CN108129587B - High-adhesion resin and preparation method and application thereof - Google Patents
High-adhesion resin and preparation method and application thereof Download PDFInfo
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- CN108129587B CN108129587B CN201711476394.8A CN201711476394A CN108129587B CN 108129587 B CN108129587 B CN 108129587B CN 201711476394 A CN201711476394 A CN 201711476394A CN 108129587 B CN108129587 B CN 108129587B
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
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Abstract
The invention belongs to the technical field of high-molecular polymerization, and discloses a high-adhesion resin, and a preparation method and application thereof. The high-adhesion resin is obtained by condensation reaction of resin with a side chain containing at least more than 2 epoxy groups and acid containing a polyphenol structure; the molar ratio of the acid containing the polyphenol structure to the epoxy groups in the resin with the side chain containing at least more than 2 epoxy groups is (0.1-1): the acid containing the polyphenol structure is an acid with an ortho-position polyphenol structure and/or an acid with other polyphenol structures, and the mass fraction of the acid with the ortho-position polyphenol structure is 50-100%. The resin shows excellent adhesion to substrates difficult to adhere, and can be used as adhesion promoters or temporary protective coatings for glass, metal, plastic and the like.
Description
Technical Field
The invention belongs to the technical field of high-molecular polymerization, and particularly relates to a high-adhesion resin, and a preparation method and application thereof.
Background
The adhesion promoter has wide application in the fields of coating, printing ink and the like, particularly on surfaces with low surface energy. The conventional adhesion promoter usually contains phosphate or siloxane groups, and the phosphate group has strong acidity, poor compatibility with other resins and good effect only on a few base materials such as metal and the like. And a large amount of phosphide is used in the process of preparing the phosphate, so that the phosphate has great harm to the environment and health. The adhesion promoter containing siloxane groups has wider application as a substitute of phosphate, but the siloxane adhesion promoter has weaker adhesion promoting effect, stronger extinction effect and slower curing speed, has poorer stability in acidic, alkaline and aqueous systems, and is difficult to meet the actual requirement.
Disclosure of Invention
In order to solve the defects in the prior art, the resin with high adhesive force is provided. The high-adhesion resin uses a compound with a polyphenol structure as an adhesion promoter, most of the compound with the polyphenol structure exists in biomass, has no potential harm to health and environment, can almost generate special physical and chemical bonding with all base materials, has excellent adhesion, and has mild property and better compatibility with other resins.
The invention also aims to provide a preparation method of the high-adhesion resin. The method is efficient and easy to implement, and can produce the required high-adhesion resin under the condition of not affecting the environment and health.
It is still another object of the present invention to provide the use of the above high adhesion resin.
The purpose of the invention is realized by the following technical scheme:
the high-adhesion resin is obtained by condensation reaction of a resin with a side chain containing at least 2 epoxy groups and an acid with a polyphenol structure, wherein the molar ratio of the acid with the polyphenol structure to the epoxy groups in the resin with the side chain containing at least 2 epoxy groups is (0.1-1): 1, the acid containing the polyphenol structure is an acid with an ortho-position polyphenol structure and/or other acids containing the polyphenol structure.
Preferably, the resin with at least 2 epoxy groups on the side chain is acrylic epoxy resin or novolac epoxy resin.
Preferably, the acrylic epoxy resin is obtained by free radical polymerization of acrylate and/or methacrylate and glycidyl methacrylate, and the number of carbon atoms in a side chain of the acrylate and the methacrylate is C1-18.
Preferably, the synthesis method of the acrylic epoxy resin comprises the following steps: heating a four-neck flask with a condensation pipe to 70-75 ℃, filling nitrogen, adding a methacrylate monomer and/or an acrylate monomer, glycidyl methacrylate, a dipropylene glycol monomethyl ether solvent and an azodiisobutyronitrile initiator, and preserving heat to obtain the acrylic acid modified acrylic acid.
More preferably, the glycidyl methacrylate is 10-50% of the total mass of the methacrylate monomer and/or the acrylate monomer, and the mass ratio of the total mass of the methacrylate monomer and/or the acrylate monomer to the dipropylene glycol monomethyl ether solvent is 1: 1, the azodiisobutyronitrile initiator is 0.5-0.7% of the total mass of a methacrylate monomer and/or an acrylate monomer, the heat preservation temperature is 70-75 ℃, and the heat preservation time is 12-13 h.
More preferably, the methacrylate monomer is at least one of methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobornyl methacrylate, tert-butyl methacrylate, n-octyl methacrylate, isooctyl methacrylate, isodecyl methacrylate, tert-butyl methacrylate, lauryl methacrylate or stearyl methacrylate; the acrylate monomer is more than one of methyl acrylate, ethyl acrylate, butyl acrylate, isooctyl acrylate, isodecyl acrylate, n-octyl acrylate, isobornyl acrylate, tert-butyl acrylate, lauryl acrylate or stearyl acrylate.
Preferably, the acid with the ortho-polyphenol structure is more than one of 3,4, 5-trihydroxybenzoic acid, 2,3, 4-trihydroxybenzoic acid, 2, 3-dihydroxy-benzoic acid or 3, 4-dihydroxy-benzoic acid; the other acids containing polyphenol structure are more than one of 2,4, 6-trihydroxybenzoic acid, 3, 5-dihydroxybenzoic acid, 2, 6-dihydroxybenzoic acid or 2, 4-dihydroxybenzoic acid; the mass fraction of the acid with the ortho-position polyphenol structure in the acid containing the polyphenol structure is 50-100%.
The preparation method of the high-adhesion resin comprises the steps of adding the resin with more than 2 epoxy groups into a four-neck flask with a condensing tube, heating to 140-150 ℃, adding acid containing a polyphenol structure, preserving heat, cooling and discharging to obtain the high-adhesion resin.
Preferably, the heat preservation temperature is 140-150 ℃, and the heat preservation time is 6-7 h.
The high-adhesion resin is applied to the fields of plastics, metals, glass and wood.
Compared with the prior art, the invention has the following beneficial effects:
1. the invention uses the compound with the polyphenol structure as the adhesion promoter, the compound with the polyphenol structure mostly exists in biomass, the provided high-adhesion resin has no health and environmental hazard, is green and environment-friendly, almost shows excellent adhesion effect on all substrates, and is good in compatibility with most of resin, paint, printing ink and the like and completely soluble in each other.
2. The high-adhesion resin can be used on the surfaces of plastic, metal, glass, wood and the like, and can increase the adhesion between a coating and a substrate.
Detailed Description
The following examples are presented to further illustrate the present invention and should not be construed as limiting the invention. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
Example 1 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, adding 30g of methyl methacrylate, 30g of butyl acrylate, 30g of isooctyl acrylate, 100g of dipropylene glycol monomethyl ether, 10g of glycidyl methacrylate and 0.5g of azobisisobutyronitrile initiator, keeping the temperature at 70 ℃ for 13 hours, and discharging to obtain the acrylic epoxy resin, which is marked as P1.
2. Synthesis of high-adhesion resin: adding P1 resin into a four-neck flask with a condenser, heating to 140 deg.C, adding 12g of 3,4, 5-trihydroxybenzoic acid, reacting at 140 deg.C for 6 hr, cooling, discharging to obtain the desired high-adhesion resin, respectively spreading on 10cm2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
Example 2 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, adding 20g of methyl acrylate, 30g of butyl methacrylate, 30g of isodecyl acrylate, 100g of dipropylene glycol monomethyl ether, 20g of glycidyl methacrylate and 0.7g of azobisisobutyronitrile initiator, keeping the temperature at 75 ℃ for 12 hours, and discharging to obtain the acrylic epoxy resin, which is marked as P2.
2. Adding P2 resin into a four-neck flask with a condenser, heating to 140 ℃, adding 12g of 2,3, 4-trihydroxybenzoic acid and 11.9g of 2,4, 6-trihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively spreading the resin on a 10cm thick film by scraping to obtain a film with a thickness of 10cm2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
Example 3 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, adding 20g of tert-butyl methacrylate, 30g of n-octyl acrylate, 20g of isodecyl methacrylate, 100g of dipropylene glycol monomethyl ether, 30g of glycidyl methacrylate and 0.5g of azobisisobutyronitrile initiator, keeping the temperature at 70 ℃ for 12 hours, and discharging to obtain the acrylic epoxy resin, which is marked as P3.
2. Adding P3 resin into a four-neck flask with a condenser, heating to 140 ℃, adding 23.9g of 2,3, 4-trihydroxybenzoic acid and 10.8g of 3, 5-dihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively spreading the resin on a 10cm thick film by a spreading method2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
Example 4 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, keeping the temperature at 70 ℃ for 12 hours, discharging 30g of butyl acrylate, 20g of isooctyl acrylate, 100g of dipropylene glycol monomethyl ether, 50g of glycidyl methacrylate and 0.5g of azodiisobutyronitrile initiator to obtain the acrylic epoxy resin, which is marked as P4.
2. Adding P4 resin into a four-neck flask with a condenser, heating to 140 deg.C, adding 5.4g of 2, 3-dihydroxybenzoic acid, reacting at 140 deg.C for 6 hr, cooling, and discharging to obtain the final product with desired heightAdhesive resin, respectively coating on 10cm2The adhesive force of the galvanized iron plate, the glass plate and the PVC plastic plate after drying is measured to be 0 grade of galvanized iron plate, 1 grade of glass plate and 1 grade of PVC plastic plate.
Example 5 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, adding 30g of isobornyl methacrylate, 40g of isodecyl acrylate, 100g of dipropylene glycol monomethyl ether, 30g of glycidyl methacrylate and 0.5g of azobisisobutyronitrile initiator, keeping the temperature at 70 ℃ for 12 hours, and discharging to obtain the acrylic epoxy resin, which is marked as P5.
2. Adding P5 resin into a four-neck flask with a condenser, heating to 140 deg.C, adding 10.8g of 2,3, 4-trihydroxybenzoic acid, reacting at 140 deg.C for 7 hr, cooling, discharging to obtain the required high-adhesion resin, respectively spreading on 10cm2The adhesive force of the galvanized iron plate, the glass plate and the PVC plastic plate after drying is measured to be 0 grade of galvanized iron plate, 1 grade of glass plate and 1 grade of PVC plastic plate.
Example 6 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, keeping the temperature at 70 ℃ for 12 hours, and discharging 70g of isobornyl acrylate, 100g of dipropylene glycol monomethyl ether, 30g of glycidyl methacrylate and 0.5g of azobisisobutyronitrile initiator to obtain the acrylic epoxy resin, which is marked as P6.
2. Adding P6 resin into a four-neck flask with a condenser, heating to 150 deg.C, adding 16.3g of 3, 4-dihydroxybenzoic acid, reacting at 140 deg.C for 6 hr, cooling, discharging to obtain the desired high-adhesion resin, respectively spreading on 10cm2The adhesive force of the galvanized iron plate, the glass plate and the PVC plastic plate after drying is measured to be 0 grade of galvanized iron plate, 1 grade of glass plate and 1 grade of PVC plastic plate.
Example 7 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, keeping the temperature at 70 ℃ for 12 hours, and discharging 50g of tert-butyl acrylate, 10g of lauryl acrylate, 10g of acrylic stearate, 100g of dipropylene glycol monomethyl ether, 30g of glycidyl methacrylate and 0.5g of azobisisobutyronitrile initiator to obtain the acrylic epoxy resin, which is marked as P7.
2. Adding P7 resin into a four-neck flask with a condenser, heating to 140 ℃, adding 13g of 3, 4-dihydroxybenzoic acid and 9.8g of 2, 6-dihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively spreading the resin on 10cm2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
EXAMPLE 8 Synthesis of acrylic epoxy resin
1. Heating a four-neck flask with a condenser pipe to 70 ℃, filling nitrogen, keeping the temperature of the four-neck flask at 70 ℃ for 12 hours, and discharging 50g of tert-butyl methacrylate, 10g of lauryl methacrylate, 10g of methacrylic stearate, 100g of dipropylene glycol monomethyl ether, 30g of glycidyl methacrylate and 0.5g of azobisisobutyronitrile initiator to obtain the acrylic epoxy resin, which is marked as P8.
2. Adding P8 resin into a four-neck flask with a condenser, heating to 140 ℃, adding 16.7g of 3, 4-dihydroxybenzoic acid, 5g of 3, 5-dihydroxybenzoic acid and 10.8g of 2,4, 6-trihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively coating the resin with 10cm of high-adhesion resin by scraping2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
EXAMPLE 9 Synthesis of high adhesion resin
Adding P1 acrylic acid epoxy resin into a four-neck flask with a condenser, heating to 140 ℃, adding 12g of 3,4, 5-trihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively spreading the resin with the thickness of 10cm by a spreading method2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
EXAMPLE 10 Synthesis of high adhesion resin
Adding 100g of phenolic epoxy resin into a four-neck flask with a condenser, heating to 140 ℃, adding 30g of 3, 4-dihydroxybenzoic acid, 10g of 2, 4-dihydroxybenzoic acid and 20g of 2, 6-dihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesionForce resin, respectively coated on 10cm2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
Example 11
Adding P2 acrylic acid epoxy resin into a four-neck flask with a condenser, heating to 140 ℃, adding 12g of 2,3, 4-trihydroxybenzoic acid and 11.9g of 2,4, 6-trihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively coating the resin with 10cm in thickness by scraping2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
Example 12
Adding 100g of novolac epoxy resin into a four-neck flask with a condenser, heating to 140 ℃, adding 20g of 2,3, 4-trihydroxybenzoic acid, 45g of 2,4, 6-trihydroxybenzoic acid and 25g of 3,4, 5-trihydroxybenzoic acid, reacting for 6 hours at 140 ℃, cooling and discharging to obtain the required high-adhesion resin, respectively coating the high-adhesion resin on 10cm of resin by scraping, and then coating the high-adhesion resin on the resin with the thickness of 10cm2The adhesive force of the steel plate, the glass plate and the PVC plastic plate is 0 grade after being dried.
Example 13
The adhesion test was carried out according to the national standard "scratch test for paint and varnish films of GBT9286-1998 paint colors and varnishes", as follows:
when a hundred-grid knife is used, the width of a knife edge is about 10 mm-12 mm, the interval is every 1 mm-1.2 mm, 10 grids are provided in total, 10 linear knife marks with the same interval appear when the straight lines are scribed, the straight lines are scribed at the vertical positions of the linear knife marks to form 100-grid squares of 10 x 10, when the hundred-grid knife is scribed, the hundred-grid knife needs to penetrate into a substrate, the hundred-grid knife cannot be cut on a coating, otherwise, the test is not established.
After the hundred grids are cut, the Tape cannot fall off when tested by using a Transparent Tape 600 Tape produced by 3M company, firstly, the Tape is pasted at the position of the hundred grids, the Tape is tightly attached by pressing down with fingers, then the Tape is torn off with instant force, and whether the paint on the material has the phenomenon of falling off or not is observed.
Rating methods and criteria:
level 0: the edges of the cuts were completely smooth without any flaking of the grid edges.
Level 1: the small pieces are peeled off at the intersection of the cuts, and the actual damage in the grid scribing area is less than or equal to 5 percent.
And 2, stage: the edges and/or intersections of the cuts are peeled off, and the area of the cuts is more than 5% -15%.
And 3, level: partial peeling or whole peeling is carried out along the edge of the cut, or partial lattices are peeled by the whole piece, and the peeling area exceeds 15-35 percent.
4, level: the edge of the cut is largely peeled off or some squares are partially or completely peeled off, and the area of the cut is more than 35-65% of the area of the grid-cutting area.
And 5, stage: there is a patch of paint falling off at the edge and intersection of the score line, with a total area of fall off greater than 65%.
The high adhesion resin of examples 1 to 12 was added to 55g of acrylic resin (AC-261, Rohm and Ha) under low-speed stirring in the proportions described in Table 1, and after stirring uniformly, 2g of wetting agent (270, diko), 1.5g of leveling agent (BYK333, bike), 0.5g of defoaming agent (Foamex810, diko) and 34.5g of deionized water were added, and ammonia was added to adjust the pH to 8, 1g of thickener (TT-935, Rohm and Ha) was added and stirred for 30min to obtain a varnish composition.
TABLE 1 compositional proportions of examples 1 to 12
The resulting A1-A13 varnish compositions were each scraped to a depth of 10cm2The steel plate, the glass plate and the PVC plastic plate were dried and then subjected to adhesion and transparency evaluations, respectively, and the results are shown in Table 2.
Table 2A1-13 application evaluation Table
From table 2, it can be seen that the coating without the high adhesion resin of the present invention has a lower adhesion than the coating with the high adhesion resin of the present invention, which indicates that the addition of the high adhesion resin of the present invention can increase the adhesion between the coating and the substrate, and the coating prepared by the addition of the high adhesion resin of the present invention has better transparency, indicating that the high adhesion resin of the present invention has good compatibility with the substrate resin.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations and simplifications are intended to be included in the scope of the present invention.
Claims (7)
1. The high-adhesion resin is characterized in that the high-adhesion resin is obtained by condensation reaction of resin with a side chain containing more than 2 epoxy groups and acid containing a polyphenol structure; the molar ratio of the acid containing the polyphenol structure to the epoxy groups in the resin with the side chain containing more than 2 epoxy groups is (0.1-1): 1, the acid containing the polyphenol structure is an acid with an ortho-position polyphenol structure and other acids containing the polyphenol structure; the acid with the ortho-position polyphenol structure accounts for 50-100% of the mass fraction of the acid with the polyphenol structure; the resin with the side chain containing more than 2 epoxy groups is acrylic epoxy resin; the acrylic epoxy resin is obtained by free radical polymerization of acrylic ester and/or methacrylic ester and glycidyl methacrylate; the number of carbon atoms of a side chain in the acrylate is C1-18, the glycidyl methacrylate accounts for 10-50% of the total mass of the methacrylate and/or the acrylate, and the acid with an ortho-position polyphenol structure is more than one of 3,4, 5-trihydroxybenzoic acid, 2,3, 4-trihydroxybenzoic acid, 2, 3-dihydroxybenzoic acid or 3, 4-dihydroxybenzoic acid; the other acids containing polyphenol structure are more than one of 2,4, 6-trihydroxybenzoic acid, 3, 5-dihydroxybenzoic acid, 2, 6-dihydroxybenzoic acid or 2, 4-dihydroxybenzoic acid.
2. The high-adhesion resin as claimed in claim 1, wherein the acrylic epoxy resin is synthesized by the following steps: heating a four-neck flask with a condensation pipe to 70-75 ℃, filling nitrogen, adding a methacrylate monomer and/or an acrylate monomer, glycidyl methacrylate, a dipropylene glycol monomethyl ether solvent and an azodiisobutyronitrile initiator, and preserving heat to obtain the acrylic acid modified acrylic acid.
3. The high adhesion resin of claim 2, wherein the mass ratio of the total mass of the methacrylate monomer and/or acrylate monomer to the dipropylene glycol monomethyl ether solvent is 1: 1, the azodiisobutyronitrile initiator is 0.5% of the total mass of the methacrylate monomer and/or the acrylate monomer, the heat preservation temperature is 70-75 ℃, and the heat preservation time is 12-13 h.
4. The high adhesion resin of claim 2, wherein the methacrylate monomer is at least one of methyl methacrylate, butyl methacrylate, isobornyl methacrylate, t-butyl methacrylate, isodecyl methacrylate, lauryl methacrylate, and stearyl methacrylate; the acrylate monomer is more than one of methyl acrylate, butyl acrylate, isooctyl acrylate, isodecyl acrylate, n-octyl acrylate, isobornyl acrylate, tert-butyl acrylate, lauryl acrylate or acrylic stearate.
5. The preparation method of the high-adhesion resin according to any one of claims 1 to 4, wherein the resin with more than 2 epoxy groups is added into a four-neck flask with a condenser, the temperature is raised to 140-150 ℃, acid containing a polyphenol structure is added, the temperature is kept, and the high-adhesion resin is obtained after cooling and discharging.
6. The preparation method of the high-adhesion resin as claimed in claim 5, wherein the temperature for heat preservation is 140-150 ℃, and the time for heat preservation is 6-7 h.
7. Use of the high adhesion resin of any one of claims 1-4 in the fields of plastics, metals, glass, wood.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003226982A (en) * | 2001-11-29 | 2003-08-15 | Kansai Paint Co Ltd | Surface treatment composition for metallic material |
| CN102079961A (en) * | 2010-11-21 | 2011-06-01 | 乐凯集团第二胶片厂 | Ultraviolet curing adhesive |
| EP3480237A1 (en) * | 2017-11-06 | 2019-05-08 | HILTI Aktiengesellschaft | Multi-component epoxy resin mass and curing agents therefor |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003226982A (en) * | 2001-11-29 | 2003-08-15 | Kansai Paint Co Ltd | Surface treatment composition for metallic material |
| CN102079961A (en) * | 2010-11-21 | 2011-06-01 | 乐凯集团第二胶片厂 | Ultraviolet curing adhesive |
| EP3480237A1 (en) * | 2017-11-06 | 2019-05-08 | HILTI Aktiengesellschaft | Multi-component epoxy resin mass and curing agents therefor |
Non-Patent Citations (1)
| Title |
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| 没食子酸改性氢化萜烯基环氧树脂多元醇的合成及性能研究;吴国民等;《林产化学与工业》;20081031;第28卷(第5期);第1-6页 * |
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