CN109251292B - Polyurethane latent curing agent, single-component polyurethane waterproof coating and preparation method - Google Patents
Polyurethane latent curing agent, single-component polyurethane waterproof coating and preparation method Download PDFInfo
- Publication number
- CN109251292B CN109251292B CN201810771535.7A CN201810771535A CN109251292B CN 109251292 B CN109251292 B CN 109251292B CN 201810771535 A CN201810771535 A CN 201810771535A CN 109251292 B CN109251292 B CN 109251292B
- Authority
- CN
- China
- Prior art keywords
- curing agent
- latent curing
- polyurethane
- waterproof coating
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/02—Polyureas
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a polyurethane latent curing agent with a structural formula of R1—CH══N—R2—N══CH—R3Wherein R is1、R2、R3Is alkyl or aryl or alkaryl, and the molecular weight of the latent curing agent is not higher than 300. The invention also discloses a single-component polyurethane waterproof coating adopting the latent curing agent and a preparation method thereof. The invention provides a polyurethane latent curing agent which has good stability, and the single-component polyurethane waterproof coating prepared by adopting the polyurethane latent curing agent is more storage-resistant and has longer quality guarantee period; the polyurethane latent curing agent of unit mass can provide more-NH 2 groups, and has small dosage and low application cost. The polyurethane waterproof coating disclosed by the invention is small in harm to a human body, environment-friendly, excellent in storage stability, excellent in performance of the obtained coating, excellent in tensile strength and tear strength, capable of being prepared by directly adopting the existing production process and production equipment, and low in production cost.
Description
Technical Field
The invention relates to the field of building waterproof coatings, in particular to a polyurethane latent curing agent, a single-component polyurethane waterproof coating and a preparation method thereof.
Background
The polyurethane waterproof paint belongs to a chemical reaction type waterproof paint, is a rubber-like high-elasticity coating film after being cured, is seamless as a whole, is called a liquid coiled material in the industry because of excellent comprehensive performance, and is widely applied in the world. The polyurethane waterproof coating in China has been developed for more than 20 years, is rich in product types and excellent in performance, and occupies an important position in the building waterproof industry.
The traditional two-component polyurethane waterproof coating has strict construction requirements, has higher requirements on the technical level of workers and is troublesome to construct; the single-component polyurethane waterproof paint does not need mixing of two components, can be directly coated and used after being unsealed, and greatly reduces construction difficulty. At present, the single-component polyurethane waterproof coating mainly comprises a moisture curing type and a latent curing type, wherein in the drying process of a coating film, the moisture curing type high-performance single-component polyurethane waterproof coating is easy to generate the defects of shrinkage cavities, pinholes, dark bubbles and the like in the coating film due to high sensitivity of a-NCO group to moisture, and the latent curing agent commonly used by the latent curing type high-performance single-component polyurethane waterproof coating is often high in using amount, high in application cost and poor in storage performance of a finished coating product.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the polyurethane latent curing agent which can stably exist in a sealed and dry environment for a long time, has small dosage and low application cost.
The invention also provides a single-component polyurethane waterproof coating adopting the latent curing agent and a preparation method thereof, and the waterproof coating has excellent storage stability, no toxicity, no pollution and excellent coating performance.
In order to realize the purpose of the invention, the following technical scheme is adopted for realizing the purpose:
a polyurethane latent curing agent with a structural formula of R1—CH══N—R2—N══CH—R3Wherein R is1、R2、R3Is alkyl or aryl or alkaryl, and the molecular weight of the latent curing agent is not higher than 300.
The prior art mostly adopts macromolecule latent curing agent with molecular weight of at least 500, however, when the molecular weight of the latent curing agent is too large, the use amount of the latent curing agent is relatively large, which can make the application of the latent curing agent expensive and the application cost high. The invention provides a micromolecule aldimine type polyurethane latent curing agent, and the polyurethane latent curing agent with unit mass can provide more-NH2Radical, amountSmall, low cost, hydrolysis of-NH2The group and-NCO form a urea bond group, so that the physical and chemical properties of the high-performance single-component polyurethane waterproof coating are improved. Compared with other latent curing agents, the polyurethane latent curing agent provided by the invention has higher chemical stability, and the single-component polyurethane waterproof coating prepared by adopting the latent curing agent is more storage-resistant and longer in quality guarantee period.
As one embodiment thereof, R1And R3Is an alkyl group having 1 to 4 carbon atoms, R2Is alkyl or aryl or alkylaryl.
In one embodiment, the compound is prepared by reacting diamine and n-alkylaldehyde. The invention preferably adopts diamine and aldehyde with low molecular weight and regular and symmetrical molecular structure, and has high reaction activity, so that the synthesis reaction can reach high reaction degree, and only water in the generated product needs to be separated in time in the synthesis reaction process, so that the synthesis reaction is carried out more completely in the forward direction.
As one embodiment, the polyurethane latent curing agent is prepared according to the following method:
s1: adding 1, 6-hexamethylene diamine and water into a reaction kettle under the protection of nitrogen, and dripping n-butyl aldehyde or propionaldehyde into the reaction kettle under stirring;
s2: and after the reaction is completed, removing water and volatile components under negative pressure to obtain the polyurethane curing agent.
As one embodiment, the polyurethane latent curing agent is prepared according to the following method:
s1: putting n-butyraldehyde or propionaldehyde and toluene into a reaction kettle under the protection of nitrogen, adding phenylenediamine into the reaction kettle under stirring, and carrying out reflux reaction for 3 hours;
s2: removing water and volatile components under negative pressure to obtain the polyurethane curing agent.
The polyurethane latent curing agent provided by the invention has the advantages of simple preparation process, low reaction condition requirement, simple preparation process, short reaction time and low preparation cost, and can be directly prepared at room temperature. The invention adopts the low molecular weight and the regular and symmetrical molecular structureDiamine and aldehyde have high reaction activity, so the synthetic reaction has high reaction degree, and water in the generated product is timely separated in the process of the synthetic reaction, so that the synthetic reaction is positively carried out completely, and residual-NH which does not participate in the reaction is generated2The polyurethane latent curing agent prepared by the invention can be directly added into the polyurethane waterproof coating without purification, and the viscosity of a finished product cannot be influenced by the reaction with-NCO groups when the polyurethane latent curing agent is added into a coating system.
Preferably, the molar ratio of amine to aldehyde is: the ratio of amine to aldehyde is 1: 2.1-2.6. Further preferably, the molar ratio of amine to aldehyde is: the ratio of amine to aldehyde is 1: 2.2-2.4.
The single-component polyurethane waterproof coating adopting the polyurethane latent curing agent is prepared from the following components in percentage by mass: 2 to 6.7 percent of diisocyanate, 25 to 50 percent of polymer polyol, 30 to 50 percent of powder filler, 10 to 20 percent of liquid filler, 1 to 2.5 percent of polyurethane latent curing agent, 0.01 to 0.5 percent of catalyst and 1 to 14 percent of diluent.
Preferably, the one-component polyurethane waterproof coating is prepared from the following components in percentage by mass: 4 to 6 percent of diisocyanate, 25 to 35 percent of polymer polyol, 35 to 42 percent of powder filler, 12 to 15 percent of liquid filler, 1.8 to 2.5 percent of polyurethane latent curing agent, 0.1 to 0.4 percent of catalyst and 9 to 13 percent of diluent.
As an embodiment, the diisocyanate is at least one of liquefied diphenylmethane diisocyanate (MDI), polymethylene polyphenyl polyisocyanate (PAPI), dicyclohexylmethane diisocyanate (HMDI), isophorone diisocyanate (IPDI); the polymer polyol is at least one of polypropylene oxide glycol (PPG), polypropylene oxide triol (PPT), polytetrahydrofuran ether glycol (PTMG), polypropylene carbonate glycol (PPC) and polycarbonate glycol (PCD); the powder filler is at least one of talcum powder, heavy calcium carbonate, light calcium carbonate and kaolin; the liquid filler is at least one of Chlorinated Paraffin (CP), diisononyl phthalate and liquid petroleum resin; the catalyst is at least one of dibutyltin dilaurate, stannous octoate, triethylamine and bismuth isooctanoate.
The latent curing type single-component polyurethane waterproof coating which does not contain free TDI is non-toxic and pollution-free, has little harm to the health of operators in the production and construction processes, and is environment-friendly. The invention adopts a method of adding a large amount of polymer polyol, greatly reduces the dosage of diisocyanate, and further lightens the harm to contact personnel and environment. Meanwhile, the self-made polyurethane latent curing agent is adopted, so that the storage stability is excellent, and the obtained coating has excellent performance, tensile strength and tear strength.
The preparation method of the single-component polyurethane waterproof coating comprises the following specific steps:
and S I: putting the polymer polyol, the powder filler and the liquid filler in the formula into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring the mixture into a reaction kettle for heating and raising the temperature, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃;
and S II: after the dehydration is finished, cooling to 80 +/-5 ℃, adding diisocyanate, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
and S III: cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
and IV: keeping the temperature at 75 +/-5 ℃, adding the polyurethane latent curing agent, keeping the temperature and stirring for 0.5 hour;
s V: adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes in vacuum, and filtering to obtain the product.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a polyurethane latent curing agent which is good in stability, and the single-component polyurethane waterproof coating prepared by adopting the polyurethane latent curing agent is more storage-resistant and longer in quality guarantee period.
(2) The polyurethane latent curing agent of the unit mass of the latent curing agent can provide more-NH2The radical and the dosage are small, and the application cost is low.
(3) The latent curing agent provided by the invention has the advantages of simple preparation process, low requirement on reaction conditions, low preparation cost, high reaction degree and suitability for mass production, and the prepared product can be directly added into the polyurethane waterproof coating without purification, and cannot react with isocyanate groups to influence the viscosity of a finished product when added into a coating system.
(4) The invention also provides the single-component polyurethane waterproof coating adopting the latent curing agent and a preparation method thereof, the polyurethane waterproof coating has little harm to a human body, is environment-friendly, has excellent storage stability, and simultaneously the obtained coating has excellent performance, tensile strength and tearing strength. In addition, the preparation process of the waterproof coating is not different from the preparation process of the common single-component polyurethane waterproof coating, the existing production process and production equipment can be directly adopted, the production cost is low, and the waterproof coating is very suitable for industrial mass production.
(5) The single-component polyurethane waterproof coating provided by the invention adopts a latent curing mode, the content of-NCO groups is controlled within a reasonable range, a structure that polyurethane groups and polyurea groups are mutually blocked is formed, and the obtained coating has better comprehensive performance.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention are described in further detail below.
Example 1
The high-performance single-component polyurethane waterproof coating comprises the following raw materials in percentage by mass:
wherein the catalyst is a mixture of triethylamine and dibutyltin dilaurate in a mass ratio of 2: 8; the molecular weight of polyoxypropylene triol 330N is 4800 and the molecular weight of polyoxypropylene diol 2000D is 2000.
The preparation method of the self-made latent curing agent A comprises the following steps: 116.20g of 1, 6-hexanediamine and 50g of water are put into a round-bottom flask under the protection of nitrogen, 160.00g of n-butyraldehyde is added from a dropping funnel under rapid stirring, and then water and other volatile components (-0.1MPa) are removed under negative pressure to obtain a product, namely a latent curing agent A.
The preparation method of the single-component polyurethane waterproof coating comprises the following steps:
(1) putting polyoxypropylene triol 330N, polyoxypropylene diol 2000D, PTMG2000, talcum powder, heavy calcium carbonate and diisononyl phthalate in a formula ratio into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring into a reaction kettle for heating and raising the temperature, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃, wherein the vacuum degree needs to be less than-0.09 MPa;
(2) after dehydration, cooling to 80 +/-5 ℃, adding liquefied MDI, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
(3) cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
(4) keeping the temperature at 75 +/-5 ℃, adding the self-made latent curing agent A, and keeping the temperature and stirring for 0.5 hour;
(5) adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes under the vacuum degree of minus 0.08MPa to minus 0.1MPa, filtering by a 100-mesh double-layer filter screen, discharging and packaging.
Example 2
The high-performance single-component polyurethane waterproof coating comprises the following raw materials in percentage by mass:
wherein the catalyst is a mixture of triethylamine and stannous octoate in a mass ratio of 2: 8.
The preparation method of the self-made latent curing agent B comprises the following steps: 116.20g of 1, 6-hexanediamine and 50g of water are put into a round-bottom flask under the protection of nitrogen, 130.00g of propionaldehyde is added from a dropping funnel under the rapid stirring, and then water and other volatile components (-0.1MPa) are removed under negative pressure to obtain a product, namely a latent curing agent B.
The preparation method of the high-performance single-component polyurethane waterproof coating comprises the following steps:
(1) putting polyoxypropylene triol 330N, PTMG2000, talcum powder, light calcium carbonate, CP52 and liquid petroleum resin which are proportioned according to a formula into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring the dispersion kettle into a reaction kettle for heating and raising temperature, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃, wherein the vacuum degree needs to be less than-0.09 MPa;
(2) after dehydration, cooling to 80 +/-5 ℃, adding liquefied MDI and HMDI, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
(3) cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
(4) keeping the temperature at 75 +/-5 ℃, adding the self-made latent curing agent B, and keeping the temperature and stirring for 0.5 hour;
(5) adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes under the vacuum degree of minus 0.08MPa to minus 0.1MPa, filtering by a 100-mesh double-layer filter screen, discharging and packaging.
Example 3
The high-performance single-component polyurethane waterproof coating comprises the following raw materials in percentage by mass:
wherein the catalyst is a mixture of bismuth isooctanoate and stannous octoate in a mass ratio of 4: 6.
The preparation method of the self-made latent curing agent C comprises the following steps: 160.00g of n-butyraldehyde and 40g of toluene are put into a round-bottom flask under the protection of nitrogen, 108.14g of phenylenediamine is added under the rapid stirring, reflux reaction is carried out for 3 hours, and then water and other volatile components (-0.1MPa) are removed under negative pressure, thus obtaining the product.
The preparation method of the high-performance single-component polyurethane waterproof coating comprises the following steps:
(1) putting polyoxypropylene triol 330N, PCD2000, kaolin, heavy calcium carbonate, diisononyl phthalate and CP52 which are proportioned according to the formula into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring the dispersion kettle into a reaction kettle for heating and raising the temperature, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃, wherein the vacuum degree is required to be less than-0.09 MPa;
(2) after dehydration, cooling to 80 +/-5 ℃, adding PAPI and HMDI, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
(3) cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
(4) keeping the temperature at 75 +/-5 ℃, adding the self-made latent curing agent C, and keeping the temperature and stirring for 0.5 hour;
(5) adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes under the vacuum degree of minus 0.08MPa to minus 0.1MPa, filtering by a 100-mesh double-layer filter screen, discharging and packaging.
Example 4
The high-performance single-component polyurethane waterproof coating comprises the following raw materials in percentage by mass:
wherein the catalyst is bismuth isooctanoate.
The preparation method of the self-made latent curing agent D comprises the following steps: 130.00g of propionaldehyde and 40g of toluene are put into a round-bottom flask under the protection of nitrogen, 108.14g of phenylenediamine is added under the rapid stirring, reflux reaction is carried out for 3 hours, and then water and other volatile components (-0.1MPa) are removed under negative pressure, thus obtaining the product, namely the self-made latent curing agent D.
The preparation method of the high-performance single-component polyurethane waterproof coating comprises the following steps:
(1) putting polyoxypropylene triol 330N, PPC2000, kaolin, talcum powder, diisononyl phthalate and liquid petroleum resin which are proportioned according to the formula into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring the dispersion kettle into a reaction kettle for heating and raising the temperature, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃, wherein the vacuum degree is required to be less than-0.09 MPa;
(2) after dehydration, cooling to 80 +/-5 ℃, adding liquefied MDI and IPDI, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
(3) cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
(4) keeping the temperature at 75 +/-5 ℃, adding the self-made latent curing agent D, and keeping the temperature and stirring for 0.5 hour;
(5) adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes under the vacuum degree of minus 0.08MPa to minus 0.1MPa, filtering by a 100-mesh double-layer filter screen, discharging and packaging.
Example 5
The high-performance single-component polyurethane waterproof coating comprises the following raw materials in percentage by mass:
wherein the catalyst is a mixture of triethylamine and dibutyltin dilaurate in a mass ratio of 1: 9.
The preparation method of the self-made latent curing agent D comprises the following steps: 130.00g of propionaldehyde and 40g of toluene are put into a round-bottom flask under the protection of nitrogen, 108.14g of phenylenediamine is added under the rapid stirring, reflux reaction is carried out for 3 hours, and then water and other volatile components (-0.1MPa) are removed under negative pressure, thus obtaining the product, namely the self-made latent curing agent D.
The preparation method of the high-performance single-component polyurethane waterproof coating comprises the following steps:
(1) putting polyoxypropylene glycol 2000D, PPC-2000, PCD-2000, talcum powder and diisononyl phthalate which are proportioned according to the formula into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring the dispersion kettle into a reaction kettle for heating and temperature rise, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃, wherein the vacuum degree is less than-0.09 MPa;
(2) after dehydration, cooling to 80 +/-5 ℃, adding IPDI, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
(3) cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
(4) keeping the temperature at 75 +/-5 ℃, adding the self-made latent curing agent D, and keeping the temperature and stirring for 0.5 hour;
(5) adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes under the vacuum degree of minus 0.08MPa to minus 0.1MPa, filtering by a 100-mesh double-layer filter screen, discharging and packaging.
Example 6
The high-performance single-component polyurethane waterproof coating comprises the following raw materials in percentage by mass:
wherein the catalyst is a mixture of triethylamine and stannous octoate in a mass ratio of 3: 7.
The preparation method of the self-made latent curing agent B comprises the following steps: 116.20g of 1, 6-hexanediamine and 50g of water are put into a round-bottom flask under the protection of nitrogen, 130.00g of propionaldehyde is added from a dropping funnel under the rapid stirring, and then water and other volatile components (-0.1MPa) are removed under negative pressure to obtain a product, namely a latent curing agent B. The preparation method of the high-performance single-component polyurethane waterproof coating comprises the following steps:
(1) putting PTMG-1000, heavy calcium carbonate, kaolin, diisononyl phthalate and liquid petroleum resin which are proportioned according to the formula into a dispersion kettle for high-speed dispersion for 0.5 hour, then transferring into a reaction kettle for heating and heating, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃, wherein the vacuum degree needs to be less than-0.09 MPa;
(2) after dehydration, cooling to 80 +/-5 ℃, adding HMDI and IPDI, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
(3) cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
(4) keeping the temperature at 75 +/-5 ℃, adding the self-made latent curing agent D, and keeping the temperature and stirring for 0.5 hour;
(5) adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes under the vacuum degree of minus 0.08MPa to minus 0.1MPa, filtering by a 100-mesh double-layer filter screen, discharging and packaging.
Performance testing
The single-component polyurethane waterproof coating provided by the embodiments 1 to 6 is subjected to performance test, the specific test method refers to GB/T16777-2008, and the specific test results are shown in Table 1.
TABLE 1
The above examples are merely illustrative for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (5)
1. The single-component polyurethane waterproof coating is characterized by being prepared from the following components in percentage by mass: 2 to 6.7 percent of diisocyanate, 25 to 50 percent of polymer polyol, 30 to 50 percent of powder filler, 10 to 20 percent of liquid filler, 1 to 2.5 percent of polyurethane latent curing agent, 0.01 to 0.5 percent of catalyst and 1 to 14 percent of diluent;
the structural formula of the polyurethane latent curing agent is R1—CH═N—R2—N═CH—R3，R1、R2、R3Is an alkyl group, the molecular weight of the latent curing agent is not higher than 300;
the polyurethane latent curing agent is prepared according to the following method:
s1: adding 1, 6-hexamethylene diamine and water into a reaction kettle under the protection of nitrogen, and dripping n-butyl aldehyde or propionaldehyde into the reaction kettle under stirring;
s2: and after the reaction is completed, removing water and volatile components under negative pressure to obtain the polyurethane curing agent.
2. The latent polyurethane curing agent according to claim 1, wherein the molar ratio of 1, 6-hexamethylenediamine to butyraldehyde or propionaldehyde is 1: 2.1 to 2.6.
3. The latent polyurethane curing agent according to claim 2, wherein the molar ratio of 1, 6-hexamethylenediamine to butyraldehyde or propionaldehyde is 1: 2.2 to 2.4.
4. The one-component polyurethane waterproof coating material of claim 1, wherein the diisocyanate is at least one of liquefied diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate, dicyclohexylmethane diisocyanate, and isophorone diisocyanate; and/or the polymer polyol is at least one of polyoxypropylene diol, polyoxypropylene triol, polytetrahydrofuran diol and polycarbonate diol; and/or the powder filler is at least one of talcum powder, heavy calcium carbonate, light calcium carbonate and kaolin; and/or the liquid filler is at least one of chlorinated paraffin, diisononyl phthalate and liquid petroleum resin; and/or the catalyst is at least one of dibutyltin dilaurate, stannous octoate, triethylamine and bismuth isooctanoate.
5. The preparation method of the one-component polyurethane waterproof coating material as claimed in any one of claims 1 to 4, which is characterized by comprising the following specific steps:
and S I: putting the polymer polyol, the powder filler and the liquid filler in the formula into a dispersion kettle for dispersion for 0.5 hour, then transferring the mixture into a reaction kettle for heating and raising the temperature, starting vacuumizing, and continuously dehydrating for 3 hours at the temperature of 110 +/-5 ℃;
and S II: after the dehydration is finished, cooling to 80 +/-5 ℃, adding diisocyanate, keeping the temperature at 80 +/-5 ℃, and stirring for reaction for 3 hours;
and S III: cooling to 75 +/-5 ℃, adding a catalyst, and reacting for 0.5 hour at the temperature of 75 +/-5 ℃;
and IV: keeping the temperature at 75 +/-5 ℃, adding the polyurethane latent curing agent, keeping the temperature and stirring for 0.5 hour;
s V: adding a diluent, cooling to 60 +/-5 ℃, defoaming for 10 minutes in vacuum, and filtering to obtain the product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810771535.7A CN109251292B (en) | 2018-07-13 | 2018-07-13 | Polyurethane latent curing agent, single-component polyurethane waterproof coating and preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810771535.7A CN109251292B (en) | 2018-07-13 | 2018-07-13 | Polyurethane latent curing agent, single-component polyurethane waterproof coating and preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109251292A CN109251292A (en) | 2019-01-22 |
| CN109251292B true CN109251292B (en) | 2021-05-18 |
Family
ID=65049038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810771535.7A Active CN109251292B (en) | 2018-07-13 | 2018-07-13 | Polyurethane latent curing agent, single-component polyurethane waterproof coating and preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109251292B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109929426B (en) * | 2019-01-25 | 2021-02-23 | 北京东方雨虹防水技术股份有限公司 | Latent curing agent type single-component polyurethane waterproof coating |
| CN110591541A (en) * | 2019-10-16 | 2019-12-20 | 远大洪雨（唐山）防水材料有限公司 | Single-component polyurethane waterproof coating production line |
| CN111662630A (en) * | 2020-06-22 | 2020-09-15 | 安徽三棵树涂料有限公司 | Low-VOC polyurethane waterproof coating and preparation method thereof |
| CN111621223A (en) * | 2020-06-22 | 2020-09-04 | 安徽三棵树涂料有限公司 | High-solid-content environment-friendly polyurethane waterproof coating and preparation method thereof |
| CN114605604B (en) * | 2022-01-27 | 2024-03-22 | 北京东方雨虹防水技术股份有限公司 | Curing agent with ionic liquid structure, preparation method and application |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0725976A (en) * | 1993-07-09 | 1995-01-27 | Mitsui Toatsu Chem Inc | Method for curing isocyanate composition containing latent curing agent |
| JPH0748430A (en) * | 1993-08-04 | 1995-02-21 | Mitsui Toatsu Chem Inc | Repairing technique by impregnation |
| JPH08325343A (en) * | 1995-05-30 | 1996-12-10 | Mitsui Toatsu Chem Inc | Waterproofing work for concrete structure |
| CA2602352C (en) * | 2005-03-28 | 2011-04-26 | Albemarle Corporation | Diimines and secondary diamines |
| EP2017260A1 (en) * | 2007-07-16 | 2009-01-21 | Sika Technology AG | Aldimines and compounds containing aldimine |
| EP2465843A1 (en) * | 2010-12-17 | 2012-06-20 | Sika Technology AG | Polyamines with secondary aliphatic amines |
| CN102807812B (en) * | 2012-09-07 | 2015-01-07 | 上海应用技术学院 | Latent curing single-component polyurethane water-proof coating and preparation method thereof |
| CN106675373B (en) * | 2016-12-26 | 2019-04-16 | 徐州卧牛山新型防水材料有限公司 | A kind of uncured polyurethane water-proof paint and preparation method thereof |
| CN107043447B (en) * | 2017-04-19 | 2019-12-03 | 江苏湘园化工有限公司 | A kind of asymmetric latency polyurethane curing agent and preparation method thereof |
| CN107118179B (en) * | 2017-05-05 | 2020-09-22 | 北京东方雨虹防水技术股份有限公司 | Imine compound, preparation method and application thereof, and single-component polyurethane waterproof coating |
-
2018
- 2018-07-13 CN CN201810771535.7A patent/CN109251292B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN109251292A (en) | 2019-01-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109251292B (en) | Polyurethane latent curing agent, single-component polyurethane waterproof coating and preparation method | |
| CN102633983B (en) | Preparation method for siloxane-terminated organosilicon block polyurethane prepolymer | |
| CN102181031B (en) | Durable polyurethane resin for sofa leather and preparation method of the durable polyurethane resin | |
| CN107142068B (en) | Thermosetting single-component polyurethane composition and preparation method thereof | |
| CN103173179B (en) | Preparation method of aqueous polyurethane adhesive for laminated composite fabrics | |
| WO2016159723A1 (en) | Polyurethane, preparing method therefor, and use thereof | |
| CN108239255B (en) | Polyurea type polyurethane coating, raw material composition and application thereof | |
| AU2014230761B2 (en) | Repair liquid for conveyor belts | |
| CN108239516B (en) | A kind of high intensity exempts from primary coat monocomponent polyurethane windshield glue and preparation method thereof | |
| CN103540254A (en) | Preparation method of single-component water-cured polyurethane waterproof paint | |
| CN101775119B (en) | Preparation method of environmental sensitive polyurethane film | |
| CN106632974A (en) | Sponge for roof of ether-ester type automobile and manufacturing process | |
| CN111116856A (en) | Single-component high-solid-content polyurethane resin and preparation method and application thereof | |
| CN112080244A (en) | High-strength and fast-curing one-component primer-free polyurethane sealant and preparation method thereof | |
| CN111876097A (en) | Prefabricated polyurethane sports floor glue and preparation method thereof | |
| CN111592851A (en) | Preparation method of water-resistant thermoplastic polyurethane hot melt adhesive | |
| CN107083227A (en) | A kind of single-component polyurethane adhesive and preparation method thereof | |
| CN102250307A (en) | Biobased micro-porous polyurethane material and preparation method thereof | |
| CN108864923A (en) | Low temperature and low humidity solidifies non-solvent single-component polyurethane water-proof paint and preparation method thereof | |
| CN113773465A (en) | Semi-rigid foam and preparation method and application thereof | |
| CN110527482B (en) | Special two-component caulking waterproof sealant for railway ballastless track and preparation method thereof | |
| CN107849422B (en) | Adhesive composition and method for producing adhesive composition | |
| KR102271145B1 (en) | Isocyanate prepolymer, moisture-curing polyurethane and eco-friendly adhesive composition comprising the same | |
| CN106147580A (en) | A kind of preparation method of one-component solvent-free type polyurethane water-repellent paint | |
| CN107629753A (en) | Water process curtain type film assembly polyurethane pouring sealant and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information |
Address after: 401220 No. 6 North Hua two road, Changshou District, Chongqing Applicant after: Chongqing Keshun New Material Technology Co., Ltd Address before: 401220 No. 6 North Hua two road, Changshou District, Chongqing Applicant before: Chongqing Ke Shun Chemical New Material Co., Ltd. |
|
| CB02 | Change of applicant information | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |