CN1990808A - Hot melt adhesive water -dispersible copolyester composition - Google Patents
Hot melt adhesive water -dispersible copolyester composition Download PDFInfo
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- CN1990808A CN1990808A CNA2006100902453A CN200610090245A CN1990808A CN 1990808 A CN1990808 A CN 1990808A CN A2006100902453 A CNA2006100902453 A CN A2006100902453A CN 200610090245 A CN200610090245 A CN 200610090245A CN 1990808 A CN1990808 A CN 1990808A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/50—Polyesters chemically modified by esterification by monohydric alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
-
- 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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a hot-melt adhesive type water dispersible copolyester composition made by copolymer of dicarboxylic with sulfonic acid metal group or derivative thereof, dicarboxylic and diol component. The composition has excellent water dispersivity, having excellent melt adhesiveness after coated to laminated material and dried, so bonded with different material firmly. Moreover, the composition can crystal quickly after boning, so formed adhesive layer has excellent thermostability, chemical fastness for orgnic solvent, hydrolytic resistance, mechanical strength and unadhesiveness when exposed in the outside. And ensuring resistance property (dimensional stability) for external stress (thermal shock) and internal stress (shrink caused by crystal of substrate resin), excellent elastic modulus and bending strength. Thanks to these properties, the composition can used as substrate film of PVC, PET, PC or PMMA, iron sheet, aluminum sheet, kinds of alloy sheet (e.g stainless steel sheet, tin plate, EGI steel sheet etc.) or adhesive layer of paper laminating, also can be used adhesive layer of other material except for the said substrate material.
Description
Technical field
The invention relates to a kind of hot melt adhesive water-dispersible copolyester composition, especially about a kind of hot-melting type water-dispersible copolyester composition that makes by dicarboxylic acid or derivatives thereof, dicarboxylic acid and the diol component copolymerization that will contain the sulfonic acid metal matrix.
Background technology
Usually, the film after the printing is used for by the packing content thing and uses the packaging application of finishing such as heat-sealing method.Yet,, therefore can not also be difficult to separately film be sealed in the directly printing of film surface because most of film is all made by resin combination.In order to address these problems, used for example to comprise the method for resin combination and another kind of resin combination coextrusion or another kind of resin combination is applied to the method on film surface.Yet, variety of issue has appearred in these methods.About these problems, because film and different with film coextrusion or the shrinkage that is applied between the resin combination on the film can form gauffer in film.In addition, because physicals is poor as affinity and heat sealability to printing ink composition, application surface also is easy to fragmentation.In addition, transparency or the glossiness of using film are low, and can not use such as the method for fusion the resin combination of using is reprocessed, and therefore can not reclaim this film.And because with an organic solvent, this film also can cause problem of environmental pollution.
In order to improve the problems referred to above that appear in the film coating resin combination, Korean Patent special permission communique 93-5141, the clear 47-40873 of Japanese Patent Laid communique, the clear 56-5476 of Japanese Patent Laid communique, the clear 56-88454 of Japanese Patent Laid communique, Japanese Patent is openly speciallyyed permit flat 4-226562 of communique etc. and is disclosed a kind of method for preparing water-dispersible copolyester composition, this method comprises and will contain dicarboxylic acid or derivatives thereof and another kind of dicarboxylic acid or derivatives thereof and the diol component copolymerization of sulfonic acid metal matrix (sulfonic acid metal base), with preparation water-dispersed resin composition; With the resin combination that makes separately or with other additive be distributed in the water or water and pure mixed solvent in.Yet, if use second-order transition temperature (the glass transition temperature of the resin that this preparation method makes, Tg) enough high, then will occur by this resin-coating is gone up layer easy fragmentation or the not enough problem of heat sealability that forms to film etc.And, then superimposed on another film or when being wound into web-like together if the second-order transition temperature of resin is very low when the film that is coated with resin, will film problem bonded to each other appears.
If do not use carrier fluid that hotmelt is formed bonding coat, then be difficult to obtain thin bonding coat; If use solvent to apply hotmelt and dryly form bonding coat as carrier fluid, though the bonding coat that may obtain to approach then, organic solvent can cause environmental pollution and Working environment is had disadvantageous effect.For this reason, but need exploitation water-soluble while of a kind of energy tackiness agent of hot melt again.
Summary of the invention
The inventor has carried out extensive studies, found that by copolymerization in the presence of acid constituents buffer reagent (acid component buffer) can make and can be dispersed in the resin combination that is essentially crystalline state in the water simultaneously with generation that reduces ethylene glycol as far as possible and the composition of adjusting raw material with dicarboxylic acid or derivatives thereof that contains the sulfonic acid metal matrix and dibasic alcohol with dicarboxylic acid.
The invention provides the hot melt adhesive water-dispersible copolyester composition, a kind of hot melt adhesive water-dispersible copolyester composition that makes by dicarboxylic acid or derivatives thereof, dicarboxylic acid and the diol component copolymerization that will contain the sulfonic acid metal matrix especially is provided.Hot melt adhesive water-dispersible copolyester composition according to the present invention has excellent water dispersible, is coated in to treat that laminated layer upward also also shows excellent metal adhesion after the drying.Thereby copolyester composition of the present invention and various material are bonded together securely.
In addition, since the bonding back of composition of the present invention rapid crystallization, the inadhesion (tack free property) when therefore the bonding coat that is formed by composition of the present invention also has excellent thermotolerance, chemical resistance, hydrolytic resistance, physical strength to organic solvent and is exposed to external environment.But also guaranteed tolerance (dimensional stability), and excellent Young's modulus and flexural strength to external stress (thermal shocking) and internal stress (contraction that is produced by the substrate resin crystallization).Because these performances, composition of the present invention can be used as polyvinyl chloride (PVC), polyethylene terephthalate (PET), polycarbonate (PC) or polymethylmethacrylate (PMMA) basement membrane, iron plate, aluminium flake, various alloy slices (as stainless steel substrates, sheet tin, electrogalvanizing (EGI) steel disc etc.), the perhaps bonding coat in the scraps of paper laminated.Composition of the present invention also can be used as the bonding coat in other material except above-mentioned body material laminated.
According to the present invention, described hot melt adhesive water-dispersible copolyester composition contains: (a) acid constituents, this acid constituents comprise that 100 weight parts do not contain the dicarboxylic acid of sulfonic acid metal matrix and the dicarboxylic acid that the 5-30 weight part contains the sulfonic acid metal matrix; (b) diol component of 20-100 weight part; And (c) acid constituents buffer compounds, be benchmark with the content of described acid constituents, the content of this acid constituents buffer compounds is 0.1-0.4 mole %.
In composition of the present invention, acid constituents buffer compounds (c) is preferably the form of faintly acid salt (conjugate base), described salt be selected from by sodium acetate, sodium bicarbonate, yellow soda ash, sodium hydrogen phosphate, Sodium Tetraborate, Potassium Hydrogen Phthalate, and the group formed of their mixture in.
Described resin combination preferably also contains the mixed solvent that makes with 100: 0 to 50: 50 ratio of mixture intermingling by with water and solvent composition, described solvent composition is selected from by the monovalent alcohol that comprises methyl alcohol, ethanol, Virahol and n-propyl alcohol with 1-15 carbon atom (monovalent alcohol), ethylene glycol such as ethylene glycol monobutyl ether, Diethylene Glycol such as Diethylene Glycol monobutyl ether, and in the group formed of ketone such as acetone and methylethylketone.
Under the preferable case, to be 0.2-0.6 deciliter/gram (30 ℃ measure down), second-order transition temperature (Tg) be 110-150 ℃ for 50-80 ℃, melting temperature (Tm) (Tm) for-30 ℃ to 10 ℃, Tc (Tc) to the limiting viscosity of resin combination.
Embodiment
Below the present invention will be described in further detail.
The invention provides the copolyester composition that makes by the dicarboxylic acid or derivatives thereof that contains the sulfonic acid metal matrix, dicarboxylic acid and diol component copolymerization, wherein, 100 weight part dicarboxylic acid and 5-30 weight part contain the dicarboxylic acid or derivatives thereof and the copolymerization in the presence of the acid constituents buffer compounds of 20-100 weight part diol component of dicarboxylic acid metal matrix.
The form that to be used for acid constituents buffer compounds of the present invention be faintly acid salt (conjugate base), described salt be selected from sodium acetate, sodium bicarbonate, yellow soda ash, sodium hydrogen phosphate, Sodium Tetraborate, Potassium Hydrogen Phthalate, and the group formed of their mixture in.Content with acid constituents is benchmark, and the content of acid constituents buffer compounds is 0.1-0.4 mole %.
Below with reference to embodiment the present invention is described in further detail.Yet, should be understood that these embodiment can not be interpreted as and limit the scope of the invention.
Embodiment 1
In the reactor that has temperature control post and condenser, add dimethyl terephthalate (DMT) (100 gram), 5-sodium sulfonate dimethyl isophthalate (15 gram), sebacic acid (50 gram), ethylene glycol (40 gram) and 1,4-butyleneglycol (30 gram) slowly rises to 150 ℃ with the temperature in the reactor then when stirring.To join in the reactor as zinc acetate (0.2 gram), tetrabutyl titanate (0.1 gram) and the sodium acetate (2 gram) of catalyzer subsequently, when stirring, the material in the reactor is heated to 235 ℃, under this temperature, carry out esterification then.When beginning to flow out as the methyl alcohol of byproduct of reaction in the reaction process, the temperature in the post remains on 100 ℃ to prevent distillation of dicarboxylic acid or diol component or evaporation.When reaction continues 5 hours, when water and methyl alcohol no longer flowed out, reaction product also changed the transparent oligopolymer of lemon yellow into by the White-opalescent attitude, showed that esterification finishes.
Weisspiessglanz (0.3 gram) is joined in the oligomeric reaction product as catalyzer, then reactor is vacuumized, simultaneously guarantee that carefully reaction mass is not disperseed, and the temperature in the rising reactor, the pressure in the reactor maintains 1 and holds in the palm and the temperature of reaction mass reaches 265 ℃ like this.Reaction mass was reacted 2 hours under said temperature and pressure, thereby make water-dispersible copolyester composition.Simultaneously, the diol component ethylene glycol and 1 that in above-mentioned steps, adds, the 4-butyleneglycol flows out as byproduct of reaction.The water-dispersible copolyester composition of gained is 0.5 deciliter/gram 30 ℃ of limiting viscosities that get with the limiting viscosity instrumentation down thus, second-order transition temperature (Tg) is that 80 ℃, melting temperature (Tm) (Tm) are 125 ℃ for-25 ℃, Tc (Tc), and said temperature records by differential scanning calorimeter.
Subsequently, the above-mentioned copolyester composition that makes (25 gram) was stirred 3 hours down at 80 ℃ in the mixed solvent of water (70 gram) and Virahol (5 gram), thereby make the dispersed copolyester dispersion of transparent water of lemon yellow.The limiting viscosity that is recorded this dispersion by brookfield's viscometer (Brookfield viscometer) under 30 ℃ is 250 centipoises (cps).
Use wire bar applicator (bar coater) dispersions obtained thickness with 20 microns to be coated on PET (polyethylene terephthalate) film of 188 micron thickness, use hot-air dry 3 minutes down at 120 ℃ then.The PET film that has bonding film on its of gained is placed on the PET film of another 188 micron thickness, and use dry laminating machine (dry laminator) under 130 ℃, they to be laminated together with 2 meters/minute the speed and the load of 3 kilogram forces, bond strength has wherein improved, and the gained result provides in following table 1.
The device that is used to measure bond strength is UTM (INSTRON; And measure T-stripping strength (180 ° of stripping strengths) handpiece speed of the load cell of 200 kilogram forces and 20 mm/min).
Embodiment 2
Adopt the mode identical to prepare copolyester composition with embodiment 1.The copolyester composition (60 gram) that makes is joined in the mixed solvent of water (105 gram) and butylcarbitol (35 gram), and stirred 3 hours down, thereby make white dispersion at 80 ℃.The limiting viscosity that is recorded this dispersion by brookfield's viscometer under 30 ℃ is 320cps.
Use wire bar applicator dispersions obtained thickness with 20 microns to be coated on the PET film of 188 micron thickness, use hot-air dry 3 minutes down at 120 ℃ then.The PET film that has bonding film on its of gained is placed on the PET film of another 188 micron thickness, and use dry laminating machine under 130 ℃, they to be laminated together with 2 meters/minute the speed and the load of 3 kilogram forces, bond strength has wherein improved, and the gained result provides in following table 1.
Embodiment 3
Adopt the mode identical to prepare copolyester composition with embodiment 1.The copolyester composition (60 gram) that makes is joined in the mixed solvent of water (105 gram) and ethylene glycol dibutyl ether (35 gram), and stirred 3 hours down, thereby make white dispersion at 80 ℃.The limiting viscosity that is recorded this dispersion by brookfield's viscometer under 30 ℃ is 310cps.
Use wire bar applicator dispersions obtained thickness with 20 microns to be coated on the PET film of 188 micron thickness, use hot-air dry 3 minutes down at 120 ℃ then.The gained PET film that has bonding film on it is placed on the PET film of another 188 micron thickness, and use dry laminating machine under 130 ℃, they to be laminated together with 2 meters/minute the speed and the load of 3 kilogram forces, bond strength has wherein improved, and the gained result provides in following table 1.
Embodiment 4
Adopt the mode identical to prepare copolyester composition with embodiment 1.The copolyester composition (60 gram) that makes is joined in the mixed solvent of water (105 gram) and ethanol (35 gram), and stirred 3 hours down, thereby make white dispersion at 80 ℃.The limiting viscosity that is recorded this dispersion by brookfield's viscometer under 30 ℃ is 330cps.
Use wire bar applicator dispersions obtained thickness with 20 microns to be coated on the PET film of 188 micron thickness, use hot-air dry 3 minutes down at 120 ℃ then.The gained PET film that has bonding film on it is placed on the PET film of another 188 micron thickness, and use dry laminating machine under 130 ℃, they to be laminated together with 2 meters/minute the speed and the load of 3 kilogram forces, bond strength has wherein improved, and the gained result provides in following table 1.
Table 1
| Embodiment | |||||
| 1 | 2 | 3 | 4 | ||
| Viscosity | 250 | 320 | 310 | 330 | |
| Outward appearance (color and luster) | Transparent | Transparent | Transparent | Transparent | |
| Bond strength (kilogram force/inch) | Initially | 2.45 | 2.21 | 2.98 | 3.95 |
| After 3 days | 2.42 | 2.20 | 2.97 | 3.79 | |
| After 7 days | 2.50 | 2.16 | 3.28 | 4.11 | |
As mentioned above, the invention provides a kind of hot melt adhesive water-dispersible copolyester composition, a kind of hot melt adhesive water-dispersible copolyester composition that makes by dicarboxylic acid or derivatives thereof, dicarboxylic acid and the diol component copolymerization that will contain the sulfonic acid metal matrix especially is provided.Hot melt adhesive water-dispersible copolyester composition of the present invention has excellent water dispersible, is coated to treat also also to demonstrate excellent fusion binding property after the drying on the laminated material.Thereby copolyester composition of the present invention and various material are bonded together securely.
And because the bonding back of present composition rapid crystallization, so the bonding coat that forms of the present composition has excellent thermotolerance, the chemical resistance to organic solvent, hydrolytic resistance, physical strength and is exposed to inadhesion under the external environment.Since the bonding back of composition of the present invention rapid crystallization, the inadhesion (tack free property) when therefore the bonding coat that is formed by composition of the present invention also has excellent thermotolerance, chemical resistant properties, hydrolytic resistance, physical strength to organic solvent and is exposed to external environment.But also guaranteed tolerance (dimensional stability), and excellent Young's modulus and flexural strength to external stress (thermal shocking) and internal stress (contraction that causes by the substrate resin crystallization).Because these performances, composition of the present invention can be used as PVC, PET, PC or PMMA basement membrane, iron plate, aluminium flake, various alloy slices (as stainless steel substrates, sheet tin, EGI steel disc etc.), the perhaps bonding coat in the scraps of paper laminated.Said composition also can be used as the bonding coat in other material except above-mentioned body material laminated.
Though for purposes of illustration have been described optimal way of the present invention, those skilled in the art will realize under the condition that does not deviate from as the disclosed scope and spirit of the present invention of claim of enclosing, and can carry out various modifications, interpolation and replacement.
Claims (5)
1, a kind of hot melt adhesive water-dispersible copolyester composition, said composition contains:
(a) acid constituents, this acid constituents comprise that 100 weight parts do not contain the dicarboxylic acid of sulfonic acid metal matrix and the dicarboxylic acid that the 5-30 weight part contains the sulfonic acid metal matrix;
(b) 20-100 weight part diol component; With
(c) acid constituents buffer compounds is a benchmark with the content of described acid constituents, and the content of this acid constituents buffer compounds is 0.1-0.4 mole %.
2, composition according to claim 1, wherein, described acid constituents buffer compounds (c) for be selected from by sodium acetate, sodium bicarbonate, yellow soda ash, sodium hydrogen phosphate, Sodium Tetraborate, Potassium Hydrogen Phthalate, and the group formed of their mixture in the form of salt of weak acid.
3, composition according to claim 1, wherein, said composition also comprises by water and solvent composition mixes the mixed solvent that makes with 100: 0 to 50: 50 ratio of mixture each other, and described solvent composition is selected from the group of being made up of the alcohol with 1-15 carbon atom, ethylene glycol, Diethylene Glycol and ketone.
4, composition according to claim 3, wherein, described solvent composition is selected from the group of being made up of methyl alcohol, ethanol, Virahol, n-propyl alcohol, ethylene glycol monobutyl ether, Diethylene Glycol monobutyl ether, acetone, methylethylketone.
5, composition according to claim 1, wherein, the limiting viscosity that described resin combination records under 30 ℃ is the 0.2-0.6 deciliter/gram, and second-order transition temperature is-30 ℃ to 10 ℃, and Tc is 50-80 ℃, and solvent temperature is 110-150 ℃.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020050133813 | 2005-12-29 | ||
| KR1020050133813A KR20070070855A (en) | 2005-12-29 | 2005-12-29 | Hot-melt adhesive type water dispersible copolyester composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1990808A true CN1990808A (en) | 2007-07-04 |
Family
ID=38213354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006100902453A Pending CN1990808A (en) | 2005-12-29 | 2006-07-07 | Hot melt adhesive water -dispersible copolyester composition |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR20070070855A (en) |
| CN (1) | CN1990808A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105603562A (en) * | 2015-12-29 | 2016-05-25 | 江苏恒力化纤股份有限公司 | Thermal resistant polyester industrial yarn and preparing method thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464959B (en) * | 2010-11-04 | 2013-05-01 | 中国石油化工股份有限公司 | Water dispersible wax-bearing hot melt adhesive composition |
| CN105506773B (en) * | 2015-12-29 | 2017-12-12 | 江苏恒力化纤股份有限公司 | A kind of high-strength middle contracting polyester industrial fiber and preparation method thereof |
| CN105506772B (en) * | 2015-12-29 | 2017-11-17 | 江苏恒力化纤股份有限公司 | A kind of heat-resistance polyester activated industrial silk and preparation method thereof |
| CN105506774B (en) * | 2015-12-29 | 2017-12-12 | 江苏恒力化纤股份有限公司 | A kind of low aberration polyester abnormal contraction composite filament and preparation method thereof |
| KR102491633B1 (en) * | 2016-06-30 | 2023-01-20 | 코오롱인더스트리 주식회사 | Thermal shrinking polyester based film, Method of manufacturing thereof and Label comprising thereof |
-
2005
- 2005-12-29 KR KR1020050133813A patent/KR20070070855A/en not_active Application Discontinuation
-
2006
- 2006-07-07 CN CNA2006100902453A patent/CN1990808A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105603562A (en) * | 2015-12-29 | 2016-05-25 | 江苏恒力化纤股份有限公司 | Thermal resistant polyester industrial yarn and preparing method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070070855A (en) | 2007-07-04 |
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Open date: 20070704 |