CN109574934A - A kind of preparation method of aliphatic urea diketone - Google Patents
A kind of preparation method of aliphatic urea diketone Download PDFInfo
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- CN109574934A CN109574934A CN201811572071.3A CN201811572071A CN109574934A CN 109574934 A CN109574934 A CN 109574934A CN 201811572071 A CN201811572071 A CN 201811572071A CN 109574934 A CN109574934 A CN 109574934A
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- diisocyanate
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- urea diketone
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- 239000004202 carbamide Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001514 detection method Methods 0.000 claims abstract description 17
- 239000003426 co-catalyst Substances 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 230000003197 catalytic effect Effects 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 claims description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 2
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 2
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 2
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 claims description 2
- OEMVAFGEQGKIOR-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCC OEMVAFGEQGKIOR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 229960004194 lidocaine Drugs 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- WBOHXLDSPBIPTP-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-4-amine Chemical group CN(C1=CC=NC2=NC=CC=C12)C WBOHXLDSPBIPTP-UHFFFAOYSA-N 0.000 claims 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- SGXQOOUIOHVMEJ-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCCCC SGXQOOUIOHVMEJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- STBLQDMGPBQTMI-UHFFFAOYSA-N heptane;isocyanic acid Chemical compound N=C=O.N=C=O.CCCCCCC STBLQDMGPBQTMI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000006555 catalytic reaction Methods 0.000 abstract description 6
- 150000002118 epoxides Chemical class 0.000 abstract 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000006471 dimerization reaction Methods 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic isocyanates Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- YWNYZQTZOONLGU-UHFFFAOYSA-N C(CC)Cl.[O] Chemical compound C(CC)Cl.[O] YWNYZQTZOONLGU-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FUCRTFHCJZBKBB-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCC FUCRTFHCJZBKBB-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QCCWVNLOJADEAV-UHFFFAOYSA-N n,n-dimethyl-1h-pyrrol-3-amine Chemical compound CN(C)C=1C=CNC=1 QCCWVNLOJADEAV-UHFFFAOYSA-N 0.000 description 1
- KCXYZMFPZHYUFO-UHFFFAOYSA-N n-methyl-n-phosphanylmethanamine Chemical class CN(C)P KCXYZMFPZHYUFO-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of preparation methods of aliphatic urea diketone, specific preparation process is as follows: under 30 DEG C -50 DEG C of normal pressure, dry nitrogen is passed through into reaction vessel, diisocyanate and preliminary catalytic agent is added thereto simultaneously, after reacting a period of time, when the content of NCO% is unchanged in detection reaction system, co-catalyst is added, until reaction monomers residual quantity be lower than 0.5%, then at 30-100 DEG C by vacuum distillation co-catalyst is isolated from reaction mixture.After the present invention carries out catalysis reaction by preliminary catalytic agent, when reaction reaches a certain level, by the way that a certain amount of epoxide is added as co-catalyst, reaction can be made to continue, so as to consume remaining isocyanate-monomer, therefore separating monomer is avoided, can effectively improve production efficiency, is more advantageous to the realization of industrialized production.
Description
Technical field
The invention belongs to powdery paints raw material preparation fields, are related to a kind of preparation side of linear (ring) aliphatic urea diketone
Method.
Background technique
In the polyisocyanates containing urea diketone, linear (ring) aliphatic urea diketone is very valuable original
Material, for example, they, which can be used as material component, prepares self-enclosed polyurethane powder coating crosslinking agent.
Monomelic aliphatic or cyclic aliphatic are subjected to dimerization reaction by catalysis reaction, form linear (ring) aliphatic urea diketone
Technology be known.Currently, there is two kinds of catalyst systems to can be used to obtain linear (ring) aliphatic urea diketone.
EP-A45995 describes catalysis of the special all alkyl amino phosphine as complete dimerization (ring) aliphatic isocyanates
The application of agent.Using preferred dimerization catalyst, i.e. hexamethyl Asia Che triamide (three (dimethylamino) phosphines), allow to prepare linear
(ring) aliphatic urea diketone.EP-A317744 describes one kind using 4- dialkylamino pyridine as catalyst, such as 4- dimethylamino pyrrole
The method of the aliphatic urea diketone of pyridine (DMAP) catalysis preparation line style (ring).But above two catalyst system all exists to (ring)
Aliphatic isocyanates have the shortcomings that catalytic activity deficiency, and when catalytic dimerization reaction reaches a certain level, dimerization reaction can not
Continue, need to isolate unreacted monomer by the method for thin-film distillation, so that there are low efficiencys for this method, in work
The shortcomings that being difficult to realize in the production of industry scale.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of aliphatic urea diketone, are catalyzed by preliminary catalytic agent
After reaction, when reaction reaches a certain level, by the way that a certain amount of epoxide is added as co-catalyst, it can make to react
Continue, so as to consume remaining isocyanate-monomer, therefore avoid separating monomer, can effectively improve production
Efficiency is more advantageous to the realization of industrialized production.
The purpose of the present invention can be achieved through the following technical solutions:
A kind of preparation method of aliphatic urea diketone, specific preparation process are as follows:
Under 30 DEG C -50 DEG C of normal pressure, dry nitrogen is passed through into reaction vessel, at the same thereto be added diisocyanate and
After reacting a period of time, when the content of NCO% is unchanged in detection reaction system, co-catalyst is added in preliminary catalytic agent, until
Reaction monomers residual quantity is lower than 0.5%, is then isolated from reaction mixture at 30-100 DEG C by vacuum distillation and is urged altogether
Agent；
Preferably, diisocyanate is isomeric pentane diisocyanate, hexane diisocyanate resin, two isocyanide of heptane
Acid esters, octane diisocyanate, nonane diisocyanate, decane diisocyanate hendecane diisocyanate and dodecane two are different
One of cyanate and isophorone diisocyanate.
Preferably, the structural formula of preliminary catalytic agent such as (I) is shown；
Wherein R in formula (I)1And R2It is the alkyl of 1 to 8 identical or different carbon atom or is connect with R1 and R2
Nitrogen-atoms is formed together 5- or 6-membered ring；
Preferably, preliminary catalytic agent is 4-dimethylaminopyridine, 4- lignocaine pyridine, 4- pyrrolidinopyridine, 4- piperazine
Pyridine and one of pyridine and 4- (4- methyl piperidine base) pyridine.
Preferably, preliminary catalytic agent is 4-dimethylaminopyridine.
Preferably, preliminary catalytic agent dosage is 1-2wt%.
Preferably, the structural formula of co-catalyst such as (II) is shown:
Wherein R in formula (II)1And R2For-H ,-CH3Or-CH2One of Cl；
Preferably, co-catalyst is epoxide, and co-catalyst is propylene oxide, ethylene oxide, epoxy butane and ring
One of oxygen chloropropane；
Preferably co-catalyst is propylene oxide.
Preferably, co-catalyst dosage is 0.25-1.5wt%, and when addition of epoxide is confidential dependent on according to often
The situation of change of the percentage composition for the reactant NCO group that rule method is measured, when the NCO content value measured in a period of time
When almost unchanged, epoxide is added and carries out further catalysis reaction.
Beneficial effects of the present invention:
It is certain by being added when reaction reaches a certain level after the present invention carries out catalysis reaction by preliminary catalytic agent
The epoxide of amount can be such that reaction continues, as co-catalyst so as to consume remaining isocyanates list
Body, therefore separating monomer is avoided, it can effectively improve production efficiency, be more advantageous to the realization of industrialized production.
The present invention does not need to separate by thin-film distillation isolation technics during preparing linear (ring) aliphatic urea diketone
Unreacted isocyanate-monomer, hence it is evident that improve production efficiency, be advantageously implemented industrialization, therefore, there is bigger application
Space and implementary value.
Specific embodiment
Embodiment 1
500g isophorone diisocyanate (IPDI) 30 DEG C, dry nitrogen and stirring under with bis- Yue amino of 10g (2%) 4-
Pyridine (DMAP) catalyst is mixed together reaction, and after 20h, detection NCO content is 27.1%, and the reaction was continued, after 30h, inspection
Surveying NCO content is 27.4%, removes unreacted monomer under 140 DEG C and 30Pa pressure using rotary evaporator.Then it just obtains
A kind of highly viscous, light yellow urea-dione polyisocyanate, free NCO group content 18.0% are obtained, monomer IPDI content is
0.6%.
Embodiment 2
500g isophorone diisocyanate (IPDI) 30 DEG C, dry nitrogen and stirring under with bis- Yue ammonia of 10g (2wt%) 4-
Yl pyridines (DMAP) catalyst is mixed together reaction.After 20h, detection NCO content is 27.3%, and the reaction was continued, after 25h,
Detecting NCO content is 27.1%, and 5g (1wt%) propylene oxide, the reaction was continued 5h is added, and detection NCO content is 20.1%, is continued
5h is reacted, detection NCO content is 17.9%, by vacuum distillation removing propylene oxide at 30 DEG C, is then just obtained a kind of high
Spend sticky, light yellow urea-dione polyisocyanate.Detecting NCO content is 18.0%, and monomer IPDI content is 0.2%.
Embodiment 3
500g isophorone diisocyanate (IPDI) 30 DEG C, dry nitrogen and stirring under with bis- Yue ammonia of 5g (1wt%) 4-
Yl pyridines (DMAP) catalyst is mixed together reaction.After 25h, detection NCO content is 29.3%, and the reaction was continued, after 30h,
Detecting NCO content is 29.5%, and 2.5g (0.5wt%) propylene oxide, the reaction was continued 10h is added, and detection NCO content is
21.1%, the reaction was continued 5h, detection NCO content are 17.6%, are carried by vacuum distillation removing propylene oxide at 80 DEG C, then just
Obtain a kind of highly viscous, light yellow urea-dione polyisocyanate.Detecting NCO content is 17.9%, and monomer IPDI content is
0.1%.
Embodiment 4
500g isophorone diisocyanate (IPDI), 50 DEG C, dry nitrogen and stirring under with bis- Yue of 10g (2wt%) 4-
Aminopyridine (DMAP) catalyst is mixed together back flow reaction.After 15h, detection NCO content is 26.5%, and the reaction was continued,
After 20h, detection NCO content is 26.1%, and 5g (1wt%) propylene oxide, the reaction was continued 8h is added, and detection NCO content is
18.2%, by vacuum distillation removing propylene oxide at 50 DEG C, then just obtain it is a kind of it is highly viscous, light yellow urea diketone is more
Isocyanates.Detecting NCO content is 17.8%, and monomer IPDI content is 0.3%.
Embodiment 5
500g isophorone diisocyanate (IPDI), 50 DEG C, dry nitrogen and stirring under with bis- Yue ammonia of 5g (1wt%) 4-
Yl pyridines (DMAP) catalyst is mixed together back flow reaction.After 22h, detection NCO content is 26.0%, and the reaction was continued, 27h
Afterwards, detection NCO content is 25.9%, and 2.5g (0.5wt%) propylene oxide, the reaction was continued 10h is added, and detection NCO content is
17.8%, pass through vacuum distillation removing propylene oxide at 100 DEG C.Then a kind of highly viscous, light yellow urea diketone is just obtained
Polyisocyanates, detection NCO content are 17.6%, and monomer IPDI content is 0.1%.
Present invention disclosed above preferred embodiment is only intended to help to illustrate the present invention.There is no detailed for preferred embodiment
All details are described, are not limited the invention to the specific embodiments described.Obviously, according to the content of this specification,
It can make many modifications and variations.These embodiments are chosen and specifically described to this specification, is in order to better explain the present invention
Principle and practical application, so that skilled artisan be enable to better understand and utilize the present invention.The present invention is only
It is limited by claims and its full scope and equivalent.
Claims (8)
1. a kind of preparation method of aliphatic urea diketone, which is characterized in that specific preparation process is as follows:
Under 30 DEG C -50 DEG C of normal pressure, it is passed through dry nitrogen into reaction vessel, while diisocyanate and primary being added thereto
After reacting a period of time, when the content of NCO% is unchanged in detection reaction system, co-catalyst is added, until reaction in catalyst
Level of residual monomers is lower than 0.5%, and co-catalyst is then isolated from reaction mixture by vacuum distillation at 30-100 DEG C.
2. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that diisocyanate is same
Divide pentane diisocyanate, hexane diisocyanate resin, heptane diisocyanate, octane diisocyanate, the nonane two of isomery different
Cyanate, decane diisocyanate hendecane diisocyanate and dodecane diisocyanate and isophorone diisocyanate
One of.
3. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that the knot of preliminary catalytic agent
Structure formula is such as shown in (I)；
Wherein R in formula (I)1And R2It is that the alkyl of 1 to 8 identical or different carbon atom or the nitrogen being connect with R1 and R2 are former
Son is formed together 5- or 6-membered ring.
4. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that preliminary catalytic agent is 4-
Dimethylamino naphthyridine, 4- lignocaine pyridine, 4- pyrrolidinopyridine, 4- piperidines and pyridine and 4- (4- methyl piperidine base) pyridine
One of.
5. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that preliminary catalytic agent is 4-
Dimethylamino naphthyridine.
6. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that preliminary catalytic agent dosage
For 1-2wt%.
7. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that the structure of co-catalyst
Formula is such as shown in (II):
Wherein R in formula (II)1And R2For-H ,-CH3Or-CH2One of Cl.
8. a kind of preparation method of aliphatic urea diketone according to claim 1, which is characterized in that co-catalyst is epoxy
Compound, co-catalyst are one of propylene oxide, ethylene oxide, epoxy butane and epoxychloropropane.
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Family
ID=65930621
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912210A (en) * | 1987-11-21 | 1990-03-27 | Huels Aktiengesellschaft | Process for the preparation of (cyclo)aliphatic uretediones |
| CN101450928A (en) * | 2007-12-04 | 2009-06-10 | 拜尔材料科学股份公司 | Preparation of uretdione polyisocyanate |
| CN104271628A (en) * | 2012-05-08 | 2015-01-07 | 巴斯夫欧洲公司 | Preparation of polyisocyanates having isocyanurate groups and their use |
-
2018
- 2018-12-21 CN CN201811572071.3A patent/CN109574934A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912210A (en) * | 1987-11-21 | 1990-03-27 | Huels Aktiengesellschaft | Process for the preparation of (cyclo)aliphatic uretediones |
| CN101450928A (en) * | 2007-12-04 | 2009-06-10 | 拜尔材料科学股份公司 | Preparation of uretdione polyisocyanate |
| CN104271628A (en) * | 2012-05-08 | 2015-01-07 | 巴斯夫欧洲公司 | Preparation of polyisocyanates having isocyanurate groups and their use |
Non-Patent Citations (1)
| Title |
|---|
| JULIE ROUTIER ET AL.,: "Heterolignans: Stereoselective Synthesis of an 11-Amino Analog of Azaelliptitoxin", 《EUR. J. ORG. CHEM.》 * |
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Application publication date: 20190405 |