CN1114331A - Ultraviolet light fast solidification paint - Google Patents
Ultraviolet light fast solidification paint Download PDFInfo
- Publication number
- CN1114331A CN1114331A CN 94111058 CN94111058A CN1114331A CN 1114331 A CN1114331 A CN 1114331A CN 94111058 CN94111058 CN 94111058 CN 94111058 A CN94111058 A CN 94111058A CN 1114331 A CN1114331 A CN 1114331A
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- parts
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- vinylformic acid
- photosensitive
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- 239000003973 paint Substances 0.000 title claims abstract description 9
- 238000007711 solidification Methods 0.000 title claims abstract description 5
- 230000008023 solidification Effects 0.000 title claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000003085 diluting agent Substances 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000003504 photosensitizing agent Substances 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 8
- 229920003257 polycarbosilane Polymers 0.000 claims description 8
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 7
- 239000003205 fragrance Substances 0.000 claims description 7
- -1 hexanediyl ester Chemical class 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 7
- XZUHEZIGAZNGJR-UHFFFAOYSA-N phenol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC1=CC=CC=C1.OC1=CC=CC=C1 XZUHEZIGAZNGJR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003607 modifier Substances 0.000 abstract description 2
- 230000003712 anti-aging effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 13
- 230000032683 aging Effects 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000000016 photochemical curing Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000002939 oilproofing Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The ultraviolet solidifying paint is made of ternary photosolidifying resin, pentatomic photosensitive diluent, photosensitive modifier, solidifying agent and levelling agent, and features quick solidification, high brightness, adhesion, toughness and thermal stability, and anti-ageing nature.
Description
The present invention relates to ultraviolet-curing paint.
Photo-curing material developed very rapid in recent years, many kinds occurred.Usually, light-cured resin is a kind of monobasic or binary mixture, and photosensitive diluent is binary or tertiary mixture.This makes that rigidity, toughness and the ageing resistance of photo-curing material are bad, and pungent odour is arranged.The photo-curing agent that tradition is used is the benzoin ether compounds, the main drawback of this photo-curing agent is: velocity of initiation is slow, cause the stable storing performance poor, flavescence is serious during polymerization, there is residual gas to emit after the decomposition, poor with the photosensitive resin consistency, and self synthesis technique complexity, synthesis material is poisonous.
Chinese patent CN1047104A has proposed a kind of ultraviolet rapid solidified tri compound optical fiber coatings, this invention coating adopts organosilicon, urethane, three kinds of dissimilar photosensitive resins of epoxy moderate as low-temperature performance, the pliability that light-cured resin has improved coating to a certain extent, the intensity height.But this coating mainly is suitable for doing optical fiber coatings, and is heat-resisting, and performances such as moisture-resistant wiping, gloss are also bad.
It is superior to the purpose of this invention is to provide a kind of fast setting, high gloss, high adhesive force, high tenacity, resistance toheat, shelf-stable, aging-resistant ultraviolet-curing paint.
To achieve the above object of the invention, coating of the present invention is made up of light-cured resin, photosensitive diluent, photosensitive properties-correcting agent, solidifying agent and flow agent; Wherein light-cured resin comprises vinylformic acid bisphenol type epoxy ester, vinylformic acid fragrance urethane and vinylformic acid fat urethane, and the parts by weight that they account in the coating are respectively 52-88 parts, 41-42 parts, 63-90 parts; Photosensitive diluent comprises Viscoat 295, pentaerythritol triacrylate, Triethylene glycol dimethacrylate, hexanediyl ester and ethylacrylic acid-2-ethoxylated ester, the parts by weight that they account in the coating are 42-61 parts respectively, 32-41 parts, 36-57 parts, 26-53 parts and 57-78 parts; Photosensitive properties-correcting agent comprises the Polycarbosilane acrylate, the weight percentage that it accounts in the coating is 8-15 parts, solidifying agent comprises ferrocene modification benzophenone photosensitizers, it accounts for, and parts by weight are 1.5-5 parts in the coating, flow agent comprises methyl acrylate and butyl acrylate copolymer, and the parts by weight that it accounts in the coating are 1-3 parts.
Light-cured resin is the main component of decision ultraviolet photocureable material physical and mechanical properties, and the many important performance to material has great influence as rigidity, viscosity, curing speed, sticking power, surface appearance, ageing-resistant performance etc.Contain epoxy group(ing), hydroxyl in the vinylformic acid bisphenol type epoxy ester molecule, these polar groups are to there being very strong sticking power by adhesion material, and film forming matter rigidity is big, and hardness is big, and ageing-resistant performance is good, but toughness is bad.In the vinylformic acid fragrance polyurethane molecular urethano group is arranged, its snappiness is good, and the film-forming rear surface is highly polished, strong adhesion, but have fragrant phenyl ring in the molecule, so ageing resistance is poor slightly, and high-and low-temperature resistance and impact property are good.In the vinylformic acid fat polyurethane molecular urethano group is arranged, thereby snappiness is good, the film-forming rear surface is highly polished, and does not have phenyl ring in the molecule, so ageing-resistant performance is outstanding especially.But the price of vinylformic acid fat urethane is the most expensive.The performance of comprehensive above three kinds of materials, the present invention has adopted above three kinds of photo-curing resin alloys, makes up for each other's deficiencies and learn from each other, and has overcome the shortcoming of one-component.
Use because photo-curing resin and the general viscosity of modifier thereof, are difficult to normal construction all than higher, so must add thinner, and this thinner is a kind of photosensitive diluent, promptly has in dilution function before solidifying and the solidification process to participate in the solidified function.Contain three activity double keys in Viscoat 295 that adopts among the present invention and the pentaerythritol triacrylate molecule respectively.Crosslinking reaction can take place in these three activity double keys under the effect of photosensitizers and UV-light, form the build network structure, increases the stiffness and ageing-resistant, the resistance toheat of this coating.These two reactive thinners play a trifunctional group cross-linking agent's effect in system.The Triethylene glycol dimethacrylate, contain two activity double keys in the hexanediyl ester molecule respectively, the key reaction of propagation can take place in these two activity double keys under the effect of photosensitizers and UV-light, form linear structure, increase the flexibility of coating, so these two reactive thinners play the effect of a bifunctional flexibilizing agent in system.Contain an activity double key in ethylacrylic acid-2-ethoxylated ester molecule, this activity double key can take place to send out under the effect of photosensitizers and UV-light with another pair key answers, thereby terminating chain increases.So this reactive thinner plays the effect of a simple function group chain terminator.The used photosensitive diluent of the present invention is water white transparency, scentless liquid.
Photosensitive properties-correcting agent adopts the Polycarbosilane acrylate to improve the thermotolerance of photoactive coating.Because contain the good Si-C key of thermostability in the Polycarbosilane acrylate,
Photo-curing agent consumption in prescription seldom but has critical influence to the many performances in the material, as polymerization velocity, stability in storage.Adopt ferrocene modification benzophenone to do the photo-curing agent among the present invention, overcome all shortcomings of using st-yrax ethers chemical combination to bring, it is few to have a consumption, and curing speed is fast, stability in storage height, the advantage of not yellowing during curing.
Flow agent adopts methyl acrylate and butyl acrylate copolymer, and good with the photosensitive resin consistency, the levelling effect is fine.
When preparing coating of the present invention, at first with the Polycarbosilane acrylate 60-80 ℃ down with ethylacrylic acid-2-ethoxylated esters dissolving, form solution A; Ferrocene modification benzophenone photosensitizers is dissolved with the Triethylene glycol dimethacrylate down at 40-60 ℃, form Solution H, methyl acrylate and butyl acrylate copolymer are diluted with pentaerythritol triacrylate under 40-60 ℃, form solution C, with A, H and C add in the reaction vessel respectively, stir after 2 hours, add vinylformic acid bisphenol type epoxy ester, add vinylformic acid fragrance urethane after half an hour, add vinylformic acid fat urethane again after half an hour, add Viscoat 295 and hexanediyl ester again after half an hour, be warming up to 45-55 ℃ after adding, stirring reaction 3 hours, discharging promptly gets product.
During use, be coated in above-mentioned coating on the article equably after, promptly curable with the UV-irradiation of wavelength 300-400nm, power 1-10kw 1-10 seconds.
Coating of the present invention is compared with traditional ultraviolet-curing paint, has that curing speed is fast, high gloss, high adhesive force, high tenacity, resistance toheat are superior, shelf-stable, aging-resistant advantage, are a kind of good ultraviolet-curing paints.
Embodiment 1
Method preparation in the by specification.Each composition weight umber is respectively,
Vinylformic acid bisphenol type epoxy ester 88
Vinylformic acid fragrance urethane 12
Vinylformic acid fat urethane 40
Viscoat 295 61
Pentaerythritol triacrylate 41
Triethylene glycol dimethacrylate 51
Hexanediyl ester 53
Ethylacrylic acid-2-ethoxylated ester 18
Polycarbosilane acrylate 15
Ferrocene modification benzophenone photosensitizers 5
Methyl acrylate and butyl acrylate copolymer 3 be above-mentioned to be prescription 1#.Embodiment 2 the same routine method preparations.
Vinylformic acid bisphenol type epoxy ester 52
Vinylformic acid fragrance urethane 41
Vinylformic acid fat urethane 63
Viscoat 295 42
Pentaerythritol triacrylate 32
Triethylene glycol dimethacrylate 36
Hexanediyl ester 28
Ethylacrylic acid-2-ethoxylated ester 51
Polycarbosilane acrylate 8
Ferrocene modification benzophenone photosensitizers 15
Methyl acrylate and vinylformic acid J ester copolymer 1 be above-mentioned to be prescription 2#.Embodiment 3 is by last routine method preparation.
Vinylformic acid bisphenol type epoxy ester 64
Vinylformic acid fragrance urethane 54
Vinylformic acid fat urethane 12
Viscoat 295 53
Pentaerythritol triacrylate 36
Triethylene glycol dimethacrylate 46
Hexanediyl ester 45
Ethylacrylic acid-2-ethoxylated ester 64
Polycarbosilane acrylate 12
Ferrocene modification benzophenone photosensitizers 35
Methyl acrylate and butyl acrylate copolymer 2 are above-mentioned for prescription 3# carries out various performance tests to the coating of above-mentioned three kinds of prescriptions, and it the results are shown in Table 1.
Table 1: the performance perameter of the coating of three kinds of prescriptions
| Test event | Testing method | Test result | ||
| 1# | 2# | 3# | ||
| The ageing-resistant moisture-resistant of outward appearance pliability (mm) paint film appearance solid content (%) viscosity (S) gloss (%) impact strength (kg.cm) adhesive force (level) water boiling resistance Waterproofing/oilproofing acid-fast alkali-proof wipe antipollution curing rate (S) heat-resisting (℃) | GB1721 GB1731 GB1729 GB1725 GB723 second method GB1743 GB1732 GB1732 48hr GB1720 normal temperature 144hr GB1734,25 ℃, 10# lubricating oil, 48hr GB1763,25 ℃, 6% H 2SO 472hr GB1763,25 ℃, 6% NaOH, 72hr GB1865-80 1000 time the interior 400hr of 3kw uv baking oven circulates 30 times with reference to ASTM | The unchanged unchanged 3000hr in water white transparency 1 smooth 〉=98 〉=220 〉=100 〉=76 1 unchanged not show-through unchanged 1.5 250 ℃ unchanged | The unchanged unchanged 3000hr in water white transparency 1 smooth 〉=98 〉=180 〉=100 〉=86 1 unchanged not show-through unchanged 2.0 220 ℃ unchanged | The unchanged unchanged 3000hr in water white transparency 1 smooth 〉=98 〉=150 〉=100 〉=74 1 unchanged not show-through unchanged 2.5 200 ℃ unchanged |
Claims (1)
1, a kind of ultraviolet light fast solidification paint, it is characterized in that it is made up of light-cured resin, photosensitive diluent, photosensitive properties-correcting agent, solidifying agent and flow agent, wherein light-cured resin comprises vinylformic acid bisphenol type epoxy ester, vinylformic acid fragrance urethane and vinylformic acid fat urethane, the parts by weight that they account in the coating are 52-88 parts respectively, 41-12 parts, 63-90 parts; Photosensitive diluent comprises Viscoat 295, pentaerythritol triacrylate, Triethylene glycol dimethacrylate, hexanediyl ester and ethylacrylic acid-2-ethoxylated ester, the parts by weight that they account in the coating are 42-61 parts respectively, 32-41 parts, 36-57 parts, 26-53 parts and 57-18 parts; Photosensitive properties-correcting agent comprises the Polycarbosilane acrylate, the parts by weight that it accounts in the coating are 8-15 parts, solidifying agent comprises ferrocene modification benzophenone photosensitizers, it accounts for, and parts by weight are 1.5-5 parts in the coating, flow agent comprises methyl acrylate and butyl acrylate copolymer, and the parts by weight that it accounts in the coating are 1-3 parts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94111058 CN1114331A (en) | 1994-07-01 | 1994-07-01 | Ultraviolet light fast solidification paint |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94111058 CN1114331A (en) | 1994-07-01 | 1994-07-01 | Ultraviolet light fast solidification paint |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1114331A true CN1114331A (en) | 1996-01-03 |
Family
ID=5034965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 94111058 Pending CN1114331A (en) | 1994-07-01 | 1994-07-01 | Ultraviolet light fast solidification paint |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1114331A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091457C (en) * | 2000-06-07 | 2002-09-25 | 湖南亚大化工建材有限公司 | Ultraviolet cured paint |
| CN1091456C (en) * | 2000-06-07 | 2002-09-25 | 湖南亚大化工建材有限公司 | Ultravoilet cured paint without irritation |
| CN101177553B (en) * | 2007-11-30 | 2010-05-19 | 华南理工大学 | A kind of composite ultraviolet light curing water-based paint and preparation method thereof |
| CN102120898A (en) * | 2009-12-31 | 2011-07-13 | 第一毛织株式会社 | Hard coating composition and laminate including a hard coating layer |
| CN101629030B (en) * | 2009-08-03 | 2012-05-02 | 重庆大学 | Coating with high weatherability and self repairability |
| CN102618151A (en) * | 2012-03-27 | 2012-08-01 | 珠海市斗门区佳家化工有限公司 | Surface light-curing odor-free paint for wood and construction technology thereof |
| CN101514274B (en) * | 2009-03-18 | 2013-01-09 | 辽宁一一三（集团）化工有限责任公司 | Ultraviolet light curing glass paint and preparation method thereof |
| CN105925170A (en) * | 2016-06-29 | 2016-09-07 | 海盐三田科技有限公司 | Solvent-free ultraviolet photocuring anti-flouring easily cleaned paint as well as preparation method and application thereof |
-
1994
- 1994-07-01 CN CN 94111058 patent/CN1114331A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091457C (en) * | 2000-06-07 | 2002-09-25 | 湖南亚大化工建材有限公司 | Ultraviolet cured paint |
| CN1091456C (en) * | 2000-06-07 | 2002-09-25 | 湖南亚大化工建材有限公司 | Ultravoilet cured paint without irritation |
| CN101177553B (en) * | 2007-11-30 | 2010-05-19 | 华南理工大学 | A kind of composite ultraviolet light curing water-based paint and preparation method thereof |
| CN101514274B (en) * | 2009-03-18 | 2013-01-09 | 辽宁一一三（集团）化工有限责任公司 | Ultraviolet light curing glass paint and preparation method thereof |
| CN101629030B (en) * | 2009-08-03 | 2012-05-02 | 重庆大学 | Coating with high weatherability and self repairability |
| CN102120898A (en) * | 2009-12-31 | 2011-07-13 | 第一毛织株式会社 | Hard coating composition and laminate including a hard coating layer |
| CN102120898B (en) * | 2009-12-31 | 2014-04-02 | 第一毛织株式会社 | Hard coating composition and laminate including a hard coating layer |
| CN102618151A (en) * | 2012-03-27 | 2012-08-01 | 珠海市斗门区佳家化工有限公司 | Surface light-curing odor-free paint for wood and construction technology thereof |
| CN105925170A (en) * | 2016-06-29 | 2016-09-07 | 海盐三田科技有限公司 | Solvent-free ultraviolet photocuring anti-flouring easily cleaned paint as well as preparation method and application thereof |
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