CN116813891B - Fatty acid modified polyester, preparation method and offset printing compound - Google Patents
Fatty acid modified polyester, preparation method and offset printing compound Download PDFInfo
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- CN116813891B CN116813891B CN202310924006.7A CN202310924006A CN116813891B CN 116813891 B CN116813891 B CN 116813891B CN 202310924006 A CN202310924006 A CN 202310924006A CN 116813891 B CN116813891 B CN 116813891B
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 63
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 63
- 239000000194 fatty acid Substances 0.000 title claims abstract description 63
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 63
- 229920000728 polyester Polymers 0.000 title claims abstract description 21
- 238000007645 offset printing Methods 0.000 title abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 title abstract description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 44
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229920005862 polyol Polymers 0.000 claims abstract description 25
- 150000003077 polyols Chemical class 0.000 claims abstract description 25
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 24
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 22
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 12
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 12
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000000539 dimer Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims description 31
- 235000021355 Stearic acid Nutrition 0.000 claims description 27
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 27
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 27
- 239000008117 stearic acid Substances 0.000 claims description 27
- 238000010438 heat treatment Methods 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 15
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 14
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 14
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 14
- 239000005642 Oleic acid Substances 0.000 claims description 14
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 14
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 14
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 7
- 244000060011 Cocos nucifera Species 0.000 claims description 7
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical group [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 7
- 235000021313 oleic acid Nutrition 0.000 claims description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000007599 discharging Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000005070 sampling Methods 0.000 claims description 5
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 6
- 229920001225 polyester resin Polymers 0.000 abstract description 4
- 239000004645 polyester resin Substances 0.000 abstract description 4
- 238000000016 photochemical curing Methods 0.000 abstract description 3
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 description 12
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
- 238000007639 printing Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000021314 Palmitic acid Nutrition 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000011087 paperboard Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The embodiment of the invention discloses fatty acid modified polyester, a preparation method and an offset printing compound, which comprise the following components in parts by mass: 17.1 to 19.8 percent of basf Sovermol750 polyol, 17.4 to 20.3 percent of trimethylolpropane, 2.6 to 3.1 percent of pentaerythritol, 15.6 to 18.1 percent of hydrogenated bisphenol A, 2 to 10 percent of monobasic fatty acid, 8.8 to 24.6 percent of p-methylbenzoic acid, 15.1 to 17.5 percent of isophthalic acid, 7.5 to 8.7 percent of terephthalic acid, 1.9 to 2.2 percent of dimer fatty acid, 0.35 to 0.41 percent of pyromellitic anhydride and 0.62 to 0.72 percent of trimellitic anhydride. 0.1 to 0.3 percent of antioxidant and 0.03 to 0.1 percent of catalyst. The invention introduces Bayer Sovermol750 polyol and trimethylolpropane into the formula for use, and improves the polymerization degree of the resin by reducing the content of monobasic fatty acid and using high-functional anhydride, thereby realizing the unification of high color concentration and high wear resistance, and the synthesized polyester resin has high color concentration, good wear resistance and high photocuring speed.
Description
Technical Field
The invention belongs to the technical field of high polymer material modification, and particularly relates to fatty acid modified polyester, a preparation method and an offset printing compound.
Background
Offset printing is one of the most widely used printing modes in the printing field. The UV (ultraviolet light curing) offset printing binders (resins) have a high pigment content and polyester resins or alkyd resins having a good pigment dispersion are generally selected as the main resin component for better color dispersion.
The color density refers to the density of color, also called saturation of color, and is a parameter indicating the selective absorption capacity of color light, that is, the reflected color density value measured under the complementary color filter. The higher the color density, the stronger the absorption capacity for the color light, that is, the higher the saturation of the color. Generally, higher color density can improve the color rendition and quality of the printed matter, and can also improve the printing efficiency and production benefit.
Wear resistance refers to resistance to mechanical friction, wear. The wear resistance is good, the quality of printed matters can be guaranteed, and the wear and damage are reduced, so that the service life of the product is prolonged. In addition, the printing ink can be applied to special printing fields, such as printing of materials such as metal cans and glass. These materials have smooth surfaces, low friction coefficients, and high hardness, which makes printing very difficult. But the wear resistance is good, the surface properties of the materials can be well adapted, high-speed and accurate printing is realized, and the quality of printed matters is ensured. Besides being applied to the printing of common products such as packaging boxes, cartons and the like, the printing ink can also be applied to special fields such as textile industry, plastic industry and the like. These industries need to perform high-speed production, and at the same time, also need to protect the surface of the product from damage, improve the wear resistance and service life of the product, and ensure the production efficiency and the product quality.
It is well known in the art of alkyd or polyester resin synthesis that the wetting characteristics and color concentration of the final product can be improved by increasing the content of monobasic fatty acids in the formulation, or by increasing the content of polyol soft segments (e.g., ethylene glycol or polyethylene glycol); however, too much incorporation of the monohydric fatty acid or the polyol soft segment may result in deterioration of the abrasion resistance of the final product.
Disclosure of Invention
The embodiment of the invention provides fatty acid modified polyester, which comprises the following components in parts by mass:
17.1 to 19.8 percent of Basoff Sovermol750 polyol,
17.4 To 20.3 percent of trimethylolpropane,
Pentaerythritol 2.6-3.1%,
15.6 To 18.1 percent of hydrogenated bisphenol A,
2-10% Of monobasic fatty acid,
8.8 To 24.6 percent of p-methylbenzoic acid,
15.1 To 17.5 percent of isophthalic acid,
7.5 To 8.7 percent of terephthalic acid,
1.9 To 2.2 percent of dimer fatty acid,
0.35 To 0.41 percent of pyromellitic anhydride,
0.62 To 0.72 percent of trimellitic anhydride.
Specifically, the basf Sovermol750 polyol has better fluidity, pentaerythritol can improve the body bone, and hydrogenated bisphenol A can keep the balance of wettability and solidification speed. Trimethylolpropane is a commonly used triol that forms the basic backbone. Isophthalic acid and terephthalic acid are commonly used dibasic acids that form the backbone of the molecule, and dimerized fatty acids can improve the flexibility of the formulation. In polyester formulations, monoacids are generally used in order to control the molecular weight and to adjust the hydroxyl number.
Preferably, the monobasic fatty acid is stearic acid, the mass fraction is 3-7%, and the mass fraction of p-methylbenzoic acid is 15-25%.
0.1 To 0.3 percent of antioxidant,
0.03 To 0.1 percent of catalyst. Specifically, the antioxidant is bht.
Specifically, the catalyst is stannous octoate.
Specifically, the monobasic fatty acid is any one of stearic acid, palmitic acid, oleic acid, coconut oleic acid, dodecanol stearic acid or lauric acid.
A method for preparing a fatty acid modified polyester comprising:
Adding 17.1-19.8% of Basoff Sovermol750 polyhydric alcohol, 17.4-20.3% of trimethylolpropane, 15.6-18.1% of hydrogenated bisphenol, 0.1-0.3% of antioxidant and 0.1% of catalyst into a reaction kettle according to the mass fraction ratio, heating at 98-105 ℃, and stirring until the components are uniformly dispersed;
Stirring 0.35-0.41% of pyromellitic anhydride and 0.62-0.72% of trimellitic anhydride for 1h at the temperature of 100-103 ℃ to carry out anhydration reaction;
Heating to 180 ℃, stopping stirring, sequentially adding 2.6-3.1% of pentaerythritol, 4.2-29.6% of monobasic fatty acid, 15.1-17.5% of isophthalic acid, 7.5-8.7% of terephthalic acid and 1.9-2.2% of dimer fatty acid, stirring, introducing nitrogen, heating to 200 ℃, preserving heat for at least 1h, heating to 210 ℃, preserving heat for at least 1h, heating to 230 ℃, preserving heat for at least 5h, sampling and measuring an acid value, introducing cold oil into a reaction kettle, cooling to below 170 ℃ and discharging after the acid value is less than 30.
Specifically, the antioxidant is bht.
Specifically, the catalyst is stannous octoate.
Specifically, the monobasic fatty acid is any one of stearic acid, palmitic acid, oleic acid, coconut oleic acid, dodecanol stearic acid or lauric acid.
A method of making a UV offset composite comprising:
Crushing the fatty acid modified polyester solid, adding trimethylolpropane triacrylate and para-hydroxyanisole, and stirring at 90-103 ℃ until the solid is completely dissolved;
adding photoinitiator, stirring to dissolve completely, adding toner, stirring for dispersing, blending into paste, and grinding with a three-roller inking machine.
In the examples of the present invention basf Sovermol 750 is a branched polyol with an average functionality of 3. According to the invention, by replacing part of trimethylolpropane with the Sovermol 750, the mechanical hardness of the resin film is improved, and the excellent performance is maintained.
The formula of the invention has low content of monobasic fatty acid, which is less than 10 percent (weight percent); the conventional monobasic fatty acid modified polyesters have relatively high monobasic fatty acid content, typically up to 15 to 30 weight percent. The lower content of monobasic fatty acid brings better film forming performance.
The hydrogenated bisphenol A is adopted to replace common micromolecular dihydric alcohol such as 1, 4-butanediol, neopentyl glycol and 1, 6-hexanediol, and the hydrogenated bisphenol A is matched with polybasic acid anhydrides such as trimellitic anhydride, pyromellitic anhydride and the like to be used, so that better balance of body bone and wettability is maintained.
The invention has the beneficial effects that: the invention introduces the formula of the basf Sovermol 750 polyol and the trimethylolpropane to use, and improves the polymerization degree of the resin by reducing the content of monobasic fatty acid and using high-functional anhydride, thereby realizing the unification of high color concentration and high wear resistance, and the offset printing compound prepared by the synthetic polyester resin has high color concentration, good wear resistance, high photo-curing speed and good wettability, and meets the requirements of high-grade UV curing offset printing resin. In addition, the production process is simpler, the time consumption is short, the energy is saved, no organic solvent is added in the reaction process, raw materials are easy to obtain, no waste gas is generated, and the method is environment-friendly and has good economic performance.
Detailed Description
In order to enable those skilled in the art to better understand the present invention, the following description will make clear and complete descriptions of the technical solutions according to the embodiments of the present invention with reference to the accompanying drawings. The examples of the present invention provide the following modified formulations of fatty acid modified polyesters, table 1 is a parameter of molecular weight and functionality of each component.
TABLE 1 component parameters
| Molecular weight | Functionality of | |
| Basoff Sovermol750 polyol | 525 | 3 |
| tmp | 134.2 | 3 |
| Pentaerythritol | 136.2 | 4 |
| Hydrogenated bisphenol a | 240.38 | 2 |
| Para-methylbenzoic acid | 136.15 | 1 |
| Stearic acid | 284.5 | 1 |
| Isophthalic acid | 166.1 | 2 |
| Terephthalic acid | 166.1 | 2 |
| Dimerized fatty acids | 146.21 | 2 |
| Pyromellitic anhydride | 218.12 | 4 |
| Trimellitic anhydride | 192.1 | 3 |
| Palmitic acid | 256.4 | 1 |
| Oleic acid | 282.46 | 1 |
| Coconut oleic acid | 343.38 | 1 |
| Dodecahydroxy stearic acid | 300.48 | 1 |
Tables 2 to 9 show the formulations of examples 1 to 8, wherein the amount of the additive was measured in kg.
TABLE 2 example 1
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 136.15 | 1 | 1 |
| Stearic acid | 455.2 | 1.6 | 1.6 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
The method for modifying polyester with fatty acid provided in example 1 is as follows:
1. Putting the Pasteur Sovermol750 polyol, the trimethylolpropane, the hydrogenated bisphenol, 0.1% of antioxidant bht and 0.1% of catalyst stannous octoate into a reaction kettle according to the mass shown in Table 2, heating at 98 ℃, and stirring until the materials are uniformly dispersed;
2. stirring pyromellitic anhydride and trimellitic anhydride for 1h at the temperature of 100 ℃ to carry out an anhydration reaction;
3. Heating to 180 ℃, stopping stirring, sequentially adding pentaerythritol, monobasic fatty acid stearic acid, isophthalic acid, terephthalic acid and dimerized fatty acid, stirring, introducing nitrogen, heating to 200 ℃, preserving heat for 1h, heating to 210 ℃, preserving heat for 1h, heating to 230 ℃, preserving heat for 5h, sampling to measure the acid value, introducing cold oil into a reaction kettle, cooling to 170 ℃ and discharging after the acid value is less than 30.
TABLE 3 example 2
The method for modifying polyesters with fatty acids provided in example 2 is as follows:
1. Putting the Pasteur Sovermol750 polyol, the trimethylolpropane, the hydrogenated bisphenol, the antioxidant bht with the mass fraction of 0.3% and the stannous octoate with the mass fraction of 0.3% into a reaction kettle according to the mass shown in the table 3, heating at 105 ℃, and stirring until the materials are uniformly dispersed;
2. Stirring pyromellitic anhydride and trimellitic anhydride for 1h at the temperature of 103 ℃ to carry out an anhydration reaction;
3. Heating to 180 ℃, stopping stirring, sequentially adding pentaerythritol, monobasic fatty acid stearic acid, isophthalic acid, terephthalic acid and dimerized fatty acid, stirring, introducing nitrogen, heating to 200 ℃, preserving heat for 1h, heating to 210 ℃, preserving heat for 1h, heating to 230 ℃, preserving heat for 5h, sampling to measure the acid value, introducing cold oil into a reaction kettle, cooling to 170 ℃ and discharging after the acid value is less than 30.
TABLE 4 example 3
The method for modifying polyester with fatty acid provided in example 3 is as follows:
1. Putting the Pasteur Sovermol750 polyol, the trimethylolpropane, the hydrogenated bisphenol, the antioxidant bht with the mass fraction of 0.2% and the stannous octoate with the mass fraction of 0.2% into a reaction kettle according to the mass shown in the table 4, heating at 100 ℃, and stirring until the materials are uniformly dispersed;
2. stirring pyromellitic anhydride and trimellitic anhydride for 1h at the temperature of 100 ℃ to carry out an anhydration reaction;
3. Heating to 180 ℃, stopping stirring, sequentially adding pentaerythritol, monobasic fatty acid stearic acid, isophthalic acid, terephthalic acid and dimerized fatty acid, stirring, introducing nitrogen, heating to 200 ℃, preserving heat for 1h, heating to 210 ℃, preserving heat for 1h, heating to 230 ℃, preserving heat for 5h, sampling to measure the acid value, introducing cold oil into a reaction kettle, cooling to 170 ℃ and discharging after the acid value is less than 30.
The preparation methods used in examples 4-14 below refer to the methods shown in examples 1-3, and are not described in detail herein.
TABLE 5 example 4
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 217.84 | 1.6 | 1.6 |
| Stearic acid | 284.5 | 1 | 1 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 6 example 5
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 245.07 | 1.8 | 1.8 |
| Stearic acid | 227.6 | 0.8 | 0.8 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 7 example 6
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 272.3 | 2 | 2 |
| Stearic acid | 170.7 | 0.6 | 0.6 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 8 example 7
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 299.53 | 2.2 | 2.2 |
| Stearic acid | 113.8 | 0.4 | 0.4 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 9 example 8
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 326.76 | 2.4 | 2.4 |
| Stearic acid | 56.9 | 0.2 | 0.2 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 10 example 9
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 340.375 | 2.5 | 2.5 |
| Stearic acid | 28.45 | 0.1 | 0.1 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 11 example 10
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 353.99 | 2.6 | 2.6 |
| Stearic acid | 0 | 0 | 0 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 12 example 11
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 136.15 | 2.4 | 2.4 |
| Palmitic acid | 256.4 | 0.2 | 0.2 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 13 example 12
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 326.76 | 2.4 | 2.4 |
| Oleic acid | 56.492 | 0.2 | 0.2 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 14 example 13
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 326.76 | 2.4 | 2.4 |
| Coconut oleic acid | 68.676 | 0.2 | 0.2 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
TABLE 15 example 14
| Feeding amount | Molar mass | Functional group | |
| Basoff Sovermol750 polyol | 262.5 | 0.5 | 1.5 |
| tmp | 268.4 | 2 | 6 |
| Pentaerythritol | 40.86 | 0.3 | 1.2 |
| Hydrogenated bisphenol a | 240.38 | 1 | 2 |
| Para-methylbenzoic acid | 326.76 | 2.4 | 2.4 |
| Dodecahydroxy stearic acid | 60.096 | 0.2 | 0.2 |
| Isophthalic acid | 232.54 | 1.4 | 2.8 |
| Terephthalic acid | 116.27 | 0.7 | 1.4 |
| Dimerized fatty acids | 29.242 | 0.2 | 0.4 |
| Pyromellitic anhydride | 5.453 | 0.025 | 0.1 |
| Trimellitic anhydride | 9.605 | 0.05 | 0.15 |
According to the invention, after the fatty acid modified polyester solid prepared in examples 1-14 is crushed, the crushed solid is put into a 200 g open iron tank, and then trimethylolpropane triacrylate and para-hydroxyanisole are added, the temperature is controlled at 90-103 ℃, and the stirring and dispersing machine is controlled to stir at a low speed of 300r/min until the solid is completely dissolved. Adding a photoinitiator 907, a photoinitiator pbz, controlling the temperature to be 90-103 ℃, and controlling the speed of a stirring and dispersing machine 300r/min to stir at a low speed until the materials are completely dissolved. The stirring speed is controlled, the toner is slowly added, the lower speed is started, the toner is stirred and dispersed at a high speed, the toner is blended into paste, and the paste is rolled and ground to the qualified fineness by a three-roller inking machine, and then the following test is carried out.
The testing method comprises the following steps:
1. color density
The fatty acid modified polyesters prepared in the above examples 1 to 14 were prepared into UV offset printing compositions according to the above preparation methods, printed on the surface of the same medium, and after the sample was printed with a color development instrument by visual method, the sample to be tested was compared with a colorimetric card.
2. Abrasion resistance
Referring to GB/T23989-2009, the color of the silver paperboard is uniformly developed by a color development instrument, after the silver paperboard is fully cured by a UV light curing machine, a sample plate is repeatedly rubbed by a cloth load of 500 g which is dipped with 95% ethanol until the ground color is exposed.
3. Curing speed
The color of the silver paperboard is uniformly developed by a color development instrument, the light curing is carried out at the speed of 20m/min, the ultraviolet light intensity is 80 mJ/square centimeter, and the finger drying method is used for determining whether the silver paperboard is completely cured.
Test results:
The color density, abrasion resistance and curing speed obtained by the formulations of examples 1 to 14 were examined in the above-described manner, and as apparent from examples 11, 12 and 14, the color density was deteriorated when stearic acid was replaced with equimolar palmitic acid, oleic acid and dodecahydroxystearic acid in the formulations of the above examples of the present invention. From example 13, it was found that when stearic acid was replaced with equimolar coconut oleic acid, the color density was not changed, the abrasion resistance was deteriorated, and the curing speed was lowered, so that stearic acid was the most preferable. Among them, examples 7 and 8 exhibited better color density and abrasion resistance, and the photo-curing speed was faster. As is clear from examples 9 and 10, the color density becomes worse as the stearic acid content is reduced, so that the test effect is best when 3 to 7% by mass of the monobasic fatty acid stearic acid is used, and 15 to 25% by mass of p-methylbenzoic acid is used.
TABLE 16 test results
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
The foregoing is only a partial embodiment of the present invention, and it should be noted that it will be apparent to those skilled in the art that modifications and adaptations can be made without departing from the principles of the present invention, and such modifications and adaptations are intended to be comprehended within the scope of the present invention.
Claims (8)
1. The fatty acid modified polyester is characterized by comprising the following components in parts by mass:
17.1 to 19.8 percent of Basoff Sovermol 750 polyol,
17.4 To 20.3 percent of trimethylolpropane,
Pentaerythritol 2.6-3.1%,
15.6 To 18.1 percent of hydrogenated bisphenol A,
2-10% Of monobasic fatty acid,
8.8 To 24.6 percent of p-methylbenzoic acid,
15.1 To 17.5 percent of isophthalic acid,
7.5 To 8.7 percent of terephthalic acid,
1.9 To 2.2 percent of dimer fatty acid,
0.35 To 0.41 percent of pyromellitic anhydride,
0.62 To 0.72 percent of trimellitic anhydride,
0.1 To 0.3 percent of antioxidant,
0.03-0.1% Of catalyst;
the monobasic fatty acid is any one of stearic acid, oleic acid or coconut oleic acid.
2. The fatty acid modified polyester of claim 1, wherein the antioxidant is bht.
3. The fatty acid modified polyester of claim 1, wherein the catalyst is stannous octoate.
4. The fatty acid modified polyester according to claim 1, wherein the monobasic fatty acid is stearic acid, the mass fraction is 3 to 7%, and the mass fraction of p-methylbenzoic acid is 15 to 24.6%.
5. A method for preparing a fatty acid-modified polyester, comprising:
Adding 17.1-19.8% of Basoff Sovermol 750 polyhydric alcohol, 17.4-20.3% of trimethylolpropane, 15.6-18.1% of hydrogenated bisphenol A,0.1-0.3% of antioxidant and 0.1% of catalyst into a reaction kettle according to the mass fraction ratio, heating at 98-105 ℃, and stirring until the components are uniformly dispersed;
Stirring 0.35-0.41% of pyromellitic anhydride and 0.62-0.72% of trimellitic anhydride at 100-103 ℃ for 1h;
Heating to 180 ℃, stopping stirring, sequentially adding 2.6-3.1% of pentaerythritol, 2-10% of monobasic fatty acid, 15.1-17.5% of isophthalic acid, 7.5-8.7% of terephthalic acid and 1.9-2.2% of dimer fatty acid, stirring, introducing nitrogen, heating to 200 ℃, preserving heat for at least 1h, heating to 210 ℃, preserving heat for at least 1h, heating to 230 ℃, preserving heat for at least 5h, sampling to measure acid value, introducing cold oil into a reaction kettle to cool until the acid value is less than 30, and discharging until the temperature is below 170 ℃;
Wherein the monobasic fatty acid is any one of stearic acid, oleic acid or coconut oleic acid.
6. The method of claim 5, wherein the antioxidant is bht.
7. The method according to claim 5, wherein the catalyst is stannous octoate.
8. A method of preparing a UV offset composite comprising:
Crushing the fatty acid modified polyester solid according to any one of claims 1 to 4, adding trimethylolpropane triacrylate and para-hydroxyanisole, and stirring at 90-103 ℃ until completely dissolved;
adding photoinitiator, stirring to dissolve completely, adding toner, stirring for dispersing, blending into paste, and grinding with a three-roller inking machine.
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