ThreeBond Technical News
Issued July 1, 2022

100

For the smooth progression of research and development
Introduction
Congratulations on the publication of the 100th issue of Technical News! The author has convincedthat this huge number of publications also reflects the corresponding great achievements in the
research and development at ThreeBond. This is an exceedingly amazing accomplishment. The
author has been organizing a laboratory at Tokyo Institute of Technology for 26 years, and during
this time the author has been carrying out research works on the creation of new polymeric materials
with over 150 master course students and 40 PhD-candidate students. The author has kept in touchwith the researchers at ThreeBond since the author first set up his laboratory, and the author has
fortunately had many occasions to participate in discussion with them while experiencing thedifficulties of research and development that differ from those in the university.
The author is a little afraid whether it will be consistent with the purpose of this Technical News, but
he would like to share his thoughts obtained from managing the laboratory and having discussion
with the researchers at ThreeBond. Although the perspective of this manuscript might be biased
towards the university side and reflect a lack of experience in the related area of work, the author
hopes this will be a good occasion for us to think together about how we can achieve smootherresearch and development.

Table of Contents
Introduction............................................................. 1
1. Sharing furthest information throughdiscussion on research works........................... 2
2. Positive and negative knowledge
accumulated at research organizations............ 4

3. To prevent negative knowledge
from occurring.................................................... 6
Closing.................................................................... 81

1.

1. Sharing furthest information
through discussion on research
works

When researchers are asked about the negative results on
their experiments, they often simply reply “it didn’t workwell”. This is a very common way of the communication
between one party who is actually doing the experiments
and the other who is actually doing the experiments
and the other who needs to know the results, when thetwo parties discuss how to proceed based on the results.
However, there is a hidden risk that something important
could be missed depending on the amount of informationthat is shared in advance between the two parties and how
the communication continues from that point on.
In the case of routine work where the party asking about
the progress has an accurate understanding of all of thespecific points of the experiment, such as the methods
used by the party conducting the experiments andthe range of conditions in which they conducted, andproperly understands the scope of potentials that needs
to be considered, the author believes that it’s possible toproceed to the next step right after sharing the simple
information. However if there’s a difference between thescopes that the party conducting the experiments has
considered and the scopes that the party asking about
the experiments has envisioned, the researchers might
miss the chance to take the results of experiment in a
fruitful direction. Many factors could play a role, suchas each party’s level of knowledge and experience, thenature of the experiment, the relationship between theparties, and people being very busy, but when not enoughinformation is shared and each party fills in the gaps
with their subjective view, unexamined areas that shouldbe pursued as possibilities may be missed because eachparty assumes that they have already been considered.
For example, when comprehensively discussing theresults of a series of experiments where parameters suchas the temperature axis, time axis, mixing ratio, andtype of catalyst can be changed, it might be difficult toaccurately discuss the true images if detailed information
about those parameters is not shared. Those matters
could include what kind of thinking those parameters
were based on, which parts were implemented, andwhat kind of results were obtained after making thoseconsiderations. As the party conducting the experimentbecomes more experienced, this relationship of trust issomething that should be strengthened considerably,
which might, however, also cause unfavorable situations.

2

That is, the party asking about the experiment will bestrengthened. This relationship of trust is somethingthat should be strengthened considerably, which might,
however, also cause unfavorable situations. That is,
the party asking about the experiment takes an overly
favorable interpretation for details that haven’t been
discussed, assuming that the party conducting theexperiment must have already considered them and ruled
them out. Even if it takes some time, the author thinks
the party conducting the experiment needs to share all
the detailed information as accurately as possible, such as
the scope they have considered, why they decided that theexperiment didn’t work well, and what happened insteadof the expected result. Additionally, it might be necessary
to devise a way for both parties to take it for granted that
all the details regarding the experiments must be shared.
The author assumes. There may not actually be muchcause for concern in ThreeBond’s case; research anddevelopment at ThreeBond proceeds exceedingly
smoothly as the researchers work toward a common goalwith the spirit of “creating our future from a single drop”,
and things are functioning smoothly enough. But atuniversities, there is often a reliance on the generosity ofeach faculty member, and the author is a little concernedthat it may be a situation where it is difficult to havesmooth discussion in future. For example, research ethics
courses have finally been introduced and classroom-based
lectures that focus on topics such as health and safetyissues, researchers’ social responsibilities and compliancewith laws and regulations have begun. However, faculty
members must still teach students through their research
activities in the lab. It is not just about learning fromexperience; the author wonders if educational programs
can then be set up that steer towards the philosophy “thewise man learns from the mistakes of others.” Now,
digressing briefly, the author has a little more to say about
universities. Even when one would consider it necessary
to take discussion one step further in order to improvethe efficiency of the research, faculty members may beconscious of the difference in status between them andstudents, and may hesitate to start such a discussion if
they get the impression that the students do not reallywant that. Another major point of self-reflection is thatmost of the professors are involved too much in various
tasks that often limit the chance to ask even a simple
question about what the results are going on. A certain
percentage of students will look for moments between
professors’ meetings to discuss even trivial things despite
this, and the author is always struck to see many of thesestudents improve at an amazing speed. Some students
can progress through continuous discussion, and there
are cases where you say “in that case, how about doing
this?” and the student triumphantly answers that they
had envisioned being asked that so they tried it already.
They’ve thought ahead, by themselves, conducted anexperiment and brought their answer to the discussion.
Some students will even research various related studies
on their own and be able to suggest a new direction to takein order to reach a solution. Those are moments that also
excite the author. The author convinces that all of thosestudents have published comprehensive and exceptional
theses, and then attained great contributions in various
areas including academia and business. This may be one
example of harmony between the party who conducts theresearch and the party who asks about the results.
On the other hand, when students are welcomed to the lab
in April every year and they commence research towards
their theses, there are some exceedingly rare cases when
the author will ask a student about their results andthey will only tell him that the research failed, and do
not provide any more information no matter how manyquestions the author asks. In such cases, it is sometimes
necessary to make the students to understand that if the
only thing being communicated is failure of the researchand no details are given at all, it’s impossible to discuss
the research any further, and there is a risk that theirresearch itself might not go any further. In some cases,
an error in interpretation of analysis data could lead toa misjudgment, so we need to delve into the issue anddiscuss it, rather than just making a subjective judgementthat it didn’t work well. For example, the research often
gets on track after the student understands how important
it is to communicate as accurately as possible about points
like how the reaction mixture looked like (for example,
whether the materials dissolved), whether the materials
were recovered without undergoing any reactions or
unexpected products formed from the analyses of thematerials. Then the students become able to discuss
what conclusions can be drawn from the results. This is
another situation where the author is delighted to watch
researchers come into their own by repeating research
activities such as subsequent one-on-one discussion,group meetings, conference presentations, and thesis
defense presentations.
The author would like to cover one more point about
universities. When renowned professor gives a retirementspeech, they often say that because it took a rather longtime before they were promoted, they had to conduct

experiments by themselves for a long time, which was,however, an irreplaceable asset for them as a researcher.
This means that working on experiments themselves led
to interesting unforeseen discoveries that can often be
missed in the indirect process of listening to student’s
reports, and the author assumes that this an expression ofuniversity professors’ own feelings about the difficulty ofholding discussion with students.
Many new trends in research come from spotting anddelving into experimental results that suggest somethinginteresting is happening—so called serendipity—. The
author thinks an important point that leads to this ishidden in those unforeseen results that get lumped into
the expression “it didn’t work well.” The author himself
also encountered unforeseen and interesting things more
often during the time that he could carry out his own
experiments than he does now, and he feels that those
discoveries rapidly broadened his research. Sometimes
the author reminisces fondly about that time, and eventoday he continues to grapple with the issue of how tofind useful information together with students the way he
did when he conducted his own experiments. The author
feels that it is important to share as many opportunities as
possible to celebrate the ups and grapple with the downs
together, no matter how trivial the results may be, to makesure his students understand that even if they are still
unable to find the answer he is very interested in talking
about mysterious phenomena that they encounter along
the way, and to place the highest priority on maintaining
an environment where students can share their unfilteredthoughts on their issues with an experiment at the timethey occur. The reality is, however, that many students
who work in a lab assume that they should only discuss
their results once they are somewhat close to findingan answer, and it takes time and effort to get them tounderstand the kind of environment the author is trying
to create. Additionally, there is an increasing age gap
between the author and his students and the time he isable to spend supervising them in the lab is decreasing alittle each year, so he feels that it is becoming increasingly
difficult to communicate smoothly about things like thiswithout junior staff. The author will now give a few
examples of serendipitous experiences he remembers
having through discussion with students. In one case,when a new polyaddition reaction was being considered,
but the goal of polymerization was not achieved, a highly
selective tandem type zipper cyclization reaction was
found to proceed quite effectively1). While the reactionthat occurred was very minor, it ended up being applied3

in synthesis reactions as Tomita Zipper Cyclization 2). In
another case, when trying to polymerize a new monomer,
it was found that a highly efficient aggregation-induced
emission (AIE) pigment happened to be created3). The
author thinks an important point here is that all of these
discoveries happened when the Ph.D. student who wasconducting the research told him that it didn’t work
well and he was able to thoroughly discuss what was
happening with an observant student.
To return to the previous topic, what has been discussed
until now applies to informal one-on-one discussion. It
can be assumed that later on the results are summarized
a little more precisely and more formal discussion is held
regularly as a group or with other groups. In addition tothe obvious points like the tension of having so manyeyes on you and the opportunity to think the results ofyour experiments over again, the author believes that thediscussion is also an effective way to get feedback frompeople whose position and point of view might differ
slightly and find new points to consider.
When a research group begins tackling a new issue, it canbe assumed that there are hidden factors that cannot be
hypothesized solely with the research method establishedby the research group. It is also important to have waysof applying outside views, such as academic conferences,
documented information, and collaborative research. Thisis another area where the author feels that ThreeBond has
a sufficient structure in place.
Incidentally, once the formal presentation and discussion
stage is reached, the author believes that the chance tohear about things that did not work well is mostly lost.
As a result, there is a tendency to end up moving in a
direction where it is usually difficult to find opportunities
to share what didn’t work well and to talk with many
people about possibilities for achieving one’s goals. Theremay be various hidden issues that need to be overcome inorder to create opportunities to present data on researchand development that is still in progress in front of a big
audience, but the author thinks it could be interesting tocreate opportunities for formal presentations that enable
active discussion of unfinished work that really needs tobe discussed and work where things are not going wellwith the group’s knowledge alone and the group thinks
they may be coming to a dead end. Obviously, there isa need to make sure the discussion operates properly sothat things do not get out of hand and lead to researchers
passing on what the author will later refer to as “bugs” toeveryone else, but it might be interesting if it functions in

4

a way that allows researchers to share knowledge about
what kind of approaches can be taken when things are
not going well and to receive suggestions they had notthought of from people who have different experiences.

2.

Positive and negative knowledge
accumulated at researchorganizations

Although trial and error is always part and parcel withresearch and development, the author believes that inmany cases, the rational way to achieve your objectives is
to make effective use of knowledge gained by researchers
before you and then explore further. It’s a process where
you’re “standing on the shoulders of giants;” applying
past knowledge as it enables the party conducting theexperiment to make smooth progress in their researchand development and achieve their objectives. The
author suggests that sharing knowledge that has been
accumulated by research organizations about what went
well with the whole group and applying it to achieve
positive results is a very efficient method. Conversely,
the author postulates that even knowledge of what wasconsidered in the past but did not work well is sharedwithin the research and development group as a whole toprovide information on methods that should be avoided,
and the group then avoids that method as they carryout their research and development work. For example,
when it comes to the policy that will be used for future
considerations by the party conducting the experiment,
what will happen if someone suggests something thatsomeone else considered in the past but did not work well?
The author assumes that they will receive the advice that
it was considered in the past but it didn’t work well so it
is best not to do it. Basically, it is effective advice in order
to avoid repeating the same mistakes. When it is clearthat the person giving the advice has the past experienceof things not going well after spending a considerable
amount of time considering all of the possibilities andtheir knowledge that it didn’t work well is quite accurate
information, it is right to decide to follow that advice
in order to avoid failures. However, related to the topic
touched on earlier, some doubts about credibility willremain if the person giving the advice omits details on
what was considered and how, or if it is found that the
judgment that it didn’t work well was actually based only
on a small consideration under only some of the possible
conditions. In those cases, the experiment may havefailed due to other factors such as human error or a flaw
with the reagent that was used at that time. In any case,even if the information has not been properly verified andthe opinion that it was not successful is presented to many
researchers, it might result in everyone believing that it
did not work well without considering factors such as thecause. The author thinks that if the opinion is expressed bya particularly trusted researcher or if multiple researchers
say something didn’t work well, this will deepen otherresearchers’ assumption in one fell swoop.
This process will create misinformation, also known asbugs, throughout the whole research and development
team. Once a bug occurs, people will no longer consider
any possibilities in that direction, and depending on thesituation, the progress of research and development could
be hindered. Guarding against bugs like this is a very
difficult issue.
The author would like to touch on a topic that is based on
experiences at his university and that he feels is slightly
relevant. The postgraduate students in the author’s lab
come from various universities and since they each havea different level of research experience, the first serious
issue that is faced is ruling out the possibility that theexperiment did not work well due to the skill level of theperson conducting. To address this, along with giving
students the chance to become familiar with how to
conduct experiments and the types of measurement
equipment in the lab, the author gets them to perform
double-checks by repeating clearly successful experimentsthat were conducted by more senior researchers and havebeen reproduced by at least several people before to see
whether they can replicate them.
Once the student gets through this process with no issues
and it is clear that they are able to replicate the resultsof their experiments, they can proceed to new research
projects. Some students’ work goes smoothly as soon as
they start working on new projects, but there are also cases
where things don’t work well at first. In many cases, thosestudents gradually get on track with encouragement fromjunior staff and senior researchers, but there are also rare
instances where the matter is discussed and suggestions
are made by the author but nothing they try works. There
are times when the author gets students to change theirresearch topic to one with a higher chance of successand they are able to put together a graduation thesis, andthrough this process of trial and error, the author createsa database in his mind for examples of things that havenot gone well. The author also thinks that when highly
skilled students whose experiments usually go extremely

well encounter something that doesn’t work well, they
add it to that database without much further thought.
The author thinks that after a while, those databases areunconsciously used as a guideline for what needs to be
avoided when setting a new task or having a discussion
with another student. Obviously it can probably be
assumed that most of the details in student’s databases
are accurate information about what does not work well,
but there may be some bugs where the method in question
actually does work, or would work under slightly different
conditions. The author thinks that there are times when weneed to carefully consider the veracity of information on
things that didn’t work well, especially if that information
will influence the future direction of research.
Now, the author would like talk about one of his
experiences of discovering a bug. A student of his had
said that an experiment hadn’t gone well. After thatstudent graduated, the author had the chance to speakwith a student who was doing somewhat related research
about the very experiment that that student thought did
not work well. The author explained as accurately as
possible about factors such as the conditions when theexperiment was conducted and why it was decided that it
hadn’t gone well, and told this student that although theauthor had thought the experiment would work, this waswhat had ended up happening. This piqued the student’s
intellectual curiosity and they tried the experiment again,
incorporating their own ideas. After a short while, thestudent came to the author smiling and explained that theexperiment had gone well with their improvements. That
breakthrough led to new developments in the research.
Additionally, when the author has a research project that
he really hopes will progress smoothly and definitely
wants to take further, he sometimes takes the very simple
method of leaving it for a little while and suggesting thata junior researcher repeat it. The most important thing,
and this is something the author’s university colleagues
feel the same way about and which they have talked
about, is that this only works if all of the students who
know the details of why the experiment did not work wellhave graduated, so you need to be patient. Otherwise,
the student who has just been assigned the project hears
from others who witnessed the negative results about how
previous researchers struggled because it didn’t work
well, and they end up putting on the brakes.
There have been many times when researchers have beentalking about a paper that has been published by a different
research group and they remark that in the past they5

approached the same problem with the same methodology
but it didn’t work well. They talk about it with a mixtureof skepticism and regret. When the author hears thesekinds of conversations, he often feels that there musthave been a serendipitous element where the successful
researchers lucked into the perfect conditions when they
conducted their research, but there are also cases where
he suspects that the research group remarking that theirresearch did not work well may have had some incorrect
assumptions in the database they created, which made itdifficult for them to be optimistic about their research.
So eliminating the bugs that have a tendency to accumulate
in research groups is also necessary in order to avoid
having other research groups and businesses sailing tosuccess with methods that were deemed as somethingthat would not work. It’s quite difficult to figure out how
to do this. This might be even more true for corporate
research and development departments as every moment
counts and you can’t take your time and use the kind of
measures mentioned earlier. Although solutions may be
far from reach, when the author has the chance to explain
to someone about something that did not work well, hetries to think back and recall as much as he can about
how correct that information was, and think a little
about whether there are any examples that can explain
why it didn’t work out. Even when the information thatsomething in the past did not work well is not a bug, hefeels that if the reason for why it did not work well can be
identified, sometimes hidden signs for new directions ofresearch can be found.

3.

To prevent negative knowledge fromoccurringThrough discussion with researchers of ThreeBond, theauthor has come to realize on many occasions that there
are difficulties you face that do not exist in university
research projects. The author will give a few brief
examples of difficulties that he feels could lead to “bugs,”
and try to think of some ways to prevent that fromhappening.

1.

Discussion about the reactivity of one
component in a productIn the development of a new product, once the outlineof the composition of the product has been settled,
the researchers sometimes focus on one component(component A) that most likely contributes to improving
performance, and examine the effects of its structure. In
this case, they try to keep the weight ratio of component

6

A to compare the performance after polymerizationand curing. However, if the chemical reaction between
component A and a different component (component B),
proceeds, for example, in a one-to-one molar ratio, it
must be important to keep the molar ratio rather than theweight ratio from the viewpoint of chemical reactions.
That is to say, when the chemical structure of component
A changes, the molar ratio of the functional groups
may change if the weight ratio remains the same, whichbrings about the inappropriate mixing ratio for smooth
polymerization and curing. If the researcher did not
notice the influence of the imbalanced molar ratio, theymight spread misinformation regarding the reactivity ofcomponent A.
In such cases, it might be preferable to change bothweights of the components A and B so that the functionalgroups being mixed keep an adequate molar ratio, while
keeping the constant total weight of the components A
and B in the product.

2.

The relationship between the structure
and reactivity of epoxy resin

On one occasion, through the discussing the reactivityof epoxy resins, it was explained to the author that epoxy
resin A was more reactive than epoxy resin B and thereason for that was discussed together. It didn’t haveanything to do with the mixing ratio issue mentioned
above, so the author tried to figure out the reason fromthe difference in their chemical structures. Since A andB have almost the same substructure, it was difficult
to explain the difference with knowledge of organic
chemistry alone, and he was unable to find an answer.
Until he happened to come across a review article thatcomments on the purity issue of the epoxy resin. Thatis, the difference in purity of epoxy resins available asindustrial products often serves as a predominant factor
that determines their polymerization and curing activity.
This fact might be well-known for researchers who workwith epoxy resin all the time, while it was impressive
for the author to know the difficulties to carry out R&D
with industrial products. Besides, in order to avoid theoccurrence of a “bug”, the author believes it necessary
to indicate clearly that the reactivity difference in thisparticular case originates from their purity difference but
not from the structural difference.

3.

The reactivity of catalysts

The author had a chance to discuss the relationshipbetween the structure of the Lewis acid catalyst andthe curing speed of a monomer component. In theirexperience, a salt of a particular metal exhibits highactivity, while that metal is preferably not to use inindustrial applications in future. Although they wanted
to switch to othrer catalyst consisting of different
metal centers. They were unable to find more active
candidates. They were struggling because the activityof catalysts was not predictable solely from their Lewis
acidity. The author also felt it reasonable to correlate
the catalytic activity with their Lewis acidity, while therelatively higher activity of the catalysts may also leadto their decompositions through hydrolysis, etc. under
the reaction conditions. This decomposition is likely tooccur, according to some literature mentioning that metal
catalysts with a similar structure undergo structuralchanges due to reactions such as hydrolysis. In cases
like this, if you put this information about metal salt
structures and variance in catalytic activity straight into
your database, you could end up with misinformationin there; you may need to take structural changes in
the catalyst into account when ranking the activity ofcatalysts. Based on this knowledge, the next step may be
to explore catalysts that have both somewhat high Lewis
acidity and stability not involving any structural changes
in use.

4.

major advances in analytical methods also for curing
reactions, the effective way to discuss reactions involvedin the polymerization and curing of the products in detailis to carry out experiments using model compounds
possessing a single reactive functional group for each andevaluate their conversion behaviors and structures.
When you’re planning to accumulate knowledge on
the reactivity and catalytic activity obtained from theexperimental results to the database mentioned above
as overarching knowledge, it would be preferable to becareful enough when you know that something happens
but you don’t know why. There might be any limits to theapplicability of such information. Besides, if you know
the adequate reasons that bring about the difference
in reactivity or activity, the information will be moretrustworthy. Therefore, the author would like to suggest
to the researchers to try to figure out the reason by
searching literature, continuing discussion, conducting
additional experiments, etc., even though they might be alittle time-consuming process.

The possibility of unforeseen reactions
with other components

In order to develop products with excellent performance
and/or those with added value curing process, multiple
components that contain plural functional groups areoften mixed in one pot so as to carry out multiple kind ofpolymerization and curing processes. In this case, there
could be unexpected reactions between functional groups
other than the ones from which you are expecting. For
example, (meth)acrylates could cause a 1,4-conjugate
addition reaction with nucleophilic agents such as amines.
Thiols may also undergo similar addition reactions if the
Lewis base or radical catalysts are present. If peroxide
initiators are employed, it is not recommended to mix
with components that serve as electron donors such asamines, which lead to any redox reactions.
Obviously, it may not be necessary to consider suchpossibilities if these reactions are very slow andnegligible under the actual storage, polymerization andcuring conditions, and/or if the polymerization andcuring reactions occur smoother than the unfavorable
side reactions. Nevertheless, it might be preferable tocarry out any control experiments by picking up someof the components from the product to know whether
unexpected reactions happen. While there have been7

Closing
When the author was asked to contribute to this issue of Technical News, the author initially intended to describe
something more technical, such as an account for the chemical reactions often employed in adhesion processes. However,before touching on the individual technical topics, as introductory remarks, the author just intended to comment onsome general matters that can happen if researchers are working as a team on some research and development projects,
which consequently covered most part of this manuscript. Although the excellent human network in the research anddevelopment divisions in ThreeBond is of an unparalleled caliber and hence it might be possible that some of the issues
described here have already been solved or have not been applicable at all to ThreeBond, the author tried to share theauthor’s experiences and thoughts to have an occasion to think together.
The author felt a sense of clarity while writing, probably because the topics covered here were quite new for the author towrite. Eventually, the topics turned out to be the main contents of this manuscript. There might be more adequate topics
to discuss, such as the importance to look at the organization as a whole and bring a balanced view to your research anddevelopment and the importance to stay attuned to issues that you should be tackling.
Since the author has not reached adequate answers to many of the issues mentioned in this manuscript, the author is alittle afraid that the contents might be premature. However, the author wishes to share the issues with the readers to start
thinking together how to solve them. Last but not least, the author strongly wishes all of you at ThreeBond the very bestin your research and development.
<References>
1) H. Kuroda, I. Tomita, T. Endo, “Novel Phosphine–Catalyzed Zipper Cyclization of Aliphatic Diyne– Dione and YneDione Systems”, Org. Lett., 2003, 5, 129–131.
2) (a) D. Ramachary, Chintalapudi Venkaiah, Patoju M. Krishna, “Stereoselective synthesis of five- memberedspirooxindoles through Tomita zipper cyclization”, Org. Lett. 2013, 15, 4714–4717. (b) N. Rocoby, “Tomita zipper
cyclization”, In Catalysis from A to Z: A Concise Encyclopedia, Wiley (2020).
3) H. Eguchi, H. Nishiyama, S. Inagi, I. Tomita, “1,2–Bis (diarylmethylene)cyclobutane as an Effective Building Block forAggregation-Induced Emissive Materials”, Asian J. Org. Chem., 2017, 6, 165–168.

Ikuyoshi Tomita
Department of Chemical Science and Engineering,
School of Materials and Chemical Technology, Tokyo Institute of Technology● ThreeBond and the slogan “Creating our future from a single drop” are trademarks or registered trademarks ofThreeBond Co., Ltd.

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