CN1325418A - Curing of resins - Google Patents
Curing of resins Download PDFInfo
- Publication number
- CN1325418A CN1325418A CN 99813045 CN99813045A CN1325418A CN 1325418 A CN1325418 A CN 1325418A CN 99813045 CN99813045 CN 99813045 CN 99813045 A CN99813045 A CN 99813045A CN 1325418 A CN1325418 A CN 1325418A
- Authority
- CN
- China
- Prior art keywords
- resin
- catalyzer
- protection
- merchandising
- called
- 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.)
- Pending
Links
Classifications
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/241—Preventing premature crosslinking by physical separation of components, e.g. encapsulation
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/12—Adsorbed ingredients, e.g. ingredients on carriers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
A method of manufacturing a product comprising at least two parts includes the steps of coating one of the parts at least partially with a resin having a trapped catalyst distributed therein, placing the parts together with the resin therebetween and releasing the catalyst into the resin to initiate curing at the desired time. The catalyst may be trapped either by encapsulation or by absorption/adsorption into the structure of a suitable substrate such as almond shell. The catalyst may be an organic peroxide, formic acid or toluene sulphonic acid. An accelerator may be used to accelerate curing.
Description
The present invention relates to a kind of modified resin of controlling the method for resin solidification and this control being provided.The present invention also comprises the application and the application of described resin in production of articles of described method.
For example in plywood production, independent plank layer is coated resin, force together and heat, to solidify this resin.Required time that is heating and curing will greatly be reduced production process.Can reduce set time by mixed catalyst in resin, but this can disturb production process itself, begin before the use of resin or in the use to solidify as meeting.
One aspect of the present invention provides a kind of method of cured resin, comprise when catalyzer discharges in the resin to cause when solidifying it is caught, mixes the catalyzer and the described resin of being caught, and discharge this catalyzer when needed and enter in the resin and solidify to cause.
Another aspect of the present invention provides a kind of a kind of method that comprises the product of two parts at least for preparing, and is included in the local at least step of coating a kind of resin on the part wherein, has been distributed with a kind of catalyzer of catching in this resin.Two portions are put together occupy in the middle of them described resin, and discharges described catalyzer solidify to cause in needs.
The present invention also comprises with the product of method for preparing and the resin that is distributed with catalyzer that uses in aforesaid method.
Can be by catalyzer being sealed or adsorption/absorption and it is captured in the structure of suitable matrix (as Pericarppium Armeniacae Amarum).
Described resin can be any of following vibrin: vinyl ester resin, resol, Resins, epoxy, acrylic resin, trimeric cyanamide/urea-formaldehyde resin, resol
Described catalyzer can be any suitable catalyzer, as: organo-peroxide, dibenzoyl peroxide for example, methylethyl ketone peroxide, cumene hydroperoxide, acetylacetone peroxide (merchandising is called Triganox 44B), TBPB tertiary butyl perbenzoate (merchandising is called TriganoxC), the tertiary butyl-2-ethylhexanoate (merchandising is called Triganox 21), t-butyl peroxy-3,5,5-tri-methyl hexanoic acid ester (merchandising is called Triganox42s), cumene hydroperoxide (merchandising is called Triganox K-80), two (4-tert-butylcyclohexyl percarbonic acid hydrogen ester (merchandising is called Perkadox 16)); Amine catalyst, for example diethyl tetramine, triethylamine isocyanic ester, boron trifluoride; UV-curing catalysts, alkyl carbonate, for example propylene and vinyl carbonate; Inorganic and organic acid is as formic acid, toluenesulphonic acids or sulfuric acid.
Described encapsulating material can be following any: gelatin, thermosetting resin, fats, paraffin, thermoplastics, polymkeric substance or silane compound or be any of the encapsulating material described in the common unsettled international application of WO98/26865 in the applicant's publication No..
Also can use accelerator as cobalt octoate (merchandising is called NL-49-P), diethyl-aniline (merchandising is called NL-64-10P), ammonium sulfate or ammonium chloride.
Described seal or the big I of coated particle in 0.5 to 1000 micron scope.
To describe embodiment of the present invention in detail by embodiment now.
In first example approach, relate to the production of glued board, on laminated wood, coat resin, laminate is stacked together and pressurizes impel their together bonding and/or heating to make resin solidification make the laminate strong binding together by being clipped in resin between adjacent layers.Must apply the quite a long time in the pressurization of routine and heating production method, for example several minutes has increased manufacturing time and manufacturing expense.According to the present invention, catalyst distribution is in whole described resin.Described catalyzer can be a propylene carbonate, vinyl carbonate or other catalyzer that is fit to, and it causes and solidifies described resin with plank between bonding successive layers.Yet,, will be difficult to or can not be satisfactorily or/and described effectively production process if solidify to cause too early or carry out too soon.For example,, can not easily be coated with laminate if carry out when laminate solidifies during at coating resin, and, even coated, the bond strength between laminate is also had adverse influence.
In order to overcome this shortcoming that may exist, come that it is caused solidified in the resin and discharge and control by sealing described catalyzer.Obtain like this to seal by the catalyst microcapsule that in the presence of encapsulating material, goes out to be coated with encapsulating material with the described Catalyst Production of ultrasonic wave radiation.Although these resin capsule of sealing are distributed in the whole resin, described coating is kept apart catalyzer and resin.In this case, resin can be resembled on the laminate that the description of front is applied to, can not begin, therefore will can not influence this process and discharge described catalyzer up to these breakage of particles and enter in the resin but solidify.Can cause producing by the described capsule of ultrasonic wave radiation or heating or some other appropriate means and break.
In a kind of encapsulating method as selection, catalyzer is adsorbed on a kind of particle surface of inertial base, and described particle is using ultrasound wave radiation coating packaged material once more.The coated particle size generally can be the 0.5-1000 micron in both cases.
Described catalyzer can be any of following material, or their mixture: organo-peroxide, as dibenzoyl peroxide, methylethyl ketone peroxide, cumene hydroperoxide, acetylacetone peroxide (merchandising is called Triganox 44B), TBPB tertiary butyl perbenzoate (merchandising is called TriganoxC), the tertiary butyl-2-ethylhexanoate (merchandising is called Triganox 21), t-butyl peroxy-3,5,5-tri-methyl hexanoic acid ester (merchandising is called Triganox42s), cumene hydroperoxide (merchandising is called Triganox K-80), two (4-tert-butylcyclohexyl percarbonic acid hydrogen esters (merchandising is called Perkadox 16); Amine catalyst, for example diethyl tetramine, triethylamine isocyanic ester, boron trifluoride; UV-curing catalysts, alkyl carbonate, for example propylene and vinyl carbonate; Inorganic and organic acid is as formic acid, toluenesulphonic acids or sulfuric acid.
Also can use accelerator as cobalt octoate (merchandising is called NL-49-P), diethyl-aniline (merchandising is called NL-64-10P).
Described encapsulating material can be following any: gelatin, thermosetting resin, fats, paraffin, thermoplastics, polymkeric substance or silane compound or be any of the encapsulating material described in the common unsettled international application of WO98/26865 in the applicant's publication No..
Described resin can be any of following resin or their any mixture: vibrin, vinyl ester resin, resol, Resins, epoxy, acrylic resin, trimeric cyanamide/urea-formaldehyde resin, resol.
In another example, catalyzer is to catch by absorbing in the suitable matrix rather than as previously described absorption.A kind of suitable matrix is a Pericarppium Armeniacae Amarum, it have help absorbing/adsorptive catalyst enters the surface in its vesicular structure.Though can use other catalyzer and resin (for example as describe in detail above), preferred described catalyzer is a formic acid, described resin is Melamine/urea-formaldehyde resin.
The method of producing Pericarppium Armeniacae Amarum formic acid/toluenesulphonic acids catalystic material is as follows:
ⅰ) at first with described formic acid/toluenesulphonic acids dissolution/go in the acetone.Acetone enters the carrier solvent of the vesicular structure of Pericarppium Armeniacae Amarum as described acid catalyst.
ⅱ) then Pericarppium Armeniacae Amarum is added in described acid/acetone mixture.
ⅲ) with described acid/acetone/Pericarppium Armeniacae Amarum mixture 20kHz, 400 watts ultrasonic fault detection 3-5 minute up to described acetone/acid absorb/adsorb to advance in the described Pericarppium Armeniacae Amarum structure.Phenomenon by the obvious thickening of described mixture can easily be observed this process.Using a reason of solvent is for ultrasonic energy is worked effectively to very firm Pericarppium Armeniacae Amarum.Require excessive liquid (being acetone) to produce air pocket.When cavitation bubble is broken, produced a large amount of energy sources/shockwave, be exactly that this energy orders about described liquid mixture and enters into described Pericarppium Armeniacae Amarum structure.
ⅳ) described acetone solvent is removed from slurry mixture, only stayed described acid catalyst and be embedded in the described Pericarppium Armeniacae Amarum by drying means.Can use condenser that described acetone is removed and recycled.Described Pericarppium Armeniacae Amarum/acid catalyst product be a kind of can quite free-pouring powder, it can easily be distributed in the resin.Use acetone to be as solvent because:
A) it has good solubility property.For example, Catalyzed by p-Toluenesulfonic Acid agent (PTSA, pressed powder) needs to be dissolved into acetone before entering into described Pericarppium Armeniacae Amarum being ordered about.
B) it has very low boiling point, and this helps it and removes in the cryodrying process.When using formic acid, this is unusual important characteristic, because this catalyzer has lower boiling point, if therefore use high drying temperature, formic acid also can be removed.
C) in described sonication process, exist acetone to keep low-down temperature (specific heat capacity characteristic) to reduce or eliminate the vaporization problem.
When described Pericarppium Armeniacae Amarum/acid catalyst is used resin dispersion, the molecule of resin too big so that they can not be easy to or enter soon in the described Pericarppium Armeniacae Amarum, therefore can not enter be embedded in structure in acid catalyst contact.Thereby can not begin the curing of described resin.Activate described acid catalyst by adding heat energy.This will cause described structure to expand and open making described resin near described catalyzer.It should be noted that this is not a kind of wrapper technology and does not use coating.Yet, if the higher package stability of final user/application requiring can apply coating.
Should be understood that above only is by embodiment embodiment of the present invention to be described, and under the situation that does not depart from scope of the present invention many variants can be arranged.For example, method of the present invention may be used in the manufacturing of any product, wherein with coating of a part or many parts and/or dipping curable resin, makes described each several part to be fixed together or as the part of production process.Felt or glass fibre can become desired shape also subsequently with described resin solidification with curable resin dipping of the present invention.Can adopt the resin prepreg stain material that uses in dirty production process, these matrix materials can be used in the following general field:
I) ship structure,
II) automotive industry-as inner/outer parts and main body panel,
III) train/aircraft structure-as inner/outer parts and main body panel,
IV) coastal waters boats and ships/field drilling is used,
V) building structure-wall (inner/outer), the roof,
VI) homely article,
VII) top coat,
VIII) flame-retardant foam body/coating/matrix material,
IX) tackiness agent of printing and paper industry,
X) tackiness agent of foundary industry use,
XI) winding filament,
XII) plastics extrusion molding,
The X III) tackiness agent,
The X IV) MDF/ shaving board,
The X V) Bulk Molding Compound,
The X VI) preimpregnation product,
The X VII) is used in the tackiness agent that uses in the concrete application of building industry.
Claims (16)
1. the method for cured resin, this method comprises the steps: capture catalyst, will cause curing when described catalyzer is discharged in the described resin; Mix described catalyzer of catching and described resin and in needs, discharge described catalyzer and in described resin, cause curing.
2. prepare a method that comprises the product of two parts at least, this method comprises the steps: upward a kind of resin of the local at least coating of a part therein, be distributed with captive catalyzer in this resin, each several part is put together, described resin clip discharges catalyzer and cause curing in described resin between them in needs.
3. claim 1 or 2 methods required for protection, wherein said catalyzer is to catch by sealing.
4. claim 3 method required for protection, wherein said encapsulating substance comprises one or more following substances:
Gelatin, thermosetting resin, fats, paraffin, thermoplastics, polymkeric substance or silane compound or be any in the disclosed encapsulating material in the international application of WO98/26865 in the applicant's publication No..
5. claim 1 or 2 method, wherein said catalyzer is to catch by absorption/absorption.
6. claim 5 method required for protection, wherein said catalyzer is hunted down by absorption/absorption and enters into the surface of Pericarppium Armeniacae Amarum.
7. claim 1 to 6 method required for protection, wherein said resin comprises one or more following vibrin: vinyl ester resin, resol, Resins, epoxy, acrylic resin, trimeric cyanamide/urea-formaldehyde resin, resol.
8. each of front claim method required for protection, wherein said catalyzer is a kind of organo-peroxide.
9. each of claim 1 to 7 method required for protection, wherein said catalyzer comprises one or more following substances: organo-peroxide, as dibenzoyl peroxide, methylethyl ketone peroxide, cumene hydroperoxide, acetylacetone peroxide (merchandising is called Triganox 44B), TBPB tertiary butyl perbenzoate (merchandising is called Triganox C), the tertiary butyl-2-ethylhexanoate (merchandising is called Triganox21), t-butyl peroxy-3,5,5-tri-methyl hexanoic acid ester (merchandising is called Triganox 42s), cumene hydroperoxide (merchandising is called Triganox K-80), two (4-tert-butylcyclohexyl peroxocarbonates (merchandising is called Perkadox 16); Amine catalyst, for example diethyl tetramine, triethylamine isocyanic ester, boron trifluoride; UV-curing catalysts, alkyl carbonate, for example propylene and vinyl carbonate; Inorganic and organic acid is as formic acid, toluenesulphonic acids or sulfuric acid.
10. catch the method for formic acid catalyzer in the Pericarppium Armeniacae Amarum, comprise the steps: formic acid dissolving or be distributed in the acetone, add Pericarppium Armeniacae Amarum in described acid/acetone mixture and with the described mixture of sonication up to described acetone and the mixt be absorbed/adsorb to advance in the described Pericarppium Armeniacae Amarum structure.
11. catch the method for toluenesulphonic acids catalyzer in the Pericarppium Armeniacae Amarum, comprise the steps: toluenesulphonic acids dissolving or be distributed in the acetone, add Pericarppium Armeniacae Amarum in described acid/acetone mixture and with the described mixture of sonication up to described pyruvic acid mixture be absorbed/adsorb to advance in the described Pericarppium Armeniacae Amarum structure.
12. claim 10 or 11 catching methods required for protection, wherein said acid/acetone mixture use the ultrasonication of 400 watts of 20kHz to survey 3 to 5 minutes.
13. the method for cured resin comprises the steps: capture catalyst, will cause curing when described catalyzer is discharged in the described resin; Mix described catalyzer of catching and described resin and discharge described catalyzer in needs and cause curing in described resin, wherein said catalyzer is caught by claim 10,11 or 12 methods required for protection.
14. claim 1 to 9 or 13 methods required for protection have wherein used a kind of accelerator to quicken to solidify.
15. claim 14 method required for protection, wherein said accelerator are cobalt octoate (merchandising is called NL-49-P), diethyl-aniline (merchandising is called NL-64-10P), ammonium sulfate or ammonium chloride.
16. product according to the method manufacturing required for protection of front claim.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9819815.3A GB9819815D0 (en) | 1998-09-12 | 1998-09-12 | Curing of resins |
| GB9909763.6 | 1999-04-29 | ||
| GBGB9909763.6A GB9909763D0 (en) | 1998-09-12 | 1999-04-29 | Cluring of resins |
| GB9819815.3 | 1999-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1325418A true CN1325418A (en) | 2001-12-05 |
Family
ID=26314359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 99813045 Pending CN1325418A (en) | 1998-09-12 | 1999-09-10 | Curing of resins |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1112303A2 (en) |
| JP (1) | JP2002524634A (en) |
| CN (1) | CN1325418A (en) |
| AU (1) | AU5870799A (en) |
| CA (1) | CA2343392A1 (en) |
| GB (1) | GB9909763D0 (en) |
| NO (1) | NO20011212L (en) |
| WO (1) | WO2000015694A2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111019554A (en) * | 2019-12-23 | 2020-04-17 | 天津环球磁卡股份有限公司 | Curing resin regulator, bi-component epoxy system adhesive and preparation method thereof |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009046251A1 (en) | 2009-10-30 | 2011-05-19 | Evonik Röhm Gmbh | Reactive 1-component road markings |
| FR2953524B1 (en) * | 2009-12-03 | 2012-12-14 | Arkema France | HIGH SPEED CROSSLINKING SYSTEM |
| WO2012148629A1 (en) | 2011-03-31 | 2012-11-01 | Ocv Intellectual Capital, Llc | Microencapsulated curing agent |
| JP5677922B2 (en) * | 2011-09-27 | 2015-02-25 | 積水化学工業株式会社 | Curing agent and / or curing accelerator encapsulating capsule, and thermosetting resin composition |
| EP2788406A1 (en) | 2011-12-08 | 2014-10-15 | OCV Intellectual Capital, LLC | Fiber reinforced resin molding compound and manufacturing method for fiber reinforced resin molded article therefrom |
| JP5964085B2 (en) * | 2012-02-13 | 2016-08-03 | 株式会社松風 | Organic peroxide-containing composite fine particles |
| US20150132592A1 (en) * | 2013-11-08 | 2015-05-14 | Ppg Industries Ohio, Inc. | Curable film-forming compositions comprising catalyst associated with a carrier and methods for coating a substrate |
| US11186528B2 (en) | 2015-07-07 | 2021-11-30 | Bae Systems Plc | PBX composition |
| ES2760908T3 (en) * | 2015-07-07 | 2020-05-18 | Bae Systems Plc | Molten explosive composition |
| EP3115348A1 (en) * | 2015-07-07 | 2017-01-11 | BAE Systems PLC | Cast explosive composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036980A (en) * | 1956-12-31 | 1962-05-29 | Union Carbide Corp | Rubber composition containing zeolitic molecular sieve and process for curing |
| GB1029732A (en) * | 1961-09-29 | 1966-05-18 | Union Carbide Corp | Improved release of agents from adsorbate-containing molecular sieves |
| JPS60168642A (en) * | 1984-02-14 | 1985-09-02 | 呉羽化学工業株式会社 | Manufacture of laminated film |
| US4808639A (en) * | 1986-07-16 | 1989-02-28 | Production Previews, Inc. | Liquid curable adhesive composition comprising a polyester resin and a microencapsulated peroxide curing agent |
| GB9623878D0 (en) * | 1996-11-15 | 1997-01-08 | Marlit Ltd | Bonding materials |
| GB9626152D0 (en) * | 1996-12-17 | 1997-02-05 | Cehmcolloids Ltd | Encapsulation |
-
1999
- 1999-04-29 GB GBGB9909763.6A patent/GB9909763D0/en not_active Ceased
- 1999-09-10 WO PCT/GB1999/002830 patent/WO2000015694A2/en not_active Application Discontinuation
- 1999-09-10 JP JP2000570228A patent/JP2002524634A/en active Pending
- 1999-09-10 CN CN 99813045 patent/CN1325418A/en active Pending
- 1999-09-10 EP EP99946287A patent/EP1112303A2/en not_active Withdrawn
- 1999-09-10 CA CA002343392A patent/CA2343392A1/en not_active Abandoned
- 1999-09-10 AU AU58707/99A patent/AU5870799A/en not_active Abandoned
-
2001
- 2001-03-09 NO NO20011212A patent/NO20011212L/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111019554A (en) * | 2019-12-23 | 2020-04-17 | 天津环球磁卡股份有限公司 | Curing resin regulator, bi-component epoxy system adhesive and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1112303A2 (en) | 2001-07-04 |
| GB9909763D0 (en) | 1999-06-23 |
| NO20011212D0 (en) | 2001-03-09 |
| NO20011212L (en) | 2001-03-09 |
| CA2343392A1 (en) | 2000-03-23 |
| AU5870799A (en) | 2000-04-03 |
| WO2000015694A3 (en) | 2000-07-13 |
| WO2000015694A2 (en) | 2000-03-23 |
| JP2002524634A (en) | 2002-08-06 |
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| C10 | Entry into substantive examination | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |