CN109355040A - A kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent and preparation method thereof - Google Patents
A kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent and preparation method thereof Download PDFInfo
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- CN109355040A CN109355040A CN201811193156.0A CN201811193156A CN109355040A CN 109355040 A CN109355040 A CN 109355040A CN 201811193156 A CN201811193156 A CN 201811193156A CN 109355040 A CN109355040 A CN 109355040A
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- anhydride
- sensitive adhesive
- acid esters
- adhesive agent
- modified propylene
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- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- 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
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention relates to pressure sensitive adhesive fields, and in particular to anhydride-modified propylene's acid esters pressure-sensitive adhesive agent and preparation method thereof.A kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, acrylate monomer including 1~80 part of lower glass transition temperatures, the acrylate monomer of 1~40 part of high glass-transition temperature, 1~20 part of acid anhydrides function monomer, 20~200 parts of organic solvent, 0.001~1 part of radical initiator, 0.1~1 part of reverse atom transfer radical polymerization catalyst, 0.1~1 part of curing accelerator and 0.1~10 part of more official's epoxy crosslinking agents.The present invention obtains the molecular weight distribution anhydride modified adhesive uniform compared with narrow structure using the polymerization of reverse atom transfer radical polymerization method, more official's epoxy crosslinking agents are added to be crosslinked, cohesive force is improved, obtains a kind of novel acrylic ester pressure-sensitive, the present invention effectively promotes the cohesive force of colloid.The invention solves the problems, such as traditional pressure sensitive xanthan molecule amount wider distribution, easily causes degumming phenomenon and the insufficient defect of heat resistance.
Description
Technical field
The present invention relates to pressure sensitive adhesive fields, and in particular to anhydride-modified propylene's acid esters pressure-sensitive adhesive agent and preparation method thereof.
Background technique
Polyacrylate pressure-sensitive refers to that monomer with unsaturated double-bond carries out radical polymerization under the action of initiator
It closes and reacts acrylate glue obtained.Polyacrylate pressure-sensitive has preferable weathering, can be prepared into all kinds of pressure sensitive adhesive tapes.
Pressure-sensitive acrylate is the most wide pressure sensitive adhesive of current application range, the weatherability and heat resistance for having the transparency good, excellent,
Without mutually separation and transport phenomena, it is particularly suitable for electric mechanical manufacturing field.Acrylate pressure-sensitive adhesive generally can not be used alone,
Due to its cohesive force deficiency, easily there is degumming or ghost phenomenon.Acrylate pressure-sensitive adhesive can introduce some bands in the synthesis process
There are reaction sexual function functional group, such as the acrylic acid derivative of carboxyl, hydroxyl.After these functional groups mix with other crosslinking agents,
Cross-linking reaction is carried out, the cohesive force of glue can be improved.The crosslinking agent being currently mainly used have epoxy resin, more official's isocyanates and
Metallic salt etc..More official's epoxy resins and carboxyl functional group reaction speed are extremely slow, to undergo maturing process long slowly.More official's isocyanides
When acid esters and hydroxy functional group cross-linking reaction, reaction condition requires strictly, to be afraid of wet gas environments, is also easy to produce many bad side reactions.
Metallic salt and carboxyl functional group cross-linking reaction binding force are weaker, and usually reaction is incomplete, while being also easy to produce metallic pollution.
Summary of the invention
Therefore, an object of the present disclosure is to provide a kind of cohesive force for improving glue, does not occur degumming phenomenon and heat-resisting
The high anhydride-modified propylene's acid esters pressure-sensitive adhesive agent of performance.
What above-mentioned purpose was realized in.
A kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, the acrylic acid including 1~80 part of lower glass transition temperatures
Ester monomer, the acrylate monomer of 1~40 part of high glass-transition temperature, 1~20 part of acid anhydrides function monomer, 20~200
The organic solvent of part, 0.001~1 part of radical initiator, 0.1~1 part of reverse atom transfer radical polymerization catalyst,
0.1~1 part of curing accelerator and 0.1~10 part of more official's epoxy crosslinking agents;It is above mass fraction.
The above technical solution can be further improved as follows.
The acrylate monomer of the lower glass transition temperatures is octadecyl acrylate, lauryl acid esters, propylene
One of the different monooctyl ester of acid, ethyl acrylate or butyl acrylate or more than one mixtures.
The acrylate monomer of the high glass-transition temperature is methyl methacrylate, ethyl methacrylate, first
One of base isobornyl acrylate, methacrylic acid cyclohexyl ester, acrylonitrile, acrylamide or styrene or more than one are mixed
Close object.
The acid anhydrides function monomer is 4- methacryloxyethyl trimellitic anhydride.
The radical initiator is the one of peroxidating Malaysia tert-butyl acrylate, dibenzoyl peroxide and azodiisobutyronitrile
Kind or two kinds of mixtures or three kinds of mixtures.
The reverse atom transfer radical polymerization catalyst includes " copper bromide and pentamethyl-diethylenetriamine " catalytic body
One of system, " copper chloride and 2,2 '-bipyridines " catalyst system or " iron chloride and triphenyl phosphorus " catalyst system or two kinds
Mixing or three kinds of mixtures.
More official's epoxy crosslinking agents are one of more official's epoxy resins and the epoxy-modified rubber of more officials or two kinds of mixing;
More official's epoxy crosslinking agents are one of more official's epoxy resins and the epoxy-modified rubber of more officials or two kinds of mixing;More official's epoxies
Resin is the resin that per molecule on average contains three or more crosslinkable epoxy groups;The epoxide number of epoxidized polybutadiene is
0.25~0.55 mol/100g and number-average molecular weight are 1000~2500.
The organic solvent is ethyl acetate, one of toluene and butyl acetate or two kinds of mixtures or three kinds of mixing
Object.
The curing accelerator is triethanolamine, dimethylaniline and 2, one in 4,6- tri- (dimethylamino methyl) phenol
Kind or more than one mixtures.
The present invention second is designed to provide a kind of cohesive force of raising glue, does not occur degumming phenomenon and heat resistance height
Anhydride-modified propylene's acid esters pressure-sensitive adhesive agent preparation method.
What above-mentioned purpose was realized in.
A kind of preparation method of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, by 1~80 part of lower glass transition temperatures
Acrylate monomer, the acrylate monomer of 1~40 part of high glass-transition temperature, 1~20 part of acid anhydrides function monomer,
20~200 parts of organic solvent, 0.001~1 part of radical initiator and 0.1~1 part of reversed atom transferred free radical are poly-
After closing catalyst mixing, after carrying out nitrogen deoxygenation 0~3 hour, temperature control carries out reversed former under nitrogen protection in 30~120 DEG C
Sub- transferring free-radical polymerization, polymerization reaction 1~50 hour, the control of number-average molecular weight after polymerization reaction for 100000~
500000, the control of molecular weight polydispersity coefficient is 1.0~1.5, and glass transition temperature (Tg) controls between -45~20 DEG C,
Reaction temperature is down between 10~30 DEG C, adds 0.1~10 part of more official's epoxy crosslinking agents and 0.1~1 part of solidification promotes
After agent is mixed, the pressure-sensitive adhesive agent of anhydride-modified propylene's acid esters is obtained;It is above mass fraction.
The present invention obtains molecular weight distribution compared with narrow structure using reverse atom transfer radical polymerization method (R-ARTP) polymerization
Uniform anhydride modified adhesive adds more official's epoxy crosslinking agents and is crosslinked, and improves cohesive force, obtains a kind of novel propylene
Acid esters pressure sensitive adhesive.
The present invention designs a kind of New Pressure-Sensitive Adhesion, which uses " acid anhydrides-epoxy " chemical crosslink reaction, cross-linking reaction
It is high-efficient, it can effectively promote the cohesive force of colloid.
The invention is synthesized using reverse atom transfer radical polymerization (R-ARTP) polymerization, solves traditional pressure sensitive glue point
The problem of son amount wider distribution, easily cause degumming phenomenon and the insufficient defect of heat resistance.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto.
Number involved in following embodiment is mass fraction.
Embodiment one is a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, is prepared by the following steps to obtain: by 40 parts
Isooctyl acrylate monomer (EHA), 10 parts of ethyl acrylate, 15 parts of butyl acrylate (BA), 3 parts of 4- methacryl
Oxygroup ethyl trimellitic anhydride (4-META), 5 parts of methyl acrylate (MMA), 3 parts of acrylonitrile, 0.01 part of free radical
Initiator peroxidating Malaysia tert-butyl acrylate (TBMA), 0.1 part of ferric trichloride, 0.2 part of triphenyl phosphorus and 100 parts of toluene are mixed
After conjunction, nitrogen deoxygenation is carried out after sixty minutes, temperature control carries out reverse atom transfer radical polymerization in 90 DEG C under nitrogen protection
(R-ARTP) polymerization reaction 10 hours, number-average molecular weight (Mn) control are 376900, and the control of molecular weight polydispersity coefficient is 1.4,
Reaction temperature is down to 30 DEG C, add 2 parts epoxidized polybutadiene (epoxide number be 0.54 mol/100g, number-average molecular weight
After 2066) being mixed with 0.1 part of 2,4,6- tri- (dimethylamino methyl) phenol of curing accelerator, anhydride-modified propylene is obtained
Acid esters pressure-sensitive adhesive agent;It is above mass fraction.
Embodiment two is a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, is prepared by the following steps to obtain: by 40 parts
Isooctyl acrylate monomer (EHA), 10 parts of octadecyl acrylate (SA), 5 parts of butyl acrylate (BA), 5 parts of 4- methyl-prop
Alkene trimethylammonium trimellitic anhydride (4-META), 4 parts of methyl acrylate (MMA), 2 parts of isobornyl methacrylate,
0.04 part of radical initiator dibenzoyl peroxide (BPO), 0.1 part of copper bromide, 0.2 part of pentamethyl-diethylenetriamine
After 80 parts of ethyl acetate mixing, after carrying out nitrogen deoxygenation 90 minutes, temperature control carries out reversed former under nitrogen protection in 80 DEG C
Sub- transferring free-radical polymerization (R-ARTP) polymerization reaction 24 hours, number-average molecular weight (Mn) control be 321400, more points of molecular weight
Dissipating coefficient control is 1.3, and reaction temperature is down to 25 DEG C, adds 1 part of epoxidation m-xylene diamine and 0.1 part of curing accelerator
After dimethylaniline is mixed, the pressure-sensitive adhesive agent of anhydride-modified propylene's acid esters is obtained;It is above mass fraction.
Embodiment three is a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, is prepared by the following steps to obtain: by 50 parts
Isooctyl acrylate monomer (EHA), 10 parts of ethyl acrylate (EA), 15 parts of butyl acrylate (BA), 5 parts of 4- metering system
Trimethylammonium trimellitic anhydride (4-META), 2 parts of methyl acrylate (MMA), 2 parts, methacrylic acid cyclohexyl ester, 0.06
The radical initiator dibenzoyl peroxide (BPO), 0.1 part of ferric trichloride, 0.2 part of triphenyl phosphorus and 70 parts of second of part
After acetoacetic ester mixing, after carrying out nitrogen deoxygenation 120 minutes, temperature control carries out reversed atom transfer certainly in 85 DEG C under nitrogen protection
When polymerizeing (R-ARTP) polymerization reaction 20 by base, number-average molecular weight (Mn) control is 265400, the control of molecular weight polydispersity coefficient
It is 1.2, reaction temperature is down to 20 DEG C, adds 1 part of trihydroxymethylpropanyltri diglycidyl ether and 0.2 part of curing accelerator three
After ethanol amine is mixed, the pressure-sensitive adhesive agent of anhydride-modified propylene's acid esters is obtained;It is above mass fraction.
Example IV is a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, is prepared by the following steps to obtain: by 40 parts
Isooctyl acrylate monomer (EHA), 20 parts of lauryl acid esters (SA), 10 parts of butyl acrylate (BA), 5 parts of 4- methyl
Acryloyl-oxyethyl trimellitic anhydride (4-META), 5 parts of methyl acrylate (MMA), 3 parts of styrene (St), 0.08 part
Radical initiator azodiisobutyronitrile (AIBN), 0.2 part of copper chloride, the 2 of 0.4 part, 2 '-bipyridines (bpy) and
After 60 parts of butyl acetate mixing, after carrying out nitrogen deoxygenation 100 minutes, temperature control carries out reversed former under nitrogen protection in 75 DEG C
Sub- transferring free-radical polymerization (R-ARTP) polymerization reaction 10 hours, number-average molecular weight (Mn) control be 234100, more points of molecular weight
Dissipate coefficient control be 1.1, reaction temperature is down to 20 DEG C, add 5 parts epoxidized polybutadiene (epoxide number be 0.28 mol/
100g, number-average molecular weight 1414) and after 0.1 part of 2,4,6- tri- (dimethylamino methyl) phenol of curing accelerator mixed,
Obtain the pressure-sensitive adhesive agent of anhydride-modified propylene's acid esters;It is above mass fraction.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (10)
1. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, it is characterised in that: including 1~80 part of lower glass transition temperatures
Acrylate monomer, the acrylate monomer of 1~40 part of high glass-transition temperature, 1~20 part of acid anhydrides function monomer,
20~200 parts of organic solvent, 0.001~1 part of radical initiator, 0.1~1 part of reverse atom transfer radical polymerization
Catalyst, 0.1~1 part of curing accelerator and 0.1~10 part of more official's epoxy crosslinking agents;It is above mass fraction.
2. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: the low glass
The acrylate monomer for changing transition temperature is octadecyl acrylate, lauryl acid esters, Isooctyl acrylate monomer, ethyl acrylate
Or one of butyl acrylate or more than one mixtures.
3. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: the high glass
The acrylate monomer for changing transition temperature is methyl methacrylate, ethyl methacrylate, isobornyl methacrylate, first
One of base cyclohexyl acrylate, acrylonitrile, acrylamide or styrene or more than one mixtures.
4. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: the acid anhydrides function
Energy monomer is 4- methacryloxyethyl trimellitic anhydride.
5. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: the free radical
Initiator be one of peroxidating Malaysia tert-butyl acrylate, dibenzoyl peroxide and azodiisobutyronitrile or two kinds of mixtures or
Three kinds of mixtures.
6. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: the reversed original
Sub- transferring free-radical polymerization catalyst include " copper bromide and pentamethyl-diethylenetriamine " catalyst system, " copper chloride and 2,2 '-
One of bipyridine " catalyst system or " iron chloride and triphenyl phosphorus " catalyst system or two kinds of mixing or three kinds of mixing.
7. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: more official's rings
Oxygen crosslinking agent is one of more official's epoxy resins and the epoxy-modified rubber of more officials or two kinds of mixing;
More official's epoxy resins are the resin that per molecule on average contains three or more crosslinkable epoxy groups;
The epoxide number of epoxidized polybutadiene is 0.25~0.55 mol/100g and number-average molecular weight is 1000~2500.
8. a kind of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 1, it is characterised in that: described organic molten
Agent is ethyl acetate, one of toluene and butyl acetate or two kinds of mixtures or three kinds of mixtures;
The curing accelerator be triethanolamine, dimethylaniline and 2, one of 4,6- tri- (dimethylamino methyl) phenol or
More than one mixtures.
9. a kind of preparation method of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent, is characterized in that:
By the acrylate monomer of 1~80 part of lower glass transition temperatures, the propylene of 1~40 part of high glass-transition temperature
Acid ester monomer, 1~20 part of acid anhydrides function monomer, 20~200 parts of organic solvent, 0.001~1 part of radical initiator and
After 0.1~1 part of reverse atom transfer radical polymerization catalyst mixing, after carrying out nitrogen deoxygenation 0~3 hour, temperature control is in 30
~120 DEG C, reverse atom transfer radical polymerization is carried out under nitrogen protection, polymerization reaction 1~50 hour, reaction temperature was down to
Between 10~30 DEG C, 0.1~10 part of more official's epoxy crosslinking agents are added and after 0.1~1 part of curing accelerator mixes,
Obtain the pressure-sensitive adhesive agent of anhydride-modified propylene's acid esters;It is above mass fraction.
10. the preparation method of anhydride-modified propylene's acid esters pressure-sensitive adhesive agent according to claim 9, is characterized in that: polymerization is anti-
Number-average molecular weight control after answering is 100000~500000, and the control of molecular weight polydispersity coefficient is 1.0~1.5, and vitrifying turns
Temperature (Tg) controls between -45~20 DEG C.
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Cited By (3)
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CN110628366A (en) * | 2019-10-31 | 2019-12-31 | 东莞市骏青电子科技有限公司 | High-viscosity pressure-sensitive adhesive, preparation method thereof and adhesive tape |
CN111320951A (en) * | 2020-04-03 | 2020-06-23 | 苏州世诺新材料科技有限公司 | Low-surface-energy temperature-resistant humidity-resistant acrylate composition and application thereof |
CN112111205A (en) * | 2019-06-20 | 2020-12-22 | 株式会社自动网络技术研究所 | Water repellent treatment agent, water repellent treatment body, electrical connection structure, and wire harness |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN112111205A (en) * | 2019-06-20 | 2020-12-22 | 株式会社自动网络技术研究所 | Water repellent treatment agent, water repellent treatment body, electrical connection structure, and wire harness |
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