CN1104481C - Reactive hotmelt adhesive - Google Patents
Reactive hotmelt adhesive Download PDFInfo
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- CN1104481C CN1104481C CN96112970A CN96112970A CN1104481C CN 1104481 C CN1104481 C CN 1104481C CN 96112970 A CN96112970 A CN 96112970A CN 96112970 A CN96112970 A CN 96112970A CN 1104481 C CN1104481 C CN 1104481C
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- butylene
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Abstract
The present invention provides liquid type reactive hot melt adhesive with excellent heat resistance, durability, mechanical physical property, working property, adhesiveness, etc., which is composed of polyurethane prepolymer containing 0.1 to 5 wt% of isocyanate groups. A compound which contains poly (ethene-butene) copolymer containing 1 to 100 mol % of hydroxy groups and contains active hydrogen, and organic diisocyanate react to obtain ethyl cyanoformate.
Description
The present invention relates to the reactive hot melt adhesive of an all good liquid type such as thermotolerance, hydrolytic resistance, mechanical-physical, binding property.
In the past, the tackiness agent aspect was known hot-melting type and a response type.
The feature of hotmelt is, will be on by adherend with the adhesive coated of thermatron heating and melting, press sticking and after fitting, make its curing by cooling, acquisition initial stage bounding force, operability is good, but its shortcoming is, fusible poor durability under the high temperature is restricted as the use range of tackiness agent.
In the hotmelt in the past, ethene-vinyl acetate copolymer (EVA), new LDPE (film grade) (LDPE), Atactic Polypropelene (APP), styrene-butadiene-styrene multipolymer (SBS), styrene-isoprene-styrene copolymer-(SIS), styrene-ethylene-styrol copolymer (SES), butyl type rubber, polyamide-based, polyester etc. are arranged.
Wherein, thermotolerance is arranged than higher in polyamide-based, the polyester, but because the relation of melt viscosity must also be set coating temperature higher, to heat-resisting difference by adherend, just can not use.
On the other hand, the bond strength of reaction-ing adhesive when high temperature is good.Yet reaction-ing adhesives such as the epoxies known to general, acrylic acid or the like, the initial stage bounding force during operation is little, need the time to solidify until reaction, so operability is poor.
Therefore studying the initial stage bounding force that has hot-melting type concurrently and the stable on heating reactive hot melt adhesive of response type.As curing reaction method in such cases, heating, oxidation, uviolizing are proposed, electron rays irradiation, moisture or moisture, binary liquid shape schemes such as (hosts/curing formulation).Wherein easy and the most practical method is to utilize moisture or moisture to be cured the type of reaction.As such method, known will have the reactive hot melt adhesive of the polyurethane prepolymer of isocyanate group (hereinafter to be referred as the NCO yl) as main component in molecular end.
For example, in the special public clear 51-47735 communique, disclose the reactive hot melt adhesive as principal constituent of the NCO terminal amino group ethyl formate pre-polymerization of forming by poly-dipropylene glycol (PPG) and tolylene diisocyanate (TDI) etc., but this polyethers of this PPG is bad as its thermotolerance of urethane of main frame tube.
The spy opens in the clear 63-251415 communique the open pure and mild diphenylmethanediisocyanate of polyester polyols (hereinafter to be referred as MDI) that is obtained by polycaprolactone polyol and hexanodioic acid and hexylene glycol, and to wait the basic terminal polyurethane prepolymer of the NCO that forms be the reactive hot melt adhesive of main component, but with the polyester is the urethane of main framing, the field that can not be used for having hydrolytic resistance.
The reactive hot melt adhesive of the isoprene that imports main hydroxyl is disclosed in the Te Kaiping 3-207782 communique, but the polyolefins of hydroxyl in the past, because remaining pair of key, and weather is poor, and functional group's number is also many, and therefore the danger of gelation often arranged.
The object of the present invention is to provide all good liquid type reactive hot melt adhesive of a kind of thermotolerance, weather resistance, mechanical properties, operability, binder performance.
For achieving the above object, a liquid type reactive hot melt adhesive of the present invention is characterised in that, it is reacted by active hydrogen-contg compound that makes poly-(ethene-butylene) multipolymer that contains 1-100 mole % hydroxyl and organic diisocyanate, and the polyurethane prepolymer that obtains, contain 0.1-5 weight % isocyanate group forms.
And the present invention is the above-mentioned tackiness agent of the mol ratio 30/70-70/30 of vinyl/butenyl in poly-(ethene-butylene) multipolymer of above-mentioned hydroxyl.
Poly-(ethene-butylene) multipolymer that contains hydroxyl that uses among the present invention, grafted ethene alkylol cpd on poly-(ethene-butylene) multipolymer that obtains by the radical polymerization of ethene and butylene or the polymerization of anionoid polymerization isoreactivity for example, obtain by handling terminal polymerization starter composition, but the crystallinity of random copolymers is minimum, bounding force is big, thereby best.
Contain the vinyl that gathers (ethene-butylene) multipolymer of hydroxyl and the mol ratio of butenyl and be preferably 30/70～70/30.In the time of beyond this scope, crystallinity increases, and melting temperature (Tm) uprises, and therefore is difficult to obtain the reactive hot melt adhesive as the purpose product.
The number-average molecular weight that contains poly-(ethene-butylene) multipolymer of hydroxyl is advisable with 500-10000, preferred 1000-9000.
During the number-average molecular weight less than 500 of poly-(ethene-butylene) multipolymer of hydroxyl, its result is roughly the same with the situation that only imports the chain extension agent in polyurethane prepolymer, is difficult to obtain import the effect of poly-(ethene-butylene) multipolymer of hydroxyl.When number-average molecular weight surpasses 10000, low with other the polyvalent alcohol or the intermiscibility of organic diisocyanate etc., and contain the viscosity degree of poly-(ethene-butylene) multipolymer of hydroxyl, thereby be difficult to obtain reactive hot melt adhesive as the purpose product.
Contain the hydroxy radical content of poly-(ethene-butylene) multipolymer of hydroxyl, be advisable with 1.5～2.5 of per 1 molecule average out to, preferred 1.8～2.0, more preferably 2.0.
During 1.5 of hydroxyl less thaies, poly-(ethene-butylene) multipolymer of hydroxyl is difficult to import in the polyurethane prepolymer molecule, and the end of the polyurethane prepolymer of acquisition is difficult to become the NCO base, very weak with the reaction of moisture behind the coating adhesive, thermotolerance, weather resistance are all very poor.When hydroxyl surpasses 2.5, during the synthesizing amino ethyl formate, produce gelation, be difficult to obtain polyurethane prepolymer along with the import volume that gathers (ethene-butylene) multipolymer of hydroxyl.
As above-mentioned (ethene-butylene) multipolymer that contains hydroxyl, concrete example is if any the HPVM-2202 of Craton liquid series.
The import volume of poly-(ethene-butylene) multipolymer of hydroxyl is 1～10 mole of % in the total amount that contains the compound bearing active hydrogen composition in the polyurethane prepolymer of the present invention.
As the compound bearing active hydrogen that contains that also can use in the present invention, except that poly-(ethene-butylene) multipolymer that can enumerate above-mentioned hydroxyl, whole compound bearing active hydrogen that contain of in polyurethane chemistry, using in addition.
For example specifically can enumerate, preferably molecular weight is 500～10000, preferred molecular weight is polymer polyamine such as macromolecule polyols such as the polyester polyol, polyether glycol, polycarbonate polyol, acrylic polyol, polyolefin polyhydric alcohol of 1000-5000 and polyethers polyamine, perhaps, the low molecular polylol of the molecular weight less than of using as the chain extension agent 500, low molecular weight polycaprolactone amine, low molecule amino alcohol, according to occasion, also can use monohydroxy-alcohol, this class of monoamine NCO base conditioning agent.Containing compound bearing active hydrogen, both can be single variety, can be that the multiple material of 2-3 constitutes by average functional group number also, but owing to generate the easy control of the molecular weight of the 2 functional polyurethane prepolymers that contain compound bearing active hydrogen, therefore preferred.These contain compound bearing active hydrogen also can comprise hydroxyl, uncle's amino, sulfonic group, phosphate etc. or their salt.
In the above-mentioned macromolecule polyol, concrete example as polyester polyol, can enumerate ethylene glycol, glycol ether, 1, the 2-propylene glycol, 1, ammediol, dipropylene glycol, 1, the 2-butyleneglycol, 1, the 3-butyleneglycol, 1, the 4-butyleneglycol, neopentyl glycol, 1, the 2-pentanediol, 1, the 3-pentanediol, 1, the 4-pentanediol, 1, the 5-pentanediol, the 2-methyl isophthalic acid, the 5-pentanediol, the 3-methyl isophthalic acid, the 5-pentanediol, 1, the 6-hexylene glycol, 2,2,4-trimethylammonium-1, ammediol, 2-ethyl-1, the 3-hexylene glycol, 2,2-diethyl-1, ammediol, 2-normal-butyl-2-ethyl-1, ammediol, the ethylene oxide adduct of two A phenol, low mass molecule alcohol class such as the propylene oxide adduct of dihydroxyphenyl propane or their mixture and, succsinic acid, hexanodioic acid, sebacic acid, nonane diacid, phthalic acid, different phthalic acid, terephthalic acid, fumaric acid, toxilic acid, oxalic acid, the polyester of third terminal hydroxyl that dihydroxy acids such as naphthalene diacid obtain through dehydration condensation, or the polycaprolactone glycol that obtains by the ring-opening polymerization of 6-caprolactone etc.
As the concrete example of polyether glycol, the polyether glycol that can enumerate a kind of of epoxide such as oxyethane, propylene oxide or mixture is obtained through ring-opening polymerization, the poly-tetramethylene glycol that tetrahydrofuran (THF) obtains through ring-opening polymerization.
As the concrete example of polycarbonate polyol, can enumerate the material that low mass molecule alcohol class used in the above-mentioned polyester polyol and diethyl carbonate obtain through taking off ethanol synthesis.
As the concrete example of polyolefin polyhydric alcohol, can enumerate the polyhutadiene that contains hydroxyl, the hydrogenation polyhutadiene of hydroxyl, the polyisoprene of hydroxyl.
As above-mentioned low molecular polylol, the low mass molecule alcohol class of using when can the above-mentioned polyester polyol of illustration synthetic.
As low molecular weight polycaprolactone amine, for example can enumerate aliphatie diamines such as quadrol, hexamethylene-diamine and, alicyclic diamine such as isophorone diamine, cyclohexanediamine and, aromatic diamines such as diaminodiphenylmethane, diaminodiphenylsulfone(DDS).
As low molecule amino alcohol, can enumerate Monoethanolamine MEA BASF, diethanolamine.
As monohydroxy-alcohol, can enumerate methyl alcohol, ethanol, propyl alcohol, Virahol etc.
As monohydroxy-alcohol, can enumerate uncle's monobasic amines such as ethamine, butylamine, Zhong Yiyuan amines such as diethylamine, dibutylamine etc.
As the organic diisocyanate that uses among the present invention, can enumerate 1, oneself two cyanates of 6-, lysinediisocyanate, isophorone diisocyanate, cyclohexyl diisocyanate, 4,4 '-dicyclohexyl methane diisocyanate, hydrogenation benzene two group diisocyanates, hydrogenation Three methyl Benzene dimethyl vulcabond, 2-methylpentane-1, the 5-vulcabond, 3-methylpentane-1, the 5-vulcabond, 2,2,4-tri-methyl hexamethylene-1, the 6-vulcabond, 2,4,4-tri-methyl hexamethylene-1, aliphatics such as 6-vulcabond, alicyclic diisocyanate, 4,4 '-MDI, 2,4 '-MDI, 4,4 '-phenylbenzene dimethylmethane vulcabond, 4,4 '-dibenzyl vulcabond, 1, the 5-naphthalene diisocyanate ester, PPDI, toluene support-2, the 4-vulcabond, toluene support-2, the 6-vulcabond, the o-Xylol vulcabond, m xylene diisocyanate, the p-Xylol vulcabond, tetramethylxylene diisocyanate etc. are difficult to xanthochromic vulcabond and composition thereof.
Wherein, from vapour pressure and in price, with 4,4 '-MDI is best.
When synthesizing polyurethane prepolymer of the present invention, can use known urethane esterification catalyzer.Specifically can enumerate organometallic compounds such as dioctyl tin dilaurate, organic amine such as triethylenediamine and its esters etc.
Polyurethane prepolymer of the present invention can be with once finishing (One-shot) method, any synthesizing in the secondary Completion Techniques, but must be that the NCO Kina sample of remaining specified amount on molecular end reacts each raw material.
The NCO content of the polyurethane prepolymer that makes thus is necessary for 0.1～5 weight %, preferred 0.5～4.5 weight %.
When NCO contained quantity not sufficient 0.1 weight %, the molecular weight of cured resin was excessive, and it is big that melt viscosity becomes, and operability is poor.And the cross-linking set in the resin of coating back is few, thereby can not get enough thermotolerances, weather resistance.When NCO content surpassed 5 weight %, the molecular weight of cured resin was too little, and physical strength is not enough.
The number-average molecular weight of polyurethane prepolymer of the present invention is with 2,000～50, and 000 for well, and is preferred 3,000～20,000, and more preferably 4,000～15,000.
The number-average molecular weight deficiency of polyurethane prepolymer 2,000 o'clock, the physical strength deficiency surpasses at 50,000 o'clock, and it is too high that melt temperature becomes, and operability is poor.
Among the present invention, also can further add to use and give adhering resin.As this resin, can enumerate terpine resin class, tree oil lipid, rosin tree lipid, terpenes-phenolic resin class etc.
As the binding property imparting agent of terpine resin class, YS Resin A, the YS resin Px of Yasuharachemical (strain) system, ピ ッ コ ラ ィ ト A, the ピ Star コ ラ イ ト S of Ha-キ ユ レ ス society system are arranged specifically.As the binding property imparting agent of tree oil lipid, the ア Le コ Application of waste river chemical industry (strain) system is specifically arranged, the エ ス コ レ ッ Star of eastern burning petroleum chemistry (strain) system, the Ha ィ レ ッ Star of Mitsui petroleum chemistry (strain) system, ッ Network エ-ス, ペ ト ロ ジ Application etc.As the binding property imparting agent of rosin tree lipid, Estergum, the Superester etc. of waste river chemical industry (strain) system are arranged specifically.The binding property imparting agent of terpenes-phenolic resin class, YS Port リ ス one, マ イ テ ィ ェ one ス etc. that specifically have Yasuharachemical (strain) to make.
Usually these give the addition of the resin of tackiness agent, with respect to urethanum 100 weight parts, being advisable below 200 weight parts, below preferred 150 weight parts.
In the present invention, also can add wax that use uses, softening agent, rubber, stablizer etc. in the ordinary hot melt adhesive.
Reactive hot melt adhesive of the present invention, can with plastics such as PET, nylon, polyethylene, polypropylene, metals such as iron, aluminium, all base materials such as cloth, timber, paper are bonding; Especially as the tackiness agent that can not obtain the polyolefins of enough bond strengths with former polyurethane resin adhesive, effective especially.
Below specify the present invention with embodiment, but the present invention is not limited by they.
Embodiment 1
In 2 liters of four-hole boiling flasks forming by stirrer, thermometer, Allihn (Allihn) cooling tube, nitrogen ingress pipe, pack into poly-(ethene-butylene) multipolymer (merchant's mouthful name: HPVW-2202, シ ユ Le society system, number-average molecular weight 3600) 1778g of hydroxyl is heated to 60 ℃.Wherein add 4,4 '-MDI 222g in 80 ℃ of urethane esterification reactions of carrying out 4 hours, after the urethane esterification reaction, carries out vacuum deaerator in 10mmHg.
The NCO content of the polyurethane prepolymer that generates is 1.2 weight %, and the viscosity of solution is 8000cp/100 ℃.
Use this polyurethane prepolymer solution (PU-1) to carry out various performance tests.
The results are shown in the table 1.
Embodiment 2
In the device identical, pack into and contain poly-(ethene-butylene) multipolymer (HPVM-2202) 1067g of hydroxyl with embodiment 1.Number-average molecular weight is 2000 3-methyl isophthalic acid, and two ends that 5-pentanediol and hexanodioic acid obtain through dehydrating condensation contain polyester (trade(brand)name: Network ラ Port-Le P2010, Network ラ レ (strain) system) 711g of hydroxyl, are heated to 60 ℃.Wherein add 4,4 '-MDI222g with embodiment 1 identical the reaction, handles, and obtains polyurethane prepolymer.
The NCO content of this polyurethane prepolymer is that the viscosity of 0.7 weight %, solution is 10000CP/100 ℃.
Use this polyurethane prepolymer solution (PU-2) to carry out each performance test.
The results are shown in the table 1.
Embodiment 3
In the device identical with embodiment 1, pack into and contain poly-(ethene-butylene) multipolymer (HPVM-2202) 667g of hydroxyl, number-average molecular weight be 5000 1, two ends that 6-hexylene glycol and hexanodioic acid obtain through dehydrating condensation contain polyester (HA-5000) 1111g of hydroxyl, are heated to 60 ℃.Wherein add 4,4 '-MDI222g reacts similarly to Example 1, after the processing, obtains polyurethane prepolymer.
The NCO content of this polyurethane prepolymer is 0.9 weight %, and the viscosity of solution is 7000cp/100 ℃.
Use this polyurethane prepolymer solution (PU-3) to carry out various performance tests.
The results are shown in the table 1.
Comparative example 1
In the device identical with embodiment 1, the number-average molecular weight of packing into is 3000 3-methyl isophthalic acid, two ends that 5-pentanediol and hexanodioic acid obtain through dehydrating condensation contain polyester (trade(brand)name Network ラ Port Le P-3010, Network ラ レ (strain) system) 1778g of hydroxyl, are heated to 60 ℃.Wherein add 4,4 '-MDI222g after reacting similarly to Example 1, handling, obtains polyurethane prepolymer.
The NCO content of this polyurethane prepolymer is 1.2 weight %, and the viscosity of solution is 9000cP/100 ℃.
Use this polyurethane prepolymer solution (PU-4) to carry out various performance tests.
The results are shown in the table 1.
(performance test)
Fusible measuring method
Use the heat seeling coating machine, separately with polyurethane prepolymer solution PU-1～4, press coating thickness 50 μ m, be coated on the aluminium sheet, fitting with polypropylene board immediately obtains bonding sample.
After this bonding sample left standstill and makes it moisture-curable through 25 ℃ * 50%RH * 1 week, measure bond strength with JIS K-6850.
The measuring method of stretching rerum natura, dynamic viscoelastic, softening temperature.
With polyurethane prepolymer solution PU-1～4, after casting by 300 μ m respectively, leave standstill through 25 ℃ * 50%PH * 1 week and to make it moisture-curable, obtain sample.
To thus obtained film, measure its stretching rerum natura, dynamic viscoelastic and softening temperature by the following method.
(1) stretching rerum natura
The film that No. 4 dumb-bell shape cutter stamping-outs of stipulating with JIS K-6301 make, with Tan Xilun (Tensilon) UTM-500 (オ リ エ Application テ Star Network (strain) system), draw speed: 200mm/ minute, measure temperature: 25 ℃, measure temperature: under 50% condition, measure the stretching rerum natura (intensity during fracture and extensibility) of film.
(2) dynamic viscoelastic
The film stamping-out that makes is become 4mm * 50mm, with レ オ バ イ Off プ ロ Application
(strain of オ リ エ Application テ Star Network) system), in frequency: 35Hz, heat-up rate: measure dynamic viscoelastic E ' under 2 ℃/minute the condition.Second-order transition temperature (Tg) is defined as E " (loss resilience rate) become the temperature when very big.Dynamic elasticity rate E ' is 25 ℃ a value.
(3) softening temperature
Film with No. 2 dumb-bell shape cutter stamping-outs of stipulating among the JIS K-6301 make adds 500gf/cm on the test film film
2Loading, press 5 ℃/minute of heat-up rates, the temperature the when stretching of test film film is reached 3 times is defined as softening temperature.
Table 1
| Embodiment | Comparative example | |||
| 1 | 2 | 3 | 1 | |
| Poly-(ethene-butylene) multipolymer (g) HPVM-2202 that contains hydroxyl | 1778 | 1067 | 667 | |
| Macromolecule polyol (g) Network ラ Port-Le P-2010 HA-5000 Network ラ Port-Le P-3010 | 711 | 1111 | 1778 | |
| Organic diisocyanate (g) 4,4 '-MDI | 222 | 222 | 222 | 222 |
| Polyurethane prepolymer (solution) (g) is called for short viscosity (cP/100 ℃) NCO content (weight %) number-average molecular weight | PU-1 8000 1.2 7000 | PU-2 10000 0.7 12000 | PU-3 7000 0.9 9000 | PU-4 9000 1.2 7000 |
| Bond strength (kgf/cm 2) | 90 | 85 | 75 | 10 |
| Intensity (kgf/ cm when the rerum natura stretching rerum natura of cured resin ruptures 2) unit elongation (%) dynamic viscoelastic Tg when rupturing (℃) E ' 25 (* 108dyn/cm 2) softening temperature (℃) | 100 500 -45 1.0 20 | 150 700 -40 1.2 40 | 300 400 -35 1.4 50 | 130 800 -45 1.1 20 |
Can learn that by above explanation reactive hot melt adhesive of the present invention is so owing to be that a liquid type can after the applying, by cooling curing, just can obtain enough initial stage bounding forces on directly being coated on by adherend behind the heating and melting.Thereafter, without heat treated NCO base and airborne moisture are reacted, solidify, so operability, weather resistance is good, and thermotolerance, hydrolytic resistance, binding property are also good.
Claims (2)
1. the reactive hot melt adhesive of a liquid type, it is characterized in that, it is by the polyurethane prepolymer that compound bearing active hydrogen and organic diisocyanate reaction obtained, contained 0.1～5 weight % isocyanate group that contains that contains poly-(ethene-butylene) multipolymer of 1～100 mole of % hydroxyl is constituted, the number-average molecular weight of poly-(ethene-butylene) multipolymer of described hydroxyl is 500～10000, and contained hydroxyl value is 1.5～2.5 in each molecule.
2. the described reactive hot melt adhesive of claim 1, the mol ratio of vinyl/butenyl is 30/70～70/30 in poly-(ethene-butylene) multipolymer of wherein said hydroxyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96112970A CN1104481C (en) | 1996-09-24 | 1996-09-24 | Reactive hotmelt adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96112970A CN1104481C (en) | 1996-09-24 | 1996-09-24 | Reactive hotmelt adhesive |
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| Publication Number | Publication Date |
|---|---|
| CN1180091A CN1180091A (en) | 1998-04-29 |
| CN1104481C true CN1104481C (en) | 2003-04-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96112970A Expired - Fee Related CN1104481C (en) | 1996-09-24 | 1996-09-24 | Reactive hotmelt adhesive |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102639615A (en) * | 2009-12-02 | 2012-08-15 | 东洋纺织株式会社 | Readily bondable polyester film for solar cells |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3199344B1 (en) * | 2016-02-01 | 2022-04-13 | Henkel AG & Co. KGaA | Electrical debonding of pu hot melt adhesives by use of conductive inks |
| EP3336115A1 (en) * | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Process for the reduction of emissions in polyurethane foams |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0790046A (en) * | 1993-09-22 | 1995-04-04 | Nippon Polyurethane Ind Co Ltd | Resin composition for damping material and damping material using the same |
| US5410011A (en) * | 1992-12-04 | 1995-04-25 | Inoac Corp. | One-component polyurethane type adhesive, and use thereof |
| JPH07179838A (en) * | 1993-12-24 | 1995-07-18 | Inoac Corp | Two-component polyurethane adhesive and its use |
| CN1120061A (en) * | 1993-10-07 | 1996-04-10 | 美国3M公司 | Binder for magnetic media |
-
1996
- 1996-09-24 CN CN96112970A patent/CN1104481C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5410011A (en) * | 1992-12-04 | 1995-04-25 | Inoac Corp. | One-component polyurethane type adhesive, and use thereof |
| JPH0790046A (en) * | 1993-09-22 | 1995-04-04 | Nippon Polyurethane Ind Co Ltd | Resin composition for damping material and damping material using the same |
| CN1120061A (en) * | 1993-10-07 | 1996-04-10 | 美国3M公司 | Binder for magnetic media |
| JPH07179838A (en) * | 1993-12-24 | 1995-07-18 | Inoac Corp | Two-component polyurethane adhesive and its use |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102639615A (en) * | 2009-12-02 | 2012-08-15 | 东洋纺织株式会社 | Readily bondable polyester film for solar cells |
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| Publication number | Publication date |
|---|---|
| CN1180091A (en) | 1998-04-29 |
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