CN105348472A - Soft-segment-modified post-chain-extended flame-retardant waterborne polyurethane and preparation method thereof - Google Patents
Soft-segment-modified post-chain-extended flame-retardant waterborne polyurethane and preparation method thereof Download PDFInfo
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- CN105348472A CN105348472A CN201510822715.XA CN201510822715A CN105348472A CN 105348472 A CN105348472 A CN 105348472A CN 201510822715 A CN201510822715 A CN 201510822715A CN 105348472 A CN105348472 A CN 105348472A
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- chain extension
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- soft section
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
Abstract
The invention relates to soft-segment-modified post-chain-extended flame-retardant waterborne polyurethane and a preparation method thereof, belonging to the field of flame retardation materials. According to the invention, polyether or polyester polyol, diisocyanate and a hydrophilic chain extender are used as raw materials; on the basis of soft segment modification by phosphorus-containing polyol, a phosphorus-containing diamine fire retardant is used as the chain extender for post chain extension, so the soft-segment-modified post-chain-extended flame-retardant waterborne polyurethane is synthesized. The preparation method has the advantages of simple operation, safety, environmental protection, etc.; and the synthesized waterborne polyurethane has good flame retardation performance and a broaden application scope.
Description
Technical field
The present invention relates to a kind of soft section of modified chain extension extinguishing waterborn polyurethane and preparation method thereof.Belong to fire retardant material field.
Background technology
According to the existing way of fire retardant in aqueous polyurethane, extinguishing waterborn polyurethane can be divided into two large classes: blended Compositional type extinguishing waterborn polyurethane and reacting fire-retardant aqueous polyurethane.Wherein, reacting fire-retardant aqueous polyurethane has good weather resistance and fire retardant the advantage such as in use can not to separate out, and is the study hotspot of current urethane.And reacting fire-retardant aqueous polyurethane is divided into soft section of modification and hard section modification two kinds.Soft section of modification typically refers to the macromole polyether glycol or polyester polyol that first synthesize with ignition-proof element, then partly or entirely polyether glycol or polyester polyol and isocyanate reaction is substituted, soft section of flame-retardant modified aqueous polyurethane has good flame retardation effect, affects little feature to glue film performance.Because soft segment molecule amount is larger, soft section after flame-retarded its ignition-proof element content general is higher, the soft section of ratio shared by whole urethane raw is also maximum simultaneously, therefore with after fire-retardant soft section alternative common soft section of part, in whole polyurethane molecular, just there is more flame-retardant composition, simultaneously less to the performance impact of glued membrane.
Rear chain extension refers to that chain extension carries out or emulsification limit, limit chain extension after emulsification in aqueous polyurethane emulsion preparation process, compared with front chain extension, rear chain extension aqueous polyurethane can reduce the consumption of organic solvent, and simple to operate, the urea key of strong polarity can also be introduced simultaneously, improve the performance of aqueous polyurethane.The rear chain extension research of aqueous polyurethane can be divided into alcohols chainextender according to the kind of chainextender, amine chain extender, resting form chainextender (as ketoimine-one azine) etc., because the reactive behavior of aminated compounds is large, and the excellent properties of the rear chain extension aqueous polyurethane obtained, therefore relatively many to its research.Rao Zhou, Xu Gewen etc. with isophorone diisocyanate (IPDI), polyether Glycols (N210), polyester diol (PBA) for main raw material, dimethylol propionic acid (DMPA) is hydrophilic chain extender, glycol ether (DEG) is small molecule chain extender, quadrol (EDA), isophorone diamine (IPDA) are rear chainextender, have synthesized a series of aqueous polyurethane emulsion.Result shows, after chain extension after diamines, stability of emulsion improves, and emulsion particle diameter diminishes, and glued membrane water-intake rate reduces, and water tolerance improves, and glued membrane tensile strength increases.
Summary of the invention
The object of the invention is a kind of soft section of modified chain extension extinguishing waterborn polyurethane and preparation method thereof.
The object of the invention is to be achieved through the following technical solutions.
A kind of soft section of modified chain extension extinguishing waterborn polyurethane, its structural formula is as follows:
Wherein R
1determined by vulcabond, R
2determined by polyether Glycols or polyester diol, R
3determined by the phosphorus-containing polyol with flame retardant effect, R
4determined by phosphorous Diamines fire retardant.
A preparation method for soft section of modified chain extension extinguishing waterborn polyurethane, concrete steps are as follows: polyether Glycols or polyester diol and the phosphorus-containing polyol with flame retardant effect dewater at 80-140 DEG C; Add butanone or acetone after being down to room temperature, then add hydrophilic chain extender; Add vulcabond again, be warming up to 80-84 DEG C and react; Be down to room temperature, then add triethylamine and carry out neutralization reaction, obtain performed polymer; In performed polymer, deionized water and the fire-retardant chainextender of phosphorous Diamines is added under stirring; Keep agitation, revolves steaming removing organic solvent and obtains soft section of modified chain extension extinguishing waterborn polyurethane.
The summation of polyether Glycols or polyester diol, phosphorus-containing polyol, hydrophilic chain extender, vulcabond, triethylamine and phosphorous diamine chain stretching agent is called total mass, hydrophilic chain extender accounts for 3 ~ 10% of total mass, and organophosphorus polyvalent alcohol small molecules accounts for 5 ~ 20% of total mass; All containing hydroxyl (-OH) in polyether Glycols or polyester diol, phosphorus-containing polyol, hydrophilic chain extender, containing isocyano (-NCO) in vulcabond; R=-NCO/-OH, need ensure 2 >=R > 1, and therefore-NCO is excessive relative to-OH, to ensure that-OH reacts completely; Contained by the addition of triethylamine and wetting ability chain extension, the mol ratio of carboxyl (-COOH) is 1:1; Diamine chain stretching agent contains two amidos (-NH2), and the mole number of amido need be less than or equal to the mole number of the rear remaining isocyano of reaction.
Described polyether Glycols comprises polytetrahydrofuran diol (PTMG) or polypropylene glycol (PPG).
Described polyester diol comprises polycaprolactone glycol (PCL) or polybutylene glyool adipate (PBA).
The described phosphorus-containing polyol with flame retardant effect comprises phenyl-phosphonic acid dibasic alcohol (PPhDH), organophosphorus polyvalent alcohol (OP550) or phosphorus chlorine antimony tri phosphoric acid ester polyether Glycols.
Described hydrophilic chain extender comprises dimethylol propionic acid, dihydroxyl half ester, methyldiethanolamine or second diamino ethyl sulfonic acid sodium.
Described vulcabond comprises tolylene diisocyanate (TDI), diphenylmethanediisocyanate (MDI) or isoflurane chalcone diisocyanate (IPDI).
The described fire-retardant chainextender of phosphorous Diamines comprises two (aminophenyl) volution pentaerythritol diphosphate (ABSPB), two aminophenyl phosphorus oxide (BAPO), two (aminophenyl) phenylphosphine oxide (BPPO) or two (3-aminophenyl) phenylphosphine oxide (BAPPO).
Beneficial effect
1, soft section of modified flame-retardant aqueous polyurethane in the present invention belongs to reacting fire-retardant aqueous polyurethane, avoids the blended emulsion caused unstable, thus makes aqueous polyurethane have good weather resistance; Not Halogen, safety and environmental protection; Good flame retardation effect.
2, soft section of modification in synthetic method of the present invention can ensure to there is more flame-retardant composition in whole polyurethane molecular; Use phosphorous Diamines fire retardant to carry out rear chain extension while introducing flame-retardant composition, can also improve the stability of aqueous polyurethane emulsion and the mechanical property of glued membrane, rear chain extension method also has simple advantage.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1
A kind of soft section of modified chain extension extinguishing waterborn polyurethane, its structural formula is as follows:
Comprise: polyether Glycols N-210, OP550, tolylene diisocyanate, dimethylol propionic acid (DMPA), triethylamine and two (aminophenyl) volution pentaerythritol diphosphate (ABSPB).Their quality and be 100g.
Get 48.6g polyether Glycols N-210,9.7gOP550 be placed in the container with tetrafluoro stirring rake, at 120 DEG C of vacuum hydro-extraction 1h, be cooled to 80 DEG C, install condensing reflux pipe additional, add appropriate butanone, be warming up to 85 DEG C, add 26.7g tolylene diisocyanate (TDI), after reaction 1h, add 6.8g dimethylol propionic acid (DMPA), continue reaction 4h.Be down to room temperature, add 5.1g triethylamine (TEA) neutralization, after 10min, performed polymer is poured in the beaker of 1L, the deionized water that 235.0g temperature is 0 ~ 10 DEG C is added while stirring under the rotating speed of blade dispersion machine 2200r/min, and add two (aminophenyl) volution pentaerythritol diphosphate (ABSPB) of 3.1g, obtain emulsion after 20min, remove butanone with Rotary Evaporators, obtain extinguishing waterborn polyurethane emulsion.The extinguishing waterborn polyurethane emulsion that takes a morsel is laid in polyfluortetraethylene plate, seasoning ten days film forming under room temperature, obtains this film to be placed in 80 DEG C of vacuum drying ovens and to be dried to example weight and no longer considerable change to occur.Testing its limiting oxygen index(LOI) is 31.0.
Embodiment 2
A kind of soft section of modified chain extension extinguishing waterborn polyurethane, its structural formula is as follows:
Comprise: polyether Glycols N-210, OP550, tolylene diisocyanate, dimethylol propionic acid (DMPA), triethylamine and two (aminophenyl) phenylphosphine oxide (BPPO).Their quality and be 100g.
Get 48.5g polyether Glycols N-210,9.0gOP550 be placed in the container with tetrafluoro stirring rake, at 120 DEG C of vacuum hydro-extraction 2h, be cooled to 80 DEG C, install condensing reflux pipe additional, add appropriate butanone, be warming up to 85 DEG C, add 26.9g tolylene diisocyanate (TDI), after reaction 1h, add 6.8g dimethylol propionic acid (DMPA), continue reaction 4h.Be down to room temperature, add 5.1g triethylamine (TEA) neutralization, after 10min, performed polymer is poured in the beaker of 1L, the deionized water that 235.0g temperature is 0 ~ 10 DEG C is added while stirring under the rotating speed of blade dispersion machine 2200r/min, and add two (aminophenyl) phenylphosphine oxide (BPPO) of 3.7g, obtain emulsion after 20min, remove butanone with Rotary Evaporators, obtain aqueous polyurethane emulsion.The aqueous polyurethane emulsion that takes a morsel is laid in polyfluortetraethylene plate, seasoning ten days film forming under room temperature, obtains this film to be placed in 80 DEG C of vacuum drying ovens and to be dried to example weight and no longer considerable change to occur.Testing its limiting oxygen index(LOI) is 29.8.
Embodiment 3
A kind of soft section of modified chain extension extinguishing waterborn polyurethane, its structural formula is as follows:
Comprise: polyether Glycols PTMG, OP550, tolylene diisocyanate, dimethylol propionic acid (DMPA), triethylamine and two (aminophenyl) volution pentaerythritol diphosphate (ABSPB).Their quality and be 100g.
Get 47.0g polyether Glycols PTMG, 9.4gOP550 be placed in the container with tetrafluoro stirring rake, at 120 DEG C of vacuum hydro-extraction 2h, be cooled to 80 DEG C, install condensing reflux pipe additional, add proper amount of acetone, be warming up to 85 DEG C, add 26.0g tolylene diisocyanate (TDI), after reaction 1h, add 6.6g dimethylol propionic acid (DMPA), continue reaction 4h.Be down to room temperature, add 5.0g triethylamine (TEA) neutralization, after 10min, performed polymer is poured in the beaker of 1L, the deionized water that 235.0g temperature is 0 ~ 10 DEG C is added while stirring under the rotating speed of blade dispersion machine 2200r/min, and add two (aminophenyl) volution pentaerythritol diphosphate (ABSPB) of 6.0g, obtain emulsion after 20min, remove butanone with Rotary Evaporators, obtain aqueous polyurethane emulsion.The aqueous polyurethane emulsion that takes a morsel is laid in polyfluortetraethylene plate, seasoning ten days film forming under room temperature, obtains this film to be placed in 80 DEG C of vacuum drying ovens and to be dried to example weight and no longer considerable change to occur.Testing its limiting oxygen index(LOI) is 32.1.
Claims (7)
1. a soft section of modified chain extension extinguishing waterborn polyurethane, is characterized in that: its structural formula is as follows:
Wherein R
1determined by vulcabond, R
2determined by polyether Glycols or polyester diol, R
3determined by the phosphorus-containing polyol with flame retardant effect, R
4determined by phosphorous Diamines fire retardant.
2. a preparation method for soft section of modified chain extension extinguishing waterborn polyurethane, is characterized in that: concrete steps are as follows: polyether Glycols or polyester diol and the phosphorus-containing polyol with flame retardant effect dewater at 80-140 DEG C; Add butanone or acetone after being down to room temperature, then add hydrophilic chain extender; Add vulcabond again, be warming up to 80-84 DEG C and react; Be down to room temperature, then add triethylamine and carry out neutralization reaction, obtain performed polymer; In performed polymer, deionized water and the fire-retardant chainextender of phosphorous Diamines is added under stirring; Keep agitation, revolves steaming removing organic solvent and obtains soft section of modified chain extension extinguishing waterborn polyurethane;
The summation of polyether Glycols or polyester diol, phosphorus-containing polyol, hydrophilic chain extender, vulcabond, triethylamine and phosphorous diamine chain stretching agent is called total mass, hydrophilic chain extender accounts for 3 ~ 10% of total mass, and organophosphorus polyvalent alcohol small molecules accounts for 5 ~ 20% of total mass; All containing hydroxyl (-OH) in polyether Glycols or polyester diol, phosphorus-containing polyol, hydrophilic chain extender, containing isocyano (-NCO) in vulcabond; R=-NCO/-OH, need ensure 2 >=R > 1, and therefore-NCO is excessive relative to-OH, to ensure that-OH reacts completely; Contained by the addition of triethylamine and wetting ability chain extension, the mol ratio of carboxyl (-COOH) is 1:1; Diamine chain stretching agent contains two amidos (-NH2), and the mole number of amido need be less than or equal to the mole number of the rear remaining isocyano of reaction.
3. the preparation method of a kind of soft section of modified chain extension extinguishing waterborn polyurethane as claimed in claim 2, is characterized in that: described polyether Glycols comprises polytetrahydrofuran diol (PTMG) or polypropylene glycol (PPG); Described polyester diol comprises polycaprolactone glycol (PCL) or polybutylene glyool adipate (PBA).
4. the preparation method of a kind of soft section of modified chain extension extinguishing waterborn polyurethane as claimed in claim 2, it is characterized in that: described in there is flame retardant effect phosphorus-containing polyol comprise phenyl-phosphonic acid dibasic alcohol (PPhDH), organophosphorus polyvalent alcohol (OP550) or phosphorus chlorine antimony tri phosphoric acid ester polyether Glycols.
5. the preparation method of a kind of soft section of modified chain extension extinguishing waterborn polyurethane as claimed in claim 2, is characterized in that: described hydrophilic chain extender comprises dimethylol propionic acid, dihydroxyl half ester, methyldiethanolamine or second diamino ethyl sulfonic acid sodium.
6. the preparation method of a kind of soft section of modified chain extension extinguishing waterborn polyurethane as claimed in claim 2, is characterized in that: described vulcabond comprises tolylene diisocyanate (TDI), diphenylmethanediisocyanate (MDI) or isoflurane chalcone diisocyanate (IPDI).
7. the preparation method of a kind of soft section of modified chain extension extinguishing waterborn polyurethane as claimed in claim 2, is characterized in that: the described fire-retardant chainextender of phosphorous Diamines comprises two (aminophenyl) volution pentaerythritol diphosphate (ABSPB), two aminophenyl phosphorus oxide (BAPO), two (aminophenyl) phenylphosphine oxide (BPPO) or two (3-aminophenyl) phenylphosphine oxide (BAPPO).
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977681A (en) * | 2017-04-07 | 2017-07-25 | 北京理工大学 | A kind of hyperbranched blending modified chain extension extinguishing waterborn polyurethane of hard section |
| CN107099132A (en) * | 2017-04-07 | 2017-08-29 | 北京理工大学 | A kind of hyperbranched blending modified chain extension extinguishing waterborn polyurethane of soft segment |
| CN107099131A (en) * | 2017-04-07 | 2017-08-29 | 北京理工大学 | A kind of hyperbranched common modified chain extension extinguishing waterborn polyurethane of blending soft and hard segments |
| CN108773119A (en) * | 2018-05-21 | 2018-11-09 | 杭州湘隽阻燃科技有限公司 | A kind of fire-retardant single-side pile composite material and the preparation method and application thereof |
| CN109134802A (en) * | 2017-06-27 | 2019-01-04 | 万华化学集团股份有限公司 | A kind of phosphor-containing halogen-free flame retardant thermoplastic polyurethane elastomer composition and its preparation method and application |
| CN109593173A (en) * | 2018-11-20 | 2019-04-09 | 高鼎精细化工(昆山)有限公司 | Have the silicon substrate thermoplastic sulfurized rubber and its synthetic method of anti-flammability |
| CN109666126A (en) * | 2018-12-24 | 2019-04-23 | 山东诺威聚氨酯股份有限公司 | Inherent flame retardant Thermoplastic polyurethane elastomer material and preparation method thereof |
| CN111825824A (en) * | 2020-08-18 | 2020-10-27 | 上海蒂姆新材料科技有限公司 | High-flame-retardant waterborne polyurethane and preparation method thereof |
| WO2021036574A1 (en) * | 2019-08-30 | 2021-03-04 | 烟台泰和新材料股份有限公司 | Modified easily dyeable meta-aramid and preparation method therefor |
| CN113389092A (en) * | 2021-05-06 | 2021-09-14 | 玖龙智能包装(东莞)有限公司 | Composite corrugated paper and preparation method thereof |
| CN115232591A (en) * | 2022-06-21 | 2022-10-25 | 嘉兴学院 | Reactive polyurethane hot melt adhesive and preparation method thereof |
| CN115505093A (en) * | 2022-09-16 | 2022-12-23 | 江苏米尔化工科技有限公司 | Preparation method of phosphorus-nitrogen-silicon flame-retardant waterborne polyurethane |
| CN115584139A (en) * | 2022-12-12 | 2023-01-10 | 佛山路桥工程技术咨询有限公司 | High-temperature-resistant flame-retardant asphalt and preparation method thereof |
| CN115678407A (en) * | 2022-11-14 | 2023-02-03 | 广东职业技术学院 | Flame-retardant modified waterborne polyurethane containing carbon nitride as well as preparation method and application thereof |
| CN115678406A (en) * | 2022-11-14 | 2023-02-03 | 广东职业技术学院 | Anticorrosive flame-retardant waterborne polyurethane and preparation method and application thereof |
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| CN107099131A (en) * | 2017-04-07 | 2017-08-29 | 北京理工大学 | A kind of hyperbranched common modified chain extension extinguishing waterborn polyurethane of blending soft and hard segments |
| CN106977681A (en) * | 2017-04-07 | 2017-07-25 | 北京理工大学 | A kind of hyperbranched blending modified chain extension extinguishing waterborn polyurethane of hard section |
| CN109134802A (en) * | 2017-06-27 | 2019-01-04 | 万华化学集团股份有限公司 | A kind of phosphor-containing halogen-free flame retardant thermoplastic polyurethane elastomer composition and its preparation method and application |
| CN109134802B (en) * | 2017-06-27 | 2023-09-19 | 万华化学集团股份有限公司 | Phosphorus-containing halogen-free flame-retardant thermoplastic polyurethane elastomer composition and preparation method and application thereof |
| CN108773119A (en) * | 2018-05-21 | 2018-11-09 | 杭州湘隽阻燃科技有限公司 | A kind of fire-retardant single-side pile composite material and the preparation method and application thereof |
| CN108773119B (en) * | 2018-05-21 | 2020-09-18 | 杭州湘隽阻燃科技有限公司 | Flame-retardant single-sided velvet composite fabric and preparation method and application thereof |
| CN109593173B (en) * | 2018-11-20 | 2022-03-18 | 高鼎精细化工(昆山)有限公司 | Silicon-based thermoplastic vulcanized rubber with flame retardance and synthetic method thereof |
| CN109593173A (en) * | 2018-11-20 | 2019-04-09 | 高鼎精细化工(昆山)有限公司 | Have the silicon substrate thermoplastic sulfurized rubber and its synthetic method of anti-flammability |
| CN109666126A (en) * | 2018-12-24 | 2019-04-23 | 山东诺威聚氨酯股份有限公司 | Inherent flame retardant Thermoplastic polyurethane elastomer material and preparation method thereof |
| WO2021036574A1 (en) * | 2019-08-30 | 2021-03-04 | 烟台泰和新材料股份有限公司 | Modified easily dyeable meta-aramid and preparation method therefor |
| CN111825824A (en) * | 2020-08-18 | 2020-10-27 | 上海蒂姆新材料科技有限公司 | High-flame-retardant waterborne polyurethane and preparation method thereof |
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Application publication date: 20160224 |