Production equipment can produce, and without increasing new equipment, have the characteristics of equipment cost is low, simple to operate, and energy in processing procedure
Consume small.
Embodiment
In order to be best understood from the present invention, with reference to embodiment, the present invention will be described in detail, but the present invention is simultaneously
It is not limited to the scope of embodiment expression.
Embodiment 1
A kind of watersoluble closed polyisocyanate curing agent of aziridine type, is prepared from the following materials：
Add 340g's in a 1000mL four-hole boiling flask protected equipped with agitating device, thermometer and logical nitrogen successively
Cohan wound water-based isocyanate curing agent 2655 (HDI trimer type), 100g propylene glycol methyl ether acetate, while with 60 turns/
Minute speed stirring side is warming up to 40 DEG C；After addition 60g aziridine stirs insulation 4 hours at 45 DEG C, 2g three second are added
Amine, be incubated at 50 DEG C the stable proved response between 2.2-3.2 of 2 hours test nco values oneself through complete.Then cool to 30 DEG C
Filtering and discharging after stirring, obtain product.Using GB 24410-2009《In indoor decorating and refurnishing materials water-borne wood coating
Limits of harmful substances》Standard detection relevant item, testing result are shown in Table 1.
The testing result of the polyisocyanate curing agent of the embodiment 1 of table 1
Embodiment 2
A kind of watersoluble closed polyisocyanate curing agent of aziridine type, is prepared from the following components：
Add 340g's in a 1000mL four-hole boiling flask protected equipped with agitating device, thermometer and logical nitrogen successively
Water-based isocyanate curing agent JY05S (HDI trimer type), the 100g propylene glycol monomethyl ether vinegar of Guangdong Ju Ying Chemical Co., Ltd.s
Acid esters, 40 DEG C are warming up to when being stirred with 60 revs/min of speed；60g aziridine is added, stirring insulation 4 hours at 45 DEG C
Afterwards, 1.8g dibutyl tin laurate is added, it is anti-that the stable proof between 2.2-3.2 of 2 hours test nco values is incubated at 50 DEG C
Should be own through complete.Then cool to 30 DEG C filtering and discharging after stirring, and obtains product.Using GB 24410-2009《Room
Limits of harmful substances in interior trim finishing material water-borne wood coating》Standard detection relevant item, testing result are shown in Table 2.
The testing result of the polyisocyanate curing agent of the embodiment 2 of table 2
Embodiment 3
A kind of watersoluble closed polyisocyanate curing agent of aziridine type, is prepared by following component：
Add 340g's in a 1000mL four-hole boiling flask protected equipped with agitating device, thermometer and logical nitrogen successively
Water-based isocyanate curing agent JY05S (HDI trimer type), the 105g propylene-glycol ethyl ether vinegar of Guangdong Ju Ying Chemical Co., Ltd.s
Acid esters, 40 DEG C are warming up to when being stirred with 60 revs/min of speed；80g methylaziridine is added, the stirring insulation 4 at 45 DEG C
After hour, 1.8g dibutyl tin laurate is added, 2 hours test nco value stabilizations are incubated at 50 DEG C to be proved between 2.2-3.2
Oneself warp of reaction is complete.Then cool to 30 DEG C filtering and discharging after stirring, and obtains product.Using GB 24410-2009
《Limits of harmful substances in indoor decorating and refurnishing materials water-borne wood coating》Standard detection relevant item.Testing result is shown in Table 3：
The testing result of the polyisocyanate curing agent of the embodiment 3 of table 3
Embodiment 4
A kind of watersoluble closed polyisocyanate curing agent of aziridine type, is prepared from the following materials：
Add 340g's in a 1000mL four-hole boiling flask protected equipped with agitating device, thermometer and logical nitrogen successively
Ten thousand China chemistry water-based isocyanate curing agent 270 (HDI trimer type), 105g propandiol butyl ether acetate, while with 60 turns/
Minute speed stirring side is warming up to 40 DEG C；80g methylaziridine is added, after being incubated 4 hours at 45 DEG C, adds 1.8g N,
N dimethyl cyclohexylamine, be incubated at 50 DEG C the stable proved response between 2.2-3.2 of 2 hours test nco values oneself through complete.Then it is cold
But be cooled to 30 DEG C stir after filtering and discharging, obtain product.Using GB 24410-2009《Indoor decorating and refurnishing materials water
Limits of harmful substances in property woodwork coating》Standard detection relevant item.Testing result is shown in Table 4.
The testing result of the polyisocyanate curing agent of the embodiment 4 of table 4
Embodiment 5
A kind of watersoluble closed polyisocyanate curing agent of aziridine type, is prepared from the following materials：
Add 500g's in a 1000mL four-hole boiling flask protected equipped with agitating device, thermometer and logical nitrogen successively
The water-based isocyanate curing agent 1470 (solid content of IPDI trimerizations build 70%) of Cohan wound, while being stirred with 60 revs/min of speed
While it is warming up to 40 DEG C；50g aziridine is added, after being incubated 4 hours at 45 DEG C, adds at 1.8g 50 DEG C of triethylamine and is incubated 2
The stable proved response between 2.2-3.2 of hour test nco value is own through completely.Then cool to 30 DEG C and filtered after stirring
Discharging, obtain product.Using GB 24410-2009《Limits of harmful substances in indoor decorating and refurnishing materials water-borne wood coating》Mark
Quasi- detection relevant item.Testing result is shown in Table 5.
The testing result of the polyisocyanate curing agent of the embodiment 5 of table 5
The watersoluble closed polyisocyanate curing agent of aziridine type and preparation method provided above the embodiment of the present invention,
It is described in detail, specific case used herein is set forth to the principle and embodiment of the present invention, and the above is real
The explanation for applying example is only intended to help the method and its core concept for understanding the present invention；Meanwhile for the general technology of this area
Personnel, according to the thought of the present invention, there will be changes in specific embodiments and applications, in summary, this theory
Bright book content should not be construed as limiting the invention.
Claims (9)
- A kind of 1. watersoluble closed polyisocyanate curing agent of aziridine type, it is characterised in that including it is following by weight percentage Raw material：Aqueous polyisocyanate curing agent 64-75%；Aziridine and/or its derivative 10-20%；Propylene Glycol Ether Ester Series Solvent 14-25%Auxiliary agent 0.2-1%.
- 2. the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 1, it is characterised in that including following Raw material by weight percentage：Aqueous polyisocyanate curing agent 65-70%；Aziridine and/or its derivative 10-15%；Propylene Glycol Ether Ester Series Solvent 18-24%Auxiliary agent 0.5-0.8%.
- 3. the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 1 or 2, it is characterised in that described Aqueous polyisocyanate curing agent be hexamethylene diisocyanate (HDI) be matrix synthesis Water-borne modification isocyanate curing agent and/or IPDI (IPDI) is the Water-borne modification isocyanate curing agent of matrix synthesis.
- 4. the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 1 or 2, it is characterised in that described Water-borne modification isocyanate curing agent includes hexamethylene diisocyanate class addition product, oneself two isocyanide acids tripolymers, hexamethylene diisocyanate (HDI) class polymer, hexamethylene diisocyanate (HDI) biuret and IPDI class addition product, isophorone two At least one of tripolymer in isocyanic ester class and IPDI class polymer.
- 5. the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 1 or 2, it is characterised in that described Aziridine and/or its derivative are selected from least one of aziridine, methylaziridine, ethylaziridine.
- 6. the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 1 or 2, it is characterised in that described Propylene Glycol Ether Ester Series Solvent is selected from propylene glycol monomethyl ether methyl esters, propylene-glycol ethyl ether acetate, propylene glycol methyl ether acetate, propane diols second At least one of ether butyl ester, propylene-glycol methyl ether butyl ester, propandiol butyl ether acetate.
- 7. the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 1 or 2, it is characterised in that described Auxiliary agent is selected from 1-METHYLPYRROLIDONE, N, N-dimethylformamide, dibutyl tin laurate, stannous octoate, N, N dimethyl ring At least one of hexylamine, triethylenediamine, triethylamine, tripropylamine, diethanol amine, triethanolamine.
- A kind of 8. preparation side of the watersoluble closed polyisocyanate curing agent of aziridine type any one of claim 1-7 Method, it is characterised in that comprise the following steps：(1) by aqueous polyisocyanate curing agent and propylene glycol alcohols solvent input reactor, heat while stirring, temperature Control is in the range of 40-50 DEG C；(2) aziridine and/or its derivative are added in reactor, temperature control at 40-50 DEG C and constantly stirring thing material, fully After reacting 2-6h, add auxiliary agent and reacted, until reaction is complete, obtain uniform solution；(3) cool to 30-35 DEG C, filtering and discharging produces.
- 9. the preparation method of the watersoluble closed polyisocyanate curing agent of aziridine type according to claim 8, its feature exist In in step (2), the reaction is all referring to nco value in 2.2-3.2.
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Cited By (4)
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| CN109180908A (en) * | 2018-11-05 | 2019-01-11 | 合肥聚合辐化技术有限公司 | A kind of blocked polyurethane curing agent of low-temperature curable and preparation method thereof |
| CN109824862A (en) * | 2018-12-26 | 2019-05-31 | 上海展辰涂料有限公司 | Isocyanate curing agent and preparation method thereof can be dispersed in a kind of water |
| CN114276510A (en) * | 2022-02-09 | 2022-04-05 | 上海健倬生物科技有限公司 | Zero free amine isocyanate modified aziridine crosslinking agent, and preparation method and application thereof |
| CN115335424A (en) * | 2020-01-27 | 2022-11-11 | 意大利亿达化料有限公司 | Macromolecular compounds and their use in compositions |
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| CN114276510A (en) * | 2022-02-09 | 2022-04-05 | 上海健倬生物科技有限公司 | Zero free amine isocyanate modified aziridine crosslinking agent, and preparation method and application thereof |
| CN114276510B (en) * | 2022-02-09 | 2023-08-11 | 上海健倬生物科技有限公司 | Zero-free amine isocyanate modified aziridine crosslinking agent, and preparation method and application thereof |
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Application publication date: 20180323 |