CN102433038A - Application of sulfonate ester in baking varnish - Google Patents
Application of sulfonate ester in baking varnish Download PDFInfo
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- CN102433038A CN102433038A CN2011102610272A CN201110261027A CN102433038A CN 102433038 A CN102433038 A CN 102433038A CN 2011102610272 A CN2011102610272 A CN 2011102610272A CN 201110261027 A CN201110261027 A CN 201110261027A CN 102433038 A CN102433038 A CN 102433038A
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- Prior art keywords
- sulphonate
- application
- baking vanish
- sulfonate
- baking
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002966 varnish Substances 0.000 title abstract description 7
- -1 sulfonate ester Chemical class 0.000 title description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 5
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 4
- 229960000655 ensulizole Drugs 0.000 claims description 4
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical group CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000004922 lacquer Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 5
- 125000003368 amide group Chemical group 0.000 abstract 1
- 239000012752 auxiliary agent Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000003459 sulfonic acid esters Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003973 paint Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000002826 coolant Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920003180 amino resin Polymers 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- NBINSWOYIKLKGL-UHFFFAOYSA-N 2-dodecylbenzenesulfonyl chloride Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(Cl)(=O)=O NBINSWOYIKLKGL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
The invention relates to the use of sulfonic acid esters in stoving lacquers; aiming at providing an auxiliary agent which can shorten the curing time of baking varnish and reduce the curing temperature of baking varnish; the technical key point is that 0.1-1.0 wt% of sulfonate is added in the baking varnish curing process; according to the application of the sulfonate in baking finish disclosed by the invention, the system gel cannot be caused when the sulfonate is added into a baking finish system, the reaction of a polymer containing hydroxyl, carboxyl or amido and a curing agent thereof can be rapidly catalyzed when the sulfonate is heated to a certain temperature, the curing temperature is reduced, and the curing time is shortened; the application range of the sulfonate is enlarged; belongs to the technical field of coating.
Description
Technical field
The present invention relates to a kind of application of sulphonate, specifically, the application of sulphonate in baking vanish belongs to technical field of coatings.
Background technology
In the baking vanish system, adding acid (like tosic acid) can obviously shorten set time, reduces solidification value, and still, these type of acidic substance also cause the system gel easily, and the stability in storage variation causes product to use at last.
In order to overcome this difficulty, generally to carry out sealing treatment to these type of acidic substance earlier, make its room temperature be in dormant state, be warming up to certain temperature and discharge acid again, the catalystsystem crosslinking reaction.Document " crosslinking feature of low-temperature quick-dry solidified paint ", Yuan Weiping, Sun Daoxing, Wang Fengying etc., Qingdao University of Science and Technology's journal (natural science edition); In August, 2007; The 28th volume discloses a kind of composite propionic acid lacquer that forms such as Hydroxylated acrylic resin A450 etc. and aminoresin, latent catalyst dead front type resin sulphonate etc. that adopts, and has the low-temperature curing characteristic; But should need join isocyanate curing agent by the amino lacquer, can process the double pack polyurethane paint; Tian Hongxing, Sun Daoxing etc., the aminoresin application in cold-setting lacquer, Shanghai coating; In December, 2009, the 47th the 12nd phase of volume, the acrylic-amino lacquer that Hydroxylated acrylic resin and aminoresin, dead front type sulphonate potential catalyst, thinner etc. are re-dubbed is disclosed; Mix with a certain proportion of polyisocyanate curing agent; Make amino polyurethane paint, this technology has reduced solidification value within the specific limits, but because this method also need add isocyanic ester when solidifying; And isocyanic ester is a violent in toxicity; Heat, naked light, oxygenant are inflammable meeting, and disengage MIC steam, oxynitride, carbon monoxide and prussic acid during burning, and these lives and properties to people bring serious threat.
Summary of the invention
To the problems referred to above, the present invention discloses and a kind ofly in baking vanish solidifies, adds sulphonate, in order to reduce solidification value, shortens set time.。
Technical scheme of the present invention is such: the application of sulphonate in baking vanish is that the accelerator during sulphonate is solidified as baking vanish uses
The application of above-mentioned sulphonate in baking vanish is characterized in that, described sulphonate addition is 0.1~1.0wt% (being that the sulphonate addition is a sulphonate weight percent 0.1~1.0%).
The application in baking vanish of above-mentioned sulphonate is characterized in that described sulphonate is used to shorten the baking vanish solidified time.
The above-mentioned application of sulphonate in baking vanish is characterized in that described sulphonate is used to reduce baking vanish solidified temperature.
Further, the application of above-mentioned sulphonate in baking vanish is characterized in that, described sulphonate is the phenylbenzimidazole sulfonic acid ester.
Advance one and mend, the application of above-mentioned sulphonate in baking vanish is characterized in that, described sulphonate is basic sulphonate for how.
Further, the application of above-mentioned sulphonate in baking vanish is characterized in that, described phenylbenzimidazole sulfonic acid ester is DBS, p-toluenesulfonic esters, to the acid dimethyl ester.
Further, the application of above-mentioned sulphonate in baking vanish is characterized in that, it is described that how basic sulphonate is dinonylnaphthalene sulfonic acid ester, docosyl napsylate.
Compared with prior art, the present invention's advantage specific as follows:
1. the application of the disclosed sulphonate of the present invention in baking vanish; This sulphonate adds the baking vanish system can not cause the system gel; Be warming up to certain temperature ability quick catalysis hydroxyl, carboxyl or the polymkeric substance of carboxamido-group and the reaction of its solidifying agent, reduce solidification value, shorten set time.
2. the application of the disclosed sulphonate of the present invention in baking vanish compared as the application of the cooling agent in the baking vanish with sulfonic amine salt, has good yellowing resistance, is applicable to tinted paints such as baking vanish varnish or white paint.
3. the application of the disclosed sulphonate of the present invention in baking vanish used as the cooling agent in the baking vanish with sulphonate and to be compared, and institute's temperature is low, has practiced thrift energy consumption.
4. the application of the disclosed sulphonate of the present invention in baking vanish enlarged the use range of sulphonate.
Principle of the present invention is such:
Sulfonic acid substance carries out the sealing treatment esterification, and high temperature (80~140 ℃) deblocking discharges acid, and the catalytic curing reaction is carried out.
Embodiment
Below in conjunction with specific embodiment the present invention is done further detailed description, but do not constitute any restriction of the present invention.
Sulphonate of the present invention is to adopt following method preparation.
Embodiment 1
100g epoxy resin E51 is dissolved in the mixed solution of 40g YLENE and 40g methyl ethyl ketone,, continues stirred for several hour to acid number, obtain final product tosic acid epoxy ester less than 10 slowly to wherein adding 10g tosic acid and 15g Virahol.
Embodiment 2
In four-hole boiling flask (band stirring, heating, condensing works), add 50g tosic acid and 50g acetone, cool off, slowly drip 30g epoxy hexane then, return to room temperature continuation stirred for several hour after dripping with mixture of ice and water.At last with unnecessary epoxy hexane and acetone remove under reduced pressure product tosic acid cyclohexyl.
Embodiment 3
In four-hole boiling flask (band stirring, heating, condensing works), add the 100g pyridine, with the mixture of ice and water cooling, and logical N
2Protection, add the 15g hexalin this moment, slowly adds Tosyl chloride 22.5g then, keeps 0 ℃, adds afterwards recovery system to room temperature reaction number hour.Products therefrom pours in the big water gaging, with dichloromethane extraction oil phase layer, cleans to acid with the vitriol oil again, uses NaHCO again
3Clean to neutral, use anhydrous magnesium sulfate drying then, boil off solvent again and get final product tosic acid cyclohexyl.
Embodiment 4
In four-hole boiling flask (band stirring, heating, condensing works), add the 100g pyridine, with the mixture of ice and water cooling, and logical N
2Protection, add the 15g hexalin this moment, slowly adds then dodecyl benzene sulfonyl chloride 28g, keeps 0 ℃, adds afterwards recovery system to room temperature reaction number hour.Products therefrom pours in the big water gaging, with dichloromethane extraction oil phase layer, cleans to acid with the vitriol oil again, uses NaHCO again
3Clean to neutral, use anhydrous magnesium sulfate drying then, boil off solvent again and get final product dodecyl toluenesulphonic acids cyclohexyl.
Embodiment 5
In four-hole boiling flask (band stirring, heating, condensing works), add 50g dinonylnaphthalene sulfonic acid and 50g acetone, cool off, slowly drip 25g epoxy hexane then, return to room temperature continuation stirred for several hour after dripping with mixture of ice and water.At last unnecessary epoxy hexane and acetone pressure reducing and steaming are got how sulfonic acid cyclohexyl of product dinonyl.
Embodiment 6
Sulphonate PT as cooling agent in polyester amino-stoving varnish system is tested
The baking vanish system that this test is selected for use adopts common polyester and melamine resin collocation system, and the two ratio was generally 2.5: 1, and the test ground is the stainless steel ground, selected 100 ℃, 120 ℃ and 150 ℃ of storing temperature, and the storing time unification is 20min.The cooling agent addition is unified to be 0.5wt%.
Hardness test: test according to GB-T6739-96.
Sticking power test: test according to QJ 990.14-1986
Yellowing resistance test: toasted back range estimation paint film and had or not flavescence.
Test result such as following table:
The damaged area of remarks: 1---less than the damaged area of 5% 2---less than the damaged area of 1/3 3---greater than 1/3
Can find out from test result; In baking vanish, add sulphonate; Effectively reduce the storing temperature (being significantly less than blank test and lower) of baking vanish system, shorten storing time, and compare with commercially available amine salt class cooling agent than general commercially available Sulfonates; Have yellowing resistance preferably, can satisfy the anti-xanthochromia requirement of baking vanish varnish system or tinted paint system.
Claims (8)
1. the application of sulphonate in baking vanish is characterized in that, is that the accelerator during sulphonate is solidified as baking vanish uses.
2. according to the application of the said sulphonate of claim 1 in baking vanish, it is characterized in that described sulphonate addition is 0.1~1.0wt%.
3. according to the application in baking vanish of the described sulphonate of claim, it is characterized in that described sulphonate is used to shorten the baking vanish solidified time.
4. according to the application of the described sulphonate of claim in baking vanish, it is characterized in that described sulphonate is used to reduce baking vanish solidified temperature.
5. the application of sulphonate according to claim 1 in baking vanish is characterized in that described sulphonate is the phenylbenzimidazole sulfonic acid ester.
6. the application of sulphonate according to claim 1 in baking vanish is characterized in that, described sulphonate is basic sulphonate for how.
7. the application of sulphonate according to claim 5 in baking vanish is characterized in that, described phenylbenzimidazole sulfonic acid ester is DBS, p-toluenesulfonic esters, to the acid dimethyl ester.
8. the application of sulphonate according to claim 6 in baking vanish is characterized in that, described how basic sulphonate is dinonylnaphthalene sulfonic acid ester, docosyl napsylate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN2011102610272A CN102433038A (en) | 2011-09-05 | 2011-09-05 | Application of sulfonate ester in baking varnish |
Applications Claiming Priority (1)
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CN2011102610272A CN102433038A (en) | 2011-09-05 | 2011-09-05 | Application of sulfonate ester in baking varnish |
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CN102433038A true CN102433038A (en) | 2012-05-02 |
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CN2011102610272A Pending CN102433038A (en) | 2011-09-05 | 2011-09-05 | Application of sulfonate ester in baking varnish |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05347019A (en) * | 1992-06-16 | 1993-12-27 | Hitachi Maxell Ltd | Magnetic recording medium |
CN1382754A (en) * | 2001-04-25 | 2002-12-04 | 金刚高丽化学 | Bottom coated polyester for anti-rust precoating outdoor metal safety guard |
WO2003074588A1 (en) * | 2002-03-01 | 2003-09-12 | Mitsui Chemicals, Inc. | Polymerizable composition containing novel cyclic sulfur compound and resin obtained by curing the polymerizable composition |
CN101065445A (en) * | 2004-12-27 | 2007-10-31 | 住友电木株式会社 | Thermosetting resin composition, thermosetting-resin molding material, and cured object obtained therefrom |
-
2011
- 2011-09-05 CN CN2011102610272A patent/CN102433038A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05347019A (en) * | 1992-06-16 | 1993-12-27 | Hitachi Maxell Ltd | Magnetic recording medium |
CN1382754A (en) * | 2001-04-25 | 2002-12-04 | 金刚高丽化学 | Bottom coated polyester for anti-rust precoating outdoor metal safety guard |
WO2003074588A1 (en) * | 2002-03-01 | 2003-09-12 | Mitsui Chemicals, Inc. | Polymerizable composition containing novel cyclic sulfur compound and resin obtained by curing the polymerizable composition |
CN101065445A (en) * | 2004-12-27 | 2007-10-31 | 住友电木株式会社 | Thermosetting resin composition, thermosetting-resin molding material, and cured object obtained therefrom |
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Application publication date: 20120502 |