CN117535026A - UV transfer printing adhesive and preparation method thereof - Google Patents

UV transfer printing adhesive and preparation method thereof Download PDF

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Publication number
CN117535026A
CN117535026A CN202311487359.1A CN202311487359A CN117535026A CN 117535026 A CN117535026 A CN 117535026A CN 202311487359 A CN202311487359 A CN 202311487359A CN 117535026 A CN117535026 A CN 117535026A
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CN
China
Prior art keywords
acrylic resin
transfer
polyether amine
modified polyurethane
amine modified
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.)
Pending
Application number
CN202311487359.1A
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Chinese (zh)
Inventor
马雅玲
石建行
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Wuhan Huagong Image Technology & Development Co ltd
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Wuhan Huagong Image Technology & Development Co ltd
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Priority to CN202311487359.1A priority Critical patent/CN117535026A/en
Publication of CN117535026A publication Critical patent/CN117535026A/en
Pending legal-status Critical Current

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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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/04—Polyurethanes
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
    • 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
    • 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
    • C09D7/65—Additives macromolecular
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/06—Unsaturated polyesters having carbon-to-carbon unsaturation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention provides a UV transfer printing adhesive and a preparation method thereof, wherein the UV transfer printing adhesive comprises the following raw materials in percentage by weight: 30% -50% of polyether amine modified polyurethane acrylic resin; 20% -30% of polyester acrylic resin; 25% -45% of active monomer; 1% -5% of a photoinitiator; compared with the prior art, the UV transfer adhesive has the characteristics of aging resistance, high toughness and the like, and solves the problem that deep groove texture patterns on a nickel plate cannot be transferred under the low-energy illumination condition in the existing UV molding production process, and the problem of energy cost is solved.

Description

UV transfer printing adhesive and preparation method thereof
Technical Field
The invention relates to the technical field of ultraviolet curing coatings, in particular to a UV transfer printing adhesive and a preparation method thereof.
Background
Currently, along with the rapid development of automotive interiors, 3C product applications and design, the diversification of appearance patterns has gradually tended to be mainstream. The embossing transfer technology is one of the important processes for turning the designed pattern to a practical product, and is the most favored one of the embossing transfer technologies as a UV embossing technology with the advantages of low VOC emission, energy saving, low curing temperature, high curing speed and the like. The curing speed of the UV transfer glue serving as a main raw material glue for UV molding is an important factor for determining mass production and yield of products.
Polyurethane resin is a main component of UV transfer printing glue and is one of resins commonly used in coating, but because polyurethane resin is generally synthesized by toxic isocyanate, the environment pollution is serious, and special polyurethane synthesized by non-isocyanate does not need isocyanate, and the polyurethane resin has the characteristics of safety and stability. The main body in the UV molding process has the characteristics of high viscosity and low curing rate, and in order to ensure molding industrialization, other resins with high curing speed are usually needed for assistance, and high-energy light is needed for production, but this affects the adjustment space of other component proportions of the whole formulation and the increase of production cost. In the existing production process, transfer printing of deep groove texture patterns on a nickel plate cannot be realized under the condition of low illumination intensity.
Therefore, based on the defects, the invention provides a UV transfer printing adhesive and a preparation method thereof.
Disclosure of Invention
Based on the expression, the invention provides the UV transfer printing adhesive and the preparation method thereof, which are used for solving the technical problems of high viscosity and slow curing rate of raw materials used by the UV transfer printing adhesive under low illumination intensity.
The technical scheme for solving the technical problems is as follows:
in a first aspect, a UV transfer paste comprises the following components in weight percent:
30% -50% of polyether amine modified polyurethane acrylic resin;
20% -30% of polyester acrylic resin;
25% -45% of active monomer;
1 to 5 percent of photoinitiator.
Further, the molecular structure of the polyether amine modified polyurethane acrylic resin is as follows:
wherein n=10 to 25.
Further, the polyester acrylic resin is an aliphatic polyester acrylic resin.
Further, the polyester acrylic resin is one or a combination of more than one of tetrafunctional polyester acrylic resin, hexafunctional polyester acrylic resin and octafunctional polyester acrylic resin.
Further, the reactive monomer is one or more of a monofunctional acrylate monomer and a difunctional acrylate monomer.
Further, the monofunctional acrylate monomer includes: isobornyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate or ethoxyethoxyethoxyethyl acrylate;
the difunctional acrylic monomer includes: tripropylene glycol diacrylate, dipropylene glycol diacrylate, 1, 6-hexanediol diacrylate or triethylene glycol diacrylate.
Further, the photoinitiator is selected from one or more of 1-hydroxy-cyclohexyl benzophenone, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 2-hydroxy-2-methyl-phenyl acetone-1, 2,4, 6-trimethylbenzoyl-ethoxy-phenyl phosphine oxide and 2-hydroxy-2-methyl-p-hydroxyethyl ether phenyl acetone-1.
In a second aspect, a method for preparing the UV transfer paste according to the first aspect, comprising:
dissolving and mixing a photoinitiator and an active monomer;
sequentially adding polyether amine modified polyurethane acrylic resin and polyester acrylic resin, stirring, dispersing and filtering.
Further, the method comprises the steps of:
before polyether amine modified polyurethane acrylic resin is added, the polyether amine modified polyurethane acrylic resin is prepared, and the method specifically comprises the following steps:
mixing polyether amine and propylene carbonate according to a molar ratio of 1:2, introducing nitrogen, stirring, heating to 110 ℃, preserving heat, and distilling under reduced pressure to obtain an intermediate product: c (C) (3n+11) H (6n+20) O (n+6) N 2 ；
Mixing the intermediate product, acrylic acid and sulfuric acid, charging nitrogen, heating to 100 ℃, stirring, and distilling the product to obtain the polyether amine modified polyurethane acrylic resin.
Compared with the prior art, the technical scheme of the application has the following beneficial technical effects:
the UV transfer printing adhesive provided by the invention is prepared by the following raw materials in percentage by weight through mutual reaction: 30-50% of polyether amine modified polyurethane acrylic resin, 20-30% of polyester acrylic resin, 30-45% of active monomer and 1-5% of photoinitiator.
Compared with the prior art, the UV transfer printing adhesive uses the polyether amine modified polyurethane acrylic resin synthesized by the non-isocyanate synthesis process as the raw material, so that the raw material used in the synthesis is safe, stable and environment-friendly, and meanwhile, the resin has the characteristics of rapid solidification, ageing resistance, good toughness and the like.
The UV transfer adhesive can copy and transfer the texture pattern of the deep groove on the nickel plate through ultraviolet light curing, and has the effect of irradiating (100 mj/cm) 2 ) Fast transfer printing is realized; the glue layer has the characteristics of ageing resistance, high toughness and the like, can be well applied to UV mould pressing, and solves the problem that deep groove texture patterns on a nickel plate cannot be transferred under the low-energy illumination condition in the existing production process, and the energy cost is high.
Drawings
Fig. 1 is a schematic diagram of a manner of performing a related performance test on a UV transfer adhesive according to an embodiment of the present invention.
Detailed Description
In order to facilitate an understanding of the present application, a more complete description of the present application will now be provided with reference to the relevant figures. Examples of the present application are given in the accompanying drawings. This application may, however, be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. It will be further understood that the terms "comprises" and/or "comprising," and/or the like, specify the presence of stated features, integers, steps, operations, elements, components, or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or groups thereof.
Abbreviations and key term definitions:
PET film: high temperature resistant polyester film.
Polyurethane resin is a main component of UV transfer printing glue and is one of resins commonly used in coating, in the prior art, isocyanate is generally used as a raw material for the synthesis of polyurethane resin, but the isocyanate has high toxicity and is easy to cause environmental pollution, and special polyurethane synthesized by non-isocyanate does not need isocyanate, and the polyurethane has the characteristics of safety and stability.
The polyurethane acrylic resin synthesized by non-isocyanate has the characteristics of strong adhesive force, good flexibility and aging resistance, but also has the defects of high viscosity, slow curing rate and the like. To ensure molding industrialization, other resins with high curing speed are usually needed for assistance, and high energy light is needed for production, but this affects the adjustment space of other component ratios of the whole formulation and the increase of production cost. The polyether amine resin has the characteristics of surface drying increase and quick curing, and the polyether amine resin and the polyurethane acrylic resin are combined to realize the advantages of quick curing, good toughness, aging resistance and the like.
Based on this, the present invention provides a UV transfer adhesive and a method for preparing the same, and embodiments of the present invention will be described in further detail with reference to the accompanying drawings and examples, which are provided to illustrate the present invention, but are not intended to limit the scope of the present invention.
Example 1
The UV transfer printing adhesive in the embodiment 1 comprises the following components in percentage by weight:
the polyether amine modified polyurethane acrylic resin is synthesized by the following method: :
(1) Adding metered polyether amine (0.2 mol) and propylene carbonate (0.4 mol) into a three-neck flask with a thermometer, an electric stirrer and a condenser, introducing nitrogen for protection, stirring, heating to 110 ℃, preserving heat for 6h, and then distilling under reduced pressure to remove residual amine to obtain an intermediate product C (3n+11) H (6n+20) O (n+6) N 2 The reaction formula is as follows:
(2) Adding the intermediate product C into a three-neck flask (3n+11) H (6n+20) O (n+6) N 2 Mixing acrylic acid and sulfuric acid, filling nitrogen to remove oxygen, heating to 100 ℃, stirring for 4 hours, and distilling the product to obtain polyether amine modified polyurethane acrylic acid prepolymer, wherein the reaction formula is as follows:
example 2
The UV transfer printing adhesive in the embodiment 2 comprises the following components in percentage by weight:
the polyether amine modified urethane acrylic resin was synthesized by the method of example 1.
Example 3
The UV transfer printing adhesive in the embodiment 3 comprises the following components in percentage by weight:
the polyether amine modified urethane acrylic resin was synthesized by the method of example 1.
Comparative example 1
The difference from the transfer paste provided in example 1 is that: the UV transfer printing adhesive in the comparative example replaces polyether amine modified polyurethane acrylic resin in the example 1 with difunctional aliphatic polyurethane acrylic resin, and specifically comprises the following components in percentage by weight:
comparative example 2
The difference from the transfer paste provided in example 1 is that: the UV transfer printing adhesive in the comparative example comprises the following components in percentage by weight:
the UV transfer adhesive related performance test was performed as follows:
dripping UV transfer glue on nickel plate by using different depth groove nickel plates (shallow groove < 10 μm; deep groove > 20 μm), covering PET film on the glue, flattening the glue by roller rolling, simultaneously curing above the membrane by using LED ultraviolet lamp synchronously, and ultravioletThe lamp power was 100mw/cm 2 And 300mw/cm 2 Checking whether glue remains on the nickel plate and whether the glue surface dries completely; and simultaneously, carrying out an ultraviolet aging resistance test on the cured coating for 168 hours by using an ultraviolet aging box, and observing whether the coating is yellow or not, wherein the test method is shown in figure 1.
Table 1 test results for examples 1, 2, 3 and comparative examples 1, 2
As shown in table 1, the UV transfer glue used in the examples of the present invention has significant advantages over the existing transfer glue.
Wherein, by the test results of comparative example 1 and comparative example 1, it can be seen that the ratio was 100mw/cm 2 Under the conditions of low illumination intensity and deeper grooves, the polyurethane acrylic resin modified by polyether amine has higher curing speed, aging resistance and low viscosity compared with polyurethane resin, so that the transfer printing of deep groove texture patterns on a nickel plate under the condition of low energy illumination can be realized in the UV molding process, thereby reducing the energy cost and improving the production efficiency.
From the test results of comparative example 1 and comparative example 2, it can be seen that the polyether amine modified urethane acrylic resin obtained by using non-isocyanate proposed by the present invention exhibits superior properties to the polyether amine modified urethane acrylic resins in the existing market.
In summary, the UV transfer printing adhesive provided by the invention is prepared by the following raw materials in percentage by weight through mutual reaction: 30-50% of polyether amine modified polyurethane acrylic resin, 20-30% of polyester acrylic resin, 30-45% of active monomer and 1-5% of photoinitiator.
Compared with the prior art, the UV transfer printing adhesive uses the polyether amine modified polyurethane acrylic resin synthesized by the non-isocyanate synthesis process as the raw material, so that the raw material used in the synthesis is safe, stable and environment-friendly, and meanwhile, the resin has the characteristics of rapid solidification, ageing resistance, good toughness and the like.
The UV transfer adhesive can copy and transfer the texture pattern of the deep groove on the nickel plate through ultraviolet light curing, and has the effect of irradiating (100 mj/cm) 2 ) Fast transfer printing is realized; the glue layer has the characteristics of ageing resistance, high toughness and the like, can be well applied to UV mould pressing, and solves the problem that deep groove texture patterns on a nickel plate cannot be transferred under the low-energy illumination condition in the existing production process and the problem of energy cost.
In the description of the present specification, reference to the term "a particular example" or "some examples" or the like means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the embodiments of the invention. In this specification, particular features, structures, materials, or characteristics may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, the different embodiments or examples described in this specification and the features of the different embodiments or examples may be combined and combined by those skilled in the art without contradiction.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims (9)

1. The UV transfer printing adhesive is characterized by comprising the following components in percentage by weight:
30% -50% of polyether amine modified polyurethane acrylic resin;
20% -30% of polyester acrylic resin;
25% -45% of active monomer;
1 to 5 percent of photoinitiator.
2. The UV transfer glue according to claim 1, wherein the molecular structure of the polyetheramine modified urethane acrylic resin is:
wherein n=10 to 25.
3. The UV transfer glue of claim 1, wherein the polyester acrylic resin is an aliphatic polyester acrylic resin.
4. The UV transfer paste according to claim 3, wherein the polyester acrylic resin is one or a combination of a tetrafunctional polyester acrylic resin, a hexafunctional polyester acrylic resin, and an octafunctional polyester acrylic resin.
5. The UV transfer glue of claim 1, wherein the reactive monomer is a monofunctional acrylate monomer and/or a difunctional acrylate monomer.
6. The UV transfer glue of claim 5, wherein the monofunctional acrylate monomer comprises: one of isobornyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate and ethoxyethoxyethoxyethyl acrylate;
the difunctional acrylic monomer includes: one of tripropylene glycol diacrylate, dipropylene glycol diacrylate, 1, 6-hexanediol diacrylate and triethylene glycol diacrylate.
7. The UV transfer glue according to claim 1, wherein the photoinitiator is selected from one or more of 1-hydroxy-cyclohexylbenzophenone, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 2-hydroxy-2-methyl-phenyl acetone-1, 2,4, 6-trimethylbenzoyl-ethoxy-phenyl phosphine oxide and 2-hydroxy-2-methyl-p-hydroxyethyl ether-phenyl acetone-1.
8. A production method for producing the UV transfer paste according to any one of claims 1 to 7, comprising:
dissolving and mixing a photoinitiator and an active monomer;
sequentially adding polyether amine modified polyurethane acrylic resin and polyester acrylic resin, stirring, dispersing and filtering.
9. The method of preparing a UV transfer paste according to claim 8, comprising:
before polyether amine modified polyurethane acrylic resin is added, the polyether amine modified polyurethane acrylic resin is prepared, and the method specifically comprises the following steps:
mixing polyether amine and propylene carbonate according to a molar ratio of 1:2, introducing nitrogen, stirring, heating to 110 ℃, preserving heat, and distilling under reduced pressure to obtain an intermediate product: c (C) (3n+11) H (6n+20) O (n+6) N 2 ；
Mixing the intermediate product, acrylic acid and sulfuric acid, charging nitrogen, heating to 100 ℃, stirring, and distilling the product to obtain the polyether amine modified polyurethane acrylic resin.
CN202311487359.1A 2023-11-07 2023-11-07 UV transfer printing adhesive and preparation method thereof Pending CN117535026A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202311487359.1A CN117535026A (en) 2023-11-07 2023-11-07 UV transfer printing adhesive and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202311487359.1A CN117535026A (en) 2023-11-07 2023-11-07 UV transfer printing adhesive and preparation method thereof

Publications (1)

Publication Number Publication Date
CN117535026A true CN117535026A (en) 2024-02-09

Family

ID=89785372

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202311487359.1A Pending CN117535026A (en) 2023-11-07 2023-11-07 UV transfer printing adhesive and preparation method thereof

Country Status (1)

Country Link
CN (1) CN117535026A (en)

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