CN112708349B - Preparation method of smooth and elastic organic silicon release agent - Google Patents

Preparation method of smooth and elastic organic silicon release agent Download PDF

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Publication number
CN112708349B
CN112708349B CN202110026780.7A CN202110026780A CN112708349B CN 112708349 B CN112708349 B CN 112708349B CN 202110026780 A CN202110026780 A CN 202110026780A CN 112708349 B CN112708349 B CN 112708349B
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vinyl
parts
release agent
smooth
weight
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CN112708349A (en
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刘鹏
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Yichang Xingyue New Material Co ltd
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Yichang Xingyue New Material Co ltd
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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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/20—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for coatings strippable as coherent films, e.g. temporary coatings strippable as coherent films
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C09J7/401—Adhesives in the form of films or foils characterised by release liners characterised by the release coating composition
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/32—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
    • D21H27/001—Release paper
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2483/00—Presence of polysiloxane
    • C09J2483/005—Presence of polysiloxane in the release coating

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Paper (AREA)
  • Adhesive Tapes (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Silicon Polymers (AREA)
  • Laminated Bodies (AREA)

Abstract

The invention relates to a preparation method of a smooth and elastic organic silicon release agent, which is characterized in that 20-30 parts by weight of vinyl-containing perfluoro polyethylene glycol modified elastic polyurethane, 80-100 parts by weight of vinyl polysiloxane, 6-12 parts by weight of hydrogen polysiloxane, 2-4 parts by weight of an anti-sticking agent and 1-3 parts by weight of an anchoring agent are added into a mixing device and stirred for 15-30 min; and adding 1-3 parts of platinum catalyst, and stirring for 1-5 min to obtain the smooth and elastic organic silicon mold release agent. The invention can be tightly adhered with the glassine paper and has the advantage of easier stripping.

Description

Preparation method of smooth and elastic organic silicon release agent
Technical Field
The invention belongs to the technical field of release materials, and relates to a preparation method of a smooth and elastic organic silicon release agent.
Background
The release agent composition is applied to the surface of various substrates such as paper, synthetic resin film, synthetic fiber, cloth, and the like, and cured to form a cured layer, whereby a film having releasability from an adhesive substance such as a pressure-sensitive adhesive can be formed. As such a release agent composition, one containing an organopolysiloxane having a siloxane unit containing a fluorine atom is known. The organic silicon coating is an important direction in the field of the anti-adhesion coating at present, and has the advantages of low surface tension, transparency, no toxicity, high temperature resistance, good weather resistance and the like, so that the organic silicon coating is widely applied to the surfaces of metals, ceramics, paper, plastics and textiles as the anti-adhesion coating or the anti-adhesion coating.
However, the conventional release agent composition has a problem of poor releasability from a silicone adhesive containing an organopolysiloxane such as dimethylpolysiloxane or methylphenylpolysiloxane as a main component, although it has excellent releasability from a cured film of an organic resin adhesive substance. As a result, the releasability from the silicone adhesive may become insufficient depending on the application. In the case of producing a tape-shaped release sheet or laminate by applying and curing a release agent composition, the tape-shaped release sheet or the like is usually wound into a roll shape and transported and stored in a wound state. In this case, it is known that a rolling pressure is applied to the center portion of the wound body in particular, but there is also a problem that the release layer is peeled off again from the adhesive substance by applying the rolling pressure. The invention increases the smoothness and elasticity of the release agent composition and obtains the organic silicon release agent with excellent stripping performance.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention aims to provide a smooth and elastic organic silicon release agent.
The invention adopts the following technical scheme that the smooth and elastic organic silicon release agent is characterized by comprising the following components in parts by weight: 20-30 parts of vinyl-containing perfluoro polyethylene glycol modified elastic polyurethane, 80-100 parts of vinyl polysiloxane, 6-12 parts of hydrogen polysiloxane, 2-4 parts of an anti-sticking agent, 1-3 parts of an anchoring agent and 2-10 parts of a platinum catalyst.
The vinyl polysiloxane is terminal vinyl polysiloxane, the viscosity is 2000-20000cp, and the vinyl content is 0.01-0.1%; the viscosity of the hydrogenous polysiloxane is 20-50cp, and the hydrogen content is 0.3-1.2%.
The anchoring agent is at least one of vinyl trimethoxy silane, vinyl tri- (beta-methoxyethoxy) silane and gamma- (methacryloyloxy) propyl trimethoxy silane.
The platinum catalyst is at least one of chloroplatinic acid-divinyl tetramethyl disiloxane, chloroplatinic acid-isopropanol and chloroplatinic acid-diethyl phthalate.
The anti-sticking agent is at least one of 4, 5-epoxy cyclohexane-1, 2-dicarboxylic acid diglycidyl ester, ethylene glycol diglycidyl ester and pentaerythritol tetraglycidyl ether.
The preparation method of the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane comprises the following steps of:
under the protection of nitrogen, adding 50-60 parts of vinyl-containing perfluoropolyethylene glycol, 6-14 parts of diisocyanate monomer and 12-25 parts of organic solvent into a reactor, starting stirring to uniformly stir the materials, heating to 60-90 ℃ and reacting for 2-3 h; and then dropwise adding 0.05-0.15 part of catalyst, continuing to react for 1-2 hours at 60-90 ℃ after dropwise adding, measuring the percentage content of-NCO in the system every 0.5 hour in the reaction process, cooling to room temperature when the percentage content of-NCO in the system reaches the target value and is less than 0.5%, and then removing the organic solvent through reduced pressure distillation to obtain the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane.
The vinyl-containing perfluoro polyethylene glycol is at least one of allyl perfluoro polyethylene glycol and isopentenyl perfluoro polyethylene glycol, and the relative molecular weight of the vinyl-containing perfluoro polyethylene glycol is 600-2000; the diisocyanate monomer is at least one of MDI, HDI and TDI; the organic solvent is at least one of ethyl acetate, acetone, butyl acetate butanone and propyl acetate; the catalyst is at least one of dibutyltin dilaurate, stannous octoate, tin naphthenate and cobalt naphthenate.
The preparation method of the smooth and elastic organic silicon release agent comprises the following steps: adding the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane, vinyl polysiloxane, hydrogen-containing polysiloxane, anti-sticking agent and anchoring agent into a mixing device according to the formula ratio, and stirring for 15-30 min; and adding a platinum catalyst in a formula amount, and stirring for 1-5 min to obtain the smooth and elastic organic silicon mold release agent.
The smooth and elastic organic silicon release agent is coated on a base material and cured at the temperature of 155-180 ℃ to obtain the release paper.
Compared with the prior art, the invention has the following advantages or beneficial results:
(1) the vinyl-containing perfluoro polyethylene glycol modified elastic polyurethane is added, and the perfluoro polyethylene glycol structure increases the oleophobicity and hydrophobicity of the organic silicon release agent, so that the organic silicon release agent is easier to peel;
(2) the toughness of the organic silicon release agent is improved due to the elasticity of the polyurethane structure, the impact resistance and the tensile resistance of the organic silicon release agent are improved, and the organic silicon release agent can be tightly attached without moving and shifting and cannot be broken when being used in the use process of release paper;
(3) the anchoring agent reacts with hydrogen-containing polysiloxane to participate in the reaction, so that the binding property of the release agent to the release paper is improved.
Detailed Description
A smooth and elastic silicone release agent of the present invention is further described below with reference to examples. It is to be understood that the specific embodiments described herein are merely illustrative of the relevant invention and not restrictive of the invention.
Example 1
The preparation method of the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane X comprises the following steps of:
under the protection of nitrogen, 54 parts of isopentenyl perfluoropolyethylene glycol, 9 parts of MDI and 18 parts of acetone are added into a reactor, stirring is started to uniformly stir the materials, and the materials are heated to 78 ℃ for reaction for 3 hours; and then dropwise adding 0.10 part of stannous octoate, continuously reacting for 2 hours at 78 ℃ after the dropwise adding is finished, measuring the percentage content of-NCO in the system every 0.5 hour in the reaction process, cooling to room temperature after the percentage content of the-NCO in the system reaches the target value and is less than 0.5%, and then removing the organic solvent through reduced pressure distillation to obtain the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane X.
Example 2
The smooth and elastic organic silicon release agent is characterized by comprising the following components in parts by weight: the modified elastic polyurethane comprises, by weight, 30 parts of vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane, 80 parts of vinyl-terminated polysiloxane (the viscosity is 5000cp, the vinyl content is 0.04%), 12 parts of hydrogen-containing polysiloxane (the viscosity is 50cp, and the hydrogen content is 0.3%), 2 parts of ethylene glycol diglycidyl ester, 3 parts of vinyl tri- (beta-methoxyethoxy) silane and 2 parts of chloroplatinic acid-divinyl tetramethyl disiloxane.
While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes, modifications and variations can be made therein without departing from the spirit and scope of the invention as defined in the following claims.

Claims (5)

1. A preparation method of a smooth and elastic organic silicon release agent is characterized in that 20-30 parts by weight of vinyl-containing perfluoro polyethylene glycol modified elastic polyurethane, 80-100 parts by weight of vinyl polysiloxane, 6-12 parts by weight of hydrogen polysiloxane, 2-4 parts by weight of an anti-sticking agent and 1-3 parts by weight of an anchoring agent are added into a mixing device and stirred for 15-30 min; adding 2-10 parts of platinum catalyst, and stirring for 1-5 min to obtain the smooth and elastic organic silicon release agent;
the anti-sticking agent is at least one of 4, 5-epoxy cyclohexane-1, 2-dicarboxylic acid diglycidyl ester, ethylene glycol diglycidyl ester and pentaerythritol tetraglycidyl ether;
the anchoring agent is at least one of vinyl trimethoxy silane, vinyl tri- (beta-methoxyethoxy) silane and gamma- (methacryloyloxy) propyl trimethoxy silane;
the preparation method of the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane comprises the following steps of:
under the protection of nitrogen, adding 50-60 parts of vinyl-containing perfluoropolyethylene glycol, 6-14 parts of diisocyanate monomer and 12-25 parts of organic solvent into a reactor, starting stirring to uniformly stir the materials, heating to 60-90 ℃ and reacting for 2-3 h; dropwise adding 0.05-0.15 part of catalyst, continuing to react for 1-2 hours at 60-90 ℃ after dropwise adding, measuring the percentage content of-NCO in the system every 0.5 hour in the reaction process, cooling to room temperature when the percentage content of-NCO in the system reaches the target value and is less than 0.5%, and then removing the organic solvent through reduced pressure distillation to obtain the vinyl-containing perfluoropolyethylene glycol modified elastic polyurethane;
the vinyl-containing perfluoro polyethylene glycol is at least one of allyl perfluoro polyethylene glycol and isopentenyl perfluoro polyethylene glycol, and the relative molecular weight of the vinyl-containing perfluoro polyethylene glycol is 600-2000; the diisocyanate monomer is at least one of MDI, HDI and TDI.
2. The method for preparing the smooth and elastic silicone release agent as claimed in claim 1, wherein the vinyl polysiloxane is terminal vinyl polysiloxane, the viscosity is 2000-20000cP, and the vinyl content is 0.01-0.1%; the viscosity of the hydrogenpolysiloxane is 20-50cP, and the hydrogen content is 0.3-1.2%.
3. The method for preparing the silicone release agent with smoothness and elasticity as claimed in claim 1, wherein the platinum catalyst is at least one of chloroplatinic acid-divinyltetramethyldisiloxane, chloroplatinic acid-isopropanol, and chloroplatinic acid-diethyl phthalate.
4. The method for preparing the smooth and elastic silicone release agent according to claim 1, wherein the organic solvent is at least one of ethyl acetate, acetone and propyl acetate.
5. The method for preparing the smooth and elastic silicone release agent according to claim 1, wherein the catalyst is at least one of dibutyltin dilaurate, stannous octoate, tin naphthenate and cobalt naphthenate.
CN202110026780.7A 2018-10-10 2018-10-10 Preparation method of smooth and elastic organic silicon release agent Active CN112708349B (en)

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CN202110026779.4A Pending CN112795309A (en) 2018-10-10 2018-10-10 Easy-to-peel glassine release paper
CN202110026780.7A Active CN112708349B (en) 2018-10-10 2018-10-10 Preparation method of smooth and elastic organic silicon release agent
CN202110026791.5A Withdrawn CN112794981A (en) 2018-10-10 2018-10-10 Vinyl perfluoropolyethylene glycol modified elastic polyurethane and application thereof

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CN113527691A (en) * 2021-06-24 2021-10-22 无锡龙驰氟硅新材料有限公司 Fluorosilicone polymer and preparation method thereof
CN115975503B (en) * 2021-10-15 2023-09-15 山东东岳高分子材料有限公司 Anchoring agent for fluorine-silicon release agent and application thereof
CN116814162A (en) * 2023-06-28 2023-09-29 太仓斯迪克新材料科技有限公司 Environment-friendly UV (ultraviolet) photo-curing release coating liquid, release film and preparation method of release film

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CN109385207B (en) 2021-06-29
CN112795309A (en) 2021-05-14
CN112708349A (en) 2021-04-27
CN109385207A (en) 2019-02-26
CN112794981A (en) 2021-05-14

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