CN114805669B - Poly (meth) acrylate and radiation-crosslinkable hot-melt adhesive based thereon - Google Patents

Poly (meth) acrylate and radiation-crosslinkable hot-melt adhesive based thereon Download PDF

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Publication number
CN114805669B
CN114805669B CN202210258447.3A CN202210258447A CN114805669B CN 114805669 B CN114805669 B CN 114805669B CN 202210258447 A CN202210258447 A CN 202210258447A CN 114805669 B CN114805669 B CN 114805669B
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meth
acrylate
acrylate monomer
methyl
alkyl
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CN114805669A (en
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顾子旭
刘旭
高超
王新龙
徐宗奎
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Suzhou Xingri Chemical Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/064—Copolymers with monomers not covered by C09J133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C09J133/16—Homopolymers or copolymers of esters containing halogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention relates to a poly (meth) acrylate and to a radiation-crosslinkable hot-melt adhesive based thereon, which consists of at least one (meth) acrylate monomer A1 selected from the group consisting of C1 to C18 alkyl groups, at least one monomer A2 of the general formula, and an ethylenically unsaturated copolymerizable photoinitiator A3. The invention also relates to the use thereof for producing adhesives, preferably pressure-sensitive adhesives for producing adhesive labels, adhesive tapes, plasters, bandages and self-adhesive films.

Description

Poly (meth) acrylate and radiation-crosslinkable hot-melt adhesive based thereon
Technical Field
The invention belongs to the technology of polymer adhesives, and particularly relates to a radiation-crosslinkable hot-melt adhesive based on poly (methyl) acrylate.
Background
For acrylate-based pressure sensitive adhesives, it is desirable to trade off between initial tack properties (adhesion to the substrate) and cohesive properties (internal strength within the adhesive layer). Thus, for example, it should adhere effectively to the steel surface, ensuring an effective flow onto the substrate surface, while having a high level of cohesion. For ease of application, the boundary condition which should be met at the same time is an extremely low melt viscosity. The prior art discloses acrylate pressure-sensitive adhesives and a preparation method thereof, but the adhesive strength of the adhesives is lower, and the adhesive requirements of adhesive materials in some special application fields cannot be met. In order to improve the adhesive performance, most of the adhesive performance is realized by modifying a main material, and at present, new acrylate adhesives with enhanced cohesive effect, effective adhesion and good flowing behavior are further required to be developed.
Disclosure of Invention
The object of the present invention is to provide radiation-crosslinkable hot-melt adhesives which have an enhanced cohesive effect and effective adhesion as well as good flow behaviour and have extremely low application viscosities.
The invention adopts the following technical scheme:
a poly (meth) acrylate prepared by polymerizing an alkyl (meth) acrylate monomer, a fluoro (meth) acrylate monomer, and an ethylenic photoinitiator; or from the polymerization of alkyl (meth) acrylate monomers, monomers having polar groups, fluoro (meth) acrylate monomers, and olefinic bond-containing photoinitiators.
A radiation crosslinkable hot melt adhesive based on poly (meth) acrylate comprising poly (meth) acrylate. Further, the poly (meth) acrylate may be used alone as a radiation crosslinkable hot melt adhesive or may be composed of the poly (meth) acrylate with other conventional components.
In the invention, the alkyl (methyl) acrylate monomer is selected from one or more of C1-C18 alkyl (methyl) acrylate monomers; preferably a C1 to C10 alkyl (meth) acrylate or a C4 to C10 alkyl (meth) acrylate or a C1 to C8 alkyl (meth) acrylate, in particular a C4 to C8 alkyl (meth) acrylate, such as methyl (meth) acrylate, ethyl acrylate, n-butyl acrylate, n-hexyl acrylate, 2-propylhexyl acrylate and 2-ethylhexyl acrylate or mixtures thereof.
In the present invention, the chemical structural formula of the fluorine-containing (meth) acrylate monomer is as follows:
wherein R is 3 Represents hydrogen or methyl, R f Represents a perfluoroalkyl group, m is 1 to 6; for example, the fluorine-containing (meth) acrylate monomer is selected from the group consisting of perfluorohexyl ethyl acrylate, perfluorohexyl ethyl methacrylate, perfluorobutyl ethyl acrylate, and perfluorobutyl ethyl acrylateA methacrylate, or a mixture of these monomers.
In the invention, the photoinitiator containing olefinic bonds is an ethylenically unsaturated copolymerizable photoinitiator and has a structural general formula of A-X-B, wherein: a is an organic group containing a benzophenone structure; x is an ester group selected from-O-C (=o) -, - (c=o) -O, and-O- (c=o) -O-, and B is a free radically polymerizable group comprising ethylenic unsaturation.
In the invention, when the poly (methyl) acrylic ester is prepared by polymerizing an alkyl (methyl) acrylic ester monomer, a fluorine-containing (methyl) acrylic ester monomer and an alkene bond-containing photoinitiator, the sum of the weight of the alkyl (methyl) acrylic ester monomer, the fluorine-containing (methyl) acrylic ester monomer and the alkene bond-containing photoinitiator is 100 percent (namely, the weight of all monomers is 100 percent), and the weight of the alkyl (methyl) acrylic ester monomer is 50 to 100 percent and does not contain 100 percent; preferably 60% -100%, and does not contain 100%; preferably 80% -100%, and does not contain 100%; preferably 90% -100%, and does not contain 100%; preferably 92% -99%; preferably 95% -98%; the amount of the photoinitiator containing olefinic bonds is 0.05 to 5 percent, preferably 0.1 to 3 percent, preferably 0.5 to 2 percent, and preferably 0.7 to 1 percent. When the poly (meth) acrylate is prepared by polymerizing an alkyl (meth) acrylate monomer, a monomer with a polar group, a fluorine-containing (meth) acrylate monomer and an ethylenic photoinitiator, the total weight of the alkyl (meth) acrylate monomer, the monomer with a polar group, the fluorine-containing (meth) acrylate monomer and the ethylenic photoinitiator is 100 percent (namely, the weight of all monomers is 100 percent), and the weight of the alkyl (meth) acrylate monomer is 50 to 95 percent, preferably 60 to 90 percent, preferably 70 to 90 percent, preferably 80 to 88 percent; the dosage of the photoinitiator containing the olefinic bond is 0.05 to 5 percent, preferably 0.1 to 3 percent, preferably 0.5 to 2 percent, and preferably 0.7 to 1 percent; the amount of the monomer having a polar group is 1% to 15%, preferably 5% to 12%, preferably 7% to 12%, preferably 8% to 11%.
The glass transition temperature of the poly (meth) acrylate prepared by the present invention is less than or equal to 10 ℃, preferably-60 ℃ to +10 ℃; k is at least 25, preferably 30 to 60, preferably 40 to 60; radiation-crosslinkable hot-melt adhesives based on poly (meth) acrylates are used as pressure-sensitive adhesives for the production of adhesive labels, adhesive tapes, plasters, bandages and self-adhesive sheets. The glass transition temperature was determined by differential scanning calorimetry (ASTA D3418-08). In the case of (radiation) crosslinkable polymers, the glass transition temperature refers to the glass transition temperature of the uncrosslinked polymer. The K value of the polymer was measured in tetrahydrofuran (1% strength solution, 21 ℃). According to Fikentscher, the K value is a measure of the molecular weight and viscosity of the polymer. The invention uses a capillary viscometer to measure viscosity, see DIN EN ISO 1628-1:2012-10. Pressure Sensitive Adhesives (PSAs) are viscoelastic adhesives that are in a dry state at room temperature, and whose cured films at room temperature have permanent tack and remain adhesive. Bonding to the substrate is instantaneously accomplished by gentle applied pressure. The hot melt adhesive is radiation crosslinkable, preferably UV crosslinkable. The term "radiation crosslinkable" means that the hot melt adhesive comprises at least one compound having at least one radiation-sensitive group and initiates a crosslinking reaction upon irradiation. Irradiation for crosslinking is preferably carried out using actinic radiation, preferably UV light, more particularly UV-C radiation. The radiation crosslinkable hot melt adhesive preferably comprises at least one photoinitiator. The photoinitiator is copolymerized into the poly (meth) acrylate. Hot melt adhesives (also known as hot melts or hot gels) are solvent-free products (i.e. not in the form of solutions or dispersions in water or organic solvents) which are more or less solid at room temperature, but flow sufficiently in the hot state and can be applied to adhesive surfaces due to the associated viscosity reduction and they produce adhesive bonds when cooled; the radiation crosslinkable hot melt adhesive may additionally be irradiated.
The poly (meth) acrylate can be prepared by copolymerizing the monomer components, optionally including a copolymerizable photoinitiator, using conventional polymerization initiators and optionally Chain Transfer Agents (CTAs), wherein the polymerization is carried out in bulk, emulsion (e.g., in water or liquid hydrocarbon) or solution at conventional temperatures. The polymer is preferably prepared at a temperature of from 70 to 120℃in the presence of from 0.01 to 10% by weight, based on the monomers, of a peroxide or azo initiator as polymerization initiator and in the presence of from 0 to 200% by weight, preferably from 5 to 25% by weight, based on the monomers, of an inert solvent, i.e.by solution polymerization or bulk polymerization. Solvents are, for example, hydrocarbons; alcohols such as methanol, ethanol, propanol, butanol, isobutanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone; ethyl acetate; nitriles such as acetonitrile and benzonitrile; or a mixture of said solvents. In a preferred embodiment, the solvent used for the polymerization is one or more ketones having a boiling point below 150℃at atmospheric pressure (1 bar). Examples of the polymerization initiator include azo compounds, ketone peroxides, and alkyl peroxides; examples are acyl peroxides such as benzoyl peroxide, dilauroyl peroxide, didecanoyl peroxide, isononyl peroxide, alkyl esters such as tert-butyl perpivalate, tert-butyl per-2-ethylhexanoate, tert-butyl per-maleate, tert-butyl per-isononanoate, tert-butyl perbenzoate, tert-amyl per-2-ethylhexanoate, dialkyl peroxides such as dicumyl peroxide, tert-butylcumene peroxide, di-tert-butyl peroxide, and peroxydicarbonates. As initiators, azo initiators can also be used, for example 2,2' -azobisisobutyronitrile, 2' -azobis (methyl isobutyrate) or 2,2' -azobis (2, 4-dimethylvaleronitrile). After polymerization in solution, the solvent may be separated off, optionally under reduced pressure, which is carried out at elevated temperature (e.g. 100 to 150 ℃). The polymer can then be used in the solvent-free state (solvent content preferably less than 2% by weight, based on all components), i.e. in the form of a melt.
The hot melt adhesive of the present invention has a zero shear viscosity at 130 ℃ of less than 60pa x s. It is used in a solvent-free, meltable form. In addition to the poly (meth) acrylate, the hot melt adhesive may contain conventional additives, with representative examples including resins, plasticizers, antioxidants, crosslinking agents, and the like. To prepare the coating, the hot melt PSA is applied to the material to be coated in the form of a melt, examples being substrates for adhesive tapes and labels, the surface being at least partially coated with the adhesive according to the invention. The hot melt PSA may be used in the form of a melt, i.e. typically at a temperature of 50 to 160 ℃, preferably 80 to 150 ℃ or more than 100 ℃. The carrier comprises a paper or a polymer film made of, for example, polyester, polyolefin (more specifically polyethylene or polypropylene), PVC, cellulose or polyacetate. After application to the carrier, the radiation crosslinkable hot melt adhesive of the invention is irradiated with high-energy radiation, preferably UV light, more particularly UV-C radiation (200-280 nm), to produce crosslinking. To this end, the coated substrate is generally placed on a conveyor belt and the belt is conveyed past a radiation source, such as a UV lamp. The degree of crosslinking of the polymer depends on the duration and intensity of the radiation. The adhesives of the invention are characterized by their surfaces exhibiting good initial adhesion and good peel strength on steel at room temperature.
Detailed Description
The present invention prepares poly (meth) acrylates and discloses radiation crosslinkable hot melt adhesives based on poly (meth) acrylates; the poly (meth) acrylate is formed by polymerization of: at least 60% by weight of at least one monomer A1, preferably chosen from n-butyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, propyl heptyl (meth) acrylate or mixtures thereof; 0.2 to 5% by weight of monomers A2;0.05 to 5% by weight of at least one ethylenically unsaturated copolymerizable photoinitiator A3; monomer A2 is as follows:
wherein R is 3 Represents hydrogen or methyl, R f Represents a perfluoroalkyl group, m is an integer between 1 and 6;
the photoinitiator A3 has a structural general formula of A-X-B, wherein: a is an organic group containing a benzophenone structure; x is an ester group selected from-O-C (=o) -, - (c=o) -O, and-O- (c=o) -O-, and B is a free radically polymerizable group comprising ethylenic unsaturation.
The poly (meth) acrylate polymer may also preferably be formed from at least one monomer having a polar group other than the monomers A1 and A2. The monomer having a polar group is, for example, a monomer in which the polar group is selected from: carboxylic acid groups, carboxylic anhydride groups, hydroxyl groups, amide groups, carbamate groups, ureido groups, piperidinyl groups, piperazinyl groups, morpholinyl groups, imidazolyl groups, and combinations of two or more of the foregoing groups. Preferred monomers having carboxylic acid groups are acrylic acid and methacrylic acid. Other monomers are also, for example, (meth) acrylamides and monomers containing hydroxyl groups, more particularly C1-C10 hydroxyalkyl (meth) acrylates. Preferred monomers having hydroxyl groups are C1-C10 hydroxyalkyl (meth) acrylates, in particular hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate.
Performance test:
k value: viscosity was measured using a capillary viscometer, see DIN EN ISO 1628-1:2012-10.
Zero shear viscosity: zero shear viscosity is the limit of the viscosity function at infinitely low shear rates. Measurements were made in plate/plate geometry using an Anton Paar rheometer. The samples were measured in oscillating shear at a low shear amplitude of 10%. The temperature was 130 ℃.
Pressure sensitive adhesive (PSA, poly (meth) acrylate Polymer) at 60g/m 2 Is drawn onto a siliconized PET film and irradiated with UV-C light; the applied film was then transferred to a PET film carrier and the PSA coated carrier was cut into test strips.
And (5) annular primary adhesion. The test specimen is bent into a ring shape, the circumference of the ring is 150mm, and the test specimen is moved downwards at a speed of 300mm/min on a clamp with an adhesive surface fastened outwards, so that the middle part of the test specimen ring is completely contacted with the central 25mm x 25mm area of the test steel plate, and the test specimen ring is separated from the test plate by a large pulling force required by the test specimen ring.
Shear strength (cohesion). To determine the shear strength, the test strips were adhered to the steel plate in a 12.5X12.5 mm bond area, rolled once using a roller weighing 1kg, and then suspended with a 1kg weight. Shear strength (cohesion) was measured under standard conditions (23 ℃ C.; 50% relative humidity). The shear strength measured is the time (in hours) taken for the heavy object to fall off. The average value is formed in each case from five measurements.
All raw materials of the invention are conventional products, and specific preparation methods and testing methods are conventional in the art.
Example 1
180g of Methyl Ethyl Ketone (MEK) was charged into a polymerization apparatus consisting of a glass reactor, a reflux condenser, a stirrer and a nitrogen inlet under a nitrogen stream, and the initial charge was heated to 80 ℃. 50g of a monomer mixture consisting of 772g of 2-ethylhexyl acrylate, 25g of perfluorohexyl ethyl methacrylate, 200g of methyl methacrylate and 8.57g Visiomer 6976 photoinitiator (containing 30% of benzophenone methacrylate) are added. When reverting to 80 ℃, 2.65g of an initiator solution containing 8g of t-butyl peroxypivalate (75% strength in mineral oil) and 45g of mek was added and the initial polymerization was carried out for 3 minutes. The remaining monomer mixture and the remaining 50.35g of initiator solution were then added over 3 hours. The temperature was then raised to 90℃and a solution of 2.67g of tert-butyl peroxypivalate (75% strength in mineral oil) in 21.7g of MEK was added over 30 minutes. The pressure is then reduced and the solvent is distilled off at a temperature of up to 135℃under 50 mbar. Subsequently, still with slow stirring, the polymer is obtained by degassing at 135℃for 1 hour under reduced pressure, K value; 1% in THF: 46, zero shear viscosity at 130℃of 20 Pa.s.
Examples 2 to 6 and comparative examples 1 to 5 were the same as example 1 except that the kinds and amounts of the respective materials were changed, as shown in Table 1:
table 1 raw materials for examples 1 to 6 and comparative examples 1 to 5 and test results
The results show that: after the A2 monomer is added into the formula, the zero shear viscosity of the polymer is effectively controlled. After irradiation crosslinking, the polymer shows good annular initial adhesion and shearing strength; after the A3 monomer is added in the formula, the cohesive force of the polymer is effectively improved and the shear strength of the adhesive is improved through irradiation crosslinking.

Claims (6)

1. A poly (meth) acrylate prepared by polymerizing an alkyl (meth) acrylate monomer, methyl methacrylate, a fluoro (meth) acrylate monomer, and an ethylenic photoinitiator, or prepared by polymerizing an alkyl (meth) acrylate monomer, acrylic acid, a fluoro (meth) acrylate monomer, and an ethylenic photoinitiator; the photoinitiator containing olefinic bonds has a structural general formula of A-X-B, wherein: a is an organic group containing a benzophenone structure; x is an ester group selected from-O-C (=o) -, - (c=o) -O, and-O- (c=o) -O-, B is a free radically polymerizable group comprising ethylenic unsaturation; the alkyl (methyl) acrylate monomer is n-butyl acrylate and/or 2-ethylhexyl acrylate; the fluorine-containing (methyl) acrylate monomer is perfluorohexyl ethyl methacrylate or perfluorobutyl ethyl acrylate; taking the sum of the weight of the alkyl (methyl) acrylate monomer, methyl methacrylate, fluorine-containing (methyl) acrylate monomer and the weight of the alkene bond-containing photoinitiator as 100 percent, the weight of the alkyl (methyl) acrylate monomer is 50 to 95 percent, and the dosage of the alkene bond-containing photoinitiator is 0.05 to 5 percent; the dosage of the methyl methacrylate is 1 to 15 percent; the total weight of the alkyl (methyl) acrylate monomer, the acrylic acid, the fluorine-containing (methyl) acrylate monomer and the alkene bond-containing photoinitiator is 100 percent, the weight of the alkyl (methyl) acrylate monomer is 50 to 95 percent, the consumption of the alkene bond-containing photoinitiator is 0.05 to 5 percent, and the consumption of the acrylic acid is 1 to 15 percent.
2. The poly (meth) acrylate according to claim 1, wherein the sum of the weight of the alkyl (meth) acrylate monomer, the methyl methacrylate, the fluorine-containing (meth) acrylate monomer and the ethylenically photoinitiator is 100%, the weight of the alkyl (meth) acrylate monomer is 60% to 90%, the amount of the ethylenically photoinitiator is 0.1% to 3%, and the amount of the methyl methacrylate is 5% to 12%; the total weight of the alkyl (methyl) acrylate monomer, the acrylic acid, the fluorine-containing (methyl) acrylate monomer and the alkene bond-containing photoinitiator is 100 percent, the weight of the alkyl (methyl) acrylate monomer is 60 to 90 percent, the consumption of the alkene bond-containing photoinitiator is 0.1 to 3 percent, and the consumption of the acrylic acid is 5 to 12 percent.
3. The method for preparing poly (meth) acrylate according to claim 1, wherein the poly (meth) acrylate is prepared by polymerizing an alkyl (meth) acrylate monomer, methyl methacrylate, a fluorine-containing (meth) acrylate monomer, and an ethylenic photoinitiator; or from the polymerization of alkyl (meth) acrylate monomers, acrylic acid, fluoro (meth) acrylate monomers, and olefinic photoinitiators.
4. The process for producing a poly (meth) acrylate according to claim 3, wherein the polymerization temperature is 70 to 120 ℃.
5. A radiation crosslinkable hot melt adhesive based on poly (meth) acrylate comprising the poly (meth) acrylate of claim 1.
6. Use of the poly (meth) acrylate according to claim 1 for the preparation of adhesives.
CN202210258447.3A 2022-03-16 2022-03-16 Poly (meth) acrylate and radiation-crosslinkable hot-melt adhesive based thereon Active CN114805669B (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5136000A (en) * 1990-08-31 1992-08-04 Herberts Gmbh Methods for preparing and using a water dilutable copolymer and aqueous coating composition prepared therewith
CN102753587A (en) * 2010-02-17 2012-10-24 株式会社钟化 Fluorine-containing (meth)acrylic (co)polymer and molded body films thereof
CN103687921A (en) * 2011-06-07 2014-03-26 巴斯夫欧洲公司 Hot-melt adhesive, containing poly(meth)acrylate that can be radiation cross-linked and oligo(meth)acrylate that has non-acrylic c-c double bonds
CN107849418A (en) * 2015-07-16 2018-03-27 巴斯夫欧洲公司 Include the hot-melt adhesive of poly- (methyl) acrylate prepared by (methyl) alkyl acrylate and (methyl) acrylate containing heterocyclic group determined
CN109503743A (en) * 2018-12-10 2019-03-22 怀化学院 Modified polyacrylate dispersion liquid
CN109563389A (en) * 2016-08-10 2019-04-02 3M创新有限公司 It is fluorinated contact adhesive

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5136000A (en) * 1990-08-31 1992-08-04 Herberts Gmbh Methods for preparing and using a water dilutable copolymer and aqueous coating composition prepared therewith
CN102753587A (en) * 2010-02-17 2012-10-24 株式会社钟化 Fluorine-containing (meth)acrylic (co)polymer and molded body films thereof
CN103687921A (en) * 2011-06-07 2014-03-26 巴斯夫欧洲公司 Hot-melt adhesive, containing poly(meth)acrylate that can be radiation cross-linked and oligo(meth)acrylate that has non-acrylic c-c double bonds
CN107849418A (en) * 2015-07-16 2018-03-27 巴斯夫欧洲公司 Include the hot-melt adhesive of poly- (methyl) acrylate prepared by (methyl) alkyl acrylate and (methyl) acrylate containing heterocyclic group determined
CN109563389A (en) * 2016-08-10 2019-04-02 3M创新有限公司 It is fluorinated contact adhesive
CN109503743A (en) * 2018-12-10 2019-03-22 怀化学院 Modified polyacrylate dispersion liquid

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