CN114316692A - Oxygen high-barrier coating, preparation method and coating method - Google Patents
Oxygen high-barrier coating, preparation method and coating method Download PDFInfo
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- CN114316692A CN114316692A CN202111569747.5A CN202111569747A CN114316692A CN 114316692 A CN114316692 A CN 114316692A CN 202111569747 A CN202111569747 A CN 202111569747A CN 114316692 A CN114316692 A CN 114316692A
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- acrylate
- barrier coating
- oxygen
- shellac
- coating
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- 238000000576 coating method Methods 0.000 title claims abstract description 71
- 239000011248 coating agent Substances 0.000 title claims abstract description 64
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 239000001301 oxygen Substances 0.000 title claims abstract description 42
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 229920001800 Shellac Polymers 0.000 claims abstract description 37
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims abstract description 37
- 239000004208 shellac Substances 0.000 claims abstract description 37
- 229940113147 shellac Drugs 0.000 claims abstract description 37
- 235000013874 shellac Nutrition 0.000 claims abstract description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 35
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 230000004888 barrier function Effects 0.000 claims abstract description 22
- 238000004132 cross linking Methods 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000013329 compounding Methods 0.000 claims abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 5
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 claims description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 238000007873 sieving Methods 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 claims description 2
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 2
- 229920003180 amino resin Polymers 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 2
- 150000001282 organosilanes Chemical class 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 abstract description 4
- 230000000670 limiting effect Effects 0.000 abstract description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 229920001688 coating polymer Polymers 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 230000035515 penetration Effects 0.000 abstract description 2
- 229920000058 polyacrylate Polymers 0.000 abstract description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- -1 Polyethylene terephthalate Polymers 0.000 description 1
- 210000002469 basement membrane Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000005010 epoxy-amino resin Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses an oxygen high-barrier coating, a preparation method and a coating method, wherein the oxygen high-barrier coating is prepared by compounding an acrylate high-barrier coating and shellac. In the invention, a crosslinking agent is subsequently added to a post-functional monomer in the acrylic polymer to form a compact reticular crosslinking structure in the curing process, so that the movement of molecular chain segments is greatly limited, and gaps among the chain segments are reduced, so that the thermal movement of the molecular chain segments of the coating polymer is limited, the free volume fraction is reduced, and the permeation path of oxygen is reduced or blocked. Meanwhile, the shellac is rich in hydroxyl and carboxyl, active groups on molecules can react with intermolecular, intramolecular and acrylate active groups in the high-temperature process and react with an added cross-linking agent, so that the molecular chain segments can form a crossed three-dimensional network structure, and the limiting effect on the molecular chain segments is enhanced. The difficulty of oxygen molecule penetration is further increased, and the oxygen barrier property is further improved.
Description
Technical Field
The invention relates to the field of coating preparation, in particular to an oxygen high-barrier coating, a preparation method and a coating method.
Background
Polyethylene terephthalate (PET) films are known for their excellent sealability, clarity, high temperature resistance and tensile strength, and can meet most packaging requirements. In recent years, it has become an important packaging material in the fields of food, medicine and cosmetics. Thus, there is an increasing demand for high performance and new functionality of PET, in particular oxygen barrier properties. Coatings are the most rapid and practical way to improve PET films due to their simple synthesis process, uncomplicated equipment requirements, versatile functionality and good adhesion to the substrate.
The invention aims to provide an oxygen high-barrier coating and a preparation method thereof, which can obviously improve the barrier of a PET film to oxygen.
Disclosure of Invention
In order to achieve the technical purpose, the first aspect of the invention provides an oxygen high-barrier coating, which comprises the following technical scheme:
an oxygen-resistant coating is prepared from acrylate and shellac through compounding.
In some embodiments, the shellac has a molecular weight of 500-.
In some embodiments, the shellac resin in the shellac is 80-92% by weight.
In some embodiments, the mass ratio of the solid matter of shellac to the solid matter of acrylic high oxygen barrier coating is 1/10-1/4.
In some embodiments, the acrylate high oxygen barrier coating is polymerized from the following monomers in weight percent: 25-75% of acrylate hard monomer; 4% -46% of acrylate soft monomer; 1-10% of pre-crosslinking monomer; the post-crosslinking monomer accounts for 5-25%.
In some embodiments, the acrylate hard monomer is one or more of methyl methacrylate, styrene, isobornyl acrylate, vinyl acetate, isobornyl methacrylate; the acrylic acid soft monomer is one or more of methyl acrylate, ethyl acrylate, butyl acrylate, isooctyl acrylate and the like; the pre-crosslinking monomer is one or more of divinylbenzene, tetramethylcyclotetrasiloxane and diallyl maleate; the post-crosslinking monomer is one or more of acrylic acid, methacrylic acid, hydroxyethyl acrylate and hydroxyethyl methacrylate.
The second aspect of the present invention provides a method for preparing an oxygen high barrier coating, which comprises:
according to the weight percentage, polymerizing an acrylate hard monomer, an acrylate soft monomer, a pre-crosslinking monomer and a post-crosslinking monomer into the acrylate high-oxygen-resistance coating;
grinding shellac into powder, and sieving with 200 mesh sieve;
placing the acrylate high oxygen resistant coating into a high-speed dispersion machine, dispersing for 30min, setting the rotating speed to be 300-600/min and the temperature to be 40-55 ℃;
adding the sampled shellac, and continuously dispersing for 1-2h to obtain the oxygen high barrier coating.
In some embodiments, the split shellac is pre-made into a solution and then placed in a high speed disperser.
The third aspect of the invention provides a coating method of an oxygen high-barrier coating, wherein before coating, a curing agent is added into the oxygen high-barrier coating, and the curing agent is one or more of metal acid ester, metal chelate, metal salt, isocyanate, organosilane, polycarbodiimide, ethylene imine, propylene imine, epoxy resin and amino resin.
The invention has the beneficial effects that:
the subsequent addition of a cross-linking agent to the post-functional monomer in the acrylic polymer forms a compact network cross-linking structure in the curing process, greatly limits the movement of molecular chain segments and reduces gaps among the chain segments, so that the thermal movement of the molecular chain segments of the coating polymer is limited, the free volume fraction is reduced, and the permeation path of oxygen is reduced or blocked.
Meanwhile, the shellac is rich in hydroxyl and carboxyl, active groups on molecules can react with intermolecular, intramolecular and acrylate active groups in the high-temperature process and react with an added cross-linking agent, so that the molecular chain segments can form a crossed three-dimensional network structure, and the limiting effect on the molecular chain segments is enhanced. The difficulty of oxygen molecule penetration is further increased, and the oxygen barrier property is further improved.
Detailed Description
The description is further elucidated with reference to specific examples. The description is to be regarded as illustrative and explanatory only and should not be taken as limiting the scope of the invention in any way.
Example 1
75g of styrene, 12.5g of ethyl acrylate, 7.5g of diallyl maleate and 5g of methacrylic acid are synthesized by free radical polymerization to obtain the acrylate high-barrier coating. Grinding 25g of shellac with molecular weight of 2000 and shellac resin content of 80% into powder, and sieving with 200 mesh sieve. Adding the acrylate high-barrier coating into a high-speed dispersion machine, dispersing for 30min at the rotating speed of 300r/min and the temperature of 55 ℃. Adding the ground shellac, and continuing to disperse for 2 hours to obtain the oxygen high barrier coating.
Adding metal chelate before coating, and stirring for 30 min.
Example 2
58g of vinyl acetate, 16g of butyl acrylate, 1g of divinylbenzene and 25g of hydroxyethyl acrylate are synthesized into the acrylate high-barrier coating through free radical polymerization. 10g of shellac with molecular weight of 500 and shellac resin content of 92% is ground into powder and sieved with 200 mesh. Adding the acrylate high-barrier coating into a high-speed dispersion machine, dispersing for 30min at the rotating speed of 600r/min and the temperature of 40 ℃. Adding the ground shellac, and continuing to disperse for 1.5h to obtain the oxygen high barrier coating.
Isocyanate was added before coating and stirred for 15 min.
Example 3
70g of methyl methacrylate, 5g of ethyl acrylate, 10g of tetravinyl cyclotetrasiloxane and 15g of maleic acid are synthesized by free radical polymerization to obtain the acrylate high-barrier coating. 15g of shellac having a molecular weight of 500 and a shellac resin content of 92% was dissolved in an ethanol solvent. Adding the acrylate high-barrier coating into a high-speed dispersion machine, dispersing for 30min at the rotating speed of 500r/min and the temperature of 50 ℃. Adding the shellac solution, and continuously dispersing for 1h to obtain the oxygen high-barrier coating.
No curing agent was added prior to coating.
Example 4
25g of styrene, 46g of isooctyl acrylate, 8g of diallyl maleate and 21g of acrylic acid are synthesized into the acrylate high-barrier coating through free radical polymerization. 14g of shellac with molecular weight of 800 and shellac resin content of 84% was ground into powder and sieved through 200 mesh. Adding the acrylate high-barrier coating into a high-speed dispersion machine, dispersing for 30min at 480r/min and at 44 ℃. Adding the ground shellac, and continuing to disperse for 1.2h to obtain the oxygen high barrier coating.
Adding metal chelate before coating, and stirring for 30 min.
Example 5
By means of free radical polymerization, 45g of vinyl acetate, 40g of butyl acrylate, 5g of divinyl benzene and 10g of hydroxyethyl methacrylate are synthesized to obtain the acrylate high-barrier coating. 18g of shellac with molecular weight of 1200 and shellac resin content of 86% was ground into powder and sieved through 200 mesh. Adding the acrylate high-barrier coating into a high-speed dispersion machine, dispersing for 30min at the rotating speed of 420r/min and the temperature of 48 ℃. Adding the ground shellac, and continuing to disperse for 1.6h to obtain the oxygen high barrier coating.
Isocyanate was added before coating and stirred for 15 min.
Example 6
60g of methyl methacrylate, 25g of methyl acrylate, 2.5g of tetravinyl cyclotetrasiloxane and 12.5g of maleic acid are synthesized into the acrylate high-barrier coating through free radical polymerization. 22g of shellac with a molecular weight of 1750 and a shellac resin content of 88% were dissolved in an ethanol solvent. Adding the acrylate high-barrier coating into a high-speed dispersion machine, dispersing for 30min at the rotating speed of 520r/min and the temperature of 52 ℃. Adding the shellac solution, and continuously dispersing for 2 hours to obtain the oxygen high-barrier coating.
No curing agent was added prior to coating.
And (3) performance testing:
comparative example 1: PET basement membrane.
Comparative example 2: common acrylate coatings.
Comparative example 3: 75g of styrene, 12.5g of ethyl acrylate, 7.5g of diallyl maleate and 5g of acrylic acid are synthesized by free radical polymerization to obtain the acrylate high-barrier coating. Adding metal acid ester before coating, and stirring for 30 min.
The test method comprises the following steps:
the coating materials of the examples of the present invention and comparative examples 2 and 3 were poured into a specific container and dried to a coating layer of a designated thickness. The oxygen transmission rate is then measured by pressing through the apparatus, the oxygen transmission rate having the unit e-15cm3·cm/cm2S.Pa. Lower test values indicate higher oxygen barrier efficiency.
The test results are shown in the following table:
the foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (9)
1. The oxygen high-barrier coating is characterized by being prepared by compounding acrylate high-barrier coating and shellac.
2. The oxygen high barrier coating of claim 1, wherein the shellac has a molecular weight of 500-.
3. The oxygen high barrier coating of claim 1, wherein the weight percentage of shellac resin in the shellac is 80-92%.
4. The oxygen high barrier coating of claim 1, wherein the mass ratio of the solid matter of shellac to the solid matter of acrylic high barrier coating is 1/10-1/4.
5. The oxygen high barrier coating of claim 1, wherein the acrylate high barrier coating is polymerized from the following monomers in weight percent:
25-75% of acrylate hard monomer;
4% -46% of acrylate soft monomer;
1-10% of pre-crosslinking monomer;
the post-crosslinking monomer accounts for 5-25%.
6. The oxygen high barrier coating of claim 5, wherein:
the acrylate hard monomer is one or more of methyl methacrylate, styrene, isobornyl acrylate, vinyl acetate and isobornyl methacrylate;
the acrylic acid soft monomer is one or more of methyl acrylate, ethyl acrylate, butyl acrylate, isooctyl acrylate and the like;
the pre-crosslinking monomer is one or more of divinylbenzene, tetramethylcyclotetrasiloxane and diallyl maleate;
the post-crosslinking monomer is one or more of acrylic acid, methacrylic acid, hydroxyethyl acrylate and hydroxyethyl methacrylate.
7. A method for preparing the oxygen high barrier coating according to any one of claims 1 to 6, comprising:
according to the weight percentage, polymerizing an acrylate hard monomer, an acrylate soft monomer, a pre-crosslinking monomer and a post-crosslinking monomer into the acrylate high-oxygen-resistance coating;
grinding shellac into powder, and sieving with 200 mesh sieve;
placing the acrylate high oxygen resistant coating into a high-speed dispersion machine, dispersing for 30min, setting the rotating speed to be 300-600/min and the temperature to be 40-55 ℃;
adding the sampled shellac, and continuously dispersing for 1-2h to obtain the oxygen high barrier coating.
8. The method for preparing oxygen high-barrier coating according to claim 7, wherein the shellac after sample separation is prepared into a solution and then put into a high-speed dispersion machine.
9. A method for coating an oxygen high-barrier coating according to any one of claims 1 to 6, wherein a curing agent is added to the oxygen high-barrier coating before coating, wherein the curing agent is one or more of a metal acid ester, a metal chelate, a metal salt, an isocyanate, an organosilane, a polycarbodiimide, an ethylene imine, a propylene imine, an epoxy resin and an amino resin.
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| CN202111569747.5A CN114316692A (en) | 2021-12-21 | 2021-12-21 | Oxygen high-barrier coating, preparation method and coating method |
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| CN202111569747.5A CN114316692A (en) | 2021-12-21 | 2021-12-21 | Oxygen high-barrier coating, preparation method and coating method |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4710228A (en) * | 1985-10-16 | 1987-12-01 | General Mills, Inc. | Edible coating composition and method of preparation |
| US20190062565A1 (en) * | 2017-08-25 | 2019-02-28 | Ppg Industries Ohio, Inc. | Metal cans coated with shellac-containing coatings |
| CN113698652A (en) * | 2021-09-09 | 2021-11-26 | 哈尔滨工业大学无锡新材料研究院 | High-oxygen barrier coating film and preparation method thereof |
-
2021
- 2021-12-21 CN CN202111569747.5A patent/CN114316692A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4710228A (en) * | 1985-10-16 | 1987-12-01 | General Mills, Inc. | Edible coating composition and method of preparation |
| US20190062565A1 (en) * | 2017-08-25 | 2019-02-28 | Ppg Industries Ohio, Inc. | Metal cans coated with shellac-containing coatings |
| CN113698652A (en) * | 2021-09-09 | 2021-11-26 | 哈尔滨工业大学无锡新材料研究院 | High-oxygen barrier coating film and preparation method thereof |
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