CN113698907A - Ultraviolet-curing laminated adhesive for labels and preparation method thereof - Google Patents
Ultraviolet-curing laminated adhesive for labels and preparation method thereof Download PDFInfo
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- CN113698907A CN113698907A CN202110976085.7A CN202110976085A CN113698907A CN 113698907 A CN113698907 A CN 113698907A CN 202110976085 A CN202110976085 A CN 202110976085A CN 113698907 A CN113698907 A CN 113698907A
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- acrylate
- labels
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- laminating adhesive
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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
- 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
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/334—Applications of adhesives in processes or use of adhesives in the form of films or foils as a label
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses an ultraviolet light curing laminated adhesive and a preparation method thereof, wherein the ultraviolet light curing laminated adhesive comprises the following components in parts by weight: 30-60 parts of polyurethane acrylate prepolymer, 20-40 parts of UV curing monomer, 3-10 parts of photoinitiator, 0.5-5 parts of wetting agent, 0.5-3 parts of flatting agent and 0.1-1 part of defoaming agent. The preparation method is simple, the operation is easy, the laminating starting speed is high and can reach 80-100 m/min, the appearance transparency of the laminated film is good, the adhesive property of the laminated film is good, and the requirement of the performance of the laminated film of the label is met.
Description
Technical Field
The invention relates to a laminated adhesive and a preparation method thereof, in particular to an ultraviolet light curing laminated adhesive for labels and a preparation method thereof.
Background
Polyurethane is a high molecular synthetic material with the performance between that of rubber and plastic, and is characterized by wide hardness adjustment range, elasticity of rubber and hardness of plastic, and good mechanical property, wear resistance and resilience. With the development of polyurethane industry, the application of polyurethane products is more and more extensive, and the performance requirements on the products are higher and higher.
The polyurethane elastomer has the advantages of good tensile strength, tear strength, impact resistance, wear resistance, weather resistance, hydrolysis resistance, oil resistance and the like. The coating is mainly used for coating materials, such as hoses, gaskets, wheel belts, rollers, gears, pipes and the like, insulators, soles, solid tires and the like. The transparent elastomer can be used for manufacturing shoes, advertisements and the like with high light transmittance.
Chinese patent CN201910339132.X provides an ultraviolet curing coated adhesive and a preparation method thereof, wherein the ultraviolet curing coated adhesive comprises the following components in parts by mass: 20-35 parts of polyurethane acrylate oligomer, 10-30 parts of first ultraviolet curing monomer, 35-60 parts of second ultraviolet curing monomer and 2-6 parts of photoinitiator; the glass transition temperature of the first ultraviolet curing monomer is 70-150 ℃, the glass transition temperature of the second ultraviolet curing monomer is-50-50 ℃, and the invention mainly solves the problems of good adhesion and transparency and the like.
Chinese patent CN201310396040.8 provides a UV-curable common laminated adhesive suitable for a thin film spraying process, which comprises the following components in parts by weight: 0-40 parts of (methyl) acrylate resin; 30-70 parts of (methyl) acrylic acid reactive diluent; 0-10 parts of a photoinitiator; and the other 0-5 parts, the invention solves the problem of coating efficiency.
Chinese patent CN201410856799.4 provides a UV film-coating glue, a film-coating machine using the UV film-coating glue and a processing method thereof, wherein the composition of the UV film-coating glue comprises the following components: the acrylate prepolymer, an acrylate monomer A, a photoinitiator and an auxiliary agent; the laminating machine comprises a paper feeder (1), a powder remover (2), a host machine (3), a UV lamp curing device (8), a paper separating machine (9) and a paper collecting table (10); the processing method comprises the steps of paper powder removal, coating of UV laminating glue on a glue film, adhesion, slitting and folding.
Chinese patent CN201610006148.5 provides an ultra-low water absorption UV curing laminating adhesive. The paint comprises the following components in parts by weight: 20-50 parts of polybutadiene modified acrylate resin, 1-15 parts of epoxidized polybutadiene modified acrylate resin, 30-60 parts of acrylic acid or methacrylic acid reactive diluent, 2-8 parts of photoinitiator, 1-15 parts of adhesion promoter and 0-3 parts of additive.
Disclosure of Invention
The invention aims to provide an ultraviolet light curing laminating adhesive for labels and a preparation method thereof.
In order to achieve the purpose, the technical scheme adopted by the invention for solving the problems is as follows: the ultraviolet light curing laminating adhesive for the label comprises the following components in parts by weight: 30-60 parts of polyurethane acrylate prepolymer, 20-40 parts of UV curing monomer, 3-10 parts of photoinitiator, 0.5-5 parts of wetting agent, 0.5-3 parts of flatting agent and 0.1-1 part of defoaming agent.
Further, the polyurethane acrylate is a related product sold in the market, such as Boxing B-2111D, Songda SD031 and the like, and can also be obtained by monomer synthesis, and the glass transition temperature Tg of the polyurethane acrylate is-30 ℃ to-100 ℃, preferably-30 ℃ to-50 ℃.
Further, the uv curable monomer comprises one or more of 1, 6 hexanediol diacrylate (HDDA), Ethylene Glycol Diacrylate (EGDA), diethylene glycol diacrylate (DEGDA), tripropylene glycol diacrylate phthalate, neopentyl glycol diacrylate (NPGDA), propoxylated neopentyl glycol diacrylate (PONPGDA), Propylene Glycol Diacrylate (PGDA), tripropylene glycol diacrylate (TPGDA), trimethylolpropane triacrylate (TMPTA), butyl acrylate, hydroxyethyl methacrylate.
Further, the photoinitiator includes benzophenone, 2, 4-dihydroxybenzophenone, thiopropoxythioanthrone, isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropanone (1173), 1-hydroxycyclohexylphenylketone (184), 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone (907), 2, 4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO), ethyl 2, 4, 6-trimethylbenzoylphenylphosphonate (TPO-L), 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone (910) 2-hydroxy-2-methyl-1- [4-, (1173) 2-hydroxyethoxy) phenyl ] -1-propanone (659), Methyl Benzoylformate (MBF), 2-Isopropyl Thioxanthone (ITX), 4-Chlorobenzophenone (CBP), and the like.
Furthermore, the wetting agent, the leveling agent and the dispersing agent are commonly used additives for UV curing products, so that the wetting, leveling and defoaming performances of the products in the application process are met, and the products can be uniformly coated on the surface of a base material.
The invention also provides a preparation method of the ultraviolet curing laminating adhesive for the label, which comprises the following steps in sequence: and adding the urethane acrylate, HDDA, CBP, 1173, TPGDA, TMPTA, wetting agent and defoaming agent into the reaction kettle in sequence, dispersing at a high speed of 500 rpm for 15 minutes, and filtering to obtain the UV-cured laminated adhesive product.
Furthermore, the polyurethane acrylate can also be prepared by polymerization of hydroxyl-terminated low molecular weight polyesters or polyethers with diisocyanates and hydroxy (meth) acrylates in a certain ratio.
Further, the hydroxyl-terminated low molecular weight polyester or polyether comprises: polyethylene glycol (PEG), propylene oxide polyether glycol (PPG), tetrahydrofuran polyether glycol (PTMG), polypropylene oxide ether (PPO), polytetramethylene oxide ether (PTMO), polybutylene glycol (PBD), Castor Oil (CO) and the like.
Further, the diisocyanate includes one or two of Toluene Diisocyanate (TDI), 4, 4-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), hydrogenated diphenylmethane diisocyanate (HMDI) hexamethylene diisocyanate (HDI0), and polyarylpolymethylene isocyanate (PAPI)
Further, the hydroxyl (meth) acrylate comprises one or two of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and 4-hydroxybutyl acrylate.
Further, the polyurethane acrylate synthesis process comprises the step of carrying out polymerization reaction on isocyanate and dehydrated hydroxyl acrylate or polyester (polyether) at a certain temperature, and terminating the reaction when the-NCO content in reactants is constant. The viscosity of the polyurethane acrylate oligomer is 1000-30000mPa.s, and the solid content is 99.9-100%.
By applying the technical scheme of the invention, the production process of the product is environment-friendly and nontoxic. The preparation method is simple, the operation is easy, the laminating starting speed is high and can reach 80-100 m/min, the appearance transparency of the laminated film is good, the adhesive property of the laminated film is good, and the requirement of the performance of the laminated film of the label is met.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail with reference to examples.
The raw materials comprise:
the ultraviolet light curing laminating adhesive comprises the following components in parts by weight: 30-60 parts of polyurethane acrylate prepolymer, 20-40 parts of UV curing monomer, 3-10 parts of photoinitiator, 0.5-5 parts of wetting agent, 0.5-3 parts of flatting agent and 0.1-1 part of defoaming agent.
The preparation process comprises the following steps:
the synthetic polyurethane acrylate can be prepared by polymerization reaction of hydroxyl-terminated low molecular weight polyester or polyether, diisocyanate and (methyl) acrylic acid hydroxyl ester according to a certain proportion.
Adding all materials of polyurethane acrylate, a UV curing monomer, a photoinitiator, a wetting agent, a leveling agent and a defoaming agent into a reaction kettle in sequence, dispersing at a high speed of 500 rpm for 15 minutes, and filtering to obtain a UV curing laminated adhesive product.
Example 1
Preferably, the polyurethane acrylate is synthesized by taking the following raw materials in parts by mass: 100 g of MDI, 20040 g of PEG, 0.2 g of dibutyltin dilaurate and 25 g of hydroxyethyl acrylate, dehydrating the PEG200, adding the MDI into a reaction vessel, heating the PEG200 and the dibutyltin dilaurate to 60 ℃ under stirring, reacting for 1 hour, dropwise adding the hydroxyethyl acrylate, reacting for 1-2 hours, and cooling to terminate the reaction to obtain the urethane acrylate (A1) when the NCO content is tested to be constant.
Taking the following raw materials in parts by mass:
urethane acrylate (a 1): 46 g of the total weight of the mixture;
UV curing monomer: HDDA30 g, TPGDA5 g, TMPTA10 g;
photoinitiator (2): 5 g CBP, 11732 g;
wetting agent: 1 g
Defoaming agent: 1 g
And adding the urethane acrylate A1, HDDA, CBP, 1173, TPGDA, TMPTA, a wetting agent and a defoaming agent into the reaction kettle in sequence, dispersing at a high speed of 500 rpm for 15 minutes, and filtering to obtain the UV-cured laminating adhesive product.
Example 2
Preferably, the polyurethane acrylate is synthesized by taking the following raw materials in parts by mass: urethane acrylate (A2) was prepared in the same manner as in example 1, except that 100 g of MDI, 80 g of PEG 40080 g, 0.2 g of dibutyltin dilaurate and 30 g of hydroxyethyl methacrylate were used.
Taking the following raw materials in parts by mass:
urethane acrylate (a 2): 40 g;
UV curing monomer: HDDA 36 g, TPGDA 3 g, TMPTA13 g;
photoinitiator (2): BP 4 g, 11732 g;
wetting agent: 1 g
Defoaming agent: 1 g
The method for preparing the ultraviolet curing coated adhesive of the present embodiment is the same as that of embodiment 1.
Example 3
Preferably, the polyurethane acrylate is synthesized by taking the following raw materials in parts by mass: MDI (100 g), PEG 20040 g, dibutyltin dilaurate (0.2 g) and hydroxypropyl methacrylate (20 g) were prepared in the same manner as in example 1 to obtain urethane acrylate (A3).
Taking the following raw materials in parts by mass:
urethane acrylate (a 3): 46 g of the total weight of the mixture;
UV curing monomer: HDDA 36 g, TMPTA10 g;
photoinitiator (2): 4 g of CBP, 11732 g;
wetting agent: 1 g
Defoaming agent: 1 g
The method for preparing the ultraviolet curing coated adhesive of the present embodiment is the same as that of embodiment 1.
Example 4
Preferably, the polyurethane acrylate is synthesized by taking the following raw materials in parts by mass: 100 g of HDI, 20060 g of PEG, 0.2 g of dibutyltin dilaurate and 40 g of hydroxyethyl methacrylate were prepared in the same manner as in example 1 to obtain a urethane acrylate (A4).
Taking the following raw materials in parts by mass:
urethane acrylate (a 4): 45 g;
UV curing monomer: HDDA30 g, TPGDA 3 g, TMPTA 8 g;
photoinitiator (2): 5 g of CBP, 11732 g;
wetting agent: 1 g
Defoaming agent: 1 g
The method for preparing the ultraviolet curing coated adhesive of the present embodiment is the same as that of embodiment 1.
Example 5
Preferably, the polyurethane acrylate is synthesized by taking the following raw materials in parts by mass: 100 g of IPDI, 20045 g of PEG, 0.2 g of dibutyltin dilaurate and 30 g of hydroxyethyl methacrylate were prepared in the same manner as in example 1 to obtain urethane acrylate (A5).
Taking the following raw materials in parts by mass:
urethane acrylate (a 5): 40 g;
UV curing monomer: HDDA35 g, TPGDA 6 g, TMPTA10 g;
photoinitiator (2): BP5 g, 11732 g;
wetting agent: 1 g
Defoaming agent: 1 g
The method for preparing the ultraviolet curing coated adhesive of the present embodiment is the same as that of embodiment 1.
Examples comparative performance testing:
and (3) comparison of film coating performance:
| transparency of | Adhesion Property | Resistance to embossing blistering | Temperature resistance, 60 DEG C | |
| Example 1 | Superior food | Superior food | Good wine | Superior food |
| Example 2 | Good wine | Superior food | Superior food | Superior food |
| Example 3 | Superior food | Superior food | Good wine | Superior food |
| Example 4 | Superior food | Superior food | Good wine | Superior food |
| Example 5 | Superior food | Superior food | Qualified | Superior food |
Note: the base material is PVC, BOPP tectorial membrane
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The ultraviolet light curing laminated adhesive for the label is characterized by comprising the following components in parts by weight: 30-60 parts of polyurethane acrylate prepolymer, 20-40 parts of UV curing monomer, 3-10 parts of photoinitiator, 0.5-5 parts of wetting agent, 0.5-3 parts of flatting agent and 0.1-1 part of defoaming agent.
2. The UV-curable laminating adhesive for labels according to claim 1, wherein the polyurethane acrylate is a commercially available product such as Boxing B-2111D, Songda SD031, etc., and can be obtained by monomer synthesis, and the glass transition temperature Tg is-30 ℃ to-100 ℃, preferably-30 ℃ to-50 ℃.
3. The uv-curable laminating adhesive for labels of claim 1, wherein said uv-curable monomers comprise one or more of 1, 6 hexanediol diacrylate (HDDA), Ethylene Glycol Diacrylate (EGDA), diethylene glycol diacrylate (DEGDA), tripropylene glycol diacrylate phthalate, neopentyl glycol diacrylate (NPGDA), propoxylated neopentyl glycol diacrylate (ponpggda), Propylene Glycol Diacrylate (PGDA), tripropylene glycol diacrylate (TPGDA), trimethylolpropane triacrylate (TMPTA), butyl acrylate, hydroxyethyl methacrylate.
4. The UV-curable laminating adhesive for labels of claim 1, wherein the photoinitiator comprises benzophenone, 2, 4-dihydroxybenzophenone, thiopropoxythioanthrone, isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropanone (1173), 1-hydroxycyclohexylphenylketone (184), 2-methyl-2- (4-morpholino) -1- [4- (methylthio) phenyl ] -1-propanone (907), 2, 4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO), ethyl 2, 4, 6-trimethylbenzoylphenylphosphonate (TPO-L), 2-dimethylamino-2-benzyl-1- [4- (4-morpholino) phenyl ] -1-butanone (910)2 -hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone (659), Methyl Benzoylformate (MBF), 2-Isopropylthioxanthone (ITX), 4-Chlorobenzophenone (CBP) and the like.
5. The method for preparing the ultraviolet curing laminating adhesive for the label according to the claims 1 to 4, characterized by comprising the following sequential steps: and adding the urethane acrylate, HDDA, CBP, 1173, TPGDA, TMPTA, wetting agent and defoaming agent into the reaction kettle in sequence, dispersing at a high speed of 500 rpm for 15 minutes, and filtering to obtain the UV-cured laminated adhesive product.
6. The method for preparing an ultraviolet-curable laminating adhesive for labels according to claim 5, wherein the urethane acrylate is prepared by polymerization of a hydroxyl-terminated low-molecular polyester or polyether with diisocyanate and hydroxy (meth) acrylate at a certain ratio.
7. The method for preparing the ultraviolet curing laminating adhesive for the label according to claim 6, wherein the hydroxyl-terminated low molecular weight polyester or polyether comprises: polyethylene glycol (PEG), propylene oxide polyether glycol (PPG), tetrahydrofuran polyether glycol (PTMG), polypropylene oxide ether (PPO), polytetramethylene oxide ether (PTMO), polybutylene glycol (PBD), Castor Oil (CO) and the like.
8. The method for preparing the UV-curable laminating adhesive for labels of claim 6, wherein the diisocyanate comprises one or two of Toluene Diisocyanate (TDI), 4, 4-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), hydrogenated diphenylmethane diisocyanate (HMDI) hexamethylene diisocyanate (HDI0), and polyarylpolymethylene isocyanate (PAPI).
9. The method for preparing an ultraviolet-curable laminating adhesive for labels of claim 6, wherein the hydroxy (meth) acrylate comprises one or both of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and 4-hydroxybutyl acrylate.
10. The method for preparing the ultraviolet curing coated adhesive for the label according to claim 6, wherein the polyurethane acrylate synthesis process comprises a step of polymerizing isocyanate and dehydrated hydroxyl acrylate or polyester (polyether) at a certain temperature, and the reaction is terminated when the-NCO content in reactants is constant.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110976085.7A CN113698907A (en) | 2021-08-24 | 2021-08-24 | Ultraviolet-curing laminated adhesive for labels and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110976085.7A CN113698907A (en) | 2021-08-24 | 2021-08-24 | Ultraviolet-curing laminated adhesive for labels and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421459A (en) * | 2013-09-04 | 2013-12-04 | 北京海斯迪克新材料有限公司 | UV solidified generality laminated adhesive suitable for thin film spraying technology |
| CN110194945A (en) * | 2018-12-03 | 2019-09-03 | 上海康达化工新材料股份有限公司 | Solvent-free Laminating adhesive of a kind of UV/EB solidification and preparation method thereof |
| CN110964477A (en) * | 2019-11-05 | 2020-04-07 | 中国人民解放军63919部队 | Thermoplastic polyurethane film or sheet ultraviolet light curing adhesive and preparation method thereof |
-
2021
- 2021-08-24 CN CN202110976085.7A patent/CN113698907A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421459A (en) * | 2013-09-04 | 2013-12-04 | 北京海斯迪克新材料有限公司 | UV solidified generality laminated adhesive suitable for thin film spraying technology |
| CN110194945A (en) * | 2018-12-03 | 2019-09-03 | 上海康达化工新材料股份有限公司 | Solvent-free Laminating adhesive of a kind of UV/EB solidification and preparation method thereof |
| CN110964477A (en) * | 2019-11-05 | 2020-04-07 | 中国人民解放军63919部队 | Thermoplastic polyurethane film or sheet ultraviolet light curing adhesive and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 曾晓鹰 等: "《电子束固化涂料及应用》", 31 December 2014, 天津大学出版社 * |
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Application publication date: 20211126 |