CN115926621A - Ultra-light release force organic silicon release agent, and preparation method and application thereof - Google Patents
Ultra-light release force organic silicon release agent, and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides an ultra-light release force organic silicon release agent, which comprises the following components in parts by weight: 100 parts of vinyl silicone oil, 0.05-0.5 part of inhibitor, 1-3 parts of cross-linking agent, 0.5-3 parts of phenyl cage type silsesquioxane, 0.5-3 parts of solvent, 0.5-1.5 parts of anchoring agent and 1-3 parts of catalyst. The organic silicon release agent can be used for preparing release materials with 1-3g/inch ultra-light release force, the release force is stable, the release force of high-temperature aging is higher than that of normal temperature by less than 10%, the silicon transfer rate is low, and the organic silicon release agent can be applied to the electronic die cutting industry with high requirements on the silicon transfer rate.
Description
Technical Field
The application relates to the field of release materials, in particular to an ultra-light release force organic silicon release agent, and a preparation method and application thereof.
Background
The organic silicon release agent is also called as an anti-sticking agent or a release agent and is mainly used for separating viscous substances and protecting pressure-sensitive adhesive coated on a substrate. Common substrates include paper such as glassine paper, polyolefin coated Paper (PCK), clay coated paper (CCK), and the like, and films such as polyethylene terephthalate (PET). With the increase of the time for laminating the pressure-sensitive adhesive on the release surface, the stable release force is a key index for investigating the performance of the release agent. The conventional organic silicon release agent has the release force of 10-20 g/inch mostly. With the development of the electronic die cutting industry, higher requirements are put forward on the release agent, firstly the release agent is required to have ultra-light release force (1-3 g/inch), secondly the release force is required to be more stable, the lower the climbing of the high-temperature aging release force relative to the normal-temperature release force is, the better the release force is, which means that the adhesive surface protected by the release film still has stable release force after being placed for a long time, and the release film is also required to have low silicon transfer rate less than 0.5%, namely, the release agent coating cannot be transferred to the adhesive surface in the process of adhering the adhesive surface so as to influence the use of the subsequent adhesive surface.
The invention aims to provide an ultra-light release force organic silicon release agent which has more stable release force and low silicon transfer rate.
Disclosure of Invention
In view of the above problems in the prior art, it is an object of the present invention to provide an ultra-light release force silicone release agent. The organic silicon release agent takes conventional vinyl silicone oil as a raw material, can achieve ultra-light release performance by adding a small amount of phenyl cage type silsesquioxane, and has more stable release force and low silicon transfer rate.
In order to realize the purpose, the technical scheme adopted by the invention is as follows:
an ultra-light release force organic silicon release agent comprises the following components: vinyl silicone oil, an inhibitor, a cross-linking agent, phenyl cage type silsesquioxane, a solvent, an anchoring agent and a catalyst.
The ultra-light release force organic silicon release agent comprises the following components in parts by weight: 100 parts of vinyl silicone oil, 0.05-0.5 part of inhibitor, 1-3 parts of cross-linking agent, 0.5-3 parts of phenyl cage type silsesquioxane, 0.5-3 parts of solvent, 0.5-1.5 parts of anchoring agent and 1-3 parts of catalyst.
Preferably, the ultra-light release force organosilicon release agent comprises the following components in parts by weight: 100 parts of vinyl silicone oil, 0.06-0.4 parts (for example, 0.06, 0.08, 0.1, 0.2, 0.25, 0.3, 0.4 parts) of inhibitor, 1.3-3 parts (for example, 1.3, 1.7, 1.9, 2.1, 2.2, 2.5, 3 parts) of cross-linking agent, 1-3 parts (for example, 1, 1.5, 2, 2.5, 3 parts) of phenyl cage type silsesquioxane, 1-3 parts (for example, 1, 1.5, 2, 2.5, 3 parts) of solvent, 0.5-1.5 parts (for example, 0.5, 1, 1.5 parts) of anchoring agent, and 1-2 parts (for example, 1, 1.5, 2 parts) of catalyst.
The ultra-light release force organic silicon release agent has the advantages that the viscosity of the vinyl silicone oil is 100-2000 mPas, preferably 200-1000 mPas, more preferably 200-500 mPas; the vinyl silicone oil contains 0.2 to 1% by mass of vinyl groups, preferably 0.3 to 0.8% by mass of vinyl groups, and more preferably 0.4 to 0.7% by mass of vinyl groups.
The ultra-light release force organosilicon release agent is characterized in that the inhibitor is one or more selected from tetramethyl tetravinylcyclotetrasiloxane, tetramethyl divinyl disiloxane, ethynyl cyclohexanol, 3, 5-dimethyl-1-hexynyl-3-ol and 3-methyl-1-dodecyn-3-ol.
The ultra-light release force organic silicon release agent is characterized in that the cross-linking agent is side hydrogen group-containing silicone oil, the viscosity of the cross-linking agent is 10-100 mPas, preferably 10-70 mPas, more preferably 15-60 mPas, and the mass content of hydrogen groups is 1.0-1.6%.
The ultra-light release force organic silicon release agent has the following structural formula, wherein the structural formula of phenyl cage type silsesquioxane (eight phenyl cage type silsesquioxane, ph-POSS) is as follows:
the ultra-light release force organic silicon release agent is characterized in that the solvent is toluene or xylene.
The ultra-light release force silicone release agent according to the invention, wherein the anchoring agent is a polysiloxane oligomer containing vinyl and epoxy groups, preferably the number average molecular weight of the polysiloxane oligomer is 500-2500. Further, the anchor may be a commonly used anchor in the art for preparing silicone release agents.
The ultra-light release force organosilicon release agent is characterized in that the catalyst is a platinum catalyst, and preferably, the platinum content is 3000-5000 ppm. Further, the catalyst may be a catalyst commonly used in the art for preparing silicone release agents, for example, the catalyst is a platinum-on-cassett catalyst.
According to the ultra-light release force silicone release agent of the present invention, further preferably, the mass ratio of phenyl cage silsesquioxane to solvent is from 0.5 to 1.2, for example, from 0.5.
According to the ultra-light release force organic silicon release agent, the phenyl cage type silsesquioxane is added as a light release additive, the release force of the organic silicon release agent can be reduced to 1-3g/inch, the release force is stable, and the release force of the high-temperature aging organic silicon release agent climbs to be less than 10% compared with the release force of the normal temperature. The preparation steps of the phenyl cage type silsesquioxane are as follows:
step 1:
dissolving phenyl triethoxysilane and alkali in a solvent, dropwise adding deionized water, and performing reflux reaction;
and 2, step:
after the reaction is finished, filtering, washing and drying the obtained white solid;
and step 3:
and recrystallizing the dried white solid to obtain the product.
Preferably, in the step 1, the base is sodium hydroxide and/or potassium hydroxide, the solvent is toluene and/or xylene, and the mass ratio of the phenyltriethoxysilane, the base, the solvent and the deionized water is 1;
preferably, in step 2, the solvent used for washing is methanol, preferably anhydrous methanol.
Preferably, in step 3, the solvent used for recrystallization is a mixed solvent of dichloromethane and acetone, wherein the volume ratio of dichloromethane to acetone is 0.5 to 2, for example, 0.5.
The invention also aims to provide a preparation method of the ultralight release force organic silicon release agent, which comprises the following steps:
step 1)
Dissolving phenyl cage type silsesquioxane in a solvent, and stirring and dissolving to obtain a phenyl cage type silsesquioxane solution;
step 2)
Uniformly mixing vinyl silicone oil and an inhibitor, adding a cross-linking agent, an anchoring agent and a phenyl cage-type silsesquioxane solution, and uniformly stirring and mixing;
step 3)
Adding a catalyst, and stirring and mixing uniformly to obtain the organic silicon release agent.
The invention also aims to provide the application of the ultralight release force organic silicon release agent in preparing release paper/release film.
Compared with the prior art, the invention has the following technical advantages:
(1) The invention takes conventional vinyl silicone oil as a main agent of the organic silicon release agent, takes lateral hydrogen-containing silicone oil as a cross-linking agent, and can obtain the organic silicon release agent with ultra-light release force by adding a small amount of phenyl cage type silsesquioxane, wherein the release force is as low as 1-3 g/inch;
(2) The organic silicon release agent provided by the invention can be coated on paper and film (such as PET) base materials, has very stable release force, and the release force of high-temperature aging rises to be less than 10% compared with the release force of normal temperature.
(3) The organic silicon release agent provided by the invention has the characteristics of stable ultra-light release force and low silicon transfer rate (the silicon transfer rate is less than 0.5%), and can be applied to the electronic die cutting industry with high requirements on the silicon transfer rate.
Detailed Description
The present invention is further illustrated by the following specific examples, which are intended to be illustrative of the invention and are not to be construed as limiting the scope of the invention.
The embodiment of the invention has the following main raw material source information:
vinyl silicone oil: ningbo Runhe high and new materials science and technology, inc.;
a crosslinking agent: ningbo Runghe high-tech materials science and technology Co., ltd;
tetramethyltetravinylcyclotetrasiloxane: win special chemical company;
ethynylcyclohexanol: shanghai Aladdin Biotechnology, inc.;
3, 5-dimethyl-1-hexyn-3-ol: fosman technologies, inc.;
3-methyl-1-dodecyn-3-ol: fosman technologies, inc.;
phenyltriethoxysilane: shandong Silicones New Material Co., ltd;
potassium hydroxide: xiong chemical corporation;
the anchoring agent can be selected from SD 8411 of Wanhua chemical group Limited company or SKM03 of Shenzhen Tianqi new material science and technology Limited company;
kast platinum catalyst: heli noble materials, inc.;
eight (isobutyl silsesquioxane): shanghai McLin Biochemical technologies, inc.
Unless otherwise specified, other raw materials and reagents in the following examples and comparative examples were all commercially available.
The test methods employed in the examples of the invention and the comparative examples are as follows:
1. the release force test method refers to GB/T2792-1998;
2. the method for testing the normal-temperature release force and the high-temperature aging release force comprises the following steps: attaching a 7475 adhesive tape on a release film, cutting the release film into sample strips with the width of 25mm, pressing the sample strips with a standard steel strip for 20h at room temperature to test that the release force is the normal-temperature release force, and pressing the sample strips with the standard steel strip for 20h at 70 ℃ to cool the sample strips, and testing that the release force is the high-temperature aging release force;
3. the silicon content testing method comprises the following steps: establishing a silicon content marking line by adopting an X-ray fluorescence diffraction spectrometer of Hitachi company for quantitative test;
4. the silicon transfer rate test method comprises the following steps: putting the sample into a methyl isobutyl ketone (MIBK) solvent, soaking for 20h in a constant temperature chamber, and measuring the silicon content on the surface of the sample before and after extraction, wherein the silicon transfer rate is (1-silicon content after soaking/silicon content before soaking) multiplied by 100%;
5. structural characterization of phenyl cage type silsesquioxane: silicon spectrum testing was performed using a Bruker AC300 NMR spectrometer, deuterated chloroform (CDCl) 3 ) Is a solvent; analyzing by using a Thermo Scientific Nicolet is 5 Fourier infrared spectrometer, taking carbon tetrachloride as a solvent, and scanning the wavelength range of 4000-500 cm -1 。
Preparation example preparation of phenyl cage silsesquioxane (Ph-POSS)
Adding 50g of phenyltriethoxysilane and 250g of toluene into a three-neck flask with magnetic stirring and a reflux condenser, adding 1g of potassium hydroxide, heating to 110 ℃, dropwise adding 7g of deionized water, refluxing for 72h at 110 ℃, stopping the reaction, filtering to obtain a white solid, washing with anhydrous methanol for 3 times, and drying the white solid in a vacuum drying oven at 70 ℃ for 36h. The dried white solid was recrystallized from a mixed solvent of 50g of methylene chloride and 50g of acetone to obtain phenyl cage silsesquioxane.
Measured by infrared spectroscopic analysis at 1135cm -1 The single peak is an asymmetric stretching vibration absorption peak of Si-O-Si and is also a characteristic absorption peak of Ph-POSS. 1595cm -1 ，3073cm -1 Is a characteristic absorption peak of a benzene ring, 997cm -1 ，1030cm -1 ，1430cm -1 Is a characteristic absorption peak of Si-Ph. Through nuclear magnetic silicon spectrum analysis and test, only one peak appears near the chemical shift delta = -76.19, which represents that only one silicon atom in Ph-POSS exists, and the structure of Ph-POSS is proved to be as follows:
comparative example 1 preparation of Silicone Release agent D1
Adding 100g of vinyl silicone oil, 0.06g of ethynyl cyclohexanol, 3g of side hydrogen-containing silicone oil and 1.5g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 245mPa & s, and the vinyl mass content is 0.63%; the viscosity of the side hydrogen group-containing silicone oil is 15mPa & s, and the mass content of hydrogen groups is 1.0%; adding 1g of Kanst platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon release agent D1.
Comparative example 2 preparation of Silicone Release agent D2
Adding 100g of vinyl silicone oil, 0.06g of ethynyl cyclohexanol, 3g of side hydrogen-containing silicone oil and 1.5g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 245mPa & s, and the vinyl mass content is 0.63%; the viscosity of the side hydrogen group-containing silicone oil is 15mPa & s, and the mass content of hydrogen groups is 1.0%; adding 2g of octa (isobutyl silsesquioxane) into a reaction kettle, uniformly stirring, adding 1g of a platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organosilicon release agent D2.
Example 1 preparation of Silicone Release agent 1
Adding 100g of vinyl silicone oil, 0.06g of ethynyl cyclohexanol, 3g of side hydrogen-containing silicone oil and 1.5g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 245mPa & s, and the vinyl mass content is 0.63%; the viscosity of the side hydrogen group-containing silicone oil is 15mPa & s, and the mass content of hydrogen groups is 1.0%; dissolving 2g of Ph-POSS in 2g of toluene, adding into a reaction kettle, uniformly stirring, adding 1g of Kansted platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon mold release agent 1.
Example 2 preparation of Silicone Release agent 2
Adding 100g of vinyl silicone oil, 0.2g of ethynyl cyclohexanol, 2.1g of side hydrogen-containing silicone oil and 1.5g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 375mPa & s, and the mass content of vinyl is 0.49%; the viscosity of the side hydrogen group-containing silicone oil is 60mPa & s, and the mass content of hydrogen groups is 1.2%; dissolving 2g of Ph-POSS in 2g of toluene, adding into a reaction kettle, uniformly stirring, adding 1.5g of Kanst platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon mold release agent 2.
Example 3 preparation of Silicone Release agent 3
Adding 100g of vinyl silicone oil, 0.3g of ethynyl cyclohexanol inhibitor, 2.2g of side hydrogen-containing silicone oil and 1g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 300 mPas, and the vinyl mass content is 0.57%; the viscosity of the side hydrogen group-containing silicone oil is 20mPa & s, and the mass content of hydrogen groups is 1.6%; dissolving 2g of Ph-POSS in 2g of toluene, adding the mixture into a reaction kettle, uniformly stirring, adding 1.5g of Kanst platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon release agent 3.
Example 4 preparation of Silicone Release agent 4
Adding 100g of vinyl silicone oil, 0.08g of ethynyl cyclohexanol, 1.7g of side hydrogen-containing silicone oil and 0.5g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 500 mPas, and the vinyl mass content is 0.43%; the viscosity of the side hydrogen group-containing silicone oil is 20mPa & s, and the mass content of hydrogen groups is 1.6%; dissolving 2g of Ph-POSS in 2g of toluene, adding into a reaction kettle, uniformly stirring, adding 1g of a Kansted platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon release agent 4.
Example 5 preparation of Silicone Release agent 5
Adding 100g of vinyl silicone oil, 0.25g of tetramethyl tetravinylcyclotetrasiloxane, 1.9g of side hydrogen-containing silicone oil and 1g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 375mPa & s, and the mass content of vinyl is 0.49%; the viscosity of the silicone oil containing lateral hydrogen groups is 20 mPa.s, and the mass content of the hydrogen groups is 1.6%; dissolving 1g of Ph-POSS in 1g of toluene, adding the mixture into a reaction kettle, uniformly stirring, adding 1.5g of Kanst platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon release agent 5.
Example 6 preparation of Silicone Release agent 6
Adding 100g of vinyl silicone oil, 0.4g of 3, 5-dimethyl-1-hexynyl-3-alcohol, 2.5g of side hydrogen-containing silicone oil and 1g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 375mPa & s, and the mass content of vinyl is 0.49%; the viscosity of the side hydrogen group-containing silicone oil is 15mPa & s, and the mass content of hydrogen groups is 1.0%; dissolving 3g of Ph-POSS in 3g of toluene, adding into a reaction kettle, uniformly stirring, adding 2g of a Kanst platinum catalyst with the platinum content of 3000ppm, and uniformly stirring to obtain the organic silicon release agent 6.
Example 7 preparation of Silicone Release agent 7
Adding 100g of vinyl silicone oil, 0.1g of 3-methyl-1-dodecyn-3-ol, 3g of side hydrogen-containing silicone oil and 1g of anchoring agent SD 8411 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 300 mPas, and the vinyl mass content is 0.57%; the viscosity of the side hydrogen group-containing silicone oil is 15mPa & s, and the mass content of hydrogen groups is 1.0%; dissolving 2g of Ph-POSS in 2g of dimethylbenzene, adding the mixture into a reaction kettle, uniformly stirring, adding 1g of Kanst platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon release agent 7.
Example 8 preparation of Silicone Release agent 8
Adding 100g of vinyl silicone oil, 0.08g of ethynyl cyclohexanol, 1.3g of side hydrogen-containing silicone oil and 1.5g of anchoring agent SKM03 into a reaction kettle, and uniformly stirring; wherein the viscosity of the vinyl silicone oil is 1000 mPas, and the vinyl mass content is 0.32%; the viscosity of the side hydrogen group-containing silicone oil is 20mPa & s, and the mass content of hydrogen groups is 1.6%; dissolving 2g of Ph-POSS in 2g of toluene, adding the mixture into a reaction kettle, uniformly stirring, adding 1g of Kanst platinum catalyst with the platinum content of 5000ppm, and uniformly stirring to obtain the organic silicon release agent 8.
Test example
The silicone release agents 1 to 8 synthesized in the above examples were applied to the corona surface of a PET film by a coater, and baked at 150 ℃ for 15 seconds to obtain release films, and the results of the test of normal temperature release force, high temperature aging release force, and silicon transfer rate are shown in table 1.
TABLE 1 Performance test results for Silicone Release agents 1-8
The release agent prepared by adding the non-phenyl cage type silsesquioxane into the formula is shown in the comparative example 1, and the release agent prepared by adding the non-phenyl cage type silsesquioxane into the formula is shown in the comparative example 2, so that when the auxiliary agent for reducing the stripping force is not added, the stripping force and the aging stripping force are both high and cannot meet the application requirement of 1-3g/inch, when the eight (isobutyl silsesquioxane) is added, the stripping force is still high and cannot be reduced to 1-3g/inch, the climbing proportion of the high-temperature aging stripping force is higher than that of the normal-temperature stripping force, and the silicon transfer rate is high; the organosilicon release agent prepared in the embodiments 1 to 8 is coated on the surface of a PET substrate, the normal temperature release force and the high temperature aging release force are both in the range of 1 to 3g/inch, and the organosilicon release agent has very stable release force, the high temperature aging release force climbs to less than 10 percent compared with the normal temperature release force, the silicon transfer rate is less than 0.5 percent, and the organosilicon release agent has low silicon transfer rate, and can be applied to the electronic die cutting industry with high requirements on the silicon transfer rate.
Claims (10)
1. An ultra-light release force organic silicon release agent comprises the following components in parts by weight:
100 parts of vinyl silicone oil, namely 100 parts of,
0.05 to 0.5 portion of inhibitor,
1-3 parts of a cross-linking agent,
0.5 to 3 portions of phenyl cage type silsesquioxane,
0.5 to 3 portions of solvent,
0.5 to 1.5 portions of anchoring agent,
1-3 parts of a catalyst.
2. The silicone release agent according to claim 1, characterized in that the vinyl silicone oil has a viscosity of 100 to 2000 mPa-s, preferably 200 to 1000 mPa-s, more preferably 200 to 500 mPa-s; the mass content of vinyl in the vinyl silicone oil is 0.2-1%.
3. The silicone release agent according to claim 1 or 2, wherein the inhibitor is selected from one or more of tetramethyltetravinylcyclotetrasiloxane, tetramethyldivinyldisiloxane, ethynylcyclohexanol, 3, 5-dimethyl-1-hexyn-3-ol, 3-methyl-1-dodecyn-3-ol.
4. The silicone release agent according to any one of claims 1 to 3, characterized in that the crosslinking agent is a side hydrogen group-containing silicone oil, the viscosity of the crosslinking agent is 10 to 100mPa · s, and the hydrogen group mass content is 1.0 to 1.6%.
5. The silicone release agent of any one of claims 1-4, wherein the phenyl cage silsesquioxane has the following structural formula:
6. the silicone release agent according to any of claims 1-5, characterized in that the solvent is toluene or xylene.
7. The silicone release agent according to any one of claims 1 to 6, characterized in that the anchor agent is a polysiloxane oligomer containing vinyl and epoxy groups.
8. The silicone release agent according to any of claims 1 to 7, characterized in that the catalyst is a platinum catalyst, preferably with a platinum content of 3000 to 5000ppm.
9. The method for preparing the silicone release agent according to any one of claims 1 to 8, characterized by comprising the steps of:
step 1)
Dissolving phenyl cage type silsesquioxane in a solvent, and stirring and dissolving to obtain a phenyl cage type silsesquioxane solution;
step 2)
Uniformly mixing vinyl silicone oil and an inhibitor, adding a cross-linking agent, an anchoring agent and a phenyl cage-type silsesquioxane solution, and uniformly stirring and mixing;
step 3)
Adding a catalyst, and stirring and mixing uniformly to obtain the organic silicon release agent.
10. Use of the silicone release agent of any one of claims 1-8 in the preparation of a release paper/release film.
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