CN107383980A - A kind of active ultra-violet absorber and its application method - Google Patents
A kind of active ultra-violet absorber and its application method Download PDFInfo
- Publication number
- CN107383980A CN107383980A CN201710478509.0A CN201710478509A CN107383980A CN 107383980 A CN107383980 A CN 107383980A CN 201710478509 A CN201710478509 A CN 201710478509A CN 107383980 A CN107383980 A CN 107383980A
- Authority
- CN
- China
- Prior art keywords
- hydroxyl
- chlorobenzotriazoles
- violet absorber
- glycidoxy
- coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/32—Radiation-absorbing paints
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
Abstract
The invention discloses a kind of active ultra-violet absorber, including 2（2 ' hydroxyls 4 '（2 ", 3 " glycidoxies）5 chlorobenzotriazoles and/or 2（2 ' hydroxyls 5 '（2 ", 3 " glycidoxies）5 chlorobenzotriazoles.Active the ultra-violet absorber resistance to migration and security of the present invention is more preferable, and compared with the active ultraviolet absorber of other reports, it has wider array of applicability, more easily Adding Way, directly can be added in coating, adhesive formulation.
Description
Technical field
The present invention relates to technical field of fine, particularly a kind of active ultra-violet absorber and its application method.
Background technology
It is well known that sightless ultraviolet is carried in natural light（290-380 nm）, its energy is high, is to cause organic material
One of an important factor for expecting degradation with aging.So the material under being typically exposed to UV needs to add certain ultraviolet absorber or light
Stabilizer.In paint solidification layer, when being polluted by sunlight, greasy dirt etc., the chain rupture of dope layer interior polymer, free radical production may be made
Raw, configuration changes etc., to making coating material gloss decline, turn to be yellow, fade, become fragile or even efflorescence etc..Or during for varnish, UV
The protected base material of direct irradiation, make to be occurred by the decline of protection materials gloss, jaundice, colour fading etc..To solve this problem, typically exist
Light stabilizer, such as ultraviolet absorber are added in material.Although in general light stabilizer persistence in organic system is preferable,
Under rugged environment, the light stabilizer of addition is still to migrate out.Have been reported that research shows ultraviolet absorber in fat
Moved out in class organomimetic phenomenon；Stripping quantity extension over time and increase, migration migration rate at initial stage is very fast, necessarily
Transition process can reach dynamic equilibrium after time；Temperature is higher, and migration rate is faster, and it is shorter to reach the time of balance, the amount of moving out
It is higher；Material is more thin more is easy to moving out for ultraviolet absorber.Ultraviolet absorber is moved out, and on the one hand makes organic layer light stability
Decline, reduce its life-span, on the other hand, if for food, medicine aspect when, to its security produce infringement.
In the development of material high additive value, high-weatherability, the demand of security are also increasingly deepened, therefore to ultraviolet
The raising of absorbent properties proposes needs.Response type ultraviolet vapor receipts are not easy to be vaporized and dissolution, obtain high security and length
The high-weatherability polymeric material of phase stabilization.
Had partial reaction type ultraviolet absorber report at present, the research of response type ultraviolet absorption agent had at nearly 20 years compared with
More article, patent and products, for example, Japanese great Zhong chemical companies production RUVA-100, Norameo company production
The Norbloc 7966 and Cyasorb-416 of CYTEC companies production, patent CN105348131, CN103321041,
CN102584727（Arranged for textile material）、CN100552125（Arranged for textile material）Deng.
It is existing problem be its reactivity, applicability it is not comprehensive.Such as RUVA-100, Norbloc 7966, Cyasorb-
The product reactivity reported in 416 and patent CN105348131 be based on acryloyl group, its reactivity be confined to there is double bond oneself
By the reaction of base, reaction needs initiator, and when being added in current material formula, initiator residual plays opposite with light stabilizer
Effect, so being typically aggregated in advance in resin in the form of copolymerization, be not easy to（Coating, adhesive）Directly add in formula
Enter.And for example, ultraviolet absorber（2,4 dihydroxyl benzophenone, 2- hydroxybenzotriazoles）, on hydroxyl can with containing activity it is different
Cyano group reacts and fixed, and still, the hydroxyl of 2 destroys original excited state intramolecular proton transfer after being reacted（By photon
Energy absorption is simultaneously converted into interior amount）Process, its unfavorable light stabilization.
The content of the invention
To solve the technical problem described in technical background, the present invention is the shortcomings that overcoming above-mentioned prior art and deficiency,
It is an object of the invention to provide a kind of ultraviolet absorber of active structure, and it can be by simply reacting to obtain.With it is other non-
Active ultraviolet absorber is compared, and active the ultraviolet absorber resistance to migration and security of invention are more preferable, the activity with other reports
Ultraviolet absorber is compared, and it has wider array of applicability, more easily Adding Way, can directly be existed（Coating, adhesive）In formula
Add.
The present invention can be achieved through the following technical solutions：
The invention discloses a kind of active ultra-violet absorber, including 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）-5-
Chlorobenzotriazole and/or 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles, its chemical constitution are as follows：
Ⅰ Ⅱ
In structural formula, structural formula I corresponds to 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles；Structural formula
II corresponding 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
In above structural formula, chemical constitution can be formed altogether with uv absorption property with multiple material
The crosslinking of valence link, UV absorbing wavelengths are 270 ~ 380 nm.
Further, 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles（Ⅰ）Preparation method
For：With 2,4- dihydroxy -5- chlorobenzotriazoles and epoxychloropropane for raw material, sodium hydroxide is catalyst, according to mol ratio 1：
1.1-5：1.1, reacted under solvents tetrahydrofurane, add base catalyst, reaction temperature is 60-80 DEG C, reaction time 2-8
H, washing after reaction terminates, dry, removal of solvent under reduced pressure and unreacted epoxychloropropane, can by column chromatography or recrystallize into
One step separating-purifying, obtains solid product I.
Further, the 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles（Ⅱ）Preparation
Method is：With 2,5- dihydroxy -5- chlorobenzotriazoles and epoxychloropropane for raw material, sodium hydroxide is catalyst, according to mole
Than 1：1.1-5：1.1, reacted under solvents tetrahydrofurane, add base catalyst, reaction temperature 60-80oC, reaction time
For 2-8 h, washing after reaction terminates, dry, removal of solvent under reduced pressure and unreacted epoxychloropropane, can by column chromatography or again
Further separating-purifying is crystallized, obtains solid product II.
A kind of application method of above-mentioned active ultra-violet absorber, adds and is used in coating or adhesive, in coating or
Addition is 0.1-6wt% in adhesive formulation.
Further, sulfydryl, amido or active ring epoxide are contained in the coating, the active ultra-violet absorber is direct
Added with formula.
Further, hydroxyl, carboxyl in the coating, while appropriate Lewis Acid metal catalysis is added in coating
Agent, and heated baking paint film.
Further, the hydroxyl is the hydroxyl outside phenolic hydroxyl group, and the amido is brothers amido.
The active ultra-violet absorber of the present invention has following beneficial technique effect：（1）It is ultraviolet to be prepared for a kind of response type
Absorbent, it can react, can be directly added into formula with various kinds of resin material；（2）Preparation method is simple；（3）The work of invention
Property ultraviolet absorber resistance to migration and security it is more preferable, compared with the active ultraviolet absorber of other reports, it has wider array of suitable
With property, can directly exist（Coating, adhesive）Added in formula.
Embodiment
In order that those skilled in the art will better understand the technical solution of the present invention, with reference to embodiment and to this
Invention product is described in further detail.
Embodiment 1
The invention discloses a kind of active ultra-violet absorber, 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzenes
And triazole, its chemical constitution are as follows：
Ⅰ
In structural formula, structural formula I corresponds to 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
10.00 g 2,4- dihydroxy -5- chlorobenzotriazoles are added in round-bottomed flask, add the g of epoxychloropropane 5,
150 ml tetrahydrofuran solvent is added, adds 1.67 g catalyst sodium hydroxide, reaction temperature 80oC, reaction time
For 2-8 h, reaction is washed after terminating, dried, and removal of solvent under reduced pressure and unreacted epoxychloropropane, end product can pass through post
Chromatography purifies, and obtains solid product I, yield 78%.
Embodiment 2
The invention discloses a kind of active ultra-violet absorber, 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzenes
And triazole, its chemical constitution are as follows：
Ⅱ
II corresponding 2- of structural formula（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
10.00 g 2,5- dihydroxy -5- chlorobenzotriazoles are added in round-bottomed flask, add the g of epoxychloropropane 10,
150 ml tetrahydrofuran solvent is added, adds 2 g catalyst sodium hydroxide, reaction temperature 80oC, reaction time 2-
8 h, reaction are washed after terminating, dried, and removal of solvent under reduced pressure and unreacted epoxychloropropane, end product can pass through column chromatography
Separating-purifying, obtain solid product II, yield 75%.
Embodiment 3
The invention discloses a kind of active ultra-violet absorber, 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzenes
And its chemical constitution of triazole is as follows：
Ⅰ
In structural formula, structural formula I corresponds to 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
The application method of above-mentioned active ultra-violet absorber, add and used in coating, addition is in formulation for coating material
0.5wt%.The coating is bi-component epoxy coating, and active ultra-violet absorber is directly added into epoxy component.
Embodiment 4
The invention discloses a kind of active ultra-violet absorber 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzenes
And triazole, its chemical constitution are as follows：
Ⅱ
II corresponding 2- of structural formula（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
The application method of above-mentioned active ultra-violet absorber, adds and is used in coating, matches somebody with somebody in hydroxy acryl acid coating
Addition is 0.5wt% in side.Lewis Acid metal catalyst, and heated baking paint film are added in coating simultaneously.
Embodiment 5
The invention discloses a kind of active ultra-violet absorber, including 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）-5-
Its chemical constitution of chlorobenzotriazole is as follows：
Ⅰ
In structural formula, structural formula I corresponds to 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
The application method of above-mentioned active ultra-violet absorber, adds and is used in adhesive, added in adhesive formulation
Measure as 0.2wt%.The adhesive is epoxy AB glue, and active ultra-violet absorber adds epoxy component.
Embodiment 6
The invention discloses a kind of active ultra-violet absorber, 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzenes
And triazole, its chemical constitution are as follows：
Ⅱ
In structural formula, II corresponding 2- of structural formula（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
The application method of above-mentioned active ultra-violet absorber, adds and is used in adhesive, the addition in viscose glue formula
For 0.1%, the adhesive is polyurethane adhesive.
Embodiment 7
The II of the 0.3 g g of above-mentioned product I and 0.3 is taken, the polyurethane paint of 100 g one pack systems is added with formula, makes stirring equal
It is even, the not transportable coating of ultraviolet absorber is obtained after dried coating film.
At the same time, in order to assess the technique effect of the present invention, correlated performance test, tool are carried out to embodiment 3~7 respectively
Body examination test result difference is as shown in table 1：
The test result of table 1
| Performance indications | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 |
| Rate of absorbing UV | >95% | >92% | >85% | >82% | >95% |
| Frosting | It is no | It is no | It is no | It is no | It is no |
Absorptivity measures absorbing state at 320 nm with fiber spectrometer at purple, and rate of absorbing UV is defined as：
ABlankFor the value of each embodiment film or adhesive film blank sample in fiber spectrum at 320 nm, ASampleFor different embodiment samples
Value of the product in fiber spectrum at 320 nm.
The foregoing is only a preferred embodiment of the present invention, not makees any formal limitation to the present invention；It is all
The those of ordinary skill of the industry can be shown in by specification and described above and swimmingly implement the present invention；It is but all familiar
Professional and technical personnel without departing from the scope of the present invention, makes using disclosed above technology contents
A little variation, modification and evolution equivalent variations, be the present invention equivalent embodiment；Meanwhile all realities according to the present invention
Variation, modification and evolution of any equivalent variations that matter technology is made to above example etc., still fall within the technology of the present invention
Within the protection domain of scheme.
Claims (6)
1. a kind of active ultra-violet absorber, it is characterised in that including 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）-5-
Chlorobenzotriazole and/or 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles, its chemical constitution are as follows：
Ⅰ Ⅱ
In structural formula, structural formula I corresponds to 2-（2 '-hydroxyl -4 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles；Structural formula
II corresponding 2-（2 '-hydroxyl -5 ' -（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles.
2. active ultra-violet absorber according to claim 1, it is characterised in that：2-（2 '-hydroxyl -4 ' -（2”, 3”-
Glycidoxy）- 5- chlorobenzotriazoles（Ⅰ）Preparation method be：With 2,4- dihydroxy -5- chlorobenzotriazoles and epoxychloropropane
For raw material, sodium hydroxide is catalyst, according to mol ratio 1：1.1-5：1.1, reacted under solvents tetrahydrofurane, add alkalescence and urge
Agent, reaction temperature are 60-80 DEG C, and the reaction time be 2-8 h, washing, drying, removal of solvent under reduced pressure and not anti-after reaction terminates
The epoxychloropropane answered, solid product I can be obtained by column chromatography or the further separating-purifying of recrystallization.
3. active ultra-violet absorber according to claim 1 or 2, it is characterised in that：The 2-（2 '-hydroxyl -5 ' -
（2 ", 3 "-glycidoxy）- 5- chlorobenzotriazoles（Ⅱ）Preparation method be：With 2,5- dihydroxy -5- chlorobenzotriazoles and
Epoxychloropropane is raw material, and sodium hydroxide is catalyst, according to mol ratio 1：1.1-5：1.1, reacted under solvents tetrahydrofurane,
Add base catalyst, reaction temperature 60-80oC, reaction time are 2-8 h, and reaction is washed after terminating, dried, and decompression removes
Solvent and unreacted epoxychloropropane are removed, solid product II can be obtained by column chromatography or the further separating-purifying of recrystallization.
A kind of 4. application method of the active ultra-violet absorber described in claim 1-3, it is characterised in that：Addition in coating or
Used in adhesive, addition is 0.1-6wt% in coating or adhesive formulation.
5. the application method of active ultra-violet absorber according to claim 4, it is characterised in that：The coating is gluing
Contain amido, active ring epoxide or sulfydryl in agent, the active ultra-violet absorber directly adds with formula.
6. active ultra-violet absorber according to claim 4, it is characterised in that：Hydroxyl, carboxyl in the coating, together
When appropriate Lewis Acid metal catalyst, and heated baking paint film are added in coating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710478509.0A CN107383980B (en) | 2017-06-22 | 2017-06-22 | A kind of activity ultraviolet absorbing agent and its application method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710478509.0A CN107383980B (en) | 2017-06-22 | 2017-06-22 | A kind of activity ultraviolet absorbing agent and its application method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107383980A true CN107383980A (en) | 2017-11-24 |
| CN107383980B CN107383980B (en) | 2019-10-25 |
Family
ID=60332546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710478509.0A Active CN107383980B (en) | 2017-06-22 | 2017-06-22 | A kind of activity ultraviolet absorbing agent and its application method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107383980B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552250A (en) * | 2020-12-14 | 2021-03-26 | 利安隆(天津)新材料科技有限公司 | Reactive benzotriazole compound, application thereof and high polymer material comprising reactive benzotriazole compound |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101717372A (en) * | 2009-11-20 | 2010-06-02 | 大连化工研究设计院 | Method for synthesizing substituted benzotriazole compound |
| CN102675823A (en) * | 2011-03-18 | 2012-09-19 | 唐来江 | Preparation process of transparent epoxy nanocomposite material for encapsulating high-power LED (light-emitting diode) |
-
2017
- 2017-06-22 CN CN201710478509.0A patent/CN107383980B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101717372A (en) * | 2009-11-20 | 2010-06-02 | 大连化工研究设计院 | Method for synthesizing substituted benzotriazole compound |
| CN102675823A (en) * | 2011-03-18 | 2012-09-19 | 唐来江 | Preparation process of transparent epoxy nanocomposite material for encapsulating high-power LED (light-emitting diode) |
Non-Patent Citations (2)
| Title |
|---|
| 丁著明等: "高分子材料稳定剂的研究进展", 《化工文摘》 * |
| 朱洪法主编: "《精细化工常用原材料手册》", 31 December 2003, 金盾出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552250A (en) * | 2020-12-14 | 2021-03-26 | 利安隆(天津)新材料科技有限公司 | Reactive benzotriazole compound, application thereof and high polymer material comprising reactive benzotriazole compound |
| CN112552250B (en) * | 2020-12-14 | 2022-04-29 | 天津利安隆新材料股份有限公司 | Reactive benzotriazole compound, application thereof and high polymer material comprising reactive benzotriazole compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107383980B (en) | 2019-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Bubalo et al. | Green extraction of grape skin phenolics by using deep eutectic solvents | |
| DE60308330T2 (en) | THIOXANTHONE DERIVATIVES AND THEIR USE AS CATIONIC PHOTOINITIATORS | |
| Miyata et al. | Synthesis of montmorillonite–viologen intercalation compounds and their photochromic behaviour | |
| Tarr et al. | Electronic absorption spectra and photodecomposition of some substituted ferrocenes | |
| Zhang et al. | UV curing of optical fibre coatings using excimer lamps | |
| EP1945678A1 (en) | Coating materials with oxygen scavenger and/or oxygen indicator function for coating or bonding and products produced therewith | |
| Liu et al. | From rosin to high adhesive polyurethane acrylate: Synthesis and properties | |
| Soni et al. | Studies on synthesis and characterization of a novel acrylic aromatic amide oligomer of aminolysed endproducts generated from pet waste with hydrazine monohydrate and its photocuring with acrylate monomers | |
| Fawcett et al. | Characterization of furfuryl alcohol oligomers by 1H and 13C NMR spectroscopy | |
| CN109942475B (en) | Single-component long-wavelength photoinitiator containing pyrrole derivatives and preparation method thereof | |
| Rosenau et al. | Chromophores in cellulosics, XI: isolation and identification of residual chromophores from bacterial cellulose | |
| Birks et al. | THE PHOTO‐DTMERS OF ANTHRACENE, TETRACENE AND PENTACENE | |
| CN107383980A (en) | A kind of active ultra-violet absorber and its application method | |
| CN112646084A (en) | Tripolyindenone derivative modified waterborne acrylic resin and preparation method thereof | |
| CN111138290A (en) | Aromatic ring-containing benzophenone derivative and preparation method and application thereof | |
| Segurola et al. | Photochemistry and photoinduced chemical crosslinking activity of acrylated prepolymers by several commercial type I far UV photoinitiators | |
| CN109160999B (en) | Vegetable oil-based epoxy prepolymer and UV curing prepolymer, and preparation method and application thereof | |
| CN106928417A (en) | A kind of modified aldehyde ketone resin, preparation method and the application in writing ink | |
| Pablos et al. | Solid polymer and metallogel networks based on a fluorene derivative as fluorescent and colourimetric chemosensors for Hg (II) | |
| Kaczmarek et al. | Strongly modified [2, 2′-bipyridyl]-3, 3′-diol (BP (OH) 2): a system undergoing excited state intramolecular proton transfer as a photostabilizer of polymers and as a solar energy collector | |
| Sawada et al. | Vinylic Rotaxane Cross‐Linker Comprising Different Axle Length for the Characterization of Rotaxane Cross‐linked Polymers | |
| CN103666053B (en) | A kind of UV curing transfer ink and preparation method thereof | |
| Wang et al. | Preparation of waterborne polyurethane film based on spirooxazine containing hydrophilic groups | |
| CN109097198B (en) | Tri-functional castor oil based UV curing prepolymer and preparation method and application thereof | |
| Zarchi et al. | Rapid and facile synthesis of acyl azides from acyl halides using a polymer-supported azide ion under heterogeneous conditions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 529000 shiheli (solvent factory), Jianghai Road, Waihai, Jiangmen City, Guangdong Province Patentee after: Qianxin Chemical Group Co.,Ltd. Address before: 529000 shiheli (solvent factory), Jianghai Road, Waihai, Jiangmen City, Guangdong Province Patentee before: JIANGMEN HANDSOME CHEMICAL DEVELOPMENT Ltd. |
|
| CP01 | Change in the name or title of a patent holder | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220216 Address after: 519000 southwest of pingwan 1st Road, petrochemical zone, Gaolan Port Economic Zone, Zhuhai City, Guangdong Province Patentee after: Zhuhai Qianxin New Material Co.,Ltd. Address before: 529000 shiheli (solvent factory), Jianghai Road, Waihai, Jiangmen City, Guangdong Province Patentee before: Qianxin Chemical Group Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220415 Address after: 529000 shiheli (solvent factory), Jianghai Road, Waihai, Jiangmen City, Guangdong Province Patentee after: Qianxin Chemical Group Co.,Ltd. Patentee after: Zhuhai Xinqian Material Co., Ltd Address before: 519000 southwest of pingwan 1st Road, petrochemical zone, Gaolan Port Economic Zone, Zhuhai City, Guangdong Province Patentee before: Zhuhai Qianxin New Material Co.,Ltd. |
|
| TR01 | Transfer of patent right |