Title：火凤凰大讲堂大师讲坛：Efficient Synthesis Strategies and Flame Retardancy
Speaker：Prof. Manfred Paul Kurt Döring (Fraunhofer Institute for Structural Durability and System Reliability)
Time：November 30, 2023 (Thursday) 16:00
Organizer：中国科学技术大学火灾科学国家重点实验室
Bio：
Prof. Manfred Paul Kurt Döring obtained his PhD degree from the University of Jena in Germany. He is currently serving as a member of the Advisory Committee for Schill+Seilacher GmbH and Schill+Seilacher Strukto GmbH, and the former Director of the Polymer Synthesis Department at the Fraunhofer Institute for Structural Durability and System Reliability in Germany. His research interests mainly focus on synthesis and technical chemistry, polymer flame retardancy, green chemistry, etc. He has led multiple scientific projects funded and supported by the German government and companies such as Airbus, BASF, and Audi. He has published over 150 peer-reviewed papers and authorized over 80 patents. He has been invited to participate in international flame retardant conferences and give more than 20 plenary/keynote presentations. Currently, he is also serving as editorial board members of more than ten international journals.
Abstract：
This presentation provides an overview of selected current developments and promising topics in the flame retardancy of polymers. At the same time, sustainable synthesis strategies are presented that lead to an optimized synthetic route of phosphorus-containing flame retardants. Based on these strategies, proposals for new synthesis chemistry approaches for monomeric and polymeric flame retardants for different applications will be presented. The evaluation of the synthesis chemical approaches is also carried out from a technical point of view.
ladies and gentlemen first of all I’d like to thank de for giving me a cordial invitation and in particular a warm welcome it’s a very nice dinner every year every night I’m here and I enjoy it was really really great thanks a lot again now to chemistry to flamey I’d like to talk today about efficient synthesis strategies and Flame responses uh uh I thought it will be interesting to discuss about these things because a lot of you guys are doing with with synthetic chemistry and of you want to do for which aim is it good or what sh shall I do to create a very efficient flame C so I hope it works okay and so I’d like to talk today about after a short introduction about this flame tent effect efficiency we a synthesis about Noble flame retardance mode of action and functionalities new synthetic strategies and starting materials flame retardance and additional effects some geny discussions radical generators as a new flame on the market and last but not least some conclusions okay first of all as I said it is really important to discuss what we are doing what is the aim what is the goal of our work should we do no we will do it so this is better okay should we do research fundamental research to collect information do some publication because this is most important or very important for you course most important is to finish your PhD or master of course this is of course we have to take care for safety for eco-friendly for life cycle impacts this is basic of fundamental research on the other hand we should look for economy for conven for costs this is going in direction of the industries looking for production is this the same your research work your synthesis your measurements compared to set what the companies are doing they have to look for green and sust and sustainable synthesis and Manufacturing what is this we will see in the next slides and of course for application okay if I want to develop a new flame Ron very important is is of course first of all flame retardant efficiency that is that what is really important you want to create a new flame R for a new PO for polymer and then the efficiency is really important on the other hand the compatibility with the polymer material properties and other adjectives and as well the processing of that polymer is important than viscosity composite operation uh we have take look after we we have to look after this uh this properties in our polymer and then we should take care on the synthesis because if we have a very complicated synthesis this is good you for for the lab it’s okay you you get your sub in your hand you can do something with that can incorporate in the polymer can do measurements and so on and so on but for other application often it is not enough we will see later on and then on the last part is environmental and health profile in Europe there is a organization so-called reach uh this reach means restriction uh evaluation and authorization of chemicals that means if a new chemical will uh come on the market we need this unfortunately it’s not expensive it is very expensive sometimes depends on the amount you will bring to the market okay this is the so-called green chemistry which is really really important if you will go for production if you will bring your synthesis in an appscale you see here there are 12 principles developed 25 years ago and going more and more important here are this the the regulations as I mentioned the process the procedure you will create for the chemistry and of course business needs and that means in other words for your synthesis it’s not only important the yield that is always important or the selectivity it’s also important this so-called atom economy or atom efficiency that uh means in other words we we’ll see it later on we should take care not only to how many product I will get you should also take care which side products and what is the amount of the side products are important because see these side products are often also very important for the final price okay now little bit more deeper in chemistry you see here the simple a simple over you of industrial phosphorus chemistry and you see a little bit the amounts here phosphate Rock so-called appetite appetite it’s um we have every year 140 million tons to uh dig it from the from the Earth but most of that of course is going to f izers in agriculture and not INF flams of course you see here the former the following processes you can do a dry process for fertilizing and you can do a wet process to isolate phosphoric acid that are only 30 million tons and or you can do a reduction to white phosphorus R by carbon uh in an electric furnace it’s about 1 million tons per year and then of course it is the whole way of phosphorus chemistry starts of a little bit sophisticated phosphorus chemistry starts with white phosphorus the easiest way is a green one because you can do an disproportionation and the one one product is ph3 you are pretty familiar with that and an other product of that reaction is hypo phosphorus acid or the the compared salts it’s about 50,000 tons per year on the other hand a very important process is the chlorination of white phosphorus final products or products are there PCL 3 PCL 5 and so on and so on that is a little bit more expensive because you start here a Cascade of new reactions here you are immediately reach to products which can handle very easily that’s why this way is cheaper okay and immediately we we will see there is a final product on flame Rance made from set sodium hypophosphite or from the free acid the so-call deal over shown over here is a classical flaming to produ produced since 20 30 years ago and you see it’s only an addition of Ayan to set compound to that molec molecule to reach the sodium salt of this phosphonic acid and incorporation of aluminium salts you get the aluminium phosphinate over here this is known as deepal the producer is clarant in Germany and Switzerland and is a very good flamor tot for engineering Plastics especially polyamides polyester and this is a simple radical addition that means very very atom efficient synthesis of that one starting from here and another very important flamon is aluminium hypophosphite it’s only salt formation of that molecule and noiz here aluminium phosphite by a simple oxidation or distination again from here as a flame tent developed by clarent in the last couple of years and this is a typical replacement for melamine polyphosphate in polyamide that means with such simple reactions we have a very nice couple of flame set one set one and Z one which are useful for some engineering plastics for example not only useful but also commercially available available but now we now take a take a little we look a little bit deeper we were here and now we look go to pcl3 we can synthesize this phosphites or phosphonates we can synthesize pcl3 from here or pcl5 and go to phosphines from pcl3 to too for example as mentioned uh and so on that means but if we look on that one we should realize the more synthetic steps means more expensive flame returns or more expensive substances on the other hand if it is fact then we should realize this flame doens shot more efficient you need less amount then of course it can be more expensive okay now here some couple of reactions starting from fos uh phosphonates for example from that molecule uh a lot of them are already known but I like to show you what is going on if you think uh if you want to synthesize such a compound for example an Amite you know this reaction very well this is a so-called OT and tot reaction here uh here shown for p pensil amine plus this fos phosphonate phosphite gives by that add under typical OT and tot reaction this phosph amide the oxidation agent is oxidizing agent is tet chlorocarbon and it’s very wonderful for the lab it works well so yield is okay but forget it for industrial application the problem is do is this one strange and expensive ingredient for the reaction and lot of side products here because in Industries you responsible for recycling or wasting and that’s why it is really important that this should very very easy and of course there is an an an more Simple Solution look here the same UCT the same starting material materials over here is the amine and here’s the phosphite and you see now we do it with Coro iodide as a catalyst and the oxidizing agent is now oxygen from Air this is really cheap compared to that one and you get the reaction the yield is okay and the only side product is water that’s is okay when you see it is 10 years 9 years old for 9 years ago they described that and not only for that direction they described 16 examples this is good for fundamental research in a lab to synthesize one product first time and to check their properties or their properties regarding the incorporation in a polymer this is more applied research if you want to go for upscaling or a production but you see the differences okay but back to that compound this hypo phosphorus acid or the hypo phosphide salt can you can uh do a simple esic developed by uh CH mam 20 years ago and you get this Easter done by a silicon this Easter is very nice but not so much synthesis was made with based on that material there are a small review again done by Professor mam you see there are some uh reaction possible starting from here and this is a really simple uh starting material as I show you for the synthesis of deepal for example you can do a lot of things starting from here and of course another publication couple of years older described that reaction and the question is perhaps we can use that one for a poly phosphor mle addition with diates or the de or Dil amides or we can formulate it in an epoxy resin an addition reaction in an epoxy resin is so-called preformulation in in the next slides suggestions are all in Orange okay uh group uh around zge leic from I CP israelian company he’s working close to New York City synthesized his Stu and did some investigations only in epoxy resin it a little is a little bit uh not so easy that synthesis because this is classical organic synthesis U but it is possible and and you can see this molecule is pretty nice because you can do a lot of synthesis with them regarding of polymerization it is interesting you can do a poly phosphor mle addition with diolates and diamides okay next reaction uh you see Michael additions uh are pretty familiar with this one we have had uh we will see a lot of more and here we have a so-called oxa Michael Edition that means we have here A drol and A die accrate all commercially available pretty NE pretty interesting and in one reaction we can synthesize this hyper branched polymer this is very interesting nowadays because based on old old uh um synthesis we developed 20 years ago these hyper branched polymers uh have a very nice effect for example in in epoxy resins or other thermosets say are stabilize the class transition temperature or even improve these and of course you can synthesize this again and then do some phosphorilation again with a phosphor mle reaction on that eates and then you have a very nice hyper branched foror compound for applications for example in epoxy ORS next problem often we have a really strange problem and this problem is shown over here on the left uh right side in Europe we have a list and this list is called svhc substances of very high concern if a chemical is listed over there then it will be banned if alternatives are possible or shown that means these substances are very very deeply investigated regarding to their toxicity or environmental benign activities and if it is really strong then they are not only a candidate there are a fixed member of that list and then this compound will be banned and one of these compound are fluorinated olome and polymers and pdfe is Teflon well known poly uh Tetra Florine poly Tetra floan means pdfe is in a lot of industrial flame rard polymeres Incorporated in a very less amount about five 0.5% for example or in particular in engineering Plastics like polyamides poly easers abs and so on and so on polycarbonates and this substance is responsible for anti- dripping this has a strong anti- dripping effect but if it this this um materials will be banned we have to look for Alternatives and one of that alternatives are described in the last years firstly in two years ago this was described the synthesis of this substance very easily formed the shift shift base and then add this sto and get this molecule that was only tested in uh epoxy resins and surprisingly the doo derivative of course it’s not surprisingly act in the gas phase or acts in the gas phase very well but there was observed a a comparable huge amount of of sha that means a condensed phase activity and so aor said that is coming from said CN groups and only one year later another group another Chinese group published this means last year recently and they use that one again formed by the shift base addition of too the So-Cal bovik reaction and you have the C8 group over here and the tested it this flame behavior in poate six and see found anti tripping properties and the reason for that they postulated that reaction that M cyanates can tralized to form this very stable aromatic rings and this is a reason for higher CH and the reason for this anti- dripping effect they postulated so but the question is now can we do this with other cyanates as I know as I said I one of my uh L reaction is the so-called Mel addition reaction shown over here we have a simple agrate and a for for derivative with a pH Bond and we have in the synthesis way a simple addition to form that final product without any side product and again or much better is the back reaction this one is a illumination that means this reaction is going back we get the accolate again and the active phosphorus unit which then does the flame R return effect okay of course we can not do this not only with doo here have we have Doo o CP here dine oxide CC and here phosphite oo and of course these are represents different effects here much more in the gas phase here more in the condensed phase and the thermal stability is growing up in that uh in that Row in that line okay then of course I checked the literature because I must not check the literature I know this uh of course the is old reaction we learned it in the third semester that means in the second year of our uh studies in chemistry the so-called guren nuggle reaction uh old reactions mostly known from known from German guys it’s difficult to uh talk but anyway he did the following he used Malo D nitr or Malo or anyway and did a reaction with alides and form this one yeah coming from here going to here get a wonderful CC double bond from a c double bond it’s not so easy but here works it well but you have here strong electron with throwing groups and this this molecule is of course able to add again with phosphites to form this one now we have phosphorus unit over here and two cyanate groups pretty easy way and there are a lot of work done here are some examples here is started from set phosphorus unit see from Z same reaction and you see very nice products Works always way very well and you see here a really a lot of groups worked in that way they did it in a simple two + two reaction or in a onep reaction in a in a two member reaction or here in a in a three member reaction in a SoCal onep reaction you everybody can look for the best way in the lab to synthesize this stuff but it is very I think this is worthful to check it you can incorporate phosphorus for flame toy and incorporate very easily this cyanates and look a little bit deeper about the anti- dripping or Char forming effect by cyanates here are a couple of more examples as a catalyst it’s now a one two three component reaction in a one port um scenario with iodine as a catalyst and another one excuse me another one here in in water with uh microwave uh application and the last one again here with a one in a onep scenario and synthesize this one very easily okay next question very important is more and more changing the flame ronance from coming from a molecular compound going to a polymer that the reason for that is as well this reach polymer are easier to get uh to get uh re reach certification say that means you can say produce or you can just upscaled much easier than compared molecular compound that’s why we take a look for the cyanate phosphorus compounds as polymers and it well uh it is it was described and look here first time this here pretty new simple reaction again we have a phosphorus containing diolate and now this is Malo d Nal and you get polymerization reaction and again this is a poly Mel addition very nice and I can only recommend to do something here uh because it is easy to synthesize and perhaps we can here change the groups or here you can do this also with Easter groups on that way or a couple of cyanate and Easter there are couple of possibilities are um um creatable this guys unfortunately did it in pla and looked not for tripping effects this is only an an review to see what is possible to syn to to create and phosphorus and different phosphorus agates you have here a lot of POS possibilities you can do this or not here are very interesting things um of course you can do you can create you can get accolades from nature if you burn meat on a or or heat it up in a pan it will smell aggressive it burns in the in the nose this stuff is acine and acine can you oxidize and you will get acrylic acid very easy and here are some synthetic and synthesis and polymerization of paste accolades in a review uh I recommend to use set compound or set one to add dopo or other phosphorous compounds and use it for polyan f we did it for this simple po accolate Easter we add Doo and in case of isopr or prople over here we get liquids which were very very effective in poly Rotan forms and here you have lacton or that special compound where the add the addition of this Doo or other compounds is possible and I think to my opinion also worthful and you have direct biobased source for this one okay another thing uh this is very this is not so so um it’s not a new stuff this is very old and commercially very well done they use the simple epoxy resin and acrylic and do an an add addition of acrylic acid then you get typically Set uh set Direction here you get this diolate adduct it’s called as Vine Easter in technical application sounds strange because it’s accrate and called vinil but anyway uh and we thought perhaps there is some there’s some chemistry possible you have your free oh groups you can do phosphorilation you have three accolate groups you can do phosphorilation and you can do this only on that side and so on and so on but much more interesting there is another stuff commercially available this is dry grol diacrylate that means C here coming from Glycerine or glycerol dry chisay and accolate as well from nature this is poor nature and very interesting because you have three o groups and you have agades and you can see here you can do a phosphor m Edition then you have a phosphorilated triol you can do add and Dot reaction then you have a an an dry phosphorated die agrate you can directly use it for coating and you can do of course a radical polymerization starting after the OT and Dot reaction you can start a poly Edition here you will get an thermoset here thermoplastic material and so on and so on this is very very versatile to my opinion and cheap biobased and commercially available surprisingly nobody did some chemistry with that until now but it’s not not not so bad okay now back to to ionic acid as well biobased uh I know this very well because the company I’m working for is doing some business with ionic acid and not only my company did it also here in China in the group of Professor Shu he did a lot of chemistry with honic acid interestingly formed that dry epoxy resin here which have near the same properties compared to ggba the basic resin on the other hand see can we can form this sto or he forms the sto derivative as epoxy resin or here do this uh uh interesting incorporation of form set epoxy resis directly from from the itronic AET the question is now epoxy resin if you look a little bit deeper you will figure out in the last 20 years there are about one or two new epoxy resins came to the market not more and the question is of course why and the answer is this synthesized a lot of interesting stuff for example here this flame retardant simple molecules this tetr promin dienol uh tgba or Doo or here some mono acid def phosphinic acid or the doo adduct to Kon and the question is if you want to bring this in an epoxy resin the simplest way is culation that means you do a reaction with epic epic rine oh thank you thank you very kind but this stuff is really toxic and the companies are working with epoxy resins don’t like this and the answer is okay before the answer will come another slide new developments are polymeres po polymeric flame rard shown over here but all is functional groups oh groups for example here and here and here and here and as I said the answer is why we can incorporate small molecules small functional molecules in epoxy resin and we can incorporate also their properties the way is very simple is a so-called Fusion process or reactive preformulation here too with a noo lism forms that one or this adduct of too with the Noak resin forms that one you have here the original resin and here the bridge or here the adduct and now you can use it without any using of Epic rain and you have the Inc not only the molecule Incorporated but also the flame retardant property okay see here some uh for the application this is an cured epoxy resin uh important is the flame is nearly the same here in that three thing in that things in that region but important is that the glass transion temperature is compared to uh the the need resin only a little bit reduced especially in particular for for this polymer and the diare over here okay next thing uh now a German group developed these polymerics poly Easter here malic acid and here ionic acid and interestingly they find two things this is selective for UV initiated cross linking that means if you irradiate this with UV you only activate this group and this not but this on the other hand is selective for ASA Michael Cross linking uh and this not and this is very interesting because this is a very nice selectivity and of course I I would think if we used instead of idic acid the doo adduct of idic acid which uh you can sometimes buy instead of this poor need ionic acid then you have now here a doo derivative but you have this uh again here active and can do as our Michel cross linking or on the other hand we can do a micel Adu of melanic acid over here and have then an intact ionic group for an UV initiated cross linking and you have Incorporated phosphorus and can do in both cases flame rant investigations ionic acid again is very important for a couple of Investigations here is in a hyper Branch polymer tough and epoxy resin with rapid stress relaxation superb solvents resistance and closed loop recyclability uh last year published again from this Chinese cook okay now back uh to small molecules with nice functionalities if you want go want to go for polymers as I said it is really important sometimes it’s not only the registration uh in Europe it’s also a lot of other advantages which poly with polymer have for example a better compatibility with the polymer if you will incorporate one polymer with another then it is a blending and the blending is much easier to handle than to bring 20% of a flame tent in your polymer uh to you will mostly is a blending for an improving of material property responsible and uh additive mostly not so uh the educt or the starting materials for this polymer of course have D functionality here’s a dorite dorite dorite or on the other hand you have a means for example this one Pine or this one Ddm or this one benzo guanine uh and interestingly perhaps these molecules should be possible to synthesize then you have phosphorus Incorporated should be possible if you use this dorites with excess of pine okay Pine itself is used in in a lot of Publications here is one by a so-called um substitution reaction that means to use a chloride and an amine is a pine two plus three functional groups and you get a thermoset or Crosslink material now between phosphorus as a phosphorus amide okay and you can do it of course as a chain molecule as a plas as a um in a in a polymeric chain shown over here here you can synthesize this D chloride and do with piperine polymeric substitution to form this thermoplastic material okay and a newer one published this year again they use dispensor guanine which is going more and more popular uh form this train again uh and they Ed some uh and they did some investigation here uh in the case of flame rency uh for pa6 it’s interesting for pa6 but uh we will see later on more or this one again dorite and now uh we synthesize this diacrylate and now we switch over from a substitution process to a poly addition substitution as you know we have always a material because we have to uh catch the ACL by an base and create some salt in the substitution process over here we have an addition proc process poly addition process uh and this is our starting material and of course we can with piperine form this polymeric stuff for example uh and then we have immediately an a coating material a resin which can be used for different application in that in that case so is this UV active okay another publication came from Saia gan from Switzerland he synthesized a very in a very um difficult manner this dienal derivative and do a poly addition with prosine to form this one especially in a reactive Extrusion very very special but anyway uh the reaction of course works well okay radical generators pretty new field uh what I mentioned about the epoxy resins which epoxy resin came out to the market in the last years the same is in in in in flams there are only couple of lens which are came out pretty new on the market uh in the last two decades uh it’s not it’s really not much it’s not no 10 News compounds were uh go gone for for upscaling or for production and here we see a very interesting order information this one a simple phosphorus compound and this one it’s a so-called no haltz haltz means hindered Amino derivative shown over here and nor means this group this is not a flame originally this is a UV stabil stabilizer UV stabilizers form can are able to form radicals in a BRI easy way and these radicals can catch other radicals these are responsible for destroying our polymer and activated by UV and a group this is a English company Thor figured out that this material produced by BSF B and this one produced by thems can form synergistic formulations especially in sin application for example poly Bryan film of oils okay sure this is very important of course for thin application more than for bulk application especially by a fs and this together can work very well as flame retardant formulation uh for example in polypropylene we will see later more um here is shown what is going on this molecule as I said can form radicals we see here the oh that’s was too fast okay we can form some s this one we can form some radicals over here pretty easily and these radicals are pretty active to catch as I said reactive radicals like h o radicals coming from UV but it’s not not only in UV irradation important it’s also in the flame retardancy very important because this AG and O radical are catalysts in our fire Circle or combustion Circle and catching them or Scavenging them will extinguish our fire this is a typical flame retardant uh acting in the gas phase and this uh radicals coming from here this flame step nor 116 this is the structure can form uh this radicals and these are able to catch this here are the radicals form but of course simple molecules are relative relatively less stable that’s why we have to stabilize this and we have two possibilities one is a so-called steric stabilization you see it over here and another one is the electronic stabilization by Electro with dra groups over here here if you do this or this you will be able to stabilize that molecule for bringing in your polymer and uh guarantee durability and reliability but on the other hand if is fire came out will it is so this radical will be well again these radicals will be formed and can catch our o and H radical the same was done not not with oxygen group here but with sulfur groups by Kain from Finland again he did a steric stabilization of set group as well as an electronic stabilization same principle and the same reaction now forming n radical and rs radical and these are very efficient and he did not only a lot of Investigations shown over here what is the real mechanism behind this action forming that one and that one and what is the action in the polymer as I said it is primary it is only a a gas phas active flame tent but he uh uh Korean company song one is buying the the pants and and do some production and this company company have a very simple slogan slogan and this is uh right over here and means the following we have a lot of flame retards on the market for a lot of applications for buk materials for foils for films for for fibers and so for Foams and so on and so on but what is the right one we need uh we we don’t need one we cannot create One Flame tent for all applications most important are synergistic effects that was their their meaning and that’s why he said okay we synthesize two different uh we upscale two different Flame doons so-called uh radical generators and do some invest do some synergistic investigations and this is shown over here you see the three flam Toons upscaled and going for production the structures will be will will I show on the next slide and you see here some sistic some Sy aristic possibilities one for for olines for Foams for abs first time we can have an nonhalogenated flame rarden solution for abs TPU Theros sets Coatings and as well wood and oh again here we see two of the commercialized structures song flame 205 and song flame 2011 and we see on the other hand flame syes and these are the known phosphorus derivatives this pz900 from Tor ahp introduced at the beginning phosphines works very well AP works but not so very well this and Z One are very very active of course also brominated stuff uh is can be active but it is also published over here from C now what is the amount necessary for get good flam tles this is for simple investigations in PP you see here for brominated stuff together with SP with antimon oxide you need 12 + 5 for v2 P 900 alone about four no classification eight no classification 15% V2 pz 900 plus one uh radical generator Fe + one V2 and 8 + 2 close to v0 that means these radical generators are not only very active they are much more active in Sy aristic formulations and I think it’s worthful to look a little bit deeper Kain itself himself as well and you see here the last publication from him so now he is combining this NS groups in one molecule with ph fate groups uh and looked for in different Manner and looked for their efficiency okay coming to the conclusion okay one hour that fits interaction between flame retards and their synthesis I hope I can you will understand now a little bit more atom efficient synthesis Roots it’s really important if you want to think in and on upscaling or on production flame tens and anti- dripping properties this is a very nice and interesting field because of um possible Banning of Teflon derivatives the classical UND dripping agents in polyamides and polyesters polymeric flame retardant are going more and more of of interest because uh they have very nice properties regarding to The Matrix polymer on the one side and uh less problems on registration uh that’s why synthetic roots are synthesis Roots uh very of of Interest new starting materials are always interesting in particular if this is cheap and very easy to get materials and last but not least some uh I discussed about radical generators especially in synergistic application now oops uh I like to thank you for your kind attention of course and uh I hope I can give you some idea and of course I I’m here for questions sure last but not least I’d like to show you some Impressions from Germany today or in this days this is close Advent site is close to Christmas and you see here Christmas markets in a small town uh there are special um beverage is hot red wine with spices and if you come close to that market you will smell this it is very very intensive and very very good and you have of course special Christmas dishes and this is only in a small town this looks in a greater one in a big town you see a lot of uh people going from hot to hot and they have special Christmas cakes and gingerbread and this mold wine very interesting most of the groups like you at night don’t get home don’t go home you go to the Christmas Market okay thank you very much for your kind attention Professor about the different kind of and the the radical generat the different thank you very much so now any question to the we want Hello very nice presentation I have one question uh when Sy when syze industrial that is uh the aut economy selectivity and yeld are important which is the most in all all three together believe me okay uh look industry is just looking for last but not least processes which are have less synthetic steps yeah I can give you I in former times I gave to my students lectures we discussed only this former times and developed synthetic steps or synthetic procedures have often a couple of steps or a few steps sometimes for drugs a lot of steps and nowadays they do develop new synthesis for the same product which reduced synthesis steps uh very in a very strong manner that means in former times perhaps eight 10 steps now only two or three it is now possible uh because you have new new um possibilities for example new catalysts new starting materials to can do this if you have a good yield you have of course low side products if you have a good SEL activity as well low side products and of course atom economy means you give you introduce only small uh so-called uh helping materials like bases or acids to to catch uh special products that means as well those side products all three things things together should be optimized yeah it’s not only the side products but uh of course if you you have a lot of side products you are responsible as a company to handles this stuff you cannot put it in the next rer it was in former times but now it’s gone you are responsible for that stuff and that’s this is money okay in your that’s the uh the radiation generator for the ABS and PP and tiv is use just c yeah NSR yeah yeah these are this this uh radical generator de developed from K yeah important I think that first yeah to I discussed with him a couple of times and he said maybe we can develop others but until now this combination of phosphorus compounds special phosphorous compounds like this p900 or phosphines and this n NSR radical generators uh for such applications are the best one and if you see this uh which songan offered if it is possible to create hogen free solutions for abs which is not possible until today in exactly or for other things TPU or or Coatings and wood wood especially there are industrial applications I show it because it is in Scandinavia where colan is coming from very very popular now to build up wooden houses they have a lot of wood and this is very very popular uh but it must be flame rard and they used this stuff um again uh for for flam for forming flamon food and this is just the PC is and and this is these things are commercial available this one and this one this is and also PC is PC and this this one this one I one and five uh I think this number they have I have only the structures for that one 2 one 2011 and 205 and this is which oh yeah this is commercial available by this British company Thor it’s they producing this in in Germany close pretty close to BSF only only 20 kilometers I can give you the address may can order [Laughter] this yeah uh I have a question how to prove the radical generator some very good question uh the best way is I should switch to another talk because to my opinion if you cannot prove something it’s only an assumption you need evidence for we did it for for D fights not for set stuff but I think it’s nearly the same we were able to detect S2 radicals he post see postul are postulating um this radicals over here of course I think it’s it should be possible to to detect this you need a special Ms technique for example or you need a special laser technique it’s not it’s much better it is possible but it is not done until now so this radic will Tri the hydrogen radical all will catch yeah will catch the the O and O and H radicals like P or B bro radicals okay it’s the same but more efficiently compar no it’s more more efficient that’s why so you need so so less amount of flamings and how much this just ah I don’t know I that is this is really it’s it’s strange I don’t like I don’t know it’s a Korean Korean Sky we want to wanted to order this SN derivatives for comparing investigations and ordered this in a company ordered that in Korea no way I called K vain of course I said Kor it’s unbelievable I think this company is selling this stuff I said yes okay and I said no we cannot order and he said he will call these guys he did it but uh now I’m four weeks 3 weeks over here in China I don’t know what is going on but I this was really terrible to get this and I don’t know why because if I going for producing I want to sell I want to earn money was really strange and as well for colan yeah so one is not a small company can they are do a lot of uh production of um U of stabilizer for for polymers U stabilizer but also other stabilizers and are famous on the market what I don’t know what’s going on it was a blendy of information too much perhaps for for one afternoon okay uh maybe maybe I think stud maybe yeah the door is [Laughter] open okay thanks very much