CN104093760B - The backboard of resin combination, two-component-type laminating adhesive, laminated film and solar cell - Google Patents
The backboard of resin combination, two-component-type laminating adhesive, laminated film and solar cell Download PDFInfo
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- CN104093760B CN104093760B CN201380008286.1A CN201380008286A CN104093760B CN 104093760 B CN104093760 B CN 104093760B CN 201380008286 A CN201380008286 A CN 201380008286A CN 104093760 B CN104093760 B CN 104093760B
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- polyol
- resin combination
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- 229920005989 resin Polymers 0.000 title claims abstract description 89
- 239000011347 resin Substances 0.000 title claims abstract description 89
- 239000012939 laminating adhesive Substances 0.000 title description 3
- 229920005862 polyol Polymers 0.000 claims abstract description 80
- 150000003077 polyols Chemical class 0.000 claims abstract description 74
- 239000004814 polyurethane Substances 0.000 claims abstract description 63
- 229920002635 polyurethane Polymers 0.000 claims abstract description 63
- 229920000728 polyester Polymers 0.000 claims abstract description 62
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 43
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 39
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 39
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 239000003822 epoxy resin Substances 0.000 claims abstract description 29
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 29
- 238000003475 lamination Methods 0.000 claims abstract description 23
- 238000009826 distribution Methods 0.000 claims abstract description 18
- 229920005668 polycarbonate resin Polymers 0.000 claims abstract description 15
- 239000004431 polycarbonate resin Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims description 41
- -1 aliphatic polyol Chemical class 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 229920006267 polyester film Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 15
- 239000011248 coating agent Substances 0.000 abstract description 10
- 238000000576 coating method Methods 0.000 abstract description 10
- 238000012360 testing method Methods 0.000 abstract description 6
- 230000032683 aging Effects 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract description 4
- 238000007711 solidification Methods 0.000 abstract description 3
- 230000008023 solidification Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
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- 238000006243 chemical reaction Methods 0.000 description 31
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- 238000003756 stirring Methods 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 24
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 13
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 13
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical group C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 11
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 6
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 6
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- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/049—Protective back sheets
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
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Abstract
The invention provides that the coating strength after solidification is strong, bonding strength is high, bonding strength can not the also excellent resin combination of outward appearance after the excellent and lamination process of the such ageing stability of deterioration in humidity resistance test, two-component-type lamination caking agent containing this resin combination, has the laminated film of the layer formed by this caking agent and the backboard of solar cell.A kind of resin combination, it contains: have branched structure in molecule, weight-average molecular weight is the scope of 10,000 ~ 100,000 and molecular weight distribution is the polyester polyurethane polyol of more than 5.0, there is in molecule branched structure, weight-average molecular weight be 10,000 ~ 50,000 scope and the molecular weight distribution polyester polyol that is less than 5.0, number-average molecular weight is the hydroxyl-containing epoxy resin of the scope of 300 ~ 5,000, and number-average molecular weight is hydroxyl polycarbonate resin and the polyisocyanates of the scope of 300 ~ 3,000.A kind of two-component-type lamination caking agent, it contains foregoing.
Description
Technical field
The present invention relates to the backboard of the resin combination of the substrate bonding excellence under wet heat condition, two-component-type lamination caking agent, laminated film and solar cell.
Background technology
In recent years, as the representative of clean energy, solar electrical energy generation just attracts attention.The backboard being arranged on the most back side of solar module is used to protect the power facility such as battery, wiring not by external environment influence and the component keeping insulativity, is the layered product utilizing caking agent to be fitted by various functional film.For the caking agent for this backboard, require it to have with high level, to polyester film, polyvinyl fluoride thin film etc., there is the high adhesion of the various films of different characteristics, the humidity resistance for also long term maintenance cementability under environment in the open.
As this backboard caking agent, propose the polyurethanes caking agent (see patent documentation 1) containing the host and solidifying agent that comprise polyester polyol, polyester polyurethane polyol and bisphenol-type epoxy resin.
Prior art document
Patent documentation
Patent documentation 1: No. 4416047th, Japanese Patent
Summary of the invention
the problem that invention will solve
But there are the following problems on ageing stability for aforementioned polyurethanes caking agent: coating strength is after hardening weak, and bonding strength can be deteriorated in humidity resistance test, but also there is the problem of the appearance poor after lamination process.
The problem to be solved in the present invention is that the coating strength after providing solidification is strong, bonding strength is high, in humidity resistance test, bonding strength can not the also excellent resin combination of outward appearance after the excellent and lamination process of the such ageing stability of deterioration, two-component-type lamination caking agent containing this resin combination, has the laminated film of the layer formed by this caking agent and the backboard of solar cell.
for the scheme of dealing with problems
The present inventor etc. are in order to solve the problem, conduct in-depth research, found that, by using the resin combination of following two-pack curing, coating strength after solidification is strong, bonding strength is high, in humidity resistance test bonding strength can not the such ageing stability of deterioration excellent, and outward appearance after lamination process is also excellent, thus complete the present invention, the resin combination of described two-pack curing uses following neccessary composition as host: have branched structure in (1) molecule, weight-average molecular weight (Mw) be 10000 ~ 100000 scope and molecular weight distribution (Mw/Mn) be more than 5.0 polyester polyurethane polyol (A), (2) in molecule, there is branched structure, weight-average molecular weight (Mw) be 10000 ~ 50000 scope and molecular weight distribution (Mw/Mn) polyester polyol (B) that is less than 5.0, and use as required compounding (3) number-average molecular weight (Mn) to be wherein the hydroxyl-containing epoxy resin (C) of the scope of 300 ~ 5000 further, (4) number-average molecular weight (Mn) is the host composition of the hydroxyl polycarbonate resin (D) of the scope of 300 ~ 3000 and (5) polyisocyanates (E) as its solidifying agent.
That is, the present invention relates to a kind of resin combination, it is characterized in that, it is using following compositions as neccessary composition:
(1) there is in molecule branched structure, weight-average molecular weight (Mw) be 10000 ~ 100000 scope and molecular weight distribution (Mw/Mn) be more than 5.0 polyester polyurethane polyol (A), and
(2) there is in molecule branched structure, weight-average molecular weight (Mw) be 10000 ~ 50000 scope and molecular weight distribution (Mw/Mn) polyester polyol (B) that is less than 5.0.
The invention still further relates to a kind of two-component-type lamination caking agent, its on the basis of aforementioned (A) composition and aforementioned (B) composition also containing (5) polyisocyanates (E) as solidifying agent.
The invention still further relates to a kind of laminated film, its adhesive linkage that there is the film of more than a kind in the group being selected from and being made up of polyester film, fluorine resin film, polyolefin film, tinsel and formed by above-mentioned two-component-type lamination caking agent.
The invention still further relates to a kind of backboard of solar cell, it has the adhesive linkage formed by above-mentioned two-component-type lamination caking agent.
the effect of invention
Resin combination of the present invention and strong containing the two-component-type lamination caking agent coating strength after hardening of this resin combination, bonding strength is high, in humidity resistance test bonding strength can not outward appearance after the excellent and lamination process of the such ageing stability of deterioration also excellent, the caking agent therefore as the backboard of laminated film and solar cell is useful.
Embodiment
Resin combination of the present invention contain in (1) molecule there is branched structure, weight-average molecular weight (Mw) is the scope of 10000 ~ 100000 and molecular weight distribution (Mw/Mn) is that the polyester polyurethane polyol (A) of more than 5.0 is as neccessary composition.
Previous polyesters polyurethane polyol (A) has branched structure in molecule, thus final cured article becomes the high material of cross-linking density, even if therefore also not swelling under wet heat condition, can maintain high adhesion.
In addition, the weight-average molecular weight (Mw) of previous polyesters polyurethane polyol (A) is the scope of 10000 ~ 100000.By making weight-average molecular weight (Mw) be in aforementioned range, cured article demonstrates high strength, becomes the resin combination of initial bonding strength excellence.And the viscosity of resin combination is suitable for coating.When the weight-average molecular weight (Mw) of previous polyesters polyurethane polyol (A) is less than 10000, there is the tendency that initial bonding strength reduces, become the resin combination being difficult to evenly coating because viscosity is low.
On the other hand, when the weight-average molecular weight (Mw) of previous polyesters polyurethane polyol (A) is more than 100000, there is the tendency that viscosity increases, therefore become the resin combination being difficult to apply.For the weight-average molecular weight (Mw) of this polyester polyurethane polyol (A), from obtaining the high and aspect of the resin combination that substrate bonding under wet heat condition is also excellent of initial bonding strength, weight-average molecular weight (Mw) is preferably the scope of 12000 ~ 90000.
The molecular weight distribution (Mw/Mn) of previous polyesters polyurethane polyol (A) is more than 5.0.Be in aforementioned range by making molecular weight distribution (Mw/Mn), the effect that the effect improved with adaptation that is base material that is that brought from low molecular weight compositions and the cured article brought from high molecular weight components become high strength can be played simultaneously, therefore become the resin combination that excellent, the initial bonding strength of substrate bonding under wet heat condition is high.When molecular weight distribution (Mw/Mn) is less than 5.0, there is the tendency of the degraded appearance after lamination process.From the aspect of the more excellent resin combination of the substrate bonding that can obtain under wet heat condition, the molecular weight distribution (Mw/Mn) of polyester polyurethane polyol (A) is preferably the scope of 5 ~ 25, is more preferably the scope of 5 ~ 15.
In addition,, viscosity excellent from the substrate bonding become under wet heat condition is suitable for the aspect of the resin combination applied, the number-average molecular weight (Mn) of previous polyesters polyurethane polyol (A) is preferably the scope of 3000 ~ 20000, is more preferably the scope of 5000 ~ 10000.
It should be noted that, in the present invention, weight-average molecular weight (Mw) and number-average molecular weight (Mn) are the values measured by the gel permeation chromatography (GPC) of following condition.
Determinator: the HLC-8220GPC that TOSOH Co., Ltd manufactures
Post: TSK-GELSuperHZM-M × 4 that the TSK-GUARDCOLUMNSuperHZ-L+ TOSOH Co., Ltd that TOSOH Co., Ltd manufactures manufactures
Detector: RI (differential refractometer)
Data processing: the MultistationGPC-8020modelII that TOSOH Co., Ltd manufactures
Condition determination: column temperature 40 DEG C
Solvents tetrahydrofurane
Flow velocity 0.35ml/ minute
Standard: monodisperse polystyrene
Sample: carried out filtering with the tetrahydrofuran solution that microfilter counts 0.2 quality % to converting with resin solid content and the material (100 μ l) that obtains
In addition, from the aspect of the substrate bonding excellence under wet heat condition, the hydroxyl value of previous polyesters polyurethane polyol (A) is preferably the scope of 5 ~ 30mgKOH/g, is more preferably the scope of 7 ~ 15mgKOH/g.When the hydroxyl value of previous polyesters polyurethane polyol (A) is greater than 30mgKOH/g, there is the tendency that wet-heat resisting cementability is deteriorated, when the hydroxyl value of previous polyesters polyurethane polyol (A) is less than 5mgKOH/g, reduce with the reactivity of solidifying agent, there is the tendency that cementability is deteriorated.
Previous polyesters polyurethane polyol (A) such as obtains by making polyprotonic acid (E), polyvalent alcohol (F), polyisocyanates (G) react.In this situation, in order to import branched structure in the molecule of polyester polyurethane polyol (A), any one the above material composition in polyprotonic acid (E), polyvalent alcohol (F) and polyisocyanates (G) uses 3 officials can above compound.
Aforementioned polybasic acids (E) can list diprotic acid (E1) and 3 officials can above polyprotonic acid (E2).
As aforementioned diprotic acid (E1), include, for example out the aliphatic dibasic acid of propanedioic acid, succinic acid, pentanedioic acid, hexanodioic acid, pimelic acid, suberic acid, nonane diacid, sebacic acid, undecane diacid, dodecanedioic acid, undecane dicarboxylic acid, tetradecane diacid, pentadecane diacid, Thapsic acid, pentadecane dicarboxylic acid, octadecane diacid, nonadecen diacid, octadecane dicarboxylic acid and so on; The aliphatics unsaturated dibasic acid of tetrahydrophthalic acid, toxilic acid, maleic anhydride, fumaric acid, citraconic acid, methylene-succinic acid, propene dicarboxylic acid and so on and acid anhydride thereof; The aliphatics unsaturated dibasic acid of tetrahydrophthalic acid, toxilic acid, maleic anhydride, fumaric acid, citraconic acid, methylene-succinic acid, propene dicarboxylic acid and so on and acid anhydride thereof; The aromatic acid of phthalic acid (Phthalicacid), Tetra hydro Phthalic anhydride, terephthalic acid, m-phthalic acid, phthalic acid (Orthophthalicacid) and so on and acid anhydride etc. thereof.
Can above polyprotonic acid (E2) as aforementioned 3 officials, include, for example out the aliphatics triprotic acids such as 1,2,5-hexane tricarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid; Aromatic series triprotic acid and the acid anhydride etc. thereof such as trimellitic acid, trimellitic acid 1,2-anhydride, 1,2,5-benzene tricarbonic acid, 2,5,7-naphthalene tricarboxylic acid.
At this, by using aforementioned 3 officials can above polyprotonic acid (E2), branched structure can be imported in the molecule of polyester polyurethane polyol of the present invention (A).
These polyprotonic acids (E) can be used alone, can also be used in combination of two or more separately.Wherein, the aspect of the resin combination applied is suitable for from the excellent and viscosity of the substrate bonding that can obtain under wet heat condition, preferably combination uses aliphatic polybasic acids and aromatic polyvalent acid, in this situation, the content shared in total polyacid constituent of preferred aliphat polyprotonic acid is the scope of 10 ~ 30 % by mole and aromatic polyvalent acid is the scope of 50 ~ 90 % by mole.In addition, from the aspect of the more excellent resin combination of the substrate bonding become under wet heat condition, the preferred hexanodioic acid of aforementioned aliphatic polybasic acids, pimelic acid, suberic acid, nonane diacid, sebacic acid, undecane diacid, dodecanedioic acid, undecane dicarboxylic acid, tetradecane diacid, pentadecane diacid, Thapsic acid, pentadecane dicarboxylic acid, octadecane diacid, nonadecen diacid, octadecane dicarboxylic acid, 1, 2, 5-hexane tricarboxylic acid, 1, 2, the carbonatoms of 4-cyclohexanetricarboxylic acid and so on is the aliphatic polybasic acids of the scope of 6 ~ 20, more preferably suberic acid, nonane diacid, sebacic acid, undecane diacid, dodecanedioic acid, undecane dicarboxylic acid, 1, 2, 5-hexane tricarboxylic acid, 1, 2, the carbonatomss such as 4-cyclohexanetricarboxylic acid are the aliphatic polybasic acids of the scope of 8 ~ 13.
In addition, for the molecular weight of adjustment previous polyesters polyurethane polyol (A), the object of viscosity, as the raw material of previous polyesters polyurethane polyol (A), the monocarboxylic acid of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, sad, n-nonanoic acid, capric acid, dodecylic acid, tetradecanoic acid, hexadecanoic acid, margaric acid, octadecanoic acid, phenylformic acid and so on also can be used.
Foregoing polyols (F) can list dibasic alcohol (F1) and 3 officials can above polyvalent alcohol (F2).
As aforementioned dibasic alcohol (F1), such as can list ethylene glycol, Diethylene Glycol, propylene glycol, 1, ammediol, 1,2,2-trimethylammonium-1,3-PD, 2,2-dimethyl-3-sec.-propyl-1, ammediol, BDO, 1,3 butylene glycol, 3-methyl isophthalic acid, 3-butyleneglycol, 1,5-pentanediol, 3-methyl isophthalic acid, 5-pentanediol, neopentyl glycol, 1,6-hexylene glycol, 1, two (methylol) hexanaphthene, 2 of 4-, the aliphatic diol of 2,4-trimethylammonium-1,3-pentanediol and so on; The ether glycol of polyoxyethylene glycol, polyoxypropylene diols and so on; The modified polyether glycol obtained by the ring-opening polymerization of the compound containing ring-type ehter bond of aforementioned aliphatic diol and oxyethane, propylene oxide, tetrahydrofuran (THF), ethyl ether, propyl glycidyl ether, butylglycidyl ether, phenyl glycidyl ether, glycidyl allyl ether and so on; The lactone polyester polyol obtained by the polycondensation of the various lactone such as aforementioned aliphatic diol and 6-caprolactone; The bis-phenol of dihydroxyphenyl propane, Bisphenol F and so on; To the bis-phenol addition of ethylene oxide, propylene oxide etc. of dihydroxyphenyl propane, Bisphenol F and so on and the alkylene oxide adducts etc. of the bis-phenol obtained.
Can above polyvalent alcohol (F2) as aforementioned 3 officials, include, for example out the aliphatic polyol of trimethylolethane, TriMethylolPropane(TMP), glycerine, hexanetriol, tetramethylolmethane and so on; The modified polyether polylol obtained by the ring-opening polymerization of the compound containing ring-type ehter bond of aforementioned aliphatic polyol and oxyethane, propylene oxide, tetrahydrofuran (THF), ethyl ether, propyl glycidyl ether, butylglycidyl ether, phenyl glycidyl ether, glycidyl allyl ether and so on; The lactone polyester polyol etc. obtained by the polycondensation of the lactone of aforementioned aliphatic polyol and 6-caprolactone and so on.
By using aforementioned 3 officials can above polyvalent alcohol (F2), branched structure can be imported in the molecule of polyester polyurethane polyol of the present invention (A).
Above-mentioned polyvalent alcohol (F) can be used alone, can also be used in combination of two or more separately.From the aspect of the resin combination of formation coating excellence, the content of aforementioned aliphatic polyol shared by total polyhydroxy reactant is preferably more than 40 % by mole, is more preferably more than 80 % by mole.In addition, from the aspect of the more excellent resin combination of the substrate bonding that can obtain under wet heat condition, aforementioned aliphatic polyol is preferably the aliphatic polyol that carbonatoms is more than 5, is more preferably aforementioned aliphatic diol.
Aforementioned polyisocyanates (G) can list diisocyanate cpd (G1) and 3 officials can above polyisocyanate compound (G2)
As aforementioned diisocyanates compound (G1), include, for example out butane-1,4-vulcabond, hexamethylene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, 2, the aliphatic diisocyanate of 4,4-trimethyl hexamethylene diisocyanate, xylylene diisocyanate, a tetramethyl-xylylene diisocyanate and so on; Hexanaphthene-1,4-vulcabond, isophorone diisocyanate, lysinediisocyanate, dicyclohexyl methyl hydride-4,4 '-vulcabond, 1, the alicyclic diisocyanate of two (isocyanatomethyl) hexanaphthene of 3-, methylcyclohexane diisocyanate, isopropylidene dicyclohexyl-4,4 '-vulcabond, norbornene alkyl diisocyanate and so on; 1,5-naphthalene diisocyanate, 4,4 '-diphenylmethanediisocyanate, 4,4 '-diphenyldimethyhnethane vulcabond, 4,4 '-dibenzyl diisocyanate, dialkyl group diphenylmethanediisocyanate, tetraalkyl diphenylmethanediisocyanate, 1, the aromatic diisocyanate etc. of 3-phenylene diisocyanate, Isosorbide-5-Nitrae-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, tetramethyl-xylylene diisocyanate and so on.
Aforementioned 3 officials such as can list in molecule the adducts type polyisocyanate compound with amino-formate bond position, the urea acid esters type polyisocyanate compound in molecule with isocyanuric acid ester ring structure by polyisocyanate compound (G2) above.
The adducts type polyisocyanate compound in previous molecular with amino-formate bond position such as can make diisocyanate cpd and polyol reaction and obtain.The diisocyanate cpd used in the reaction include, for example out as the various diisocyanate cpds illustrated in aforementioned diisocyanates compound (G1), and they can be used alone, can also be used in combination of two or more separately.In addition, the polyol compound used in the reaction can list as the various polyol compounds illustrated in foregoing polyols (F), the polyester polyol etc. that makes polyvalent alcohol and polyprotonic acid react and obtain, these compounds can be used alone, can also be used in combination of two or more separately.
The aforementioned urea acid esters type polyisocyanate compound in molecule with isocyanuric acid ester ring structure such as can make diisocyanate cpd and monohydroxy-alcohol and/or diol reaction and obtain.The diisocyanate cpd used in the reaction include, for example out as the various diisocyanate cpds illustrated in aforementioned diisocyanates compound, and they can be used alone, can also be used in combination of two or more separately.In addition, as the monohydroxy-alcohol used in the reaction, include, for example out hexanol, 2-Ethylhexyl Alcohol, octanol, nonylcarbinol, n-undecane alcohol, n-dodecane alcohol, n-tridecane alcohol, n-tetradecanol, Pentadecane alcohol, n-heptadecane alcohol, Octadecane alcohol, NSC 77136 alcohol, eicosanol, 5-ethyl-2-nonyl alcohol, Exxal 12, 2-hexyl decyl alcohol, 3, 9-diethyl-6-tridecyl alcohol, the different hendecanol of the different heptyl of 2-, 2-Standamul G, 2-decyl tetradecanol etc., as dibasic alcohol, illustrative aliphatic diol etc. in foregoing polyols (F) can be listed.These monohydroxy-alcohols and dibasic alcohol can be used alone, can also be used in combination of two or more separately.
At this, by using aforementioned 3 officials can above polyisocyanate compound (G2), branched structure can be imported in the molecule of polyester polyurethane polyol of the present invention (A).
These polyisocyanates (G) can be used alone, can also be used in combination of two or more separately.Wherein, from the aspect of the resin combination of the bonding strength excellence that can obtain under wet heat condition, preferably aforementioned 3 officials can above polyisocyanate compound (G2), more preferably urea acid esters type polyisocyanate compound.In addition, resin combination is adjusted to from easy the aspect being suitable for the viscosity applied, preferably combination uses aforementioned diisocyanates compound (G1) and aforementioned 3 officials can above polyisocyanate compound (G2).In this situation, excellent and demonstrate the aspect of the resin combination being suitable for the viscosity applied from the substrate bonding that becomes under wet heat condition, both mass ratioes [(G1)/(G2)] are preferably the scope of 50/50 ~ 5/95, be more preferably the scope of 40/60 ~ 10/90, be particularly preferably the scope of 30/70 ~ 15/85.
3 officials used when manufacturing previous polyesters polyurethane polyol (A) can composition above can be any one in aforementioned polybasic acids (E2), foregoing polyols (F2) and aforementioned polyisocyanates compound (G2), but as previously mentioned, in the resin combination of the bonding strength excellence that can obtain under wet heat condition and the aspect of previous polyesters polyurethane polyol (A) can be manufactured easily with the shorter time, preferably use polyisocyanate compound (G2).
As the method manufacturing previous polyesters polyurethane polyol (A), include, for example out following method etc.: under the existence of esterifying catalyst, aforementioned polybasic acids (E) and foregoing polyols (F) is made to react in the temperature range of 150 ~ 270 DEG C and obtain polyester polyol, then, under the existence of urethanation catalyst, this polyester polyol and aforementioned polyisocyanates (G) are reacted in the temperature range of 50 ~ 100 DEG C.
In addition, resin combination of the present invention contain in (2) molecule there is branched structure, weight-average molecular weight (Mw) is the scope of 10000 ~ 50000 and molecular weight distribution (Mw/Mn) is that the polyester polyol (B) of less than 5.0 is as neccessary composition.
Previous polyesters polyurethane polyol (A) has branched structure in molecule, thus final cured article becomes the high material of cross-linking density, even if therefore also not swelling under wet heat condition, can maintain high adhesion.
Foregoing polyester polyols (B) has branched structure in its molecule, thus especially when for laminating adhesive, contributes to improving initial cementability and wet-heat resisting cementability.
In addition, the weight-average molecular weight (Mw) of foregoing polyester polyols (B) is the scope of 10000 ~ 50000.By making weight-average molecular weight (Mw) be in aforementioned range, cured article demonstrates high strength, becomes the resin combination of initial bonding strength excellence.And the viscosity of resin combination is suitable for coating.When the weight-average molecular weight (Mw) of foregoing polyester polyols (B) is less than 10000, there is the tendency that initial bonding strength reduces, become the resin combination being difficult to evenly coating because viscosity is low.On the other hand, when the weight-average molecular weight (Mw) of foregoing polyester polyols (B) is more than 50000, become owing to there is tendency that viscosity increases the resin combination being difficult to apply.For the weight-average molecular weight (Mw) of this polyester polyol (B), from obtaining the high and aspect of the resin combination that substrate bonding under wet heat condition is also excellent of initial bonding strength, weight-average molecular weight (Mw) is preferably the scope of 12000 ~ 40000.
The molecular weight distribution (Mw/Mn) of foregoing polyester polyols (B) is lower than 5.0.By making molecular weight distribution (Mw/Mn) be in aforementioned range, when being used as two-component-type lamination caking agent, the effect of the excellent appearance after lamination process can be played.When the molecular weight distribution (Mw/Mn) of foregoing polyester polyols (B) is more than 5.0, when being used as two-component-type lamination caking agent, there is the tendency that initial bond reduces.The molecular weight distribution (Mw/Mn) of foregoing polyester polyols (B) is preferably the scope of 1.0 ~ 5.0, is more preferably the scope of 2.0 ~ 4.0.
In addition,, viscosity excellent from the substrate bonding become under wet heat condition is suitable for the aspect of the resin combination applied, the number-average molecular weight (Mn) of foregoing polyester polyols (B) is preferably the scope of 3000 ~ 20000, is more preferably the scope of 5000 ~ 10000.
In addition, from the aspect of the substrate bonding excellence under wet heat condition, the hydroxyl value of foregoing polyester polyols (B) is preferably the scope of 5 ~ 30mgKOH/g, is more preferably the scope of 7 ~ 15mgKOH/g.
Foregoing polyester polyols (B) such as obtains by making polyprotonic acid (E) and polyvalent alcohol (F) react.In this situation, in order to import branched structure in the molecule of polyester polyol (B), any one the above material composition in polyprotonic acid (E) and polyvalent alcohol (F) uses 3 officials can above compound.
The material same with the reaction raw materials of previous polyesters polyurethane polyol (A) can be used as the polyprotonic acid (E) of the reaction raw materials of foregoing polyester polyols (B) and polyvalent alcohol (F).
As the method manufacturing foregoing polyester polyols (B), include, for example out following method etc.: under the existence of esterifying catalyst, aforementioned polybasic acids (E) and foregoing polyols (F) are reacted in the temperature range of 150 ~ 270 DEG C.
Resin combination of the present invention contains above-mentioned polyester polyurethane polyol (A) and polyester polyol (B) as host composition necessary in two-pack curing composition, even if also can show the aspect of high adhesion from the fluorine system base material such as PVF (fluorinated ethylene propylene) film, PVDF (poly(vinylidene fluoride)) film low to usual cementability, preferably also containing the hydroxyl-containing epoxy resin (C) that number-average molecular weight (Mn) is the scope of 300 ~ 5000.When the number-average molecular weight (Mn) of aforementioned epoxy resins (C) is less than 300, sufficient bonding strength cannot be obtained; When number-average molecular weight (Mn) is more than 5000, the solvability in resin combination of the present invention reduces.Wherein, from the solvability in resin combination of the present invention and the more excellent aspect of the substrate bonding under wet heat condition, number-average molecular weight (Mn) is more preferably the scope of 400 ~ 2000.
As aforementioned hydroxyl-containing epoxy resin (C), include, for example out the bisphenol-type epoxy resin of bisphenol A type epoxy resin, bisphenol f type epoxy resin and so on; The biphenyl type epoxy resin of biphenyl type epoxy resin, tetramethyl biphenyl type epoxy resin and so on; Dicyclopentadiene-phenol addition reaction-type epoxy resin etc.These hydroxyl-containing epoxy resin can be used alone, can also be used in combination of two or more separately.In the middle of these, from the aspect of the resin combination of the substrate bonding that can obtain under wet heat condition and initial bonding strength excellence, preferred bisphenol-type epoxy resin.
From the aspect of the resin combination of the substrate bonding excellence become under wet heat condition, resin combination of the present invention preferably also contains the hydroxyl polycarbonate resin (D) that number-average molecular weight (Mn) is the scope of 300 ~ 3000 on the basis of above-mentioned each composition.When number-average molecular weight (Mn) is less than 300, sufficient bonding strength cannot be obtained; When number-average molecular weight (Mn) is more than 3000, the solvability in resin combination of the present invention reduces.Wherein, from the solvability in resin combination of the present invention and the more excellent aspect of the substrate bonding under wet heat condition, more preferably number-average molecular weight (Mn) is the scope of 400 ~ 2000.
From the aspect becoming the more excellent resin combination of solidified nature, the hydroxyl value of aforementioned hydroxyl polycarbonate resin (D) is preferably the scope of 20 ~ 300mgKOH/g, is more preferably the scope of 40 ~ 250mgKOH/g.In addition, from the aspect of the substrate bonding excellence under wet heat condition, optimization polycarbonate glycol.
Aforementioned hydroxyl polycarbonate resin (D) such as can be manufactured by the method making polyvalent alcohol and carbonyl agent carry out polycondensation.
As the polyvalent alcohol used in the manufacture of aforementioned hydroxyl polycarbonate resin (D), include, for example out as the various polyvalent alcohols illustrated in foregoing polyols (F).
Polyvalent alcohol can be used alone, can also be used in combination of two or more separately.
The carbonyl agent used in the manufacture of the aforementioned polycarbonate resin (D) containing hydroxyl include, for example out ethylene carbonate, Texacar PC, methylcarbonate, diethyl carbonate, dibutyl carbonate, diphenyl carbonate etc.
These can be used alone, can also be used in combination of two or more separately.
Resin combination of the present invention contains previous polyesters polyurethane polyol (A) with following ratio, foregoing polyester polyols (B), aforementioned hydroxyl-containing epoxy resin (C) and aforementioned hydroxyl polycarbonate resin (D), relative to summation 100 mass parts of previous polyesters polyurethane polyol (A) with foregoing polyester polyols (B), aforementioned hydroxyl-containing epoxy resin (C) is the scope of 5 ~ 20 mass parts and aforementioned hydroxyl polycarbonate resin (D) is the scope of 5 ~ 20 mass parts, what formed various base material thus is excellent in adhesion, even if the resin combination of high substrate bonding also can be maintained under wet heat condition.
In addition, previous polyesters polyurethane polyol (A) in resin combination of the present invention counts the scope of preferably 10:50 ~ 90:10 in mass ratio with the compounding ratio of foregoing polyester polyols (B), is particularly preferably the scope of 20:80 ~ 50:50.
Resin combination of the present invention preferably uses aforementioned polyisocyanates (E) as curing agent component.This polyisocyanates (E) include, for example out as the various polyisocyanates listed by aforementioned polyisocyanates (G).These polyisocyanates (E) can be used alone one, also can combinationally use two or more.
In these polyisocyanates (E), be less likely to occur the aspect of xanthochromia from caking agent film, preferred aforementioned aliphatic diisocyanate compound.In addition, from the aspect of the base material excellent adhesion under wet heat condition, preferred aforementioned urea acid esters type polyisocyanate compound.
Resin combination of the present invention contains previous polyesters polyurethane polyol (A), foregoing polyester polyols (B), aforementioned hydroxyl-containing epoxy resin (C), aforementioned hydroxyl polycarbonate resin (D) and polyisocyanates (E) as neccessary composition.In the present invention, to make in previous polyesters polyurethane polyol (A), foregoing polyester polyols (B), aforementioned hydroxyl-containing epoxy resin (C) and aforementioned hydroxyl polycarbonate resin (D) ratio [OH]/[NCO] of the mole number [NCO] of isocyanate group contained in the total mole number [OH] of contained hydroxyl and aforementioned polyisocyanates compound (E) be 1/1 ~ 1/2 scope, be more preferably 1/1.05 ~ 1/1.5 scope, become the resin combination of solidified nature excellence thus.
Resin combination of the present invention can also contain all kinds of SOLVENTS.Aforementioned solvents include, for example out the ketone compounds of acetone, methylethylketone (MEK), methyl iso-butyl ketone (MIBK) and so on, the cyclic ether compounds of tetrahydrofuran (THF) (THF), dioxolane and so on, the ester compound of methyl acetate, ethyl acetate, butylacetate and so on, the aromatic series compounds of toluene, dimethylbenzene and so on, the alcohol compound etc. of Trivalin SF, cellosolve, methyl alcohol, Virahol, butanols, propylene glycol monomethyl ether and so on.These compounds can be used alone one, also can combinationally use two or more.
Resin combination of the present invention can also contain the various additives such as UV light absorber, antioxidant, silicon class additive, fluorine class additive, rheology control agent, defoamer, static inhibitor, antifogging agent further.
Resin combination of the present invention can use aptly as the two-component-type lamination caking agent for bonding various plastics film.
Aforementioned various plastics film include, for example out the film formed by polycarbonate, polyethylene terephthalate, polymethylmethacrylate, polystyrene, polyester, polyolefine, epoxy resin, melamine resin, tri acetyl cellulose resin, polyvinyl alcohol, ABS resin, norbornene resin, cyclic olefin resinoid, polyimide resin, polyfluoroethylene resin, polyvinylidene fluoride resin etc.Even if to by the film being difficult to bonding polyfluoroethylene resin especially in above-mentioned various film, polyvinylidene fluoride resin is formed, two-component-type lamination caking agent of the present invention also demonstrates high adhesion.
When being bonded to each other by aforementioned various film, the usage quantity of two-component-type lamination caking agent of the present invention is preferably 2 ~ 10g/m
2scope.
Use two-component-type lamination caking agent of the present invention multiple films bonding and the laminated film that obtains has following feature: be not easy to peel off even if also have under wet heat condition between high adhesion, film.
Therefore, two-component-type lamination caking agent of the present invention can be suitably used for waiting the laminated film purposes used under rugged environment without, as this purposes, include, for example out the caking agent the etc. during backboard of manufacture solar cell.
Embodiment
Below enumerate concrete synthesis example, the present invention will be described in more detail for embodiment, but the present invention is not limited to these embodiments.It should be noted that, in following example, " part " and " % " in case of no particular description, represents " mass parts " and " quality % " respectively.
It should be noted that, in the embodiment of the present application, number-average molecular weight (Mn) and weight-average molecular weight (Mw) are measured by the gel permeation chromatography (GPC) of following condition.
Determinator: the HLC-8220GPC that TOSOH Co., Ltd manufactures
Post: TSK-GELSuperHZM-M × 4 that the TSK-GUARDCOLUMNSuperHZ-L+ TOSOH Co., Ltd that TOSOH Co., Ltd manufactures manufactures
Detector: RI (differential refractometer)
Data processing: the MultistationGPC-8020modelII that TOSOH Co., Ltd manufactures
Condition determination: column temperature 40 DEG C
Solvents tetrahydrofurane
Flow velocity 0.35ml/ minute
Standard: monodisperse polystyrene
Sample: filter with the tetrahydrofuran solution that microfilter counts 0.2 quality % to converting with resin solid content and the material (100 μ l) that obtains
(synthesis example 1-1) [synthesis of polyester polyurethane polyol (A1)]
Neopentyl glycol 1131 parts, m-phthalic acid 737 parts, Tetra hydro Phthalic anhydride 342 parts, sebacic acid 534 parts, trimellitic acid 1,2-anhydride 20 parts and organic titanic compound 1.3 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, after being cooled to 100 DEG C, is 80% with diluted ethyl acetate to solids component.Then, the isocyanurate-modified body (SUMIDURN-3300 of hexamethylene diisocyanate is dropped into; SumitomoBayerUrethaneCo., Ltd. manufactures) 124 parts, hexamethylene diisocyanate 25 parts, in flask, pass into drying nitrogen and stir, while be heated to 70 ~ 80 DEG C to carry out urethane reaction.Stopped reaction when isocyanic ester containing ratio is less than 0.3%, obtains that number-average molecular weight is 5700, weight-average molecular weight is 35000 and hydroxyl value is the polyester polyurethane polyol of 10.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyurethane polyol (A1).
(synthesis example 1-2) [synthesis of polyester polyurethane polyol (A2)]
Neopentyl glycol 1155 parts, m-phthalic acid 755 parts, Tetra hydro Phthalic anhydride 325 parts, sebacic acid 507 parts, trimellitic acid 1,2-anhydride 20 parts and organic titanic compound 1.3 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, after being cooled to 100 DEG C, is 80% with diluted ethyl acetate to solids component.Then, the isocyanurate-modified body (SUMIDURN-3300 of hexamethylene diisocyanate is dropped into; SumitomoBayerUrethaneCo., Ltd. manufactures) 247 parts, hexamethylene diisocyanate 40 parts, in flask, pass into drying nitrogen and stir, while be heated to 70 ~ 80 DEG C to carry out urethane reaction.Stopped reaction when isocyanic ester containing ratio is less than 0.3%, obtains that number-average molecular weight is 7800, weight-average molecular weight is 88000 and hydroxyl value is the polyester polyurethane polyol of 12.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyurethane polyol (A2).
(synthesis example 1-3) [synthesis of polyester polyurethane polyol (A3)]
Neopentyl glycol 1144 parts, m-phthalic acid 753 parts, Tetra hydro Phthalic anhydride 464 parts, sebacic acid 373 parts, trimellitic acid 1,2-anhydride 19 parts and organic titanic compound 1.3 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, after being cooled to 100 DEG C, is 80% with diluted ethyl acetate to solids component.Then, the isocyanurate-modified body (SUMIDURN-3300 of hexamethylene diisocyanate is dropped into; SumitomoBayerUrethaneCo., Ltd. manufactures) 132 parts, hexamethylene diisocyanate 13 parts, in flask, pass into drying nitrogen and stir, while be heated to 70 ~ 80 DEG C to carry out urethane reaction.Stopped reaction when isocyanic ester containing ratio is less than 0.3%, obtains that number-average molecular weight is 5000, weight-average molecular weight is 51000 and hydroxyl value is the polyester polyurethane polyol of 17.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyurethane polyol (A3).
(synthesis example 1-4) [synthesis of polyester polyurethane polyol (A4)]
Neopentyl glycol 941 parts, 1 is dropped in the flask with stirring rod, temperature sensor, bead tube, 6-hexylene glycol 201 parts, m-phthalic acid 757 parts, Tetra hydro Phthalic anhydride 301 parts, hexanodioic acid 68 parts, sebacic acid 470 parts, trimellitic acid 1,2-anhydride 19 parts and organic titanic compound 1.3 parts, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, after being cooled to 100 DEG C, is 80% with diluted ethyl acetate to solids component.Then, the isocyanurate-modified body (SUMIDURN-3300 of hexamethylene diisocyanate is dropped into; SumitomoBayerUrethaneCo., Ltd. manufactures) 132 parts, hexamethylene diisocyanate 13 parts, in flask, pass into drying nitrogen and stir, while be heated to 70 ~ 80 DEG C to carry out urethane reaction.Stopped reaction when isocyanic ester containing ratio is less than 0.3%, obtains that number-average molecular weight is 5500, weight-average molecular weight is 32000 and hydroxyl value is the polyester polyurethane polyol of 11.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyurethane polyol (A4).
(synthesis example 2-1) [synthesis of polyester polyol (B1)]
Neopentyl glycol 828 parts, m-phthalic acid 588 parts, Tetra hydro Phthalic anhydride 274 parts, sebacic acid 407 parts, trimellitic acid 1,2-anhydride 15 parts and organic titanic compound 1.0 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, obtains that number-average molecular weight is 6700, weight-average molecular weight is 22000 and hydroxyl value is the polyester polyol of 12.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyol (B1).
(synthesis example 2-2) [synthesis of polyester polyol (B2)]
Neopentyl glycol 1114 parts, m-phthalic acid 717 parts, Tetra hydro Phthalic anhydride 456 parts, sebacic acid 407 parts, trimellitic acid 1,2-anhydride 19 parts and organic titanic compound 1.0 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, obtains that number-average molecular weight is 6200, weight-average molecular weight is 23000 and hydroxyl value is the polyester polyol of 15.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyol (B2).
(synthesis example 2-3) [synthesis of polyester polyol (B3)]
Neopentyl glycol 985 parts, 1 is dropped in the flask with stirring rod, temperature sensor, bead tube, 6-hexylene glycol 70 parts, m-phthalic acid 600 parts, terephthalic acid 144 parts, Tetra hydro Phthalic anhydride 349 parts, hexanodioic acid 25 parts, sebacic acid 514 parts, trimellitic acid 1,2-anhydride 19 parts and organic titanic compound 1.3 parts, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, obtains that number-average molecular weight is 6000, weight-average molecular weight is 20000 and hydroxyl value is the polyester polyol of 13.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyol (B3).
(comparing synthesis example 1-1) [synthesis of polyester polyurethane polyol (a1)]
Neopentyl glycol 1130 parts, m-phthalic acid 759 parts, Tetra hydro Phthalic anhydride 342 parts, sebacic acid 534 parts and organic titanic compound 1.2 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, after being cooled to 100 DEG C, is 80% with diluted ethyl acetate to solids component.Then, drop into hexamethylene diisocyanate 108 parts, in flask, pass into drying nitrogen and stir, while be heated to 70 ~ 80 DEG C to carry out urethane reaction.Stopped reaction when isocyanic ester containing ratio is less than 0.3%, obtains that number-average molecular weight is 10000, weight-average molecular weight is 22000 and hydroxyl value is the polyester polyurethane polyol of 9.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyurethane polyol (a1).
(comparing synthesis example 1-2) [synthesis of polyester polyurethane polyol (a2)]
Neopentyl glycol 1210 parts, m-phthalic acid 679 parts, Tetra hydro Phthalic anhydride 346 parts, hexanodioic acid 539 parts, trimellitic acid 1,2-anhydride 20 parts and organic titanic compound 1.2 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, after being cooled to 100 DEG C, is 80% with diluted ethyl acetate to solids component.Then, the isocyanurate-modified body (SUMIDURN-3300 of hexamethylene diisocyanate is dropped into; SumitomoBayerUrethaneCo., Ltd. manufactures) 132 parts, hexamethylene diisocyanate 25 parts, in flask, pass into drying nitrogen and stir, while be heated to 70 ~ 80 DEG C to carry out urethane reaction.Stopped reaction when isocyanic ester containing ratio is less than 0.3%, obtains that number-average molecular weight is 5500, weight-average molecular weight is 32000 and hydroxyl value is the polyester polyurethane polyol of 12.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyurethane polyol (a2).
(comparing synthesis example 2-1) [synthesis of polyester polyol (b1)]
Neopentyl glycol 1088 parts, m-phthalic acid 727 parts, Tetra hydro Phthalic anhydride 336 parts, sebacic acid 524 parts, trimellitic acid 1,2-anhydride 19 parts and organic titanic compound 1.2 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, obtains that number-average molecular weight is 2300, weight-average molecular weight is 5000 and hydroxyl value is the polyester polyol of 50.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyol (b1).
(comparing synthesis example 2-2) [synthesis of polyester polyol (b1)]
Neopentyl glycol 1105 parts, m-phthalic acid 898 parts, Tetra hydro Phthalic anhydride 421 parts, hexanodioic acid 272 parts, trimellitic acid 1,2-anhydride 19 parts and organic titanic compound 1.2 parts is dropped in the flask with stirring rod, temperature sensor, bead tube, while pass into drying nitrogen and stir in flask, be heated to 230 ~ 250 DEG C and carry out esterification.Stopped reaction when acid number is below 1.0mgKOH/g, obtains that number-average molecular weight is 7200, weight-average molecular weight is 21000 and hydroxyl value is the polyester polyol of 15.It is obtained with diluted ethyl acetate the resin solution that solids component is 62%, as polyester polyol (b2).
The epoxy resin (C) used in examples and comparative examples of the present invention is below shown.
Epoxy resin (C1): bisphenol A type epoxy resin (" EPICLON860 " that Dainippon Ink Chemicals manufactures) epoxy resin (C2) of number-average molecular weight (Mn) 470, epoxy equivalent (weight) 245g/eq: the bisphenol A type epoxy resin (" JER1001 " that Mitsubishi chemical Co., Ltd manufactures) of number-average molecular weight (Mn) 900, epoxy equivalent (weight) 475g/eq
The polycarbonate resin (D) used in examples and comparative examples of the present invention is below shown.
Polycarbonate polyol (D1): the polycarbonate diol (" DURANOLT5651 " that Asahi Kasei Corporation manufactures) of number-average molecular weight (Mn) 1000, hydroxyl value 10mgKOH/g
The polyisocyanates (E) used in examples and comparative examples of the present invention is below shown
Polyisocyanates (E1): the isocyanurate-modified body (" SUMIDURN3300 " that SumitomoBayerUrethaneCo., Ltd. manufacture) of hexamethylene diisocyanate
(embodiment 1)
Polyester polyol (B1) solution 90 parts of gained in polyester polyurethane polyol (A1) solution 10 parts of gained in aforementioned Production Example 1-1, aforementioned Production Example 2-1, aforementioned epoxy resins (C1) 10 parts, foregoing polycarbonates polyvalent alcohol (C1) 10 parts and aforementioned polyisocyanates (D1) 10 parts are obtained by mixing resin combination, make assess sample by following main points, evaluate by method shown below.Result is shown in table 1.
(making of assess sample)
Using 125 μm of thick PET film (" X10S " that Dongli Ltd. manufactures) as base material, by the resin combination of gained in above-described embodiment 1 with the quality of the solids component after solvent seasoning for 5 ~ 6g/m
2the mode of scope carry out application, the 25 μm of thick fluorine resin films (" AFLEX25PW " that Asahi Glass Co., Ltd manufactures) and obtain laminated film of then fitting.By its slaking 72 hours at 50 DEG C, obtain assess sample.
(evaluate 1): outward appearance for the assess sample made of preceding method, from fluorine resin film side with visual valuation laminated appearance.
Zero: the level and smooth △ of film surface: film surface exist a small amount of arc crater ×: there is multiple arc crater (depression) in film surface
(evaluating 2): the mensuration of the bonding force under wet heat condition is for the assess sample made of preceding method, use tensile testing machine (" AGS500NG " that SHIMADZU Co., Ltd. manufactures), under the condition of peeling rate 300mm/min, intensity N/15mm, carry out T-shaped stripping test, its intensity is evaluated as bonding force.The initial bonding force of evaluation of measuring sample, and 121 DEG C, expose 25 hours, 50 hours, 75 hours under humidity 100% environment after the bonding force of sample.
(evaluate 3): the initial bonding force of the assess sample that the evaluation comparison of humidity resistance measures in aforementioned evaluation 2 and 121 DEG C, expose 75 hours under humidity 100% environment after the bonding force of sample, be that the sample of more than 60% of initial bonding force is evaluated as zero by the bonding force after exposure, be evaluated as △ by more than 40% and lower than the sample of 60%, the sample lower than 40% is evaluated as ×.
(embodiment 2 ~ 14)
Except by the formula change of resin combination be as Suo Shi table 1 ~ 2 except, operation makes assess sample similarly to Example 1, and evaluates.Evaluation result is shown in table 1 ~ 2.
(comparative example 1 ~ 10), except being changed into except as Suo Shi table 3 ~ 4 by the formula of resin combination, operation makes assess sample similarly to Example 1, and evaluates.Evaluation result is shown in table 3 ~ 4.
[table 1]
[table 2]
[table 3]
[table 4]
Claims (10)
1. a resin combination, is characterized in that, it is using following compositions as neccessary composition:
(1) there is in molecule branched structure, weight-average molecular weight (Mw) be 10000 ~ 100000 scope and molecular weight distribution (Mw/Mn) be more than 5.0 polyester polyurethane polyol (A),
(2) there is in molecule branched structure, weight-average molecular weight (Mw) be 10000 ~ 50000 scope and molecular weight distribution (Mw/Mn) polyester polyol (B) that is less than 5.0,
(3) number-average molecular weight (Mn) is the hydroxyl-containing epoxy resin (C) of the scope of 300 ~ 5000,
(4) number-average molecular weight (Mn) is the hydroxyl polycarbonate resin (D) of the scope of 300 ~ 3000,
And polyisocyanates (E),
Described polyester polyurethane polyol (A) makes polyprotonic acid (E), polyvalent alcohol (F) and 3 officials can react as neccessary composition and obtain by polyisocyanate compound (G2) above,
Described polyprotonic acid (E) is the aliphatic dibasic acid 10 ~ 30 % by mole of more than 8 and the dicarboxylic acid component of aromatic acid 50 ~ 90 % by mole containing carbonatoms, described polyvalent alcohol (F) is the aliphatic polyol 40 ~ 100 % by mole of more than 5 containing carbonatoms
Described polyester polyol (B) is by the aliphatic dibasic acid containing carbonatoms more than 8 10 ~ 30 % by mole and the dicarboxylic acid component of aromatic acid 50 ~ 90 % by mole and aliphatic polyol 40 ~ 100 % by mole of polyester polyols formed of carbonatoms more than 5.
2. resin combination according to claim 1, wherein, described polyester polyurethane polyol (A) is polyester polyurethane polyol polyisocyanates (G) being reacted as neccessary composition and obtains, and described polyisocyanates (G) contains diisocyanate cpd (G1) and 3 officials with the scope that both mass ratioes (G1)/(G2) is 50/50 ~ 5/95 can above polyisocyanate compound (G2).
3. resin combination according to claim 2, wherein, the scope of the hydroxyl value of described polyester polyurethane polyol (A) is 5 ~ 30mgKOH/g.
4. resin combination according to claim 1, wherein, described polyester polyurethane polyol (A) makes 3 officials can react as neccessary composition and obtain by polyisocyanate compound (G2) above.
5. resin combination according to claim 1, wherein, the scope of the hydroxyl value of described polyester polyol (B) is 5 ~ 30mgKOH/g.
6. resin combination according to claim 1, wherein, ratio [OH]/[NCO] of the mole number [NCO] of isocyanate group contained in the total mole number [OH] of contained in described polyester polyurethane polyol (A), described polyester polyol (B), described epoxy resin (C) and described polycarbonate resin (D) hydroxyl and described polyisocyanate compound (E) is the scope of 1/1 ~ 1/2.
7. resin combination according to claim 1, wherein, relative to summation 100 mass parts of described polyester polyurethane polyol (A) with described polyester polyol (B), contain described epoxy resin (C) with the scope of 5 ~ 20 mass parts, and contain described polycarbonate resin (D) with the scope of 5 ~ 20 mass parts.
8. a two-component-type lamination caking agent, it contains the resin combination according to any one of claim 1 ~ 7.
9. a laminated film, its adhesive linkage that there is the film of more than a kind in the group being selected from and being made up of polyester film, fluorine resin film, polyolefin film and tinsel and formed by caking agent according to claim 8.
10. a backboard for solar cell, it has the adhesive linkage formed by caking agent according to claim 8.
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| JP2012-095546 | 2012-04-19 | ||
| JP2012095546 | 2012-04-19 | ||
| PCT/JP2013/061507 WO2013157604A1 (en) | 2012-04-19 | 2013-04-18 | Resin composition, two-part laminating adhesive, laminated film, and backsheet for solar cell |
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| JP5787202B2 (en) * | 2013-09-06 | 2015-09-30 | Dic株式会社 | Polyester polyol, polyol agent for laminating adhesive, resin composition, curable resin composition, laminating adhesive, and solar cell backsheet |
| JP6210307B2 (en) * | 2013-12-24 | 2017-10-11 | Dic株式会社 | Resin composition, two-component laminating adhesive, laminated film and solar cell backsheet |
| WO2016010132A1 (en) * | 2014-07-18 | 2016-01-21 | Dic株式会社 | Adhesive for solar-cell backsheet, polyol composition for solar-cell backsheet adhesive, solar-cell backsheet, and solar cell module |
| CN104231204B (en) * | 2014-09-18 | 2017-08-29 | 东莞市吉鑫高分子科技有限公司 | A kind of TPUE used for solar batteries and preparation method thereof |
| JP2019034466A (en) * | 2017-08-15 | 2019-03-07 | 東洋製罐グループホールディングス株式会社 | Gas barrier film laminate |
| JP7137937B2 (en) * | 2018-03-09 | 2022-09-15 | 三井化学株式会社 | Laminating adhesives and packaging materials |
| TW202206519A (en) * | 2019-06-27 | 2022-02-16 | 日商旭化成股份有限公司 | Polyisocyanate composition, composition for film formation, film, film laminated body, adhesive resin composition, adhesive resin cured product, composition for coating materials, and coating material cured product |
| CN112143437A (en) * | 2020-09-08 | 2020-12-29 | 沈阳化工研究院有限公司 | Lithium battery aluminum plastic film outer layer adhesive resin and preparation and application thereof |
| CN116761867A (en) * | 2021-02-02 | 2023-09-15 | Dic株式会社 | Adhesive, laminate and packaging material |
| CN113462341B (en) * | 2021-07-01 | 2022-12-09 | 河南省科学院化学研究所有限公司 | Double-component solvent-free reaction type polyurethane hot melt adhesive |
| JP7190542B1 (en) | 2021-07-16 | 2022-12-15 | 大日精化工業株式会社 | glue |
| WO2023286644A1 (en) * | 2021-07-16 | 2023-01-19 | 大日精化工業株式会社 | Adhesive |
| CN115073715A (en) * | 2021-10-22 | 2022-09-20 | 上海联景高分子材料有限公司 | Polyester polyol for adhesive, and preparation method and application thereof |
| JP2023151005A (en) | 2022-03-31 | 2023-10-16 | 日東シンコー株式会社 | Hot-melt adhesive sheet |
| JP2023150988A (en) | 2022-03-31 | 2023-10-16 | 日東シンコー株式会社 | Hot-melt adhesive sheet |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102099434A (en) * | 2008-07-16 | 2011-06-15 | 东洋油墨制造株式会社 | Polyurethane adhesive for outdoor use |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3915371B2 (en) * | 2000-05-29 | 2007-05-16 | 大日本インキ化学工業株式会社 | Laminate adhesive composition with excellent hot water resistance |
| JP4744138B2 (en) * | 2004-12-24 | 2011-08-10 | バンドー化学株式会社 | Transdermal preparation |
| US8734943B2 (en) * | 2011-04-22 | 2014-05-27 | Dic Corporation | Resin composition, two-pack type adhesive for laminates, multilayer film, and back sheet for solar cells |
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2013
- 2013-04-18 JP JP2013539032A patent/JP5413704B1/en active Active
- 2013-04-18 WO PCT/JP2013/061507 patent/WO2013157604A1/en active Application Filing
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| CN102099434A (en) * | 2008-07-16 | 2011-06-15 | 东洋油墨制造株式会社 | Polyurethane adhesive for outdoor use |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5413704B1 (en) | 2014-02-12 |
| JPWO2013157604A1 (en) | 2015-12-21 |
| TWI557148B (en) | 2016-11-11 |
| TW201348280A (en) | 2013-12-01 |
| WO2013157604A1 (en) | 2013-10-24 |
| CN104093760A (en) | 2014-10-08 |
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