CN108689977A - A kind of compound depolymerizing agent and its application method of δ-valerolactone polymer - Google Patents
A kind of compound depolymerizing agent and its application method of δ-valerolactone polymer Download PDFInfo
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- CN108689977A CN108689977A CN201810716148.3A CN201810716148A CN108689977A CN 108689977 A CN108689977 A CN 108689977A CN 201810716148 A CN201810716148 A CN 201810716148A CN 108689977 A CN108689977 A CN 108689977A
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- depolymerizing agent
- compound
- valerolactone
- depolymerizing
- polymer
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Abstract
Present invention relates particularly to a kind of compound depolymerizing agent of δ-valerolactone polymer and its application methods.Compound depolymerizing agent includes depolymerizing agent, stabilizer and deicer, the depolymerizing agent is by stannous octoate and/or 1,3- disubstituted imidazole Cabbeens form, the stabilizer is made of the one or more of alkyl phosphorous acid, aromatic series phosphorous acid, hydroxy phenylpropionic acid, benzyl alcohol or hydroquinone, and the deicer is made of the one or more of clay, aluminium oxide, silica gel, zeolite, calcium chloride, calcium carbonate or saleratus.The application method of the compound depolymerizing agent includes the following steps:By δ-valerolactone polymeric seal in container, and fusing is heated under 85~95 DEG C of water bath conditions;δ-valerolactone polymer after fusing is transferred in four-hole bottle, condenser pipe is connected on four-hole bottle, compound depolymerizing agent is added into four-hole bottle, is heated, is stirred after standing reaction, δ-valerolactone crude product is obtained by the reaction.
Description
Technical field
The invention belongs to chemical technology fields, and in particular to a kind of compound depolymerizing agent of δ-valerolactone polymer and its use
Method.
Background technology
δ-valerolactone (Delta-Valerolactone) also known as 1,5- valerolactones, tetrahydrochysene-α-pyranone, ring valerolactone
Deng.δ-valerolactone is a kind of colourless or light yellow liquid with aromatic odor, is slightly soluble in water, be soluble in ethyl alcohol, ether, benzene,
Acetone and other organic solvent, when standing, easily polymerize itself.δ-valerolactone is a kind of important organic intermediate raw material, easily with oneself
The esters such as lactone polymerize, generate polyactide, because polyactide have it is soft, transparent, degradable, can be used to handle wound in medical field
Mouthful etc..There is δ-valerolactone aromatic odor can be additionally used in the daily chemical products such as suncream, daily detergent;With good flexible
Property, plasticity, are widely used in synthesizing optical substance, such as the raw material of liquid crystal.
δ-valerolactone is a kind of chemical substance that strain energy is high, can be polymerized to polymer certainly at normal temperatures.Production and
Certain polymerization can also occur in distillation process, long-time continuous production can cause due to the polymerization of δ-valerolactone except being expected
Outage.The δ-valerolactone resting period grows easy autohemagglutination and forms colourless or lurid solid, it is therefore desirable to which exploitation is a kind of new
The depolymerizing agent of type, to ensure to produce long-term normal operation, product shelf life extends, and is current urgent problem to be solved.
Currently, the documents and materials not yet in terms of δ-valerolactone depolymerization disclose report both at home and abroad.But about similar
The depolymerization of substance caprolactone polymers reports that United States Patent (USP) US4360682 reports a kind of in dihydroxy benzenes series compound
Hydroquinone stablize caprolactone, but mainly stablize coloration, without preferable inhibition.Patent CN104292205A, will
It is one or more of as polymerization inhibitor in primary amine, secondary amine or tertiary amine compounds, it is under conditions of 0~200 DEG C, caprolactone is oligomeric
Object and polymerization inhibitor are stirred, and are sealed, and have certain polymerization inhibition effect.Patent CN104557846A, in 6-caprolactone rectifying
In the process, polymerization inhibitor monomer diethyl hydroxylamine and polymerization inhibitor monomer tert-butyl catechol, hydroquinone and adjacent nitre are separately added into
One or more of base phenol, as a result the purity of 6-caprolactone increases, while reducing the generation of polymerisation, also solves
The problem of equipment blocks in production process.Patent CN104292206A, with the first, second, third and fourth main group in the periodic table of elements and
In 8th race one or more of oxide, hydroxide or carbonate of element be used as polymerization inhibitor, temperature be 100~
Under conditions of 500 DEG C and 0.5~80kpa of pressure, caprolactone polymers depolymerization can be made.To make the δ-valerolactone polymer having polymerize
Depolymerization, makes solid polymer become liquid monomer, and inventor has carried out a series of scientific experiment research.
Invention content
The purpose of the present invention is to provide the compound depolymerizing agent of δ-valerolactone polymer, in the δ-penta that can be formed to polymerization
Ester carries out depolymerization and effectively prevents polymerizeing again for δ-valerolactone, prevents δ-valerolactone polymer from generating and its to line equipment
Blocking.
The present invention provides following technical scheme:A kind of compound depolymerizing agent of δ-valerolactone polymer, the compound depolymerizing agent
Including depolymerizing agent, stabilizer and deicer, the depolymerizing agent is by stannous octoate and/or 1,3- disubstituted imidazole Cabbeens composition, institute
State one or more of the stabilizer by alkyl phosphorous acid, aromatic series phosphorous acid, hydroxy phenylpropionic acid, benzyl alcohol or hydroquinone
Composition, the deicer by clay, aluminium oxide, silica gel, zeolite, calcium chloride, calcium carbonate or saleratus it is one or two kinds of with
Upper composition.
Further, in mass, the depolymerizing agent:Stabilizer:Deicer is (50~150):(1~10):(5~
15)。
Preferably, the depolymerizing agent is by stannous octoate and 1,3- disubstituted imidazole Cabbeens composition;In mass, octanoic acid is sub-
Tin:1,3- disubstituted imidazole Cabbeens:Stabilizer:Deicer is 60:40:5:15.
The application method of the compound depolymerizing agent, includes the following steps:
Step 1:By δ-valerolactone polymeric seal in container, and fusing is heated under 85~95 DEG C of water bath conditions;
Step 2:δ-valerolactone polymer after fusing is transferred in four-hole bottle, condenser pipe is connected on four-hole bottle, it is described cold
Solidifying pipe connects reception device, and compound depolymerizing agent is added into four-hole bottle, heats, and stands reaction 0.3h~0.5h, then stirring is anti-
1~5h is answered to obtain δ-valerolactone crude product.The reception device is vacuum distillation fraction receiver/head.
Further, the temperature reacted described in step 2 is controlled at 150~240 DEG C.
Further, the absolute pressure reacted described in step 2 is controlled in 0MPa~0.1MPa.
Further, compound depolymerizing agent accounts for 0.1~2wt% of δ-valerolactone polymer in step 2.
δ-valerolactone polymer depolymerizing agent of the present invention, there is following positive effect:Depolymerizing agent raw material sources of the present invention are rich
Rich, at low cost, preparation process is simple;Under the action of depolymerizing agent of the present invention, depolymerization process mild condition is easy to operate;This hair
Bright depolymerizing agent achieves δ-valerolactone polymer excellent depolymerization effect, and yield can reach after δ-valerolactone polymer depolymerization
90% or so, depolymerization product purity can reach 80% or more, and coloration is less than 10Hazen, and moisture is less than 700ppm, economical
Benefit is apparent, has good commercial introduction value.
Specific implementation mode
Following embodiment is not used to limit protection scope of the present invention for illustrating the present invention.Unless otherwise specified, real
Apply the conventional means that technological means used in example is well known to those skilled in the art.
Embodiment 1
A kind of compound depolymerizing agent of δ-valerolactone polymer, the compound depolymerizing agent include depolymerizing agent, stabilizer and deicer, institute
Depolymerizing agent is stated to be made of stannous octoate and/or 1,3- disubstituted imidazole Cabbeens;Stabilizer selects alkyl phosphorous acid;Deicer is selected
Calcium carbonate.With depolymerizing agent:Stabilizer:Deicer is 100:5:The ratio of 15 (by mass) carrys out the compound depolymerizing agent of mixed preparing.
Depolymerization experiment according to 6 groups of the content difference point of stannous octoate in compound depolymerizing agent and 1,3- disubstituted imidazole Cabbeens into
Row, the 1st group:Without stannous octoate, only 1,3- disubstituted imidazole Cabbeens;2nd group:Stannous octoate and 1,3- disubstituted imidazole Cabbeens
Mass ratio be 1:4;3rd group:The mass ratio of stannous octoate and 1,3- disubstituted imidazole Cabbeens is 2:3;4th group:Stannous octoate
Mass ratio with 1,3- disubstituted imidazole Cabbeens is 3:2;5th group:The mass ratio of stannous octoate and 1,3- disubstituted imidazole Cabbeens
It is 4:1;6th group:Without 1,3- disubstituted imidazole Cabbeens, only stannous octoate.
The depolymehzation step of δ-valerolactone polymer is as follows:It respectively will be in the 300g δ-penta that melted under 85~95 DEG C of water bath conditions
Ester polymer is placed in the four-hole boiling flask of 6 500mL, is then respectively adding the compound depolymerizing agents of 3.6g, and electric jacket heats, 200 DEG C
Under the conditions of stand reaction 0.5h, be stirred to react 5h.After depolymerization, by sample weighing, its yield, and further sampling point are calculated
The purity, coloration and moisture of δ-valerolactone in division object.
As a result it shows:Stannous octoate:1,3- disubstituted imidazole Cabbeens:Alkyl phosphorous acid:Calcium carbonate is 60:40:5:15 (press
Quality meter) when, the yield of δ-valerolactone is higher, is 90.26%;Depolymerization product purity is 84.27%;Coloration is 6;Moisture
For 639ppm.The compound depolymerizing agent of different ratio refers to table 1 to the depolymerization situation of δ-valerolactone polymer.
The depolymerization situation of the lower δ-valerolactone polymer of the compound depolymerizing agent effect of 1 different ratio of table
Embodiment 2
With depolymerizing agent:Stabilizer:Deicer mass ratio is 100:5:15 ratio carrys out mixed preparing depolymerizing agent.Wherein depolymerizing agent is
The mass ratio of stannous octoate and 1,3- disubstituted imidazole Cabbeens, stannous octoate and 1,3- disubstituted imidazole Cabbeens is 3:2;Stabilizer
It is made of the one or more of alkyl phosphorous acid, aromatic series phosphorous acid, hydroxy phenylpropionic acid, benzyl alcohol or hydroquinone;It removes
Aqua is made of the one or more of clay, aluminium oxide, silica gel, zeolite, calcium chloride, calcium carbonate or saleratus.
Depolymerization experiment is according to point 5 groups of progress of the difference of stabilizer and deicer in compound depolymerizing agent, the 7th group:Stabilizer is
Hydroxy phenylpropionic acid, deicer are calcium carbonate and aluminium oxide, and the mass ratio of calcium carbonate and aluminium oxide is 1:1;8th group:Stabilizer is
Benzyl alcohol, deicer are calcium carbonate;9th group:Stabilizer is alkyl phosphorous acid, and deicer is calcium carbonate;10th group:Stabilizer is
Alkyl phosphorous acid, deicer are aluminium oxide;11st group:Stabilizer is alkyl phosphorous acid and hydroquinone, alkyl phosphorous acid and right
The mass ratio of benzenediol is 1:1, deicer is calcium chloride.
The depolymehzation step of δ-valerolactone polymer is as follows:It respectively will be in the 300g δ-penta that melted under 85~95 DEG C of water bath conditions
Ester polymer is placed in the four-hole boiling flask of 5 500mL, is separately added into the compound depolymerizing agents of 3.6g, electric jacket heating, 200 DEG C of conditions
Lower standing reacts 0.5h, is stirred to react 5h.After depolymerization, by sample weighing, its yield, and further sampling analysis solution are calculated
The purity, coloration of δ-valerolactone, moisture in poly- product.
As a result it shows:Under identical depolymerizing agent, different stabilizers, deicer is added, there is depolymerization effect, but it is sad
The combined effect of stannous+1,3- disubstituted imidazoles Cabbeen+alkyl phosphorous acid+calcium carbonate is preferable, and the yield of δ-valerolactone is higher,
It is 90.75%;Depolymerization product purity is 85.69%;Coloration is 8;Moisture is 656ppm.Under the effect of different composite depolymerizing agent
The depolymerization situation of δ-valerolactone polymer see the table below 2.
The depolymerization situation of the lower δ-valerolactone polymer of 2 different composite depolymerizing agent of table effect
3 comparative examples of embodiment
The δ-valerolactone polymer of 300g is placed in the four-hole boiling flask of 500mL, electric jacket heating, is stood under the conditions of 200 DEG C anti-
0.5h is answered, 5h is stirred to react.After depolymerization, by sample weighing, its yield, and further δ-penta in sampling analysis product are calculated
Purity, coloration and the moisture of lactone.
The results show that the yield of δ-valerolactone is 10.23%;Purity is 41.32wt%.It is shown in Table 3.
The depolymerization situation of 3 control group of table
Group | Yield (%) | Purity (wt%) |
12 (controls) | 10.23 | 41.32 |
Embodiment 4
A kind of compound depolymerizing agent of δ-valerolactone polymer, the compound depolymerizing agent include depolymerizing agent, stabilizer and deicer, institute
Depolymerizing agent is stated to be made of stannous octoate and 1,3- disubstituted imidazole Cabbeens;Stabilizer selects alkyl phosphorous acid;Deicer selects carbon
Sour calcium.With stannous octoate:1,3- disubstituted imidazole Cabbeens:Alkyl phosphorous acid:Calcium carbonate is 60:40:5:15 (by mass)
Ratio carrys out the compound depolymerizing agent of mixed preparing.
Depolymerization experiment is according to 3 groups of progress of the difference of depolymerization reaction temperature point:13rd group, reaction temperature is 180 DEG C;14th
Group, reaction temperature are 200 DEG C;15th group, reaction temperature is 220 DEG C.
The depolymehzation step of δ-valerolactone polymer is as follows:It respectively will be in the 300g δ-penta that melted under 85~95 DEG C of water bath conditions
Ester polymer is placed in the four-hole boiling flask of 3 500mL, is separately added into the compound depolymerizing agents of 3.6g, electric jacket heating, 200 DEG C of conditions
Lower standing reacts 0.5h, is stirred to react 5h.After depolymerization, by sample weighing, its yield, and further sampling analysis production are calculated
The purity, coloration of δ-valerolactone, moisture in object.
The results show that when reaction temperature is 200 DEG C, yield is higher, is 91.19%;The purity of depolymerization product is
84.93%;Coloration is 9;Moisture is 612ppm.The depolymerization situation of δ-valerolactone polymer, is shown in Table at a temperature of differential responses
4。
The depolymerization situation of δ-valerolactone polymer at a temperature of 4 differential responses of table
Embodiment 5
A kind of compound depolymerizing agent of δ-valerolactone polymer, the compound depolymerizing agent include depolymerizing agent, stabilizer and deicer, institute
Depolymerizing agent is stated to be made of stannous octoate and 1,3- disubstituted imidazole Cabbeens;Stabilizer selects alkyl phosphorous acid;Deicer selects carbon
Sour calcium.With stannous octoate:1,3- disubstituted imidazole Cabbeens:Alkyl phosphorous acid:Calcium carbonate is 60:40:5:15 (by mass)
Ratio carrys out the compound depolymerizing agent of mixed preparing.
Depolymerization experiment is according to point 3 groups of progress of the difference of depolymerization reaction pressure, the 16th group:Reaction pressure is 0MPa;17th group:
Reaction pressure is 0.02MPa;18th group:Reaction pressure is 0.04MPa.
The depolymehzation step of δ-valerolactone polymer is as follows:It respectively will be in the 300g δ-penta that melted under 85~95 DEG C of water bath conditions
Ester polymer is placed in the four-hole boiling flask of 3 500mL, is separately added into the compound depolymerizing agents of 3.6g, electric jacket heating, 200 DEG C of conditions
Lower standing reacts 0.5h, is stirred to react 5h.After depolymerization, by sample weighing, its yield, and further sampling analysis production are calculated
The purity, coloration of δ-valerolactone, moisture in object.
The results show that when reaction pressure is 0MPa, δ-valerolactone yield is 90.49%;The purity of depolymerization product is
85.53%, coloration 8;Moisture is 642ppm.The depolymerization situation of δ-valerolactone polymer, is shown in Table under differential responses pressure
5.The reaction pressure is absolute pressure.
The depolymerization situation of δ-valerolactone polymer under 5 differential responses pressure of table
Embodiment 6
A kind of compound depolymerizing agent of δ-valerolactone polymer, the compound depolymerizing agent include depolymerizing agent, stabilizer and deicer, institute
Depolymerizing agent is stated to be made of stannous octoate and 1,3- disubstituted imidazole Cabbeens;Stabilizer selects alkyl phosphorous acid;Deicer selects carbon
Sour calcium.With stannous octoate:1,3- disubstituted imidazole Cabbeens:Alkyl phosphorous acid:Calcium carbonate is 60:40:5:15 (by mass)
Ratio carrys out the compound depolymerizing agent of mixed preparing.
Depolymerization experiment accounted for according to compound depolymerizing agent dosage the difference points 4 groups of the mass percent of δ-valerolactone polymer into
Row, the 19th group:Compound depolymerizing agent dosage is the 0.42wt% of δ-valerolactone polymer;20th group:Compound depolymerizing agent dosage is δ-
The 0.83wt% of valerolactone polymer;21st group:Compound depolymerizing agent dosage is the 1.2wt% of δ-valerolactone polymer;22nd group:
Compound depolymerizing agent dosage is the 1.67wt% of δ-valerolactone polymer.
The depolymehzation step of δ-valerolactone polymer is as follows:It respectively will be in the 300g δ-penta that melted under 85~95 DEG C of water bath conditions
Ester polymer is placed in the four-hole boiling flask of 4 500mL, is separately added into the compound depolymerizing agent of 1.25g, 2.5g, 3.6g, 5g, electric jacket
It heats, reaction 0.5h is stood under the conditions of 200 DEG C, is stirred to react 5h.After depolymerization, by sample weighing, its yield is calculated, is gone forward side by side
The purity, coloration of δ-valerolactone, moisture in one step sampling analysis product.
The results show that when compound depolymerizing agent dosage is the 1.2wt% of δ-valerolactone polymer, the yield of δ-valerolactone compared with
Height is 90.81%;The purity of depolymerization product is 84.87%;Coloration is 9;Moisture is 621ppm.Different composite depolymerizing agent
The depolymerization situation of δ-valerolactone polymer is shown in Table 6 under dosage.
The depolymerization situation of δ-valerolactone polymer under 6 different composite depolymerizing agent dosage of table
Examples 1 to 6 show after δ-valerolactone polymer depolymerization crude product purity 82%~90%, coloration 4~9,
Moisture is in 610ppm~700ppm, and for yield 75%~91%, δ-valerolactone polymer depolymerization effect is preferable.
Embodiment 7
Further to investigate the stability of gained depolymerizing substance, 22 groups of crude products that Examples 1 to 6 depolymerization is gone out place water white transparency
Vial in, Room-temperature seal preserve 3 months, observe its color state within every 1 month, the stability of depolymerization crude product examined
It examines, the results show that preferable using the δ-valerolactone crude product stability that depolymerization of the present invention goes out, storage 3 months is unchanged.It is shown in Table 7.
It is subsequent by the way that the further rectifying of the depolymerized product, purification processes, δ-valerolactone product quality is significantly improved, and reaches production
Product sale requires.
Depolymerization sample product storage stability obtained by the different embodiments of table 7
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Any one skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (7)
1. a kind of compound depolymerizing agent of δ-valerolactone polymer, which is characterized in that the compound depolymerizing agent is by depolymerizing agent, stabilizer
It is formed with deicer,
The depolymerizing agent is made of stannous octoate and/or 1,3- disubstituted imidazole Cabbeens,
The stabilizer by alkyl phosphorous acid, aromatic series phosphorous acid, hydroxy phenylpropionic acid, benzyl alcohol or hydroquinone one kind or two
Kind composition described above,
The deicer by clay, aluminium oxide, silica gel, zeolite, calcium chloride, calcium carbonate or saleratus one or more
Composition.
2. compound depolymerizing agent according to claim 1, which is characterized in that in mass, the depolymerizing agent:Stabilizer:It removes
Aqua is(50~150):(1~10):(5~15).
3. compound depolymerizing agent according to claim 1, which is characterized in that the depolymerizing agent is taken by stannous octoate and 1,3- bis-
It is formed for imidazole carbenes;In mass, stannous octoate:1,3- disubstituted imidazole Cabbeens:Stabilizer:Deicer is 60:40:5:
15。
4. the application method based on compound depolymerizing agent described in claim 1, which is characterized in that include the following steps:
Step 1:By δ-valerolactone polymeric seal in container, and fusing is heated under 85~95 DEG C of water bath conditions;
Step 2:δ-valerolactone polymer after fusing is transferred in four-hole bottle, condenser pipe is connected on four-hole bottle, it is described cold
Solidifying pipe connects reception device, and compound depolymerizing agent is added into four-hole bottle, heats, and stands reaction 0.3h~0.5h, then stirring is anti-
1~5h is answered to obtain δ-valerolactone crude product.
5. the application method of compound depolymerizing agent according to claim 4, which is characterized in that the temperature reacted described in step 2
Degree control is at 150~240 DEG C.
6. the application method of compound depolymerizing agent according to claim 4, which is characterized in that is reacted described in step 2 is exhausted
Pressure is controlled in 0MPa~0.1MPa.
7. the application method of compound depolymerizing agent according to claim 4, which is characterized in that compound depolymerizing agent accounts in step 2
0.1~2wt% of δ-valerolactone polymer.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1706878A (en) * | 2005-04-15 | 2005-12-14 | 浙江大学 | Metal-less N-heterocyclic carbone catalyst and its prepn process |
CN101100527A (en) * | 2002-12-26 | 2008-01-09 | 国际商业机器公司 | Catalytic depolymerization of polymers containing electrophilic linkages using nucleophilic reagents |
CN105017205A (en) * | 2015-07-17 | 2015-11-04 | 江苏红太阳新材料有限公司 | Epsilon-caprolactone polymerization inhibitor and application thereof |
US20170247350A1 (en) * | 2016-02-29 | 2017-08-31 | Regents Of The University Of Minnesota | Recovery of monomer from polyurethane materials by depolymerization |
-
2018
- 2018-06-30 CN CN201810716148.3A patent/CN108689977A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101100527A (en) * | 2002-12-26 | 2008-01-09 | 国际商业机器公司 | Catalytic depolymerization of polymers containing electrophilic linkages using nucleophilic reagents |
CN1706878A (en) * | 2005-04-15 | 2005-12-14 | 浙江大学 | Metal-less N-heterocyclic carbone catalyst and its prepn process |
CN105017205A (en) * | 2015-07-17 | 2015-11-04 | 江苏红太阳新材料有限公司 | Epsilon-caprolactone polymerization inhibitor and application thereof |
US20170247350A1 (en) * | 2016-02-29 | 2017-08-31 | Regents Of The University Of Minnesota | Recovery of monomer from polyurethane materials by depolymerization |
Non-Patent Citations (2)
Title |
---|
I. S. MEGNA,ET AL: "THE DEPOLYMERIZATION OF POLY-ɛ-CAPROLACTONE WITH TITANIUM CATALYSTS", 《POLYMER LETTERS》 * |
M.GRUVEGÅRD,ET AL: "RANDOM COPOLYMERS OF 1,5-DIOXEPAN-2-ONE", 《J.M.S.-PURE APPL. CHEM.》 * |
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Application publication date: 20181023 |