CN111393597B - Siloxane modified cardanol derivative prepolymer and preparation method and application thereof - Google Patents
Siloxane modified cardanol derivative prepolymer and preparation method and application thereof Download PDFInfo
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- CN111393597B CN111393597B CN202010475094.3A CN202010475094A CN111393597B CN 111393597 B CN111393597 B CN 111393597B CN 202010475094 A CN202010475094 A CN 202010475094A CN 111393597 B CN111393597 B CN 111393597B
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- cashew nut
- nut shell
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- silane
- shell oil
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/778—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur silicon
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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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
Abstract
The invention belongs to the technical field of high molecular polymerization, and discloses a siloxane modified cardanol derivative prepolymer and a preparation method and application thereof. Putting cashew nut shell oil alcohol, isocyanate-based propyl silane and a catalyst into a reaction kettle under the protection of nitrogen, reacting at 80-90 ℃, sampling, monitoring an NCO characteristic peak by using a Fourier infrared spectrometer until the NCO characteristic peak disappears completely, cooling, filtering and discharging to obtain the siloxane modified cardanol derivative prepolymer; the molar ratio of OH of the cashew nut shell oil alcohol to NCO of the isocyanate propyl silane is 1: (0.5 to 1). The cashew nut shell oleyl alcohol can be interacted with the pigment through large pi conjugation or hydrogen bonds, can improve the wettability of the pigment, and is used for dispersing the pigment. Meanwhile, the cardanol derivative prepolymer is grafted to the surface of the pigment, so that the storage stability of the pigment is greatly improved.
Description
Technical Field
The invention belongs to the technical field of high polymer polymerization, and particularly relates to a siloxane modified cardanol derivative prepolymer and a preparation method and application thereof.
Background
Pigments are often present in the form of powder or particles, and when applied to the fields of paints, inks, and the like, it is generally necessary to stably disperse pigment particles in the paints or inks by adding a pigment dispersant or stabilizer. With the increasing application of paint and printing ink, the using amount of pigment and dispersing auxiliary agent thereof also increase, but the currently used pigment dispersing agent is generally prepared by non-renewable non-environment-friendly raw materials and does not meet the current requirement of green and environment protection.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides a siloxane modified cardanol derivative prepolymer. The siloxane modified cardanol derivative prepolymer is obtained by modifying cashew nut shell oil polyalcohol by adopting an organic siloxane structure. Cashew nut shell oil polyalcohol is a nontoxic and natural renewable non-food chain raw material, the main chain of the cashew nut shell oil polyalcohol is a long carbon chain structure containing unsaturated double bonds, and an aromatic ring is directly connected with the long carbon chain. Compared with other natural vegetable oil renewable polyols such as castor oil, palm oil and soybean oil, the pigment has more excellent water resistance and chemical resistance and lower viscosity, and has excellent wetting effect on pigment dispersion.
Another object of the present invention is to provide a method for preparing the siloxane-modified cardanol derivative prepolymer. The method is efficient and easy to implement, has low requirements on process equipment and operating environment, and is green and environment-friendly.
Still another object of the present invention is to provide a use of the above siloxane-modified cardanol derivative prepolymer.
The purpose of the invention is realized by the following technical scheme:
putting cashew nut shell oil alcohol, isocyanate-based propyl silane and a catalyst into a reaction kettle under the protection of nitrogen, reacting at 80-90 ℃, sampling, monitoring an NCO characteristic peak by using a Fourier infrared spectrometer until the NCO characteristic peak disappears completely, cooling, filtering and discharging to obtain the siloxane modified cardanol derivative prepolymer; the molar ratio of OH of the cashew nut shell oil alcohol to NCO of the isocyanate propyl silane is 1: (0.5 to 1).
Preferably, the cashew nut shell oil alcohol is more than one of cardanol, alkoxy modified cardanol, cashew nut shell oil polyester dihydric alcohol, modified cashew nut shell oil polyalcohol, cashew nut shell oil branched-chain type polyalcohol and cashew nut shell oil phenolic resin polyalcohol, the hydroxyl value of the cashew nut shell oil alcohol at 25 ℃ is less than or equal to 200mgKOH/g, and the viscosity is less than or equal to 3000 cps.
Preferably, the isocyanato propyl silane is more than one of 3-isocyanato propyl trimethoxy silane, 3-isocyanatopropyl methyl dimethoxy silane, 3-isocyanatopropyl triethoxy silane and 3-isocyanatopropyl methyl diethoxy silane.
Preferably, the catalyst is 0.2-0.6 per mill of the total mass of the cashew nut shell oil alcohol and the isocyanatopropyl silane.
Preferably, the catalyst is an organobismuth catalyst or/and an organozirconium catalyst.
Preferably, the reaction time at 80-90 ℃ is 4-6 h.
The photocuring colored paint composition comprises the siloxane modified cardanol derivative prepolymer, polyurethane acrylate, an organic pigment, a photoinitiator, a reactive diluent, a leveling agent and a defoaming agent.
Preferably, when the total amount of the photo-curing colored paint composition is 100 parts by mass, the siloxane modified cardanol derivative prepolymer is 0.5-1 part, the polyurethane acrylate is 40-55 parts, the organic pigment is 5-10 parts, the photoinitiator is 2-4 parts, the reactive diluent is 35-45 parts, the leveling agent is 0.5-1 part, and the defoaming agent is 0.2-1 part.
More preferably, the photoinitiator is an initiator 184, and the reactive diluent is one or more of 2-phenoxyethyl acrylate, ethoxylated pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate, and propoxylated trimethylolpropane triacrylate; the leveling agent is more than one of BYK-333, BYK371 or BYK373, and the defoaming agent is BYK-088, BYK055 or BYK 020; the organic pigment is isoindolinone, pyrrolopyrroledione, benzimidazolone or quinacridone.
The siloxane modified cardanol derivative prepolymer is applied to a pigment dispersing agent or a stabilizing agent.
Compared with the prior art, the invention has the following beneficial effects:
1. according to the invention, a siloxane structure of hydrolytic condensation is introduced into cashew nut shell oil alcohol molecules, the siloxane structure of the siloxane modified cardanol derivative prepolymer can form a stable chemical covalent bond with a polyhydroxy structure on the surface of the pigment through hydrolytic condensation, and an unstable non-covalent bond between the cashew nut shell oil alcohol and the pigment is converted into a stable covalent bond, so that the cardanol derivative prepolymer is grafted to the surface of the pigment, and the storage stability of the pigment is greatly improved.
2. The cashew nut shell oleyl alcohol can be interacted with the pigment through large pi conjugation or hydrogen bonds, can improve the wettability of the pigment, and is used for dispersing the pigment.
3. The invention introduces siloxane structure by adopting the addition reaction of isocyanate and hydroxyl, has simple operation process, low requirements on process equipment and operation environment and stable batch.
4. The siloxane modified cardanol derivative prepolymer prepared by the invention is prepared from non-toxic and natural renewable non-food chain raw materials, and is safe and environment-friendly.
Detailed Description
The following examples are presented to further illustrate the present invention and should not be construed as limiting the invention. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
The manufacturers of the organobismuth catalysts or organozirconium catalysts used in the examples of the present invention are the leading chemical companies in the united states.
Example 1
Putting cashew nut shell oil polyester diol (viscosity of 1400cps at 25 ℃ and hydroxyl value of 75mgKOH/g), 3-isocyanatopropyl trimethoxy silane and an organic bismuth catalyst into a reaction kettle equipped with a high-low temperature circulating pump, a thermometer and a stirring rod, reacting for 4 hours under the constant temperature condition of 90 ℃ under the protection of nitrogen in the whole process, sampling every 0.5 hour, monitoring the condition of an NCO characteristic peak by adopting a Fourier infrared spectrometer, and when the NCO peak disappears completely, cooling, filtering and discharging to obtain the siloxane modified cardanol derivative prepolymer. Wherein the molar ratio of OH of cashew nut shell oil polyester diol to NCO of 3-isocyanatopropyl trimethoxy silane is 1: 0.5, the organic bismuth catalyst is 0.2 per mill of the total weight of the cashew nut shell oil polyester dihydric alcohol and the 3-isocyanate propyl trimethoxy silane.
Example 2
Putting cashew nut shell oil phenolic resin dihydric alcohol (the viscosity is 1000cps at 25 ℃ and the hydroxyl value is 175mgKOH/g) 3-isocyanate propyl methyl dimethoxy silane and an organic bismuth catalyst into a reaction kettle provided with a high-low temperature circulating pump, a thermometer and a stirring rod, reacting for 6 hours under the constant temperature condition of 80 ℃ under the protection of nitrogen in the whole process, sampling every 0.5 hour, monitoring the condition of an NCO characteristic peak by adopting a Fourier infrared spectrometer, and when the NCO peak disappears completely, cooling, filtering and discharging to obtain the siloxane modified cardanol derivative prepolymer. Wherein the molar ratio of OH of the cashew nut shell oil phenolic resin dihydric alcohol to NCO of 3-isocyanatopropyl methyldimethoxysilane is 1: 1, the organic bismuth catalyst is 0.6 per mill of the total weight of the cashew nut shell oil phenolic resin dihydric alcohol and the 3-isocyanate propyl methyl dimethoxy silane.
Example 3
Putting cashew nut shell oil branched polyol (viscosity is 2900cps at 25 ℃, hydroxyl value is 175mgKOH/g), 3-isocyanatopropyl triethoxysilane and an organic bismuth catalyst into a reaction kettle equipped with a high-low temperature circulating pump, a thermometer and a stirring rod, reacting for 5 hours under the condition of constant temperature of 85 ℃ under the protection of nitrogen in the whole process, sampling every 0.5 hour, monitoring the condition of an NCO characteristic peak by adopting a Fourier infrared spectrometer, and cooling, filtering and discharging to obtain the siloxane modified cardanol derivative prepolymer when the NCO peak completely disappears. Wherein the molar ratio of OH of the cashew nut shell oil branched polyol to NCO of 3-isocyanatopropyl triethoxysilane is 1: 0.8, the organic bismuth catalyst is 0.4 per mill of the total weight of the cashew nut shell oil branched-chain polyol and the 3-isocyanate propyl triethoxysilane.
Application example
When the total mass of the photocuring colored paint composition is 100 parts, the photocuring colored paint composition comprises 0.5-1 part of siloxane modified cardanol derivative prepolymer, 40-55 parts of polyurethane acrylate, 5-10 parts of organic pigment, 2-4 parts of photoinitiator, 35-45 parts of active diluent, 0.5-1 part of leveling agent and 0.2-1 part of defoaming agent. Wherein the photoinitiator is an initiator 184, and the reactive diluent is more than one of 2-phenoxyethyl acrylate, ethoxylated pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate and propoxylated trimethylolpropane triacrylate; the leveling agent is more than one of BYK-333, BYK371 or BYK373, and the defoaming agent is BYK-088, BYK055 or BYK 020; the organic pigment is isoindolinone, pyrrolopyrroledione, benzimidazolone or quinacridone.
Specifically, the siloxane-modified cardanol derivative prepolymers prepared in examples 1 to 3, color organic pigments (e.g., pigment red, pigment yellow, etc.), a photoinitiator 1173, a reactive diluent, a leveling agent, and urethane acrylate (W500, manufactured by guangzhou five-element materials science and technology ltd) were uniformly ground with stirring at a low speed to obtain a photocurable color paint composition, the components of which are shown in table 1.
TABLE 1 composition of the photocurable pigmented coating compositions
The siloxane-modified cardanol derivative prepolymers obtained in examples 1 to 3 were subjected to performance evaluation according to the standard "evaluation of storage stability of GBT33327-2016 ultraviolet-curable coating material". The resulting photocurable colored paint composition was charged into a metal can in an amount of about 15mm from the mouth of the can at the surface of the sample, which was then covered tightly with a can lid, and the mass of the sample (to an accuracy of 0.01g) was weighed, and after standing for one month naturally, the metal can was opened for evaluation. The photocurable colored paint composition was coated on a plastic plate, and after photocuring, the coating effect was evaluated, and the results are shown in table 2.
1. The degree of sedimentation was checked and evaluated on the following scale, and the results are shown in Table 2.
10 level: the pigment is completely suspended and has no change compared with the original state of the colored paint;
and 8, stage: the color paint has obvious sedimentation touch feeling, a small amount of deposited pigment appears on the adjustable knife, no obvious resistance is generated when the adjustable knife is pushed by the knife surface, and the color paint can be easily and uniformly mixed again;
and 6, level: the dead weight of the knife can not fall on the bottom of the container, the knife passes through the pigment block and is difficult to move by using the knife surface of the knife, and the knife edge of the knife is moved along the edge of the can with slight resistance, but the colored paint can be easily and uniformly mixed again;
4, level: the dead weight of the knife can not fall to the bottom of the container, the knife passes through the pigment block and is difficult to push by the knife surface of the knife, and the knife edge of the knife is pushed along the edge of the can with slight resistance, but the colored paint can be easily and uniformly mixed again;
and 2, stage: when the adjustable knife is forced to penetrate through the pigment sedimentation layer, the knife face of the adjustable knife is difficult to move, the knife edge of the adjustable knife is moved along the edge of the tank, so that the adjustable knife has obvious resistance, and the adjustable knife can be remixed into a uniform state;
level 0: the hard lumps formed and could no longer be remixed with liquid into a homogeneous paint by hand stirring within 5 min.
2. The granules and the gum lumps were examined and evaluated, and the results are shown in table 2.
After the photocuring colored paint compositions I-IV are stirred uniformly, the mixture is filtered by a filter screen with the diameter of 150 mu m, and the condition of particles or rubber blocks on the filter cloth is observed and evaluated according to the following grades:
10 level: no gel at all; and 8, stage: almost no gel; and 6, level: a small amount of gel; 4, level: a medium amount of gel; and 2, stage: a plurality of gels; level 0: the gel was complete.
3. Viscosity change was checked and evaluated, and the results are shown in table 2.
If the evaluation grade of the particles and the rubber blocks is more than or equal to 6, the viscosity of the filtered sample is tested according to the viscosity test method before storage (GBT9751.1-2008), the test temperature is (23 +/-0.2) DEG C, and the viscosity change value is calculated (C)
v1The viscosity of the sample after storage is expressed in pas; v. of0The original viscosity of the sample before storage is in pas). According to change of viscosityChemical value, rated on the following scale:
10 level: t is less than or equal to 5 percent; and 8, stage: 5% < t < 15%; and 6, level: 15% < t less than or equal to 25%; 4, level: 25% < t less than or equal to 35%; and 2, stage: t is less than or equal to 45 percent and is 35 percent; level 0: t > 45%.
4. Surface effect of the coating film: after the coating was applied to a plastic substrate and photocured, the surface of the formed coating film was observed for the presence of a granular feel and smoothness and gloss, and the surface effect of the coating film was evaluated in accordance with the following criteria. Very good: the surface has no granular feel, and is flat and high in gloss; good: a small amount of particles are arranged on the surface, and the surface gloss is good; poor: the surface has a grainy feel and is poor in surface gloss.
TABLE 2 evaluation of the Properties of the photocurable pigmented coating compositions I to IV
As can be seen from table 2, without adding the siloxane-modified cardanol derivative prepolymer of the present invention, the pigment easily aggregated and settled in the paint, and the storage stability was poor; and the formed film has granular feel and poor gloss, which indicates that the siloxane modified cardanol derivative prepolymer has poor dispersion wettability in resin and is difficult to grind uniformly. The siloxane modified cardanol derivative prepolymer is good in storage stability and film coating effect, so that the siloxane modified cardanol derivative prepolymer has good wettability on pigment, the dispersibility of the pigment in resin can be greatly improved, and the cardanol derivative prepolymer is grafted to the surface of the pigment due to the fact that a stable covalent bond is formed between cashew nut shell oil polyalcohol and the pigment, and the storage stability of the pigment is greatly improved.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations and simplifications are intended to be included in the scope of the present invention.
Claims (4)
1. The photocuring colored paint composition is characterized by comprising siloxane modified cardanol derivative prepolymer, polyurethane acrylate, organic pigment, photoinitiator, active diluent, leveling agent and defoaming agent;
when the total mass of the photocuring paint composition is 100 parts by mass, the siloxane modified cardanol derivative prepolymer is 0.5-1 part, the polyurethane acrylate is 40-55 parts, the organic pigment is 5-10 parts, the photoinitiator is 2-4 parts, the reactive diluent is 35-45 parts, the leveling agent is 0.5-1 part, and the defoaming agent is 0.2-1 part;
the photoinitiator is an initiator 184, and the active diluent is more than one of 2-phenoxyethyl acrylate, ethoxylated pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate and propoxylated trimethylolpropane triacrylate;
the leveling agent is more than one of BYK-333, BYK371 or BYK 373;
the defoaming agent is BYK-088, BYK055 or BYK 020; the organic pigment is isoindolinone, pyrrolopyrrole dione, benzimidazolone or quinacridone;
putting cashew nut shell oil alcohol, isocyanate-based propyl silane and a catalyst into a reaction kettle under the protection of nitrogen, reacting at 80-90 ℃, sampling, monitoring an NCO characteristic peak by using a Fourier infrared spectrometer until the NCO characteristic peak disappears completely, cooling, filtering and discharging to obtain the siloxane modified cardanol derivative prepolymer; the molar ratio of OH of the cashew nut shell oil alcohol to NCO of the isocyanate propyl silane is 1: (0.5 to 1);
the cashew nut shell oleyl alcohol is more than one of cardanol, alkoxy modified cardanol, cashew nut shell oil polyester dihydric alcohol, cashew nut shell oil branched-chain type polyhydric alcohol and cashew nut shell oil phenolic resin polyhydric alcohol, the hydroxyl value of the cashew nut shell oleyl alcohol at 25 ℃ is less than or equal to 200mgKOH/g, and the viscosity is less than or equal to 3000 cps;
the isocyanate propyl silane is more than one of 3-isocyanate propyl trimethoxy silane, 3-isocyanate propyl methyl dimethoxy silane, 3-isocyanate propyl triethoxy silane or 3-isocyanate propyl methyl diethoxy silane.
2. The photocurable colored paint composition according to claim 1, wherein the catalyst is 0.2-0.6 ‰ of the total mass of cashew nut shell oil alcohol and isocyanatopropyl silane.
3. The photocurable colored paint composition according to claim 1, wherein the catalyst is an organobismuth catalyst or/and an organozirconium catalyst.
4. The photocurable colored paint composition according to claim 1, wherein the reaction time at 80-90 ℃ is 4-6 h.
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| CN114539099A (en) * | 2022-03-25 | 2022-05-27 | 苏州世名科技股份有限公司 | Double-bio-based light-cured polyurethane acrylate oligomer and preparation method thereof |
| CN116102930B (en) * | 2022-12-29 | 2023-09-12 | 广东邦固化学科技有限公司 | Protective layer coating for cold stamping film and preparation method thereof |
| CN116023628B (en) * | 2023-02-21 | 2023-09-12 | 广州海豚新材料有限公司 | Bio-based silicon-containing polyurethane, preparation method thereof and microfiber leather |
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